Sesquiterpene coumarins and related derivatives from Ferula pallida

Six new compounds-two sesquiterpene coumarins, pallidones A and B (1, 2), and four related derivatives, pallidones C-F (3-6), as well as two known sesquiterpene coumarins, feselol (7) and conferol (8), have been isolated from the EtOAc extracts of the roots of Ferula pallida. All structures of these compounds were determined on the basis of spectral evidence, especially 2D NMR ((1)H-(1)H COSY, HSQC, HMBC, and NOESY) and HRMS. The possible biosynthetic pathway of pallidones C-F (3-6) is discussed.     

Traditional uses, phytochemistry and pharmacology of asafoetida (Ferula assa-foetida oleo-gum-resin)-a review

The old traditional phytomedicine asafoetida, an oleo-gum-resin obtained from the roots of different Ferula assa-foetida, is used in different countries for various purposes. Asafoetida is not only used as a culinary spice but also traditionally used to treat various diseases, including asthma, gastrointestinal disorders, intestinal parasites, etc. This oleo-gum-resin has been known to possess antifungal, anti-diabetic, anti-inflammatory, anti-mutagenic and antiviral activities. A wide range of chemical compounds including sugars, sesquiterpene coumarins and polysulfides have been isolated from this plant. Recent studies have shown new promising antiviral sesquiterpene coumarins from this old phytomedicine. The present review summarizes the information concerning the traditional uses, phytochemistry and biological activities of asafoetida.     

阜康阿魏中倍半萜香豆素类化学成分研究

 目的对伞形科阿魏属植物阜康阿魏(Ferula fukanensis K.M.Shen)根中的倍半萜香豆素类活性成分进行分离纯化和结构确定。方法利用普通硅胶柱色谱和中压制备色谱等多种色谱技术进行反复分离纯化,根据理化性质和现代波谱技术(EI-MS,¹H-NMR,¹³C-NMR)进行结构鉴定。结果从阜康阿魏根中分离得到5个倍半萜香豆素类化合物,分别鉴定为umbelliprenin(Ⅰ),fekolone(Ⅱ),badrakemone(Ⅲ),lehmannolone(Ⅳ),assafoetidin(Ⅴ)。结论化合物Ⅰ～Ⅴ为首次从该植物中分离得到。     

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.     

The genus Stephania (Menispermaceae): Chemical and pharmacological perspectives

The plants of the genus Stephania (Menispermaceae) are widely distributed, and have long been used in folk medicine for the treatment of various ailments such as asthma, tuberculosis, dysentery, hyperglycemia, malaria, cancer and fever. Over 150 alkaloids together with flavonoids, lignans, steroids, terpenoids and coumarins have been identified in the genus, and many of these have been evaluated for biological activity. This review presents comprehensive information on the chemistry and pharmacology of the genus together with the traditional uses of many of its plants. In addition, this review discusses the structure-activity relationship of different compounds as well as recent developments and the scope for future research in this aspect.     

Natural and synthetic 2,2-dimethylpyranocoumarins with antibacterial activity

A new efficient synthetic approach to the natural coumarins 5-hydroxyseselin (5), 5-methoxyseselin (3), and (+/-) cis-grandmarin (9) is described as well as the synthesis of some new derivatives in the 5-methoxyseselin series (10-15). The natural coumarins 7-hydroxyalloxanthyletin (6), alloxanthoxyletin (8), and dipetalolactone (7) have also been obtained as secondary products. The type of fusion of the pyrano ring in all cases has been established by 2D NMR spectroscopy. The compounds have been studied for their in vitro antibacterial activity, which has been compared with that of some previously synthesized seselin derivatives. The most active compounds were 3, 7, 8, 11, and 14. Some structure-activity relationships are discussed.     

阿魏的化学成分研究

目的:研究准格尔阿魏Ferula songorica Pall.ex Spren in Roem.et Schult的化学成分.方法:利用各种色谱方法进行分离纯化,根据波谱解析、理化常数分析及文献对照进行结构鉴定.结果:从阿魏根茎95%乙醇提取物中分离得到3个化合物,分别为2,4-二羟基-α-氧代-苯乙酸(1),3,3',4,4'-联苯四甲酸(2),2,4-二羟基苯甲酮(3).结论:化合物2是新天然产物,化合物1为首次从该植物中分离得到.     

Sesquiterpene phenylpropanoid and sesquiterpene chromone derivatives from Ferula pallida

Four novel compounds-two sesquiterpene phenylpropanoid derivatives, pallidones G (1) and H (2), and two sesquiterpene chromone derivatives, pallidones I (3) and J (4)-have been isolated from the roots of Ferula pallida. Their structures were determined on the basis of NMR and HREIMS evidence.     

Farnesylamine from the ant Monomorium fieldi Forel

(2E)- and (2Z)-Farnesylamine were detected in the extracts of the myrmicine ant Monomorium fieldi Forel from Australia. Their structures were established by direct comparison with synthetic (2E)- and (2Z)-farnesylamine. This finding of a sesquiterpene is unique in a genus known to produce unbranched fatty acid derived alkaloids and amines. Additionally, while farnesylamine has not been reported from natural sources, the synthetic material has been shown to have a variety of biological activities.     

Sesquiterpene lactones from the roots of Ferula varia and their cytotoxic activity

The ethyl acetate-soluble fraction from a MeOH extract of the roots of Ferula varia gave six new sesquiterpene lactones (1-6) and five known sesquiterpenes (7-11). Their structures were established on the basis of spectroscopic evidence. The cytotoxic activities of 1-11 were evaluated against selected human cancer cell lines. Compound 4 showed significant selective cytotoxicity against multidrug-resistant cancer cells (KB-C2). The cytotoxicities of compounds 1, 3, 5, 8, and 11 against KB-C2 cells were enhanced in the presence of nontoxic concentrations of colchicine.     

Estrogenic activity of chemical constituents from Tephrosia candida

In a continued investigation of medicinal plants from the genus Tephrosia, phytochemical analysis of a methylene chloride-methanol (1:1) extract of the air-dried aerial parts of Tephrosia candida afforded two new 8-prenylated flavonoids, namely, tephrocandidins A (1) and B (2), a new prenylated chalcone, candidachalcone (3), a new sesquiterpene (4), and a previously reported pea flavonoid phytoalexin, pisatin (5). The structures of 1-4 were established by spectroscopic methods, including HREIMS