Dedicated to the discovery of novel medicines from the natural sources. Desperately seeking solutions for the > Global Climate Change > Loss of Biodiversity > Population Explosion > Famine
Silphion was an ancient medicinal gum-resin; most likely obtained from a Ferula species growing i... more Silphion was an ancient medicinal gum-resin; most likely obtained from a Ferula species growing in the Cyrene region of Libya ca. 2500 years ago. Due to its therapeutic properties and culinary value, silphion became the main economic commodity of the Cyrene region. It is generally believed that the source of silphion became extinct in the first century AD. However, there are a few references in the literature about the cultivated silphion plant and its existence up to the fifth century. Recently, a rare and endemic Ferula species that produces a pleasant-smelling gum-resin was found in three locations near formerly Greek villages in Anatolia. Morphologic features of this species closely resemble silphion, as it appears in the numismatic figures of antique Cyrenaic coins, and conform to descriptions by ancient authors. Initial chemical and pharmacological investigations of this species have confirmed the medicinal and spice-like quality of its gum-resin supporting a connection with t...
... SESQUITERPENE LACTONES FROM CHROMOLAENA OPADOCLINIA NH ELSAYED,* MAHMUT MISKi, ALAN T. WHITTE... more ... SESQUITERPENE LACTONES FROM CHROMOLAENA OPADOCLINIA NH ELSAYED,* MAHMUT MISKi, ALAN T. WHITTEMORE and TOM J. MABRY The Department of Botany ... Quijano, L., Calderon, JS, Gomez, GF, Garduno, JT and Rios, CT (1980) Phytochemi.stry 19, 1975. ...
Abstract Seventeen natural coumarin derivatives; badrakemin (1), 14′-acetoxybadrakemin (2), badra... more Abstract Seventeen natural coumarin derivatives; badrakemin (1), 14′-acetoxybadrakemin (2), badrakemone (3), 14′-acetoxybadrakemone (4), colladonin (5), colladonin acetate (6), 14′-acetoxycolladonin (7), karatavicinol (8), deltoin (9), smyrnioridin (10), marmesin (11), osthol (12), oxypeucedanin (13), oxypeucedanin hydrate (14), isoimperatorin (15), scopoletin (16), and umbelliprenin (17), were tested against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE), the sister enzymes that play a critical role in the pathology of Alzheimer’s disease as well as tyrosinase (TYR) as the target for Parkinson’s disease. The tested coumarins were more selective against BChE, where the coumarins 2, 5, 8, and 15 (IC50 = 30.3 μM, 29.2 μM, 37.2 μM, and 50.1 μM, respectively) displayed higher BChE inhibition than the reference (galanthamine, IC50 = 60.2 μM) at 100 μg/mL. Only four coumarins (2, 5, 9, and 15) showed inhibition against AChE. Binding conformations of the coumarins (2, 5, 8, 9, and 15) within the active sites of AChE and BChE were explored via molecular docking experiments. The docked compounds were oriented by the interactions with the oxyanion hole and the peripheral anionic site residues of AChE/BChE. The coumarin derivatives 1–17 was found to have no or low inhibition (2.03 ± 0.92 %–12.91 ± 0.40 %) against TYR at 100 μg/mL. Our findings revealed that coumarins could be promising lead compounds for designing novel anti-Alzheimer drug candidates.
Preliminary 2-day cancer cell screening assays indicated that the dichloromethane extract of the ... more Preliminary 2-day cancer cell screening assays indicated that the dichloromethane extract of the roots of Heptaptera cilicica showed relatively strong cytotoxic activity. Eleven sesquiterpene coumarin ethers with potent and selective cytotoxic activities were isolated from the dichloromethane extract of the roots of H. cilicica. Furthermore, revised spectroscopic data for 14′-acetoxybadrakemone (4) and complete NMR spectroscopic assignments for colladonin (6) and colladin (7) are reported.
