And Unit 5: stems, leaves and roots

Chapter 9: 176-191, chapter 10: 196-215

Stem and leaf crops from biennials (plants that complete their lifecycle in 2 years)
 biennial species use roots not only for absorption but storage
 farmers interested in a root crop wait as long as possible to gather the most amount of nutrients – at
the end of the first years growth

biennials grown as annual leafy crops

 cabbage and its relatives
o Brassicacea- cabbage and relatives- canola oil and mustard  have a pungent flavour due to
the mustard oil glycosides found in them
o Mustard oil glycosides- have sulfur containing antipredator compounds that repel pathogens,
insects, animals ..
o This compound is shown to have many health benefits
o Vegetables that are produced by modifications of shoots of brassica species – cabbage, Brussel
sprouts, kale, broccoli cauliflower = cole crops
 Grown today as annuals but their ancestors were biennial or perennial
o The native species Brassica oleracea (ancestor of the cole group) is thought to have been
cultivated 650 BC by the greeks
o The plants first cultivated developed a waxy coating that protected them from salt damage 
evident in modern crops (contributes to their resistance to drought and cold)
o Cabbage preservation  sauerkraut provided sources of vitamin C
o Cabbages grown in warmer climates can bolt: produce a flowering shoot
o Cabbage: formed when their lateral meristem of primary shoot don’t elongate and inner leaves
don’t expand
o Brussel sprouts: produced when axillary buds form small lateral heads
o Cauliflower and broccoli: inflorescences of the cabbage plant and treated as different varieties
 Broccoli: mass of fertile flower buds
 Cauliflower: proliferation of the stem tips – forming a mass of tissue= curds
 Chard
o Believed to have been eaten by humans in the Mediterranean region

o
 celery
o Apiaceae-known for its culinary herbs and biennial root crops like carrots and parsnips
 o Celery is commonly grown as vegetables
o Celery: edible parts are leaf petioles- an axillary bud is at the bottom of each stalk
 Contains high levels of nitrites- used as a preservative in nitrite free (inorganic nitrite/
nitrate free) meat products
 Lettuce and its allies
o Asteraceae family- characteristic heads of many small flowers
o 4500 BC cultivation- Egypt
o modern lettuce is derived from L. serriola- biennial species from the Mediterranean
o lettuce heads are formed by the suppression of lateral buds ( bolt if not picked soon enough)
o endives and chicory: belong to the genus Cichrium (lettuce belongs to Lactuca)
 Belgian endives come from the perennial species cichorium intybus
 Chicory roots are often roasted and ground into powder
 Spinach (spinachia oleracea)
o Member of the AMaranthaceae family
o Native to western Asia
o Contains compounds that inhibit iron absorption
o Folic acid- a vitamin necessary for synthesis of amino acids was isolated from spinach
 Other greens
o Arugula, dandelion greens, mustard green, radiccio, mache and watercress

Perennial vegetables: artichokes and asparagus

 The perennial habit:
o Care in soil preparation because the plants remain in olace for many years
o Cultivation is delayed 2 or more years after planting to allow plants to become well established
with root reserves
o Perennial temperate vegetable crops are generally replanted every 15-25 years
 Artichokes ( cynara scolymus) : means earth thorn
o Asteraceae family
o Cultivated for their immature flower heads
o Planted using suckers or basal branches
o High carbohydrate component  inulin (humans cant digest this)
 Asparagus (asparagus officinalis)
o Native to southern Europe, Eastern Asia and northern Africa
o Sprout rapidly from underground rhizomes
o Contains folate

Vegetables from bulbs

 Onions, leeks, garlic, shallots and chives
o Alliaceae family
o Onions, shallots and garlic originated in central Asia
o Leek originated in the Near East
 All cultivated in Egypt
o Onions- grown for their single, large bulb
o Garlic- grown for its clusters of bulbs – called a clove
o Leeks- edible parts are the swollen white basal portion and green leaf blades
o Chives- eaten solely for their leaves
o Onions contain the most sugar
 o All allium species seem to have medicinal properties
o Sulfur compounds- are released when the cells of an onion are ruptured (what makes you
cry) form sulfuric acid when dissolved in fluid covering our eyes
 This reaction can be avoided by freezing onion before cutting or cutting in water

Biennial root crops:

 High in calories but lower in carbohydrates than other storage crops
 Families that yield the major biennial root crops: Brassicacea- mustard, Apiaceae- carrot and
Amaranthaceae- beet
 Of the mustard and cabbage family- turnips and rutabagas are the 2 major root crops
o The edible part is the hypocotyl (where the stem and root meet).
 Turnips originate in Europe and Asia
 Rutabaga: more nutritious but more pronounced flavour
o Polyploidy between cabbage and turnip
o Cultivars are selected for use as an oilseed crop
 Radish- the red colour is a mutation
 Roots of the carrot family:
o Apiaceae- carrots and parnsips
o Carrots store reserves in the main taproot (cortex)
o Original domestications of carrot where purple or white
 Purple carrots contain anthocyanins- health benefits
 Orange colour in carrots= beta carotene – contains vitamin A (benefit for eyes)
o Parsnips: native to Mediterranean
 The beet family (beta vulgaris)
o Provides 3 other crop plants: mangel- wurzel (used as stock feed) , swiss chard and sugar beet
 Differ in position of the hypocotyl
o Yam beans (Jicamas)- poisonous when mature
 Sold highly in mexico

Starchy tubers, rhizomes and roots

 Functions of tubers and rhizomes
o Tubers and fleshy fruits were among the main food gathered by pre-agricultural people
o Can be used in propagation
 Irish potatoes: 4th as a major food staple (behind wheat, corn and rice)
o Cultivated for at least 7000 years
o People in the Andes preserve them using a certain freeze thaw drying method freezing
ruptures the cells , then they squeeze out water , over several days of repetition, a dry mass of
cellulose is formed (chuno) – keeps for months
o If allowed to turn green- they produce solanine a poisonous glycoalkaloid
o Became a staple in Ireland in the 18th century, potato blight lead to mass starvation
o The common potato is a tetraploid
o Domesticated 10,000 years ago in Peru  wild species solanum brevicaule
o Mainly propagated by tubers (most are male sterile)
 Yams (second most important tuber)
o True yams belong to the Dioscorea genus
o Independent domestication in Africa, Asia and South America
 Other tubers: taro, eddoe, dasheen, cocoyam (malangas, yautias or tannias) and canna/ achira
 o Dasheens are staples in tropical Pacific areas
o Tubers used as a powdered starch

Starchy root crops

 Manioc:
o Predominantly starch- 50% of global production in Africa
o Domestication in Brazil
o High carbohydrate content but low protein content and no vitamins
o Contain poisonous compounds that must be removed before eating  form hydrogen cyanide
when cut, bruised etc
o Cassava with the glycosides still in them = konzo disease (paralysis of the legs)
o Sweet maniocs- have little or no glycosides
o Bitter maniocs- large amount of glycosides
 Sweet potatoes (impomoea batatas)
o Native to south America
o Temperate areas grown as a annual and grown as a perennial in tropical areas
o True roots – they lack root scars
o Small amount of protein, some sugar and a lot of beta carotene
o China is the worlds leading producer

