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In addition to the antiflatulent, emollient, antifungal, antihemorrhoidal, antioxidant, anthelmintic effects, Prangos species have been used to stop bleeding and for the treatment of wounds and scars in central Asia and Turkey. In the present study, the compounds were isolated using chromatographic methods, and their structures were identified by 1H NMR and direct comparison with the reference compounds where available. Fifteen known coumarins were isolated from the dichloromethane extract as osthol, murraol, auraptenol, peroxyauraptenol, 4'-senecioiloxyosthol, meranzin hydrate, scopoletin, umbelliferone, isoimperatorin, oxypeucedanin, oxypeucedanin hydrate, oxypeucedanin methanolate, gosferol, psoralen, and marmesin. The cytotoxic activities of all isolated compounds from dichloromethane extract of P. turcica roots were evaluated using MTT assay on human adenocarcinoma (prostate PC-3) cells. 4'-senecioiloxyosthol, oxypeucedanin methanolate, gosferol, psoralen, peroxyauraptenol and marmesin were tested for the first time on the PC-3 cell line. Osthol and peroxyauraptenol showed the highest cytotoxic activity with IC50 values of 65 and 72 µg/mL, respectively. Additionally, auraptenol, scopoletin, gosferol, psoralen, 4'-senecioiloxyosthol and dichloromethane extract of root part (Pt/R/DCM) demonstrated moderate to low cytotoxic activity. Consequently, the most potent compounds, osthol and peroxyauraptenol, may be used as a lead compound to develop effective drug substances to treat prostate cancer.

Cytotoxic activities of the fruit extracts of Heptaptera triquetra (Vent.) Tutin were investigated on the colon cancer COLO205 and KM12 cell lines. The dichloromethane extract of the fruits of H. triquetra showed the highest cytotoxic activities with IC50 values of 9.3 and 5.3 ug/mL on the COLO205 and KM12 cell lines, respectively. Whereas, the ethyl acetate extract of the fruits showed moderate cytotoxic activity with IC50 values of 22.3 ug/mL against the KM12 cell lines.

Cytotoxic activities of the fruit extracts of Heptaptera anatolica (Boiss.) Tutin were investigated on the colon cancer COLO205 and KM12 cell lines. The dichlorometh-ane extract of the fruits of H. anatolica showed the best cytotoxic activities with IC50 values of 17.9 and 15.1 ug/mL on the COLO205 and KM12 cell lines, respectively. Whereas, the ethyl acetate extract of the fruits showed moderate cytotoxic activity with IC50 values of 23.4 ug/mL against the KM12 cell lines.

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.

© 2021 Phytochemical Society of EuropeSeventeen 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.

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&prime, acylated osthol derivatives including a novel coumarino-alkaloid, neopapillarine) demonstrated selective cytotoxic activity in A498 and UO31 renal cancer cell lines.

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.

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&prime, acetoxybadrakemin (7) were observed at nanomolar level against the UO31 kidney cancer cell line.

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.

Ethnopharmacological relevance 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. Aim of the study 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. Materials and methods 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. Conclusion 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.

The dichloromethane extract of the roots of Prangos hulusii, a recently described endemic species from Turkey, has yielded nine known and one new prenylated coumarins. The structures were elucidated by spectroscopic methods and direct comparison with the reference compounds where available. The root extract and its prenylated coumarins exhibit antimicrobial activity against nine standard and six clinically isolated strains at a concentration between 5 and 125 µg/mL. In particular, the new coumarin, 4′-senecioiloxyosthol (1), displayed 5 µg/mL MIC (Minimum Inhibitory Concentration) value against Bacillus subtilis ATCC 9372, murraol (4) and auraptenol (5) showed 63 µg/mL MIC value against Klebsiella pneumoniae ATCC 4352 and Bacillus subtilis ATCC 9372, and isoimperatorin (9) exhibited 16 µg/mL MIC value.

Annual Meeting of the American-Society-of-Pharmacognosy on Natural Products at a Crossroad - Current and Future Directions -- JUL 14-17, 2013 -- St Louis, MO, WOS: 000338695100234, …, Amer Soc Pharmacognosy

Annual Meeting of the American-Society-of-Pharmacognosy on Natural Products at a Crossroad - Current and Future Directions -- JUL 14-17, 2013 -- St Louis, MO WOS: 000338695100236 The genus Ferula comprises more than 180 species and is the largest genus of Apiaceae in Asia. There are 23 species of Ferula in Turkey and 17 of them are endemic. Ferula species are rich sources of sesquiterpenes with wide structural variety. The phytochemical investigations of several Ferula species growing in Turkey has yielded many sesquiterpenes with antibacterial, antifungal, anticancer, antioxidant, P-glycoprotein inhibitor, immune modulator and hormonal activities. Chemical structures, chemical transformations, biological activities, biosynthetic and chemotaxonomic significance of the sesquiterpenes isolated from Anatolian Ferula species will be presented. Amer Soc Pharmacognosy

Annual Meeting of the American-Society-of-Pharmacognosy on Natural Products at a Crossroad - Current and Future Directions -- JUL 14-17, 2013 -- St Louis, MO WOS: 000338695100223 … Amer Soc Pharmacognosy

Using a high throughput colorimetric bioassay three aporphine alkaloids, annonaine, nornuciferine and roemerine, were isolated and identified as the CD45 protein tyrosine phosphatase inhibitor metabolites of Rollinia ulei . The nor-aporphine alkaloids, anonaine ( 1 ) and nornuciferine ( 3 ), exhibited more potent inhibitory activity than that of the N-methylated alkaloid roemerin ( 2 ).