Ferula pisidica is a novel endemic species found in the vicinity of Karaman province of inner Med... more Ferula pisidica is a novel endemic species found in the vicinity of Karaman province of inner Mediterranean Region of Turkey. F. pisidica is morphologically distinct from F. haussknechtii and F. brevipedicellata by habit, sheaths, terminal leaf lobes, and mericarp size as well as by chemotaxonomic differences. The new species is described by morphological, carpological, ecological and phytochemical characteristics. Its relationships with the other related species and proposed conservation status will be reviewed.
Several simple and prenylated coumarin derivatives were isolated from the dichloromethane extract... more Several simple and prenylated coumarin derivatives were isolated from the dichloromethane extract of the root of Neocryptodiscus papillaris based on moderate cytotoxic activity of the extract in COLO205, KM12 and MCF7 cancer cells. While the major prenylated furanocoumarin derivatives and osthol isolated from the dichloromethane extract were responsible for the activity in the colon and breast cancer cell lines, the 4′-acylated osthol derivatives including a novel coumarino-alkaloid; neopapillarine) demonstrated selective cytotoxic activity in A498 and UO31 renal cancer cell lines.
Seven known sesquiterpene coumarins and a new sesquiterpene coumarin, anatolicin (8), were isolat... more Seven known sesquiterpene coumarins and a new sesquiterpene coumarin, anatolicin (8), were isolated from the dichloromethane extract of the roots of Heptaptera anatolica. Structures of these compounds were elucidated based on their spectral properties. While some of these sesquiterpene coumarins showed modest cytotoxic activity against COLO205, KM12, A498, UO31, and TC32 cancer cell lines, selective cytotoxicity of anatolicin (8) and 14′-acetoxybadrakemin (7) were observed at nanomolar level against the UO31 kidney cancer cell line.
Acta Crystallographica Section C Crystal Structure Communications, 1992
C 26 H 34 O 6 cristallise dans P2 1 2 1 2 1 avec a=7.766, b=11.809, c=27.219AZ=4, T=223K; affinem... more C 26 H 34 O 6 cristallise dans P2 1 2 1 2 1 avec a=7.766, b=11.809, c=27.219AZ=4, T=223K; affinement jusqu'a R=0.051. Ce compose a ete isole du Ferulago Antiocha. Le cycle a 10 chainons adopte une conformation bateau chaise, presque identique dans les details a celle observee pour les sesquiterpenoides caracterises precedemment. Les doubles liaisons trands sont toutes deux deformees , comme le montrent les angles de torsion C2-C1-C10-C9 et C3-C4-C5-C6 de -162.4 et -159.6°
Silphion was an ancient medicinal gum-resin; most likely obtained from a Ferula species growing ... more Silphion was an ancient medicinal gum-resin; most likely obtained from a Ferula species growing in the Cyrene region of Libya ca. 2500 years ago. Due to its therapeutic properties and culinary value, silphion became the main economic commodity of the Cyrene region. It is generally believed that the source of silphion became extinct in the first century AD. However, there are a few references in the literature about the cultivated silphion plant and its existence up to the fifth century. Recently, a rare and endemic Ferula species that produces a pleasant-smelling gum-resin was found in three locations near formerly Greek villages in Anatolia. Morphologic features of this species closely resemble silphion, as it appears in the numismatic figures of antique Cyrenaic coins, and conform to descriptions by ancient authors. Initial chemical and pharmacological investigations of this species have confirmed the medicinal and spice-like quality of its gum-resin supporting a connection with the long-lost silphion. A preliminary conservation study has been initiated at the growth site of this rare endemic Ferula species. The results of this study and their implications on the regional extinction event, and future development of this species will be discussed.