Sweets from stems, roots, leaves and fruits

 Sugar comes from the stem or root of a plant
 Sucrose is a disaccharide produced by chemical bonding of glucose and fructose
 Sucrose is the primary sugar stored in the phloem – not commonly stored in fruits, roots or tubers
 Sugar cane:
o Perennial grass
o Easily propagated by means of setts
o Setts: part of the stem that includes lateral buds and a circle of cells that give rise to
adventitious roots
 The adventitious root can absorb nutrients until a new shoot roots are formed  once
they do this cane plants put out tillers that give rise to new stalks
 Raw sugar production and refining
o Crystallized sugar is made by processing the juice of cut sugar cane or harvested sugar beets
o Canes are sent to mills where they are rolled and crushed to express the juice
o Boiling, clarifying with calcium hydroxide, filtering, evaportating and separating raw crystals
from molasses
o Raw cane sugar is used to make rum
o Refining raw sugar is done in refineries
o Sugar refining:
 Crystals dissolved into heavy syrup, filtered (through charred bone) – formation of
white crystals
 Other plant sources of sweeteners
o Sorghum molasses
o Date palm
o Sugar maple
o Stevia
o Monk fruit
Unit content
Vegetative plant parts as food
 Biennials: have a 2 year life cycle
o During the first year- they grow vegetatively and generally store energy in a root, tuber or other
storage organs  then go dormant in the winter
o The stored energy is used in the spring to accelerate growth and reproductive structures and
seeds are produced the second season
o After this the plant dies
o Ideal because they store a lot in their roots after the first season, they don’t flower during their
first year – rich in many nutrients
o Brassica oleraceae- domesticated to produce a variety of crops like kale, broccoli, Brussel
sprouts, cabbage…
o Bolting: when a plant (typically a biennial) produces flowers in the first year (this occurs in
cabbage species )
o Cabbage: slected to produce one large swollen stem
o Brussel sprouts: axillary buds develop
o Broccoli and cauliflower: edible parts are the developing inflorescence
 Broccoli- eat the mature flowers
 Cauliflower- eat proliferating stem tips (curds)
 Perennials
o Plants that live for many years
o Need several years to reach maturity but then generally flower every year
o Artichokes- we consume the immature inflorescence
o Asparagus- we consume the young unexpanded shoots

Fact- nearly half the global sugar supply comes from sugar beets

 Root and tuber crops

o Potato- the most important vegetative crop in terms of caloric intake
o 4th most important crop – most important non grain staple in the world
o native to south America – eaten for at least 13,000 years and domesticated 10,000 years ago in
Peru
o late blight caused a potato famine in Ireland
o after the Ireland incident- fungicides were created
 Bordeaux mixture – one of the first fungicides that helped control the disease

Fact- sweet potatoes are not yams

- True yams are tropical vines that develop large tubers and represent the second most important tuber
in terms of production
- Sweet potatoes are native to south America where they have been consumed for at least 8000 years
o Evidence of sweet potatoes have been found in New Zealand
 This data suggests that there was contact among these people before European contact
in the new world

Before sugar was available from sugar cane or beet- the most common source of sugar was maple sugar
Potato diversity:
Peru: the real gold of the incas| global 3000 video
- 4000 varieties grow in Peru
- what is the national potato centre: conservation institution in Lima Peru dedicated to preserving
potato diversity using a combination of plant tissue culture and cryptopreservation. This institute also
conserves a number of other less known tuber crops indigenous to the area
- how does the international potato centre work with other farmers?
o Farmers bring new varieties and knowledge about agronomy and other traits to the centre- in
return the centre provides farmers with disease free planting material and access to other
varieties

Unit 6: herbs, spices and perfumes

Chapter 13: page 261-289

Overview:
 Herbs, spices and perfumes affect our CNS via neural connections from the taste buds or olfactory bulb
 Value of herbs and spices sparked the exploration of the world in the 15 th century

Chemistry and ecology

 Essential oils: volatile oil with a characteristic scent
o Volare means to fly from volatile
 Only molecules that have a molecular weight of less than 300-400 mass units, neutral in pH and have a
high vapour pressure reach out scent receptors
o Light weight molecules are usually tarpenes
 Volatile oils are found in specialized cells, glands or vessels that can occur in all parts of the plant
o When combined with resins= oleoresins
 Many oils are created by plants in nature to attract animals, others like thymol is secreted from the
glands on plant leaves and stems
 Herbs and spices may have health benefits like aiding digestion, calming smooth muscles

Herbs and spices

 Herb- botanical definition refers to a non woody plant  annual or perennial as long as the stems do
not form any wood
 Spice- no botanical definition but is loosely applied to an assortment of dried barks, roots, seeds, fruits
and flower parts that provide us with pungent essential oils
 Herbs and spices history
o Garlic and onions used as flavoring agents goes back to 1500 BC
o Spices were used for religious ceremonies, embalming and cremation
o Embalming dates back to 3500 BC in Egypt
o The greeks established Alexandria (Cairo) as the Mediterranean trade centre
o Wealth brought to Italian cities by the spice trade helped foster the cultural rebirth = the
renaissance
Herbs and spices of the Mediterranean regions
 Herbs of the mint family
o The mint family (Labiatae) provides many flavorful plant leaves- rosemary, thyme, oregano,
basil, sage and mint
 Often sold as whole, crushed or powered dried form
o Basil (ocimum bascilicum) – native to Africa or Asia but the early Greeks knew it very well
  Integral in Italian and Thai cooking
o Mint- genus Mentha
 In ancient times spearmint was widely used but now peppermint is more common
 Used as a digestive aid
 Cultivated in the US

o Marjoram and oregano are closely related

 Both perennials belonging to the genus Origanum
o Rosemary
 Symbol for remembrance – seems to have effects on reducing memory loss
o Sage was the most commonly used in medicine for classical Greek times through the Middle
Ages
 Associated with wisdom and memory
 Mixes well with oils and fats- used in processed meats
o Thyme- genus thymus
 Thymol – crystalized phenol constituent of thyme oil has some antiseptic and fungicidal
properties used in mouthwash, cough drops and cleaning products

 Herbs of the mustard family

o 2 genera in the brassicacea family brassica (mustard) and horseradish
 2 mustard sepcies – one producing black seeds and the other producing yellow seeds
 each produces a specific oil when mixed in water
 mustard gas doesn’t come from mustard plants but a group of synthetically produced
compounds called thioethers that contain sulfur (contained in mustard)
o horseradish – contains glycoside sinigrin that decomposes in water to form mustard oil
 other herbs from temperate asia and Europe
o bay leaves are often considered a spice than an herb (even though they are leaves)
 they come from a tree- why they might be included among the spices
o saffron – most costly of all herbs and spices
 comes from the stigmas of a crocus
 high demand due to its taste and yellow colour
o tarragon- native to Russia
 one of the most popular herbs in Europe

 spices of the Asian tropics

o the species that led to European exploration of the world came mostly from India and SE Asia
o of all the Asian spices the most important is black pepper
o Piper nigrum is native to India and Sri Lanka
o Brazil is the worlds largest producer, the US is the largest consumer
o In history, 2 of the most important spices were cinnamon and cassia (both sold under the name
cinnamon)
 Obtained from bark
o Other spices that come from tropical tress include cloves, nutmeg and mace
 Cloves come from unopened flower buds
 The only spice that comes from flower buds are capers
 Cloves are native to Indonesia
 Cloves used in manufacturing Indonesian cigarettes
  Nutmeg and mace are 2 differently flavoured spices from the same fruit Myristica
fragrans
 The aril that surrounds the seed= mace
 The seed inside = nutmeg
 Nutmeg trees produce sex identifying flowers only after they are about 6 years
old
 Nutmeg is toxic in large amounts and produces hallucinogenic effects
o Been used to induce abortions
 Some other spices
o Cardamom, ginger and turmeric are members of the ginger family  native to S Asia
 Ginger comes from the rhizome of a ginger plant, yields an oleoresin used to flavor
things
 Turmeric produces yellow rhizomes that are dried and ground and used in curry powder
 Galangal
 Grass family- lemon grass (same genus as citronella)
 Spices of the new world
o Capsicum peppers, vanilla and allspice
o Peppers rank with corn, cotton, potatoes and tobacco as the most important crops of American
origin
o Paprika is from dried peppers – capsicum annuum
o Chilli powder is a mixture of oregano, cumin, garlic and red peppers
o Capsaicin- the compound in red peppers that causes a burning sensation
 Hotness is measured in Scoville units
o Vanilla- Orchidaceae family (familys only crop)
 Perennial vines native to central and south America
 The vanilla bean fruit is an accessory capsule
 2nd to saffron as most expensive  elaborate processing techniques
o allspice comes from the same family as cloves but native to central America and the Indies
 allspice refers to the flavor of dried green fruits
 almost all production occurs in Jamaica
o Epazote
o Achiote

