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Phytochemical and Phytotherapeutic Properties of Annona Squamosa, Annona

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Pelagia Research Library


Asian Journal of Plant Science and Research, 2015, 5(8):28-33

ISSN : 2249-7412
CODEN (USA): AJPSKY

Phytochemical and phytotherapeutic properties of Annona squamosa, Annona


reticulata and Annona muricata: A review
Suneel Kumar A.1*, Venkatarathanamma V.2 and Naga Saibabu V.3
1
Department of Biochemistry, Acharya Nagarjuna University, Nagarjunanagar, Andhra Pradesh, India
2
Department of Zoology, Acharya Nagarjuna University, Nagarjunanagar, Andhra Pradesh, India
3
Department of Biotechnology, Acharya Nagarjuna University, Nagarjunanagar, Andhra Pradesh, India
_____________________________________________________________________________________________

ABSTRACT

Medicinal plants and phytogenic products have used for treatment of various diseases from ancient times in the
folklore medicine all over the world. Crude plants extracts are now considered a valuable source for natural
products used in the development of medicines against various diseases, for the development of pharmaceutical
preparations and for novel biomedical research. Annona squamosa, Annona reticulata and Annona muricata are
shrubby evergreen plants widely distributed in West Indies and Central America and widely cultivating in India and
tropical regions of Asia for their edible fruits and medicinal values. These plants have been used for centuries as
traditional folk medicine for the treatments of various diseases and also used as insecticide. The plants are
considered to be a good source of vitamins, minerals, plant proteins, fibers, etc. as well as the plant is supposed to
have tremendous pharmacological importance. The present review aims to present a brief overview of the medicinal
use as well pharmacological value of the plants focusing for the current research work on chronic inflammatory
disease arthritis.

Keywords: Annona squamosa, Annona reticulata and Annona muricata, Taxonomical classification, Phytochemical
constituents and Phytotherapeutic effects.
_____________________________________________________________________________________________

INTRODUCTION

Under the classification of flowering plants Annonaceae where it is also known as custard apple family [1]
composed of trees, shrubs and rarely lianas [2]. The genus prefix Annona is derived from a Latin word ‘anon’
which means ‘yearly produce’ that refers the production of fruits to the plants of this family.

Under the genus of Annona, around 2300-2500 species and more than 130 genera are currently classified [3]. The
plants belong to this family mostly distributed in tropic regions, where very rarely some species observed in
temperate regions. Approximately 900 species are Neotropical, 450 are Afrotropical and the some are Indo-
Malayasian. Among 130 genera of Annonaceae family, 7 genera very commonly available and widely distributed
[4]: Annona, Anonidium, Rolliania, Uvaria, Melodorum, Asimina and Stelechocarpus.

Because of easy availability of Annona genus in India, the present study was planned on plants of this genus
according to the available literature and depending on the availability of the plants; three plants of Annonacea family
named Annona squamosa Linn, Annona reticulata Linn, Annona muricata Linn were selected. Leaves of these
plants were taken for the present study.

• Botanical Description
The Annona genus belongs to the Annonaceae family, class Magnoliopsida and order Magnoliales.

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Annona squamosa L.: small semi evergreen well branched straggling shrub grows up to 7 meters in height. The bark
thin, gray and woody in nature and with extensively branched tap root system. Leaves are simple, alternative, oblong
lanceolate or elliptic, pellucid-dotted, peculiarly scented, 5.0 to 15.0 cm x 1.9 to 3.8 cm in size. Flowers are
greenish, fleshy, drooping, extra axillary, more on the leafy shoot than on the older wood. Fruits have many carpels
with lozenge shaped on a central torus, fused into an irregular globose or heart shaped tubercled, yellowish green
syncarpium with thick scaly or knobby skin, the pulp sweet, fragrant with white to light yellow in colour. The seeds
oblong, deep brownish black, aril shinning, covered with whitish pulp [5].