Ten aglycones and six glycosides of luteolin and apigenin were identified from the leaves of Salv... more Ten aglycones and six glycosides of luteolin and apigenin were identified from the leaves of Salvia palaestina Bentham (Labiatae). Among them cirsimaritin showed a high activity against Staphylococcus aureus, Staphylococcus epidermidis, Escherichia coli, Klebsiella pneumoniae, Proteus vulgaris, and Pseudomonas aeruginosa, while the others have little or no activity against the same bacterial strains.
The diastereo- and enantioselective microbial oxidation of a mixture of racemic cis/trans-chrysan... more The diastereo- and enantioselective microbial oxidation of a mixture of racemic cis/trans-chrysanthemols to the corresponding stereoisomeric chrysanthemic acids by Aspergillus species is described. Of the three microorganisms which were found capable of oxidizing racemic cis/trans-chrysanthemols, A. ochraceus ATCC 18500 showed complete enantioselectivity for (+)-stereoisomers [(+)-trans-chrysanthemol and (+)-cis-chrysanthemol), whereas A. flavipes ATCC 1030 and ATCC 11013 showed complete enantioselectivity for the (+)-cis-chrysanthemol but a time-dependent enantioselectivity during oxidation of trans-chrysanthemol [oxidation of (+)-trans-chrysanthemol prior to (-)-trans-chrysanthemol]. The diastereoselectivity of all three microorganisms was time dependent, in that the trans-stereoisomers were oxidized prior to the cis-isomers.
We have compiled information about the medicinal plants used in folk medicine in the district of ... more We have compiled information about the medicinal plants used in folk medicine in the district of Antakya. Since its establishment by King Seleucus I in 300 B.C., Antakya (old Antioch) has hosted nearly 20 civilizations. Antakya, neighboring Northwestern Syria, is located on the western end of the "Silk Road" and was one of the great centers of Graeco-Roman world. Today, Antakya is a cosmopolitan city in which Arabic and Turkish are widely spoken, and where distinct ethnic and religious communities, such as Arab Alawite, Arab Christian, Arab Sunni, Turk Sunni, Armenian, and Jewish, have been living together in harmony for centuries. In addition, the rich flora in the vicinity of Antakya also renders the area interesting in terms of ethnobotanical fieldwork. This study aimed to compile the information about plants used for medicinal purposes by local people in the district of Antakya. This city is a significant region in terms of ethnobotanical fieldwork, owing to its cosmopolitan structure, long history, relatively preserved traditional community structure, and rich flora. Furthermore, we sought to compare the ethnomedicinal data geographically, cross-culturally, and historically. The ethnobotany of medicinal plants used in the district of Antakya has been investigated through two separate studies; one was conducted in 1975, interviewing 29 people, and the other was conducted in 2011-2013, interviewing 182 people. The use value (UV) and informant consensus factor (FIC) values of the plants were calculated. In order to interpret the authenticity and sources of the compiled ethnomedicinal information, previous publications that contain information about the similar medicinal uses of plants identified in our region were reviewed and evaluated meticulously. A comparison with the data obtained from other regions of Turkey and from other Mediterranean regions, as well as a cross-cultural analysis between the ethnic groups within the study area, was performed by implementation of the Jaccard index (JI) RESULTS: Throughout the study, information about 202 medicinal plant taxa was compiled. Among these plants, 39 have either not yet been mentioned in ethnobotanical or medicinal studies, or have been used for a medicinal purpose other than those encountered in the literature review. The ethnomedicinal information we gathered from the study area exhibits close similarities to the ethnomedicinal information of other Southern and Eastern Mediterranean countries where Arabic is spoken, as well as to that of Northern and Western Mediterranean countries where Latin languages are spoken. In addition to these similarities, in most cases, this ethnomedicinal information shows hybrid features of ethnomedicinal knowledge from Eastern and Western Mediterranean countries. Based on a literature survey, we found that the cited medicinal uses for 43 plants have also been corroborated by other various biological testings. This finding strongly suggests the importance of ethnobotanical studies in the development of new medicines. We believe that this study has compiled rich ethnomedicinal information that reflects the cosmopolitan structure of Antakya in a very good way.