Perfumes
 How perfumes are made
o Originally they were derived from natural sources
o Extraction methods must use substances in which volatile oils dissolve in
o Fixatives – added to help retard rapid dissipation of volatile compounds
o The basic ingredients used in perfume are odorants
 Concretes, absolutes, distilled and fractional distilled, resinoids and tinctures
 Concretes: purest of the natural odorants are obtained by immersing fragrant plant
products in a hydrocarbon solvent that penetrates the tissues and dissolves the oils
 Resinoids: resins are dissolved in organic solvents , the solvent is evaporated from the
oil under pressure
 Absolute- produced when a concrete is extracted in a more concentrated state with
alcohol (alcohol evaporates)
 Most perfumes are mixtures of absolutes
  Expression: obtaining oils from citrus peels using a hydraulic press
 Distillation and fractional distillation – most common methods to exract natural
fragrances
 Exposing plant to steam that is super heated
 Volatile oils float on the surface once steam has cooled – this is then skimmed
 Different fractions of the steam are condensed the fragrant compounds can be
separated
 Inexpensive and rapid
 Tinctures –extract medicinal compounds and fragrant oils
o Often less expensive to synthesize a compound than to extract it from a natural source
 Pure not mixtures
 From oils to perfumes
o Perfume making is an art that blends different fixatives and odorants

Course content
Chemistry and biology of herbs and spices
 Essential/ volatile oils: aromatic compounds produced by plants that are responsible for their scent or
capture their essence
o Not oils but a complex group of compounds consisting of trapenes
o The term oil is used because these compounds are usually hydrophobic and share properties
with true oils
 Essential oils tend to be toxic to the plant (phytotoxic)
o Produced in structures of the plant where they are physically separated  leaves, roots, stems
and fruit and can be many specialized structures
 Play a variety of roles in the life of plants like:
o Antimicrobial- help plants defend against pathogens
o Attract deter insects and attract pollinators
o Include tissue responses – used to elicit plants defense response

Herbs vs spice
Herb: any non woody or herbaceous plant not always derived from leaves (dill seed)
Spice- has no real definition – often used in reference to plants used for flavouring or scent that originate from
temperate regions like mint or oregano – refer to seasoning from plants native to warmer regions like black
pepper or cloves

 Why is saffron so expensive?

o Spice obtained from the stigma of Crocus sativus
o An entire acre of saffron is required to yield 2.5-5.5kg of dried spice- requiring 462000
stigma/kg
o These stigma are hand collected and the low yields and high labour make it expensive
 What is the only herb/ spice obtained from the orchid family?
o Vanilla
 Need to know: the mint family (Lamiaceae) contributes the most species used as herbs and spices

Historical uses of spices

 Ancient Egypt (5200-4500 BC)
o Used as far as 3500 BC for embalming
 o According to Herodotus, myrrh, cassia, cinnamon, cumin anise, marjoram and other aromatic
spices were used in embalming
o Many spices used in Egypt were not native to Egypt- lead to the development of important
trade routes throughout the Middle East, China and India as early as 1400 BC
 Ancient Greece (400-300 BC)
o Established Alexandria (Cairo) as an important Mediterranean trade centre
o Herbs were described botanically and used in medicine
 Roman empire
o Romans used herbs and spices for medicine, perfume, wine, lamp oils and incense that lead to
further development of the trade routes
o The fall of the roman empire diminished the trade routes and the Arabs took control of
Alexandria
 The dark ages (641-1096 AD)
o After the fall of the Roman Empire, availability of spices from Europe declined
o The few available herbs were mainly cultivated in monasteries
o Spice trade did not resume until after the beginning of the crusades in 1096 AD
 Europe during the crusades (1096- 1300 AD)
o Crusades led to Europeans being exposed to scents and flavours not available since the fall of
the Roman empire
o Led to increased demand throughout Europe and re-establishment of trade routes
o Venice and Genoa were important trade centres in Europe contributed to the renaissance
 Europe after the crusades (1300 AD)
o 1429- spicers were given a charter by the king of England to spell spices en gross
o this was a driving force for global exploration such as voyages in Africa that lead to navel trade
routes and expansion of Asia
o capture of Constantinople in 1493 severed existing trade routes and put pressure to develop
routes by sea

video: king of spices

 how did Europeans take control of the pepper trade
o kept secrets about pepper to themselves
 where are the main pepper cultivation regions
o Malaysia (saloac), Indonesia and Brazil
 how is pepper cultivated and processed in various ways
o grown close to the equator
o Spice grows on vines grown on standards
o Harvest from may to august
o white pepper: dried out in the sun, packed into sacs and soaked in a stream for up to 2 weeks-
bacterial process allows pericarps to separate from inner cores, second drying, cleaned then
shipped
o black pepper:
 what is the difference between black, white and long pepper
 Need to know: pepper was a highly valued commodity that started colonial expansion and started wars

Perfumes
 Now almost all made from synthetic compounds
  The goal of natural extraction was to purify the plants while minimizing any degradation or chemical
changes in the process
 Perfumes are soluble in non polar solvents and are extracted using these chemicals (hexane)
 The most common extraction method is steam distillation- steam is passed through the plant material,
condensed and collected
 NOTE: essential oils are not composed of oils

Unit 7: medicinal plants

Chapter 14: page 290-317

Overview:
 Major classes of plant compounds used medicinally are steroidal sapinogens or cardiac glycosides and
alkaloids
 The most effective pain killers used today: the opiates – still obtained from plants and aspirin is based
on salicin present in several different plants
 Tropane alkaloids found in members of the tomato family are used as muscle relaxants and analgesics
 Production of human hormones for birth control, treating inflammation and Addison’s disease provide
a chemical backbone needed to produce complex compounds
 80% of the world population depends on traditional herbal medicine
 US: plants provide 10% of the active ingredients for drugs
 Fungi is the source of many antibiotics  penicillin