Annona reticulata L.: small deciduous or semi deciduous tree grows up to 10 meters. The bark is rough, thin and
chocolate brown, 1.4-4.0 mm thick, becoming double quilled when dry. Leaves are oblong, lanceolate, reticulate,
pellucidpunctate, with unpleasant odour, glabrous above and glaucous and pubescent beneath when young; lateral
nerves 8-11 pairs, petiole up to 2 cm long. Flowers are bisexual, drooping, greenish white, fleshy, solitary, leaf
opposed or 2-4 on short extra axillary branchlets. Fruit is globose, 5-10 cm in diameter, yellowish-green when ripe;
Berries many heart shaped syncarpium with pentagonal areoles, seeds smooth and black in colour. The tree has a
robust, deep penetrating root system with abundant root fibres [5, 6].

Annona muricata L.: small evergreen tropical tree with low branching and bushy grows up to 7 to 9 meters in
height, Native of tropical America and Caribbean region of West Indies. Leaves are leathery with unpleasant odour,
broadly elliptic to obovate, 5.8 – 19.0 cm x 3.7 -8.1 cm, sometimes slightly unequal. Flowering starts at the age of 3
years and flowers leaf opposed on the old wood, greenish yellow, usually 3, fleshy, triangular, saccate at the base.
The fruit skin is leathery and covered with curved, soft, pliable spines with cream coloured pulp inside divided into
segments. Seeds are black, oval with smooth finishing surface [5, 7].

• Vernacular Names
Annona squamosa L.: custard apple, sugar apple, sweet apres in English, sharifa in Hindi, sitaphalam in Telugu and
corossolier, cailleux, pommiercannelle in French [8].

Annona reticulata L.: Jamaican apple, bullock's heart, netted custard apple and Sweetsop in English, Lonang and
Nona kapri in Malaysia, Noinong in Thailand, Anonacolorada, Anona de seso, Anonaroja in Spanish,
Corossolsauvage, Bois Cachiman and cachiman in French and in Hindi it is called as Luvun, Ramphal and Nona [9].
Annona muricata L.:graviola, guyabano or soursop in English, asguanabana in Spanish, huanaba in Guatemala,
zopote de viejas in Mexico, cabeza de negro in Venezuela, catoche in Argentina, jaca do para in Netherlands and
lakshmanaphal or jangli or mullaraamaphala in India [10].

• Distribution
Thethree plants are native of tropical America, particularly Caribbean region of West Indies West Indies. Because of
its edible fruit widely distributed throughout the tropical regions and warmer sub-tropics [5].

• Phytochemistry
Annona squamosa L. reported to contain alkaloids, amino acids, glycosides, saponins, carbohydrates, flavonoids,
tannins, proteins, phytosterols and phenolic compounds. The various chemical constituents isolated from leaves,
stem and roots of the plant including anonaine, norcorydine, aporphine, isocorydine, coryeline and glaucine [11].
Leaves of this plant found to have Anonaine, Borneol, Camphor, Benzyltetrahydroisoquinoline, car-3-ene,
Camphene, Carvone, β -Caryphyllene, Farnesol, 16-Hetriacontanone, Geraniol, Hexacontanol, Higemamine,
Limonine, Methylheptenone, p-(hydroxybenzyl)-6,7-(2-hydroxy,4-hydro) isoquinoline, Eugenol, Linalool
acetate,Isocorydine, Menthone, Methylsalicylate, Methyl anthranilate, n-Octacosanol, b-Pinene, Stigmasterol, α-
Pinene, β-Sitosterol, Rutin, Thymol 4-(2-nitro-ethyl-1)-1-6-((6-o-β-D-xylopyranosy1-β-D-glucopyranosyl)-oxy)
benzene and n-Triacontanol[12]. Oil extracted from leaves contain germacrene D, β-elemene, sabinene, α and β-
pinenes, bicyclogermacrene, T-cadinol and T-muurolol; The fruit oil determined for spathulenol, bornyl acetate,
germacreneD,borneol and verbenone [13]. A new acetogeninsquamone isolated from stem bark and it also contains
bullatacin, bullatacinone, liriodenine and (-) kaur-16-en-19-oic acid [14]. The bark found to contain the 1H-
cycloprop(e) azulene, bisabolene, germacrene D, bisabolene epoxide, kaur-16-ene and caryophyllene oxide are the
major constituents found in the bark. The branches also determined for liriodenine, moupinamide, annonaine and
sachanoic acid. Chloroform extract of the plant contain an active constituents Annotemoyin[15].Annonacin A,
annonastatin, saponins like stigma-5,24 (28)-dien-3β-ol-α-L-rhamnoside, squamostatin A, annonin I, VI, VIII, XIV
and XVI [16]. From the seeds about 30 acetogenins were Isolated like squamocins B to N, coumarinoligans,
annotemoyin and squamocin, annonastatin, squamocinetc[17, 18]. Alkaloids like Liriodenine, oxoanalobine and β
caryophyllene, α -humulene, α pinene, α-gurjunene found in the roots [19, 20].