Silphion was an ancient medicinal gum-resin; most likely obtained from a Ferula species growing i... more Silphion was an ancient medicinal gum-resin; most likely obtained from a Ferula species growing in the Cyrene region of Libya ca. 2500 years ago. Due to its therapeutic properties and culinary value, silphion became the main economic commodity of the Cyrene region. It is generally believed that the source of silphion became extinct in the first century AD. However, there are a few references in the literature about the cultivated silphion plant and its existence up to the fifth century. Recently, a rare and endemic Ferula species that produces a pleasant-smelling gum-resin was found in three locations near formerly Greek villages in Anatolia. Morphologic features of this species closely resemble silphion, as it appears in the numismatic figures of antique Cyrenaic coins, and conform to descriptions by ancient authors. Initial chemical and pharmacological investigations of this species have confirmed the medicinal and spice-like quality of its gum-resin supporting a connection with t...
... SESQUITERPENE LACTONES FROM CHROMOLAENA OPADOCLINIA NH ELSAYED,* MAHMUT MISKi, ALAN T. WHITTE... more ... SESQUITERPENE LACTONES FROM CHROMOLAENA OPADOCLINIA NH ELSAYED,* MAHMUT MISKi, ALAN T. WHITTEMORE and TOM J. MABRY The Department of Botany ... Quijano, L., Calderon, JS, Gomez, GF, Garduno, JT and Rios, CT (1980) Phytochemi.stry 19, 1975. ...
Abstract Seventeen natural coumarin derivatives; badrakemin (1), 14′-acetoxybadrakemin (2), badra... more Abstract Seventeen natural coumarin derivatives; badrakemin (1), 14′-acetoxybadrakemin (2), badrakemone (3), 14′-acetoxybadrakemone (4), colladonin (5), colladonin acetate (6), 14′-acetoxycolladonin (7), karatavicinol (8), deltoin (9), smyrnioridin (10), marmesin (11), osthol (12), oxypeucedanin (13), oxypeucedanin hydrate (14), isoimperatorin (15), scopoletin (16), and umbelliprenin (17), were tested against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE), the sister enzymes that play a critical role in the pathology of Alzheimer’s disease as well as tyrosinase (TYR) as the target for Parkinson’s disease. The tested coumarins were more selective against BChE, where the coumarins 2, 5, 8, and 15 (IC50 = 30.3 μM, 29.2 μM, 37.2 μM, and 50.1 μM, respectively) displayed higher BChE inhibition than the reference (galanthamine, IC50 = 60.2 μM) at 100 μg/mL. Only four coumarins (2, 5, 9, and 15) showed inhibition against AChE. Binding conformations of the coumarins (2, 5, 8, 9, and 15) within the active sites of AChE and BChE were explored via molecular docking experiments. The docked compounds were oriented by the interactions with the oxyanion hole and the peripheral anionic site residues of AChE/BChE. The coumarin derivatives 1–17 was found to have no or low inhibition (2.03 ± 0.92 %–12.91 ± 0.40 %) against TYR at 100 μg/mL. Our findings revealed that coumarins could be promising lead compounds for designing novel anti-Alzheimer drug candidates.
Preliminary 2-day cancer cell screening assays indicated that the dichloromethane extract of the ... more Preliminary 2-day cancer cell screening assays indicated that the dichloromethane extract of the roots of Heptaptera cilicica showed relatively strong cytotoxic activity. Eleven sesquiterpene coumarin ethers with potent and selective cytotoxic activities were isolated from the dichloromethane extract of the roots of H. cilicica. Furthermore, revised spectroscopic data for 14′-acetoxybadrakemone (4) and complete NMR spectroscopic assignments for colladonin (6) and colladin (7) are reported.