History:
 Mystical agents were thought to cause illness and cures for illnesses were thought to be from plants
and animals
 Discovery by trial and error
o Knowledge passed slowly because it was passed from generation to generation by word of
mouth
 Sumerian drawings of opium poppy – 2500 BC
 The use of herbs in medicine comes from the Code of Hammurabi- series of tablets carved under the
direction of King of Babylon in 1770 BC
o The tablets mention henbare, licorice and mint
 Egyptians recorded their knowledge on temple walls and in documents like Ebers papyrus (1550 BC)
o Contained over 700 medicinal formulas
o Many recipes contained these species: cannabis, aloe, castor, and mandrake
 Greece (500-300 BC) contributed significant knowledge to medicine
o Hippocrates- father of medicine  first to discuss illness and their treatment in a rational way
 Believed that sickness was caused by bodily errors not spirits
o Aristotle: compiled a list of medicinal plants after Hippocrates , his best student Theophrastus
founded the science of botany and provided the first thorough account of opium and its effects
o In a ship wreck (140-120 BC) evidence of medicinal objects – bleeding cup, drug vials and tins of
circular tablets
 The drugs found were from alfalfa, carrots, radishes, parsley, celery, wild onion, cabbage
and yarrow (were prescribed in ancient Greece)
o Dioscorides (40-90 BC) made the most significant Greek contribution- 5 volume encyclopedia of
1000 simple drugs (inaccurate) – prototype for future pharmacopeias
  Often said that this encyclopedia put back medicinal advances 1500 years
 Following greek precedents, the monks in Europe produced herbals (manuals) for the identification
and preparation of plants of medicinal value
o Until the invention of the printing press- herbals only available to a small number of people
 The availability of printed herbals was the prelude to the discovery of some truly effective pant derived
medicines
 During the renaissance: da Vinci influence and paracelus created art broke tradition by burning the
works of the greeks (mentioned above)
o He believed that God put signs in the plants as how to use them to treat illness (red sap for the
treatment of blood disorders) = doctrine of signatures
o Paracelus contributed to medicine by writing a textbook on surgery and introducing the
chemicals like mercury for treating syphilis
 17 and 18th century= hypothesis testing
th

o Edward Jenner- provided a framework for testing medicines = discovered the process of
vaccinations
o William withering: experiments with foxglove extracts as remedies for heart problems
( considered the beginning of modern pharmacology)
 th
19 century: anesthesia was introduced and Joseph Lister use of chemicals to prevent infection
 20th century – large advancement
o morphine, quinine, ephedrine
o structure of compounds and their synthesis
o synthetics
 in the US- natural products stopped being studied for medical uses since 1950s because:
o disdain for old-fashioned medicine
o pharmaceutical companies have been reluctant to assume the screening and testing programs
o many biochemists don’t think it is necessary to rely on plants
 holistic treatment – used around the world. The technique is to treat imbalances and treatments are
aimed at restoring balance

the chemistry of plant derived medicines

 fatty acids, essential oils, gums and resins, alkaloids and steroids are used in modern drugs
 oils and gums are used as purgatives (promote rapid elimination of material from intestinal tract) and
as carriers in many drug preparations
 volatile oils and resins: penetrate tissues and used as antiseptics
 steroids and alkaloids are the 2 major classes of plant derived medicine
o glycosides: compound that yields glucose when hydrolyzed (medically active form of a
compound)
o steroids: 4 carbon rings (backbone)
 addition of sugar to the backbone = steroidal glycosides
 secondary products because no direct physiological functions for steroids have been
found in plants
 milkweed contains steroidal glycosides (monarchs aren’t poisoned by this compound
and it acts as a poison that deters predators)
o alkaloids: cyclic chemicals grouped together because they contain nitrogen an usually have an
alkaline reaction
 were first considered secondary products but they do sometimes enter primary c
 many extremely poisonous to humans
 locoweed, deadly nightshade and hemlock
  one of the most importnant steps in deriving medicine from alkaloids is the
determination of standard doses
 other alakoloids: papaverine (poppy), quinine, colchicine (crocus), ephedrine, nicotine,
reserpine (snake root) and strychnine (reserpine)

plants formerly important in medicinal treatment

 the worst diseases that historically affected humans: malaria and leprosy
o treatments came from plants
o leprosy: Joseph Rock went on a hunt to find chaulmoogra ( a plant that the Vedas mentioned
treated it)
 chaulmoogra was the only effective treatment
o malaria was treated by steeping pieces of cinchona bark in water (discovered in south America)
 Jesuits proclaimed this was a cure and thus many people decided not to take it
 Cinchona was accepted in 1681 and 1820 quinine its active ingredient was extracted
 1944 cinchona was synthesized and then after chemically similar alkaloids were made –
reducing the need for natural quinine
 quinine is also the bitter part of tonic- gin and tonic – use of the natural quinine
 ephedrine: obtained by soaking the dried stem in ma huang ( a gymnosperm)  now produced
synthetically
o stimulant prescribed in china also for the treatment of high BP, asthma and hay fever
 white willow (salix alba): soaking willow leaves were placed on the body that ached
o the active ingredient that alleviated pain = salicin  compound name = aspirin
 coca (erythroxylum coca)- cocaine – chew the leaves mixed with lime
o first discovered its medicinal use in 1884 by an assistant to Freud that noticed it caused
numbing
o cocaine has never been synthesized but similar alkaloids have: procaine and lidocaine

plants important in medicine today:

 steroids and cardiac glycosides
o hormone: substance produced in one part of the body that affects the functioning of tissues or
organs in other places
 adrenal gland, pituitary, adrenal gland and sex organs produce the most steroidal
hormones
 sex hormones: estrogen, testosterone, progesterone and androgen
 adrenal cortex: cortisone
o 1940s it was discrovered that certain members of the yam genus ( dioscorea) contain saponins
o saponin: make a soap like foam when shaken with water, have additional rings added to the
steroid backbone  otherwise they are similar to the human sex hormones
o agave sisalana and other species of dioscorea and species of the asparagus and bean families
contain compounds that form sapogenins saporins with one or more sugars attached
 dioscerea species yield diosgenin which is a good starting point for chemical synthesis
 used in birth control pills – for the production of hormones that regulate the
menstrual cycle
 cortisone and hydrocortisone are synthesized from diosgenin  treat allergic
reactions, arthritis and Addison’s disease (malfunction of the adrenal glands)
 this backbone structure is used to produced anabolic steroids
o cardiac glycosides: like saponin are compounds that foam in water but have different rings
attached to the steroid backbone
  can improve circulation, relieve fluid retention and help kidney disease
 withering – found foxglove as an effective treatment for heart disease
 the chemical responsible for the effects of foxglove (digitalis purprea) was
digitoxin and digitalin
 alkaloids
o analgesics: drugs that reduce pain
o one of the most common analgesics= from the opium poppy (papaver somniferum)
o early use of opium for psychological purposes
o 4% harvested is used for medicinal purposes  cultivation is often prohibited (like the US)
o obtaining opium: fertilized, swollen capsules are slashed by a worker backing through fields-
cuts have to be deep enough to cut the latex capsules
 capsules can be tapped 3-10 times
 the latex is dried overnight before collection
 in ancient times the wax was powdered and dissolved in liquid
o 26 alkaloids isolated from opium  morphine, codeine, etc
o morphine: most potent pain killer (very addictive)
 mixed with scopolamine to produce a twilight sleep (during labor and delivery)
o codeine: milder and less likely to form addicitions
 in many prescription and over the counter drugs
o papaverine: primarily treats internal spasms of the intestinal tract
 component of compounds used to treat diarrhea
o noscapine: cough suppressant
 reduces deaths due to strokes and has anticancer properties
o thebaine: stimulant that is converted into pain killers like oxycodone and naloxone
o members of the potato family are used to treat muscle spasms
 hyposcyamine, atropine and scopolamine = tropane alkaloids (identified from atropa)
 all contain a nitrogen containing ring structure
 most commonly extracted from atropa belladonna, hypcyamus niger , D.
muticus, buboisia myoporiodes and D. leichtardtii
 usually only the leaves are dried and put in solvent
 belladonna/ deadly nightshade: cause pupil dilation
o prescribed for stomach and bladder cramps, prevents nausea and
vomiting by motion sickness , treatment of tremors in people with
parkinson’s and people before surgery to reduce salivation
 these alkaloids- especially atropine are used to treat nerve gas poisoning
(organophosphates)
o atropine increase heart rate
 hellebore- used to treat heart disease
 cinchona- known primarily for quinine- also produces 30 other alkaloids
 quinidine – used to treat heart disease (interferes with beta blockers and
antidepressants)
o snake root (Rauwolfia serpentina)- useful for treating snake bites and lunacy
 principle alkaloid = reserpine regulating hypertension by lowering blood pressure and
relaxing heart muscle
 reserpine was isolated in Switzerland and is most commonly extracted from the root
 treated people with schizophrenia
 plants that battle cancer
 o plant alkaloids have some effect- act by interfering with mitotic cell division and slows cell
growth
o periwinkle (catharanthus roseus)- folk treatment for diabetes, it has been used to treat
leukemia
 active chemicals- vinblastine and vincristine
 used in hogkins disease
o podophyllum / mayapple- an antitumor alkaloid genus
 active compound is podophyllotoxin and alpha / beta peltatin (found in rhizomes)
 podophyllotoxin is very toxic but is used in the semisynthetic derivatives of etoposide
and teniposide – treats testicular cancer and breast and lung cancer
o taxol- drug used to treat breast and uterine cancer (taxus brevifolia)/ the pacific yew
 pacific yew= tree of death- taxol is isolated from the bark
 became the number 1 selling cancer drug
 the pacific yew trees number declined- hard to obtain
o noscapine: one of the opium poppy alkaloids- antimitotic , anticancer agent- treatment for
melanomas
o autumn crocus- the alkaloid colchicine- extracted from the corms- interferes with cell division
 most common use is inflammation and pain due to gout
o campotothecin- from the Chinese tree- used to produce synthetic compounds that act by
disrupting successful DNA synthesis leading to cell death
 active compounds = topotecan and irinotecan = complex cyclic alkaloids

