Daucane sesquiterpenes from Ferula hermonis

The dried roots of Ferula hermonis yielded three new daucanes, (1R,4R)-4-hydroxydauca-7-ene-6-one (1), (1R,4R)-4-hydroxydauca-7-ene-6,9-dione (2), and (1R,3S,8S)-3-ethoxy-8-angeloyloxydauca-4-en-9-one (3), together with the three known sesquiterpenes, ferutinin, teferidin, and (+)-alpha-bisabolol. The structures of compounds 1-3 were elucidated on the basis of spectroscopic evidence. The effect of these compounds on the proliferation of estrogen-dependent MCF-7 cells was evaluated, and it was found that compounds 1 and 3 exhibited proliferative activity, whereas 2 showed an antiproliferative effect.     

Antimicrobial antioxidant daucane sesquiterpenes from Ferula hermonis Boiss

Seventeen daucane sesquiterpenoid esters, including a new one (4), were isolated from the root of Ferula hermonis Boiss. The structures of the isolated compounds were elucidated on the basis of spectroscopic evidence and correlated with known compounds. The relative stereochemistry of the new compound was determined using 2D NOESY and the most stable and the lowest energy conformation was determined using molecular modelling. The antimicrobial activity was evaluated by determination of MIC using the broth microdilution method against six bacterial strains and one fungal strain (Pseudomonas aeruginosa PAO1, Escherichia coli, Bacillus subtilis ATCC6633, Mycobacterium bovis BCG Pasteur, Mycobacterium tuberculosis H37Rv, Staphylococcus aureus ATCC6538 and Candida albicans SC5314). There was a significant indication that compounds 15, 16, 17 demonstrated potent activity against Gram +ve (S. aureus, B. subtilis), as well as Mycobacterium strains M. bovis BCG and M. tuberculosis H37Rv. None of the isolated compounds exhibited a significant antifungal activity. In the antioxidant study using the DPPH assay method, the highest radical scavenging activity was observed for compounds 15, 16, 17.     

Antiinflammatory sesquiterpenes from the root oil of Ferula hermonis

Ferula hermonis Boiss. (Apiaceae), commonly known as ‘Shilsh‐el‐zallouh’, ‘Hashishat‐al‐kattira’ or ‘The Lebanese viagra’, is a small shrub that grows abundantly on the Hermon Mountain between Syria and Lebanon. The seeds and roots of this plant have long been used in the Middle East as an aphrodisiac, and for the treatment of frigidity and impotence for both men and women. The antiinflammatory properties of three major daucane esters, ferutinin (1) teferin (2) and teferidin (3), isolated from the root oil of Ferula hermonis, were assessed by the carrageenan‐induced oedema model in rats. The antiinflammatory effect of both 1 and 2 was observed with a dose of 100 mg/kg, while compound 3 did not show any antiinflammatory activity; conversely it produced a significant proinflammatory effect 2 and 3 h after carrageenan injection. Copyright © 2010 John Wiley & Sons, Ltd.     

New sesquiterpenes from Ferula sinaica

The CH2Cl2 extract of Ferula sinaica afforded twelve sesquiterpenes including three new daucanes, 14-hydroxyvaginatin, 4 beta, 8 beta, 9 alpha-trihydroxy-6 alpha-p-hydroxy-benzoyloxydaucane, and isolancerotriol.     

Antifungal Compounds from the Rhizome and Roots of Ferula hermonis

The antifungal activity of hexane, dichloromethane, methanol and aqueous extracts from the rhizome and root of Ferula hermonis was assayed in vitro by the agar disk diffusion method against a panel of human opportunistic and pathogenic fungi. Among them, the hexane and dichloromethane extracts showed the highest activity particularly against the dermatophytes Microsporum gypseum and Tricophyton mentagrophytes as well as the yeast Candida lactis‐condensi. Activity‐guided fractionation of both extracts using an agar overlay bioautographic method led to the isolation of two antifungal compounds which were identified as the daucane aryl esters jaeschkeanadiol p‐hydroxybenzoate (ferutinin) and jaeschkeanadiol benzoate (teferidin). Determination of minimal inhibitory concentration (MIC) and minimal fungicidal concentration (MFC) values of both compounds evidenced a stronger antifungal activity for ferutinin than for teferidin. Particularly, T. mentagrophytes was the most sensitive strain with MIC and MFC values ranging from 8 to 256 µg/mL. Copyright © 2012 John Wiley & Sons, Ltd.     