International Congress on Natural Products Research on Global Change, Natural Products and Human Health/8th Joint Meeting of AFERP, ASP, GA, PSE and SIF -- JUL 28-AUG 01, 2012 -- New York, NY WOS: 000307042801555 … Amer Soc Pharmacognosy (ASP), Soc Med Plant & Nat Prod Res (GA), Italian Soc Phytochem (SIF), Phytochem Soc Europe (PSE), French Speaking Soc Pharmacognosy (AFERP)

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°

In addition to several known daucane aryl esters 11 new daucane esters and a new phenyl propanoid ester were isolated from the roots of Ferula rigidula. The structures of the new esters were elucidated by spectral analyses.

In addition to the known sesquiterpene-coumarin samarcandin and two known phenylpropanoids, two new cyclic farnesyl-coumarin and two new cyclic farnesyl-chromone derivatives were isolated from the benzene extract of the roots of Ferula communis subsp. communis. Structures of the new compounds were elucidated by spectral methods.

In addition to the known phenylpropanoid myristicin, the petrol extract of the roots of Ferulago antiochia yielded six new germacrane esters and a new alloaromadendrane ester. The structures were elucidated by spectral and chemical methods.

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°

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.

The well-known germacrolide, eupatoriopicrin, and two additional sesquiterpene lactones, were isolated from Perityle vaseyi . The latter two lactones, one a novel guaianolide and the other a known germacrolide, both contain unusual ten carbon diester side chains attached at C-8. The chemical evidence, in conjunction with morphological data, suggest that Perityle, and hence the subtribe Peritylinae, should be placed in the tribe Heliantheae.

Eleven sesquiterpene lactones, six of which are new, were identified from Piptothrix pubens . All but one of the compounds contained a C 10 -diester attached at C-8. The taxonomic implications of these results are discussed.

Fourteen daucane esters together with a known propiophenone 3,4-methylenedioxy-5-hydroxy-propiophenone, were isolated from Ferula communis subsp. communis . Except for the 6-( p -anisic acid) ester of jaeschkeanadiol all these esters are new. Structures were elucidated using spectral properties of the esters and their partial hydrolysis products. X-ray diffraction analysis of one of the compounds confirmed its structure including the stereochemical assignments made on the basis of spectral data.

The chloroform extract of the leaves of Onopordon tauricum yielded 10 sesquiterpene lactones, including a new elamanolide and four new eudesmanolides. The structures of the new compounds were elucidated by chemical transformations and modern spectral methods.

In addition to three known thymol esters and five known sesquiterpene lactones, two new germacrolides and a new diterpene diester were isolated from the dichloromethane extract of the aerial parts of Piptothrix sinaloae . Structures for the new compounds were elucidated by chemical transformations and spectral methods. The current taxonomic status of P. sinaloae is discussed on the basis of both morphological and secondary metabolite data.

In addition to the known sesquiterpene lactone pinnatifidin, and the flavones 6-methoxyacacetin and 6-methoxyapigenin, the dichloromethane extract of the aerial parts of Decachaeta ovatifolia afforded four new sesquiterpene lactones: a germacranolide 7α-hydroxycostunolide, a guaianolide 4α,15-dihydro-7α-hydroxy-3-desoxyzaluzanin C and two eudesmanolides, 7α-hydroxysantamarine and 7α-hydroxyreynosin. The structure of 7α-hydroxycostunolide was confirmed by X-ray analysis.

Ten new apiene-type humulenoid esters were isolated from the root of Ferula haussknechtii . The structures were elucidated by spectroscopic methods.

Together with the known daucene ester 14- p -anisoyloxy-dauc-4,8-diene, a new ester, fercomin and the first known daucane-γ-lactone, fercolide, were isolated from Ferula communis subsp. communis . Structures for these compounds were elucidated on the basis of their spectral properties and the structure of fercomin was confirmed by X-ray analysis. A revised structure of vaginatin is discussed.

One known and four new germacranolide-type sesquiterpene lactones were obtained from the dichloromethane extract of Chromolaena opadoclinia .

Two new salicyloyl and angeloyl esters of jaeschkeanadiol, together with the known benzoic, p -hydroxybenzoic, p -methoxybenzoic and vanillic acid esters, were isolated from Ferula elaeochytris . A new ketone, 3-hydroxy-4,5-methylenedioxypropiophenone, was also obtained.

Four new sesquiterpene lactones, 11β,13-dihydroxyepitulipinolide, 11β,13-epoxyepitulipinolide, 3β-acetoxy-11β,13-epoxyepitulipinolide and 11β,13-epoxy-8β-acetoxy-α-cyclocostunolide as well as the known lactone epitulipinolide, were isolated from the aerial parts of Bartlettina karwinskiana .