other medicinal plants

 Artemisia annua- wormwood related species antimalarial compound
o Used in china
o Artemisinin – tricyclic compound (not an alkaloid) and doesn’t contain nitrogen
o Less effective because the plasmodium (parasite) becomes resistant to it
 Plantain species are sources of psyllium- colloid mucilage used for intestinal problems
o Relieves irritations caused by constipation or diarrhea
 Aloe species- soothing gels
o Burns, ringworm, sores
o The soothing agent is the pulp scraped form under the epidermis
o Latex containing anthraquinone glycosides- used as a purgative (irritates the intestine)
 Chymopapain an enzyme from papaya
o This enzyme is used because of its dissolution of proteins
o Injecting this enzyme inti soft tissue of the spinal column relieves pressure of adjacent nerves-
treats slippage of disks in the spinal column
 Costs $800 million and 12 months of research and development to bring a new drug to the market
 Star anise- a cooking spice, diuretic, digestive aid, gas reducer
o The plant produces shikimic acid used to produce ostltavivir phosphate that relieves symptoms
of the flu

Dietary and herbal supplements

 Herbal remedies: ginko, Echinacea, milk thistle, st johns wort and chamomile
 These products are allowed for sale as herbal remedies if no claims are made for medicinal efficacy=
labelled as dietary supplements
o Exempt from regulation by US food and drug administration
o Problem that testing effectiveness is in the hands of the public
Unit content
Plants referred to as natures chemists

Medicinal plants: a historical perspective

 Earliest written records were found on clay tablets in Mesopotamia from 2600-3000BC
o Plants mentioned on the tablets: cedar, licorice and poppy  still used for their medicinal
properties
 Other sources of medicinal records: Egyptian writings contained in the “Ebers Papyrus” written in 1500
BC – describing 700 drugs
o Ayurvedic literature from India- several texts describing 1250 medicinal plants
o Chinese pharmacopeia- developed by many authors between 2700 BC and now containing 6000
herbs
o Several Greek books like “history of plants” by Theophrastus around 300 BC
o 1932- 70% of organic monographs in the British pharmacopeia were on plant derived products
 with the discovery of microbial produced compounds and advances in synthetic chemistry that plants
lost their predominance in drug development
o despite their new sources- 25% of prescription drugs in NA are based on compounds originally
derived from plants
 75-80% of the worlds population still relies on traditional medicine for their primary health care

medicinal plant products: where do they come from?

 Europe- 1300 plants are used medicinally with up to 90% coming from the wild
 Globally- 2/3 of the 50,000 species of medicinal plants are collected from the wild
 4000- 10,000 species of medicinal plants are endangered

cultivation of medicinal plants:

 domestication and cultivation of medicinal plants has advantages over collecting plants from the wild:
o reliable botanical identification
o reliable yields of plant material- cultivation increases ability to meet consumer demands and
predict yearly harvests
o standardized post-harvest practices: cultivation increases consistency of harvested material
o provides alternative crops for farmers- diversify agricultural practices
 example: case of American Ginseng- listed as an endangered species- cultivation and strict regulations
on collection help reduce the threat of extinction
 challenges to medicinal plant cultivation:
o low germination rates, slow growth, requirement for specific conditions
 medicinal plants are biologically active due to their chemical profiles production of secondary
metabolites
o secondary metabolite: compounds not usually integral to basic metabolism but function to
attract animals and help plants avoid infection , parasitism and predation
 protection from pathogens, herbivores and environmental stresses
 production of these compounds requires the allocation of significant resources
 agricultural practices for cultivation need to be optimized to promote accumulation of
the secondary metabolites

secondary metabolites
 alkaloids:
 o first alkaloid= morphine – isolated by Serturner in 1806
o the term alkaloid was first used by Carl Meissner in 1819
 original definition of alkaloid was – pharmacologically active, nitrogen containing basic
compound of plant origin
 this definition has spanned to cover compounds produced by organisms other than
plants- some that are pharmacologically inactive and some are neutral not basic
o alkaloids are produced by 20% of plant species- 12000 described
o many are precursors to synthetic drugs
o alkaloids are grouped into several classes- based on chemical structure
o based on chemical structure- 2 main divisions
 heterocyclic or non-heterocyclic
 heterocyclic alkaloids are further divided into 14 groups according to their ring structure
o biosynthesis of most begins with L-amino acids (like tryptophan, tyrosine, lysine , arginine…)
these amino acids are often combined with steroidal, secoiridoid or terpenoid moieties
 terpenoids
o many primary and more than 25,000 secondary metabolites
o terpene is derived from the german “terpetin”- the first terpenes were derived from turpentine
o also called isoprenoids- common occurrence of isoprene as a product of decomposition
o classified based in the number of 5 carbon isoprene units
o the first terpene compounds studied has 2 isoprene units but were considered base units so
they were called monoterpenes
o terpenes with 1 isoprene unit: hemiterpenes
o terpenes with 2 isoprene unit: monoterpenes
o 3 isoprene units: sesquinterpenes
o 4 isoprene units: diterprenes
o large diversity due to the number of bonds they can have with each other an alterations in
configuration during synthesis
o initial steps of terpene biosynthesis:
 starts with isopentenyl diphosphate (IPP)- synthesized through the acetate/ mevalonate
path
 2 IPP molecules combined through action of IPP isomerase = geranyl diphosphate (GPP)
 GPP converted into farnesyl diphosphate (FPP) followed by geranylgernanyl
diphosphate (GGPP) by enzymes specific for each step
o Play an importnant role in primary and secondary metabolism
o Provide many pharmaceuticals like artemisinin and taxol
o Sesquiterpenes and monoterpenes are constituents of essential oils and resins
o Larger terpnes= rubber
o Produced in large amounts in the plant, hydrophobic- produced in specialized structures like
laticifer cells in the rubber tree, resin ducts or glandular trichomes
 Phenylpropanoids
o Account for 40% of organic carbon circulating the biosphere
o Phenylpropanoid- phenylpropranoid- acetate pathway is the primary- but not the sole route of
synthesis for phenolic compounds in plants
 Compounds produced through this pathway= lignans, flavanoifs, coumarins,
furanocoumarins and stilbenes
o Play a role in plants as structural components, pigments, defense compounds etc
 o Phenolics typically possess or had possessed one or moe acidic hydroxyl groups attached to an
aromatic ring
o The phenylpropranoid pathway begins with the conversion of phenyalanine to cinnamic acid or
tyrosine into p- coumaric acid by phenylalanine/ tyrosine ammonia lyase