Sesquiterpenes from Ferula penninervis

The ethyl acetate soluble extract of the dried roots of Ferula penninervis gave 17 new sesquiterpenes [15 of the guaiane-type, ferupennins A-O (1-15), and two of the eudesmane-type, 1alpha-hydroxy-2-oxo-5alpha,7beta,11betaH-eudesm-3-en-6alpha,12-olide (16) and penninervin (17)] and nine known sesquiterpenes. The structures of the new compounds were elucidated on the basis of spectroscopic evidence and X-ray analysis. The absolute configuration of ferupennin A (1) was determined by a modified Mosher method.     

Daucane phytoestrogens: a structure-activity study

The estrogenic activity of a series of analogues of the daucane ester ferutinin (1a) modified at the acyl moiety was investigated in a yeast screen containing the human estrogen receptor alpha. Rather strict structure-activity relationships were observed. Thus, while the parent polyol (jaeschkeanadiol, 2a) was inactive, the presence of a p-hydroxybenzoyl moiety was necessary for activity in the yeast screen. Homologation and vinylation were both detrimental for activity, as were methylation of the p-hydroxyl substituent and the introduction of oxygen functions on the adjacent carbons.     

Sesquiterpene coumarins from Ferula gumosa

A new sesquiterpene coumarin, gumosin (1), two new sesquiterpene coumarin glycosides, gumosides A (2) and B (3), and 10 known compounds, namely, cauferoside (4), feselol (5), conferoside, ferilin, ferocaulidin, ligupersin A, conferol, and daucosterol, and the phenolic compounds acantrifoside E and 4-hydroxybenzoic acid 4-(6-O-sulfo)glucopyranoside, were isolated from a methanolic extract of Ferula gumosa roots. The structures of 1-3 were elucidated by spectroscopic data interpretation. The cytotoxic activity of the sesquiterpene coumarin derivatives was evaluated against a small panel of cancer cell lines.     

Polysulfide derivatives from Ferula foetida

The ethyl acetate-soluble fraction from a methanol extract of Ferula foetida has afforded six new sulfide derivatives, (E)-3-methylsulfinyl-2-propenyl sec-butyl disulfide (foetisulfide A) (1), (Z)-3-methylsulfinyloxy-2-propenyl sec-butyl disulfide (foetisulfide B) (2), (E)-3-methylsulfinyloxy-2-propenyl sec-butyl disulfide (foetisulfide C) (3), bis(3-methylthio-2E-propenyl) disulfide (foetisulfide D) (4), 3,4,5-trimethyl-2-thiophenecarboxylic acid (foetithiophene A) (5), 3,4,5-trimethyl-2-(methylsulfinyloxymethyl)thiophene (foetithiophene B) (6), along with six known compounds. The structures of 1-6 were established on the basis of spectroscopic studies, with the elucidation of 5 confirmed by single-crystal X-ray crystallography.     

Eremophilane sesquiterpenes from Ligularia macrophylla

New eremophilane sesquiterpenes, 6beta-sarracinoyloxy-1beta,10beta-epoxy-furanoeremophilane (1), 6alpha-angeloyloxy-10betaH-furanoeremophil-1-one (2), 1alpha-hydroxy-9-deoxycacalol (3), and 1beta-hydroxy-11(R,S)-8-oxoeremophil-6,9-dien-12-al (4a+4b), together with five known sesquiterpenes (5-9) were isolated from the roots and rhizomes of Ligularia macrophylla. The structures were elucidated by spectroscopic methods including 2D NMR techniques, and the structure of 1 was confirmed by a single-crystal X-ray diffraction experiment. The compounds were also evaluated for cytotoxic activity against human lung carcinoma (A-549) and human breast adenocarcinoma (MCF-7) and were found to show only very weak cytotoxicity.     

Cytotoxic sesquiterpenes from Aplysia dactylomela

Three new chamigrenes, compound 1, acetyldeschloroelatol 2 (2-bromo-1,1,9-trimethyl-5-methylenespiro[5.5]undec-8-en-3-yl acetate), and acetylelatol 4 (2-bromo-8-chloro-1,1,9-trimethyl-5-methylenespiro[5.5]undec-8-en-3-yl acetate), and the known metabolites deschloroelatol 3, elatol 5, 8-acetylcaespitol 6, and caespitol 7 have been isolated from the sea hare Aplysia dactylomela. The structures of 1, 2, and 4 were determined on the basis of spectroscopic evidences. The in vitro cytotoxicity of six of these compounds against two cancer cell lines (HeLa and Hep-2) and nontumoral Vero cells was evaluated. The results support the hypothesis that the acetate derivatives decrease the toxicity of the corresponding alcohols in a strategy to store toxic metabolites acquired through the diet.     