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Annona reticulata L. leaves reported for annoreticuin, isoannoreticuin and annonaretin; oil extracted from leaves
contain monoterpenes, sesquiterpenes, (E, E) farnesyl acetate, ar-turmerone, benzyl benzoate and gamma-terpinene
as the major constituents [21]. (-) kaur-16-en-19-oic acid, 16α-hydroxy-(-)kaurn-19-oic acid and methyl 17-
hydroxy--(-)kaurn-19-oic acid was determined from stem bark of Annona reticulate. The extracts of seed determined
for rolliniastatin 1, N-fattyacyltryptamines, 7-1actone acetogenin and cis-/trans-isomurisolenin, acetogenins like cis-
/trans-bullatacinone, annoreticuin-9-one, bullatacin, annoreticuin, cis-/trans-murisolinone and squamocin. Other
terpenes such as spathenelol, muurolene, copaene and eudesmol were also reported [22, 23]. Two cyclopeptides, the
cycloheptapeptidecycloreticulin C and the cyclohexapeptideglabrin was isolated from the seeds methanol extract
and Sequence and three-dimensional structure of cycloreticulins A and B, new cyclooctapeptides was also identified
[24]. Aequaline, asimilobine, liriodenine and norushinsunine was isolated from roots [20]. Anonaine, norcorydiene,
roemerine, norisocorydine, corydine, linalool, carvone, squamocin-I, samoquasine A, squamocin-B, motrilin,
squamocenin, phenolic, kaurenoic acid and nonphenolic alkaloids, two crystalline alkaloids - muricine, muricinine,
(2, 4-cis and trans)-squamolinone, (2, 4-cis and trans)-9-oxoasimicinone, bullacin B are the phytochemical
constituents reported in Annona reticulata [25].

Annona muricata was revealed the presence of carbohydrates, phenolic compounds, flavonoids, alkaloids,
coumarins, glycosies, phytosterols, quinones, steroids, proteins, saponins and terpenoids [26]. The ethanolic extracts
of leaves contain high content of iron, phosphorous and also contains Annohexocin, murihexocins A and B,
muricoreacin and murihexocin C. The methanolic extracts of roots contain a new acetogenins called CohibinsA and
B and sabadelin which intermediate in the biosynthesis of mono-THF acetogenins [27].