Ferula pisidica is a novel endemic species found in the vicinity of Karaman province of inner Med... more Ferula pisidica is a novel endemic species found in the vicinity of Karaman province of inner Mediterranean Region of Turkey. F. pisidica is morphologically distinct from F. haussknechtii and F. brevipedicellata by habit, sheaths, terminal leaf lobes, and mericarp size as well as by chemotaxonomic differences. The new species is described by morphological, carpological, ecological and phytochemical characteristics. Its relationships with the other related species and proposed conservation status will be reviewed.
Several simple and prenylated coumarin derivatives were isolated from the dichloromethane extract... more Several simple and prenylated coumarin derivatives were isolated from the dichloromethane extract of the root of Neocryptodiscus papillaris based on moderate cytotoxic activity of the extract in COLO205, KM12 and MCF7 cancer cells. While the major prenylated furanocoumarin derivatives and osthol isolated from the dichloromethane extract were responsible for the activity in the colon and breast cancer cell lines, the 4′-acylated osthol derivatives including a novel coumarino-alkaloid; neopapillarine) demonstrated selective cytotoxic activity in A498 and UO31 renal cancer cell lines.
Seven known sesquiterpene coumarins and a new sesquiterpene coumarin, anatolicin (8), were isolat... more Seven known sesquiterpene coumarins and a new sesquiterpene coumarin, anatolicin (8), were isolated from the dichloromethane extract of the roots of Heptaptera anatolica. Structures of these compounds were elucidated based on their spectral properties. While some of these sesquiterpene coumarins showed modest cytotoxic activity against COLO205, KM12, A498, UO31, and TC32 cancer cell lines, selective cytotoxicity of anatolicin (8) and 14′-acetoxybadrakemin (7) were observed at nanomolar level against the UO31 kidney cancer cell line.
Acta Crystallographica Section C Crystal Structure Communications, 1992
C 26 H 34 O 6 cristallise dans P2 1 2 1 2 1 avec a=7.766, b=11.809, c=27.219AZ=4, T=223K; affinem... more C 26 H 34 O 6 cristallise dans P2 1 2 1 2 1 avec a=7.766, b=11.809, c=27.219AZ=4, T=223K; affinement jusqu'a R=0.051. Ce compose a ete isole du Ferulago Antiocha. Le cycle a 10 chainons adopte une conformation bateau chaise, presque identique dans les details a celle observee pour les sesquiterpenoides caracterises precedemment. Les doubles liaisons trands sont toutes deux deformees , comme le montrent les angles de torsion C2-C1-C10-C9 et C3-C4-C5-C6 de -162.4 et -159.6°
Silphion was an ancient medicinal gum-resin; most likely obtained from a Ferula species growing ... more Silphion was an ancient medicinal gum-resin; most likely obtained from a Ferula species growing in the Cyrene region of Libya ca. 2500 years ago. Due to its therapeutic properties and culinary value, silphion became the main economic commodity of the Cyrene region. It is generally believed that the source of silphion became extinct in the first century AD. However, there are a few references in the literature about the cultivated silphion plant and its existence up to the fifth century. Recently, a rare and endemic Ferula species that produces a pleasant-smelling gum-resin was found in three locations near formerly Greek villages in Anatolia. Morphologic features of this species closely resemble silphion, as it appears in the numismatic figures of antique Cyrenaic coins, and conform to descriptions by ancient authors. Initial chemical and pharmacological investigations of this species have confirmed the medicinal and spice-like quality of its gum-resin supporting a connection with the long-lost silphion. A preliminary conservation study has been initiated at the growth site of this rare endemic Ferula species. The results of this study and their implications on the regional extinction event, and future development of this species will be discussed.
Ten aglycones and six glycosides of luteolin and apigenin were identified from the leaves of Salv... more Ten aglycones and six glycosides of luteolin and apigenin were identified from the leaves of Salvia palaestina Bentham (Labiatae). Among them cirsimaritin showed a high activity against Staphylococcus aureus, Staphylococcus epidermidis, Escherichia coli, Klebsiella pneumoniae, Proteus vulgaris, and Pseudomonas aeruginosa, while the others have little or no activity against the same bacterial strains.