New sesquiterpenes from Pluchea arabica

Two new sesquiterpenes, godotol A (1) and godotol B (2), were isolated from Pluchea arabica. Their structures were determined by analysis of NMR data. The absolute configurations of 1 and 2 were established by Mosher ester methodology. The godotols displayed weak activity against bacteria and the brine shrimp larvae. They were also inactive in the DPPH antioxidant assay.     

Minor sesquiterpenes from Maytenus chubutensis

Four new minor dihydro-beta-agarofuran-skeleton sesquiterpenes, 9 beta-benzoyloxy-1 alpha,2 alpha,6 beta-triacetoxy-15-hydroxydihydro-beta- agarofuran [1], 9 beta-benzoyloxy-1 alpha,2 alpha,6 beta,15-tetracetoxydihydro-beta-agarofuran [6], 9 alpha-benzoyloxy-1 alpha,2 alpha,6 beta-triacetoxy- 8 alpha,15-dihydroxydihydro-beta-agarofuran [7], and 9 alpha-benzoyloxy-1 alpha,2 alpha,6 beta,8 alpha-tetracetoxy-15- hydroxydihydro-beta-agarofuran [8] were isolated from the aerial parts of Maytenus chubutensis and identified by spectroscopy and chemical reactions.     

New sesquiterpenes from Capsicum annuum

The ethyl acetate soluble fraction of a MeOH extract of the dried stems and roots of Capsicum annum gave 10 new sesquiterpenoids (1-10) and nine known compounds. The structures of the new compounds were elucidated on the basis of spectroscopic evidence. The isolated new compounds were evaluated for their cytotoxic activities.     

Muurolane sesquiterpenes from illicium tsangii

A dichloromethane extract of Illicium tsangii has yielded five novel muurolane sesquiterpenes (1, 2, 6, 7, 9) and three new menthane monoterpenes (10-12) in addition to several known compounds. Biogenetic relationships among the sesquiterpenes are discussed.     

New daucane esters from Ferula tingitana

In addition to the three known daucane esters (2,3,8) and one phenylpropanoid (9), the petroleum ether extract of the roots of Ferula tingitana yielded four new daucane esters: 14-p-anisoyloxy-dauc-4,8-diene (1), acetyltingitanol (4), acetyldesoxodehydrolaserpitine (5), and 4-beta-hydroxy-6-alpha-p-hydroxybenzoyloxy-10-alpha-angeloyloxy dauc-8-ene (6). A possible biogenetic pathway for 1,5-cis- and 1,5-trans-daucanes is presented.     

大果阿魏化学成分的研究

目的：对大果阿魏根部的化学成分进行研究。方法：采用硅胶柱色谱、Sephadex LH-20柱色谱以及重结晶等方法分离纯化,根据理化性质和谱学数据鉴定化合物的结构。结果：从大果阿魏根部分离得到6个化合物,分别鉴定为lehmannolone（Ⅰ）、sinkianone（Ⅲ）、lehmannoloneA（Ⅲ）、farnesiferolC（Ⅳ）、fekrynol（Ⅴ）、assafoetidin（Ⅵ）。结论：化合物Ⅱ-Ⅵ均为首次从该植物中分得。     

Three new sesquiterpenes from Croton arboreous

Three new sesquiterpenes, 5alpha,7alpha,10betaH-3-patchoulen-2-one (1), 5alpha,7alpha10betaH-4(14)-patchoulen-2alpha-ol (2), and 9alpha,10beta-dihydroxy-2beta,4beta-peroxy-1alpha,5beta,7alphaH-guaiane (3), were isolated from the aerial parts of Croton arboreous along with 14 known compounds. The structures of these compounds were determined on the bases of their spectroscopic data (IR, UV, OR, 1D and 2D NMR, and MS). The anti-inflammatory activity against ear edema in mice produced by 12-O-tetradecanoylphorbol-13-acetate (TPA) was evaluated for all the pure compounds and showed that compounds 4-7 are active.     

New eudesmane sesquiterpenes from Plectranthus cylindraceus

Three new eudesmane sesquiterpenes, plectranthone (1), desacetylplectranthone (2), isodeacetylplectranthone (3), and the three known flavonols pachypodol, casticin, and chrysosplenol D were isolated for the first time from the aerial parts of Plectranthus cylindraceus. Their structures have been established on the basis of spectral data. The structures and relative stereochemistries of 1 and 2 were confirmed by single-crystal X-ray analysis.