Questions:
1. Where/ when was the first written record of medicinal plant use?
- Sumaria- 2600-300 BC
2. What percentage of monographs in the british pharmacopeia were plant products in 1932 and what -
displaced the prevalence of plant based drugs in modern medicine?
- 70%- microbial based compounds and synthetic chemistry displaced the prevalence of plant based
drugs in modern medicine
3. What % of modern drugs are based on plant derived compounds and how important is pant based
medicine today?
- 25%- 75-80% of worlds population still relies on traditional medicine – using a large number of plants
4. Where do we get our medicinal plant material and what impact does this have on plant populations?
- Most comes from the wild
- Ex. Of the 1300 plants used in Europe about 90% and 2/3 of the 50,000 species used globally are
harvested from the wild
- 4000-10,000 species of medicinal plant are endangered – primarily due to wild harvesting
5. what are 5 problems wit harvesting medicinal plants from the wild?
- Plants can be misidentified and substituted with the wrong plants
- Unpredictable yields
- Unknown quality due to genetic and diversity
- Non uniform processing
- Threatens natural populations
6. What endangered species has been protected and developed into a major north American industry
through cultivation
- American Ginseng- highly endangered and was threated by overharvest
- Now- widely cultivated (Ontario is a leading producer) and has developed into a sizable industry that
does not require plants to be harvested from the wild
7. What 3 challenges exists with cultivating medicinal plants
- Many difficult to cultivate with poor seed germination and specific ecological requirements
- Some grow slowly or have low yields
- General belief that wild harvest is better
8. What are secondary metabolites and what are 3 main groups
- compounds not usually integral to basic metabolism but function to attract animals and help plants
avoid infection, parasitism and predation”. In contrast, primary metabolites are those that are required
for plant growth and survival. In reality, the line between these groups is often blurred and it is not as
clear cut as we may like. The three main groups of secondary metabolites are: 
- Alkaloids, terpenes, and phenylpropanoids.

9. What is an alkaloid and what was the first isolated alkaloid

- The definition of an alkaloid is blurry, but the original definition was a “pharmacologically active,
nitrogen-containing basic compound of plant origin”. This has been expanded since then, but this is still
often used as a working definition. The first alkaloid that was isolated was morphine, in 1806.
10. How common are alkaloids and how diverse is this group
 - is estimated that about 20% of plants produce alkaloids and there are over 12 000 known alkaloids.
Within this group, there are several classifications and sub-groups, demonstrating the extent of the
diversity.
11. How are alkaloids synthesized?
- Due to the diversity of alkaloids, there is no single metabolic pathway for their synthesis. However,
most are synthesized from various amino acids which contribute the nitrogen.
12. How many tarpenes are there and what is the basic building block?
- Over 25 000 terpenoids have been described that are classified as secondary metablolites making this
the largest class of secondary metabolites. In addition, many terpenoids considered primary
metabolites also exist. The basic building block is the 5 carbon isoprene molecule, although they are
not directly synthesized from this compound.
13. Why are monoterpenes comprised of 2 isoprene molecules not 1?
- Early researchers working in this area first encountered monoterpenes and believed that that this 10
carbon unit was the basic building block. As such, they called them momoterpenes. While this later
proved to be false, the nomenclature was already established and if still used today.
14. How can a group of compounds all built with the same 5 carbon building blocks lead to 25000 different
structures?
- these simple compounds can be altered in what seems like an endless number of ways to create a
variety of structures. It is important to realize that this process is more than just polymerization and
can lead to great diversity.
15. What are some uses of tapenes?
-  medicinal properties, including the current front line antimalarial artemisinin, some are volatile and
aromatic making them useful as fragrances, while some such as rubber molecules are incredibly large
and are important for structural uses.
16. What are the phenylpropanoids , how common are they and what role do they play in the plant?
- This is a class of compounds synthesized primarily from phenylalanine and includes a diverse group of
compounds including phenolics, flavonoids, and anthiocyanins. This group of compounds accounts for
approximately 40% of organic carbon circulating in the biosphere. It is hard to imagine that these
“secondary” metabolites are not important to plants….These diverse compounds play a rage of roles in
the plant including structural support, plant defense, pigmentation, and protection from abiotic
stresses.

Details on the history of medicinal plants

 Dioscoride: wrote De Materia Medica libre- 5 volume encyclopedia that discusses uses and selection of
600 medicinal plants
o Was a standard botanical reference until the 15th century and served as a prototype for future
pharmacopeias
 Until 17th century- Avicennas Canon of medicine was a book widely used in Europe and the middle east
 Until the end of the 15th century herbals written in Euroope showed little originality- based on Arab
commentaries or Greek and Latin writings
 Beginning of 16th century- renaissance botanists and scholaras began to reconcile their native flora with
those described by dioscoride
 First notable people to reject botanical thought was Theophrastus Von Hohenheim – Paracelus
o Doctrine of signatures- like the shell of a walnut as a sign that walnuts should be used to treat
brain ailments
 17 century- scientific approach
th

o formulated hypothesis and tested effecst-

 o William witering- initiated western pharmacology through stufy od botanical drugs  foxglove
(digitalis purprea)
 Foxglove treatment for heart disease
 th
20 century- discovery of widespread use of morphine, quinine and ephedrine

alkaloid producing medicinal plants

 scopolamine – tropane alkaloid
o widely found members of the solanacea family  deadly nightshade family
o very poisonous
o medieval times- eye drops from scopolamine to dilate pupils
 isoquinoline alkaloids isolated from members of the poppy family (Papaveraceae)
o isoquinoline alkaloids= morphine, codeine and papaverine – found in the opium poppy
 all share basic structure and many are biologically active
 latex from opium = opium- complex mix of chemicals used medicinally since 600 BC
 before the 19th and 20th century opium was smoked or powdered and dried and put in a
drink (wine)
o quinolone alkaloids: quinine and quinidine – used to treat malaria
 Jesuits would use tea made form the cinchona tree to treat malaria
 It tooks 150 years to figure out that quinolone alkaloids were responsible for its effects
 1944- synthesized quinine in the lab

terpenoid producing medicinal plants

 cinchina spp. And Artemisia annua have been used traditionally to treat malaria
 17th century Jesuits made tea made from cinchona tree bark to treat malaria
 artemisinin is an active compound in A. annua and is now the first line treatment for malaria
 quinine is no longer used due to a resistance built by plasmodiums
 NOTE- dr. youyou tu won won a nobel prize in 2015 for her discovery of artemisinin
 Catharanthus roseus and taxus spp possess compounds now used as chemotherapies
o Neither traditionally used to treat cancer- medicinal properties discovered through random
screening
o Vincrtisine and vinblastine and taxol were potent anti cnacer compounds
o Getting taxol from T. brevifolia (the plant that produces it) was hard because it is endagrgered
 Scientists were able to use a close relative as an alternative source of taxol
o Scientistsi could not get enough vincristine and vinblastine from C. roseus so other methods
were developed
 Taxol is a complex molecule derived from taxol brevifolia

Phenylpropanoid producing medicinal plants

 Large class of compounds derived from phenylalanine
 Phenyl ring – majoriy of phenolic compounds are capable of scavenging free radicals- led to association
that foods rich in flavonoids like anthocyanins are super foods due to antioxidant effect (under debate)
 Simple phenolics can be identified by their phenyl 6- carbon ring and 3 carbon side chain
 hydroxycinnamic acids, cinnamic aldehydes, and monolignols are all simple phenolics, however they
differ by a carboxylic, aldehyde and alcohol located on the 3-carbon side chain. 