A new biogenetic precursor’s epoxymurins A and B isolated from stem bark. The seed extracts contains a new
monotetrahydrofuran namely murisolin, two new cytotoxic γ-lactones namely corossolone and corossolin, a new
acetogenins; muricatetrocins A and B, gigantetrocin B, muricatacin, solamin and epomuricenins A and B [20].
Annonaceousacetogenins, C-35 and C-37 mono-epoxy unsaturated compounds epomuricenins A and B, and
epomusenins A and B and Two new mono-epoxy saturated C-35 representatives, epomurinins A and B were isolated
from fruit pulp methylene chloride extract [28]. Annohexocin, annomutacin, annomuricin A to E, annonacinone,
corossolone, cis-annonacin, annomontacin, annonacin, epomuricenin A & B, cis-corossolone, corepoxylone,
corepoxylone, annomuricatin A & B, cohibin A to D, donhexocin, montanacin, muricatetrocin A & B muricatin D,
annopentocin A to C, gigantetrocin A & B, gigantetronenin, goniothalamicin, montecristin, corossolin,
gigantetrocinone, iso-annonacin, muracin A to G, muricatalin, muri-catenol, gigantetrocin, murihexocin 3,
muricatalicin, muricatocin A to C, muricoreacin, murihexocin A to C, muricapentocin, muricin H, muricin I,
rolliniastatin 1 & 2, uvariamicin I & IV, coronin, javoricin, murisolin, solamin, annocatalin, xylomaticin, robustocin,
annomonicin and murihexol were the few annonaceousacetogens in graviola [29].

• Phytotherapeutic Effects
Annona squamosa L. possess a number of pharmacological and medicinal properties which are as follows; the
various solvent extracts of Annona squamosa leaf inhibited the different strains of the bacteria like Vibrio
alginolyticus, Staphylococcus aureus, Bacillus subtilis and Staphylococcus epidermidis. The aqueous extract of the
leaves inhibit the pathogenicity of Staphylococcus aureus, Pseudomonas aeruginosa and Escherichia coli[30]. The
plant extract contains 16β, 17-dihydroxy-ent-kauran-19-oic acid which is having antiviral activity against HIV[31].
The seed extract has anthelmintic activity against Haemonchuscontortus, the ethyl acetate extract inhibited the
hatching of egg [32]. The methanolic extract of the leaves showed antiplasmodial activity by inhibiting the
chloroquine sensitive strain 3D7 and chloroquine resistant strain Dd2 of Plasmodium falciparum [33]. The
ethanolic extracts of root showed molluscicidal activity by killing the Biomphalariaglabrata, the leaf, bark and root
also having molluscicidal activity by showing toxicity in snails (Lymnaea acuminate) [34]. The hexane extract of
seed is very effective in killing the head lice [35]. The plant has mosquito repellent activity by showing larvicidal
effect against Aedesadopictus, C. quinquefascinits and Anopheles stephensi [36]. The seed extracts also having
pesticidal activity by showing lethal effects against Triboliumcastaneum [37]. The ethanolic and aqueous extracts of
leaves and roots possess anti-diabetic and antihyperglycaemic activity [38, 39]. The various extracts of leaves
showed antioxidant properties by different in vitro screening models [40]. Aqueous extracts of leaves showed anti
hyperlipidaemic activity and wound healing properties [30, 41] and alcoholic and aqueous extracts of leaves were
screened for hepatoprotective activity [42]. Twelve different acetogenins showed antitumor activity by inhibiting the
growth of elective for certain types cancer cell lines using MTT method [43] and also aqueous and ethanolic bark
extracts of Annona squamosa was evaluated by determining the frequency of micronucleated polychromatic
erythrocytes (MnPCEs) and chromosomal aberrations against the mutagenicity [44]. The seed extract of Annona
squamosa Linn was investigated for post coitus antifertility activity [45] and the diterpinoids isolated from stem
showed anti platelet activity [46]. The bark and leaves possessed cytotoxicity, analgesic, anti-inflammatory activity
[47] and anti-ulcer activity [48].