The diastereo- and enantioselective microbial oxidation of a mixture of racemic cis/trans-chrysan... more The diastereo- and enantioselective microbial oxidation of a mixture of racemic cis/trans-chrysanthemols to the corresponding stereoisomeric chrysanthemic acids by Aspergillus species is described. Of the three microorganisms which were found capable of oxidizing racemic cis/trans-chrysanthemols, A. ochraceus ATCC 18500 showed complete enantioselectivity for (+)-stereoisomers [(+)-trans-chrysanthemol and (+)-cis-chrysanthemol), whereas A. flavipes ATCC 1030 and ATCC 11013 showed complete enantioselectivity for the (+)-cis-chrysanthemol but a time-dependent enantioselectivity during oxidation of trans-chrysanthemol [oxidation of (+)-trans-chrysanthemol prior to (-)-trans-chrysanthemol]. The diastereoselectivity of all three microorganisms was time dependent, in that the trans-stereoisomers were oxidized prior to the cis-isomers.
We have compiled information about the medicinal plants used in folk medicine in the district of ... more We have compiled information about the medicinal plants used in folk medicine in the district of Antakya. Since its establishment by King Seleucus I in 300 B.C., Antakya (old Antioch) has hosted nearly 20 civilizations. Antakya, neighboring Northwestern Syria, is located on the western end of the "Silk Road" and was one of the great centers of Graeco-Roman world. Today, Antakya is a cosmopolitan city in which Arabic and Turkish are widely spoken, and where distinct ethnic and religious communities, such as Arab Alawite, Arab Christian, Arab Sunni, Turk Sunni, Armenian, and Jewish, have been living together in harmony for centuries. In addition, the rich flora in the vicinity of Antakya also renders the area interesting in terms of ethnobotanical fieldwork. This study aimed to compile the information about plants used for medicinal purposes by local people in the district of Antakya. This city is a significant region in terms of ethnobotanical fieldwork, owing to its cosmopolitan structure, long history, relatively preserved traditional community structure, and rich flora. Furthermore, we sought to compare the ethnomedicinal data geographically, cross-culturally, and historically. The ethnobotany of medicinal plants used in the district of Antakya has been investigated through two separate studies; one was conducted in 1975, interviewing 29 people, and the other was conducted in 2011-2013, interviewing 182 people. The use value (UV) and informant consensus factor (FIC) values of the plants were calculated. In order to interpret the authenticity and sources of the compiled ethnomedicinal information, previous publications that contain information about the similar medicinal uses of plants identified in our region were reviewed and evaluated meticulously. A comparison with the data obtained from other regions of Turkey and from other Mediterranean regions, as well as a cross-cultural analysis between the ethnic groups within the study area, was performed by implementation of the Jaccard index (JI) RESULTS: Throughout the study, information about 202 medicinal plant taxa was compiled. Among these plants, 39 have either not yet been mentioned in ethnobotanical or medicinal studies, or have been used for a medicinal purpose other than those encountered in the literature review. The ethnomedicinal information we gathered from the study area exhibits close similarities to the ethnomedicinal information of other Southern and Eastern Mediterranean countries where Arabic is spoken, as well as to that of Northern and Western Mediterranean countries where Latin languages are spoken. In addition to these similarities, in most cases, this ethnomedicinal information shows hybrid features of ethnomedicinal knowledge from Eastern and Western Mediterranean countries. Based on a literature survey, we found that the cited medicinal uses for 43 plants have also been corroborated by other various biological testings. This finding strongly suggests the importance of ethnobotanical studies in the development of new medicines. We believe that this study has compiled rich ethnomedicinal information that reflects the cosmopolitan structure of Antakya in a very good way.
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