Video: finding medicines in plants (unit 7 and 8)

Segments 1-6
1. How does the video claim people first started using medicinal plants?
 o Knowledge was observed from nature and wild animals
o Birds decorate their nests with fragrant aromatic plants – to protect them from illness  same
plants humans use
o Chimpanzees-eats bitter sap of plants to cure intestinal problems- worms (veroneia)
traditional cure used in Africa
2. How many remedies were described in the Ancient Sumarian tablets?
o 600 remedies  proved that knowledge of medicinal plants originated a long time ago
3. Why would they ingest medicinal plants with beer?
o Plants were ground to release the favourable elements
o Alcohol makes the plant effective
o Flour and oil
4. What is the Ebers Papyrus?
o Written in 1550 BC
o Found in an Egyptian tomb
o Catalogues 150 herbal plants and preparations
o Incantations that physicians recite
o Encyclopedia of ancient medicine
o 850 texts to treat diseases , also beauty tips
5. Paracelsus is known for the misguided doctrine of signatures, but how did he help advance modern
medicine?
o Leonardo Da Vinci- distilling
o Laid foundations of modern pharmacology
6. Why are plants still useful for discovering new pharmaceuticals?
o Active chemicals in plants used as guidelines
o Jenner- first vaccine (led to vaccine for rabies)
o Willow bark (Bayer)
 Aspirin – basis for pharmaceuticals
 Molecular chemistry reduces dependency on wild species (synthesized molecules)
7. How are new plants screened?
o Extractions are made in 3months and 6months – have results
o Vegetative material is ground to a powder
o Solvent injected into tubes with powder to extract molecules
o Each test tubes has solvent and dissolved molecules
o Next step- screening robot  extracts are brought into contact with targets (cultures of
diseased cells, parasites etc)
o Activity when in contact with target- determine what molecule is responsible
o Extract broken down into sub extracts that are separated= pure molecule
o Test biological properties – identify chemical structure
o Semi synthesis- replacing atoms – part natural and synthetic
8. How has technology improved this process?
o 5-10,000 tests a day or even 100,000 tests a day (robots)
o chromatography- visualize and measure quantity of molecules in extracts
9. How much material is needed to complete these tests
o 1kilo of vegetation = 1 mg extract
10. What is periwinkle used for?
o Naval bean derived from periwinkle
o Used as an anticancer medicine
11. How much periwinkle is needed to produce the drug?
o Tons of dried leaves
o 4 tons needed to make 1 kilo of active drug= 20, 000 doses of the IV drug
12. How do they decide how the drug should be administered?
o determine solubility and stability
o naval bean is injected intravenously
13. How many people have access to the full range of modern drugs
o Consumers = rich countries (France)
o Those able to consume drugs is limited – is declining
o 800 million have access to all available medicines – probably drop to 600 million
14. How do most traditional healing systems differ from modern Western medicine?
o Other healing methods- holistic view (body in its entirety- spiritual..)
o Grew in 1970s
o Attack cause instead of treating symptoms
o African- medicinal plants – large wealth associated with it
15. How many plants are used in Chinese traditional medicine?
o 3000 native plants- 300 used in medicine
o use plants, minerals and other natural elements
o bond between body and mind- traditional medicine
o disease= imperfection in disharmony
 massage, acupuncture etc.
o pharmacopeia- 5000 years old- natural products transformed and prepared in many ways
 costs to consumer is reliable
o west- logic that new drugs must be on the market (many of the same drugs under different
names)
o France over 8000 listed but only 600 effective (250 are actually useful according to WHO but
only 70 medicines important)

16. Why are many countries looking toward traditional medicines again? 

o Nutraceuticals  food industry

17. What pilot program is ongoing in Tuscany? 

o Department of herbal medicine in a hospital in Giuseppe

o Treatment and medicine administered are reimbursed by social security
o 6000 patients treated by this department
o took a while to get approved and become permanent

18. Why is it difficult to get medicinal plants accepted in modern medicine? 

o Policies
o Authorization is hard to obtain for medical plants
 Molecule and receptor sites
 Bring about effects by a combination of molecules
o Europe- allow medicinal plants- same legislation as food products nutraceuticals (food and
medicine)
  Nutraceuticals- food with medicinal properties without toxicity
 Rapid growth of these products
 This new legislation – future of medicinal plants

Unit 8: ethnobotany
Readings:
The discovery of medicines from plants: a current biological perspective
 In the last 50 years- new changes in the process of searching for new drugs
 Screening advances: robotics equipment that can conduct large numbers of conductor based assays
and improved analytical equipment – more efficient at determining structure of an active compound
 The only non- automated process is collecting and processing plant material
 These advances also change legal regulations and ethics for access to biological resources
o Reason for the trend of natural products research shift from large pharmaceutical companies to
being based largely around university organic chemistry groups
 United states National Cancer Institute’s program is important because of its long history, large scale
and opposed the efforts of large pharmaceutical companies
o NCl was one of the first programs with the capacity to evaluate systematically large numbers of
plant extracts
o Reinvented in 1989- new 60 tumor cell line panel for evaluation of plant and marine samples
 1993- national institues of health launched the international cooperative biodiversity groups – a
program funded by many top sources  aimed to assemble multi institutional teams to conduct
natural products drug discovery in ways that promoted economic growth and conservation of natural
resources
 screening has produced many important drugs:
o taxol from taxus brevifolia
o camptothecin from camptotheca acuminate
 the results of these programs – yielding few drugs from plants

innovation of the drug pipeline:

 pipeline for the discovery of plant derived drugs starts with collection of plant material 
extracted evaluated in bio assays  active compounds isolated and structures determined 
preclinical trials
 screening:
o samples are not really random or representative to diversity of an area (biggest and most
common plants collected ) random selection methods improved
 efforts to plants that were thought to be biologically active like plants used as traditional
medicines, fish poisons and other toxic plants
 selective collection of plants used medicinally in indigenous cultures
 plants that are relatives to plants with biologically active compounds

innovation in handling extracts

 activity if potentially useful bioactive compounds may not be detected during screening
 equipment developed to separate complex mixtures of natural products into fractions and making sure
there was adequate amount of compound in each fraction – improved discovery

innovation in bioassay
 important- 80-90s – development of in-vitro bioassays and their automation (9KB tumor line cell and
leukemia cell lines at the NCL  60 cancer cell lines )
  assays can be a poor indicator of general biological activity
o whole cell lines and in vivo assays to be better for general biological activity

innovation in structure determination

 after the identification of an active extract- isolate active compounds and separate novel bioactive
compounds  dereplication
 HPLC, and other chromatography and spectrometry methods are used to separate and isolate samples