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Annona reticulata L. ethanolic extract of leaves evaluated for antioxidant activity by different in vitro screening
methods [40]. The ethanol extracts of seed showed a potent cytotoxic activity against four cancer cell lines Hep.G2,
Hep.2, 3, 15, KB and CCM2. Ethanol and aqueous extract of roots were evaluated for in vivo anticancer activity
against melanoma cells in mice and MDA-MB-435 human melanoma cells was used to screen the in vitro anticancer
model by the MTT [3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide] colorimetric assay [49, 50, 51].
The ethanol extract of leaves revealed antinociceptive activity [52] and the aqueous extracts of stem bark showed
significant effect on CNS depressant, analgesic and anti-inflammatory activities [53, 54]. Tea prepared using roots is
used as a treatment for fevers and the bark as a powerful astringent is used as anti-dysenteric and vermifuge.

Annona muricata L is a medicinal plant used as a natural remedy for different diseases. Several studies
demonstrated that the bark and leaves had anti-spasmodic, anti-hypertensive, vasodilator, hypotensive and cardio
depressant effects in animals. The traditional uses documented as anti-cancerous, anti-diabetic, anti-bacterial, anti-
fungal, anti-malarial, anti-mutagenic, emetic, anti-convulsant, sedative, insecticidal and urine stimulant. It is also
having anti-viral (against Herpes simplex), cardio tonic, digestive stimulant, nerviness, febrifuge, vermifuge,
pediculocide and analgesic properties. The extracts of this plant also screened for anti-parasitic, astringent, anti-
leishmanial, anti-depressant and cytotoxic activities [55]. Extracts of Annona muricata were also shown to be
effective cytotoxic effeagainst T47D cell line, two human (H8 and H125) cancerous cell lines, non-cancerous
immortalized rat GI epithelial cell line, CEM-SS cell line, HL-60 cell line, MDR breast cancer cell line, non-
transformed immortalized pancreatic epithelial cell line HPNE and U973 cancer cell line [56]. The leaves aqueous
extracts was revealed significant anti-hypertensive activity without affecting the heart rate [57]. Aqueous extracts of
leaves and seeds showing high contents of proteins, phenols, non-enzymatic components like vitamin-C and
vitamin-E, enzymatic components like Super Oxide Dismutase (SOD) and Catalase was having high antioxidant
power [40, 58]. Leaf extract exhibit a broad spectrum of anti-microbial activity against B. subtilis, Staph aureus, K.
pneumonia, P. vulgaris, etc. responsible for common bacterial diseases like pneumonia, diarrhea, UTIs and skin
infections. Aqueous extracts of Annona muricata exhibit an antibacterial effect against S. Aureus and Vibrio
Cholerae. The ethanolic extract of leaf shows highest antibacterial activity towards Pseudomonas aeruginosa and
Staphylococcus aureus [59]. Methanolic extracts of Annona muricata showed significant anti-diabetic activity by
reducing serum total cholesterol, LDL and VLDL and a significant increase in HDL and anti-atherogenic index [60].
Annona muricata leaf extracts of different solvents has therapeutic effects against anti-diabetic [55],
hepatoprotective [61], wound healing, anti-nociceptive and anti-Inflammatory activities [62].

CONCLUSION

From the above mentioned detailed literature survey it is clearly understood that different solvents extracts of
Annona squamosa, Annona reticulata and Annona muricata have different traditional and pharmacological uses.
The pharmacological uses of these plants extracts reported for their anti-microbial, antiplasmodial, anti-viral, anti-
mutagenic, anti-ulcerogenic, anti-nociceptive, anti-inflammatory, anti-cancer, cytotoxicity, anti-diabetic, anti-
hyperlipidaemia, antioxidant and hepatoprotective activity etc.

All these above mentioned literature review relates the potential benefits of using these plants as medicine for
microbial infection, acute inflammation, diabetes associated with oxidative stress. Moreover, these literature reports
warrant and provide us a new avenue for the commencement of our research work in these medicinal plants for
screening their chronic anti-inflammatory effect related to arthritis associated 5-Lipoxygenase pathway and
oxidative stress by using different animal and cell line models.

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