New ethical framework for natural products discovery

 After a united nation convention – worldview was changed on access to biological resources
o Commitment to protect diversity, use biological resources sustainably and to equitably share
benefits that arose from their use- drug (this last point has had a large effect on discovery of
natural products )
o Introduction of access and benefit agreements complicated collecting programs
Enigma of low discovery rates
 Microbes have yielded many new drugs
 No highly publicizes new drugs derived from plants
 Reasons for no new discoveries
o Compounds with drug potential already discovered
o Discovery paradigm flawed
o Redundancy among secondary metabolites
o Preparation of samples for bio assays- masking of compounds
o Sensitivity and physiological relevance of enzyme based assays
o Surveyed small amount of land for collection
o Most reasonable explanation: working with crude extracts or simple fractions containing
compounds that may interfere with each other
 Most new compounds are reported from a single species
 Potential issues with plant collection
o Preserved- dried samples don’t have the same chemical composition as living plants
o Ethnobotany
o collecting rates results in higher discovery rates

future potential of plants as a source of drug leads

 135 drugs form plants as they occur in nature from the 2000-60,000 plants that have been screened
 screening efforts have probably covered less than 10% of the plant species
o NCI has screened less than 35000 plant species
 No agreement among botanists about the number of plant species that exist – why it is hard to decide
what percentage have been screened (estimates are between 231413- 420,000 plants)- upper limit
probably exaggerated
 Taking into consideration of these estimates we should be able to produce 540-653 20-23,000
 Signifies that there is still potential to find new plants that can be used as drugs

Second renaissance of plant natural products discovery/ conclusion

 Large scale efforts in the 80s and 90s led to development of new innovative technologies to evaluate
larger numbers of plants more thoroughly and efficiently
 Only a small amount of plants have been evaluated and studied thoroughly
 Many active compounds in plants guide chemists to make synthetic drugs
 Other groups than plants that can yield drugs
Ethnobotany: the study of people- plant relationships ( Nolan and Turner)
Intro
 Regions of high biological diversity correlate with regions of highest linguistic and cultural diversity

Development of ethnobotany
 1893- Harshberger proposed a new field of study (based on the World fair collection) = ethnobotany
o his cultural assumptions are no longer accepted
o lead to a more realistic approach
 1994- Richard Ford- published “tree ring” schematic that represented evolution of ethnobotany
 Richard Evans Schultes – Amazonian healers – inspired ethnobotany work
 Classification – Harold Conklin – observations of an agricultural group in the Philippines
o Discovered lexicon of plants – over 18000 terms
 Then came knowledge of indigenous people about traditional land and resource management
 Most ethnobotanists are in india
 Examples of some ethnobotanical research: paleoethnobotany, historical ecology, medical.
Classification systems . cognitive symbolic etc.
 Most important current tasks= development of ethical protocols for the study of traditional ecological
knowledge
o Associated with biodiversity research, bioprospecting and cultural conservation
 Ethnobotany is closely linked to ethnoecology
o Ethnoecology- interpreting complex resource management strategies
o Safeguarding biodiversity is a goal through memory banking- documentation of indigenous
knowledge and technologies
 Trend in ethnobotany- dynamics between human populations and plant foods and medicines that have
historic significance in maintaining human health
o Chili peppers, seaweed, black berries and mushrooms – valued for role in maintaining cultural
identity as edible food AND for their powerful healing virtues
 Highlight how information is transferred among generations
 Focus of survival of plant based knowledge at its source

Methods in ethnobotany
 First task for many ethnobotanists- develop a research question
o Choosing a research site based on the question
o Technique of participant observation – used among ethnobotanists that work with indigenous
groups
 Adopt the lives and routines of the people they want to learn about
o Identify key respondents in a community community elders
 Collect voucher specimens – necessary for ethnobotanical research

Classic case studies and their contributions

 Moerman: identified evolutionary properties that explained why certain families were used as
medicinal plants (rose, bean and mint)
o These families produce alkaloids and other compounds with bioactive properties that serve as
chemical defense mechanisms
 Paleoethnobotany- ethnobotany of past human societies
o Human bodies found
o James Dickson et al
 o The stomach contents of otzi (oldest body found) – 80> species of bryophytes, pollen and hazel
o Point: plants allowed for a deep understanding of history to be conducted and traced
 Identification of the origin of disease – Cycad toxicity- found in cyanobacteria
Course content:
Stages in discovering new drugs from plants:
- Ethnobotany, plant collections, extract prep, bio assay guided fractionation and isolation
Ethnobotanical enquiry toward the traditional use of plants as medicines has facilitated the discovery of many
active chemicals like:
- Quinine (cinchona spp.), artemisinin (Artemisia annua), and digitoxin (digitalis spp.)

Ethnobotany:
 Ethnobotany: is the study of people- plant relationships
 Richard Evans Schultes – father of modern ethnobotany
o Spent extensive time studying and living amongst many indigenous groups to counter prior
beliefs by demonstrating the complex nature of indigenous knowledge
 Multi- disciplinary field – plant taxonomy, nutrition, pharmacognosy, phytochemistry, palynology,
ecology, conservation biology, anthropology, political science, geography, environmental studies,
economics, linguistics and philosophy= ethnobotany
 Key component to modern ethnobotany: participant observation in which ethnobotanists assimilate
within a group/ community by taking on daily activities of the people they want to learn from
 Can lead to bioprospecting- the search for plant and animal species from which the medicinal drugs
and other commercially valuable compound can be obtained
o Can lead to biopiracy of indigenous knowledge
 CBD- convention of biological diversity – treaties to protect property of indigenous
people
 Before conducting ethnobotanical studies:
o Identify key inforamnts
o Take voucher specimen of any plant under study
 Plant voucher- dried plant specimen that was collected in the field in order to document
its ethnobotanical use
o Prepare voucher specimen and submit to local herbaria for identification
o Partnership with communities that are equitable and responsible through implementation of
ethical protocols for the study of traditional knowledge

Drug discovery
 Time and money at each stage of drug development
 7 stages:

o
 discovery using: ethnobotanical leads, taxonomic investigations, random screening
 random plant screening- large group of diverse plants
 ethnobotanically guided collection- information provided by key informants
 examples:
o vincristine and vinblastine were discovered through random screening of the periwinkle
o artemisinin was discovered through examination of traditional Chinese medicine
 test for activity: crude extract is made by soaking plant material in a solvent (alcohol, water, butane ,
methanol)  resulting extract is a chemically complex mixture with many chemical structures
 preliminary screening: evaluating extracts for a specific medicinal effect
o false positive and negatives because:
 medicinally active constituents are at very low concentrations – don’t yield an effect in
their bioassay (false negative)
 medicinal activity of one chemical is masked by another
 chemical complexity interferes with screening technique (false positive )
 to limit likelihood of false positives and negatives: fractionate crude extract by applying different
chromatography techniques
o separation into pure compounds

o
 extracts evaluated for bioactivity using bioassays
 bioassay: scientific approach used to measure the potency of a substance by observing its effect on a
biological system
o hippocartic screening- injecting animals with extracts and observing effects
o assays use cell lines, enzymes or animal models
 bioassay guided fractionation
o crude extract is fractioned further screening using a bioassay  extracts that show activity
are further separated and re-screened for activity  continuation until isolation of a single
active compound
discovery of new drugs is low due to:
 biologically active compounds are low in abundance within complex mixtures – not detected
 false positives or negatives
 interference caused by compounds that interact with light based detection
 adequate drug targets unavailable or not developed
 elaborate and costly methods

biopiracy and bioprospecting

 convention that changed guidelines in ethnobotany had a 3rd implication that equity was needed
among a discovery
 if a company wants to bioprospect abroad- they have to ask local and national authorities for
permission to collect specimen and show they are committed to sharing any benefits that may arise
from the research
 this has made plant collection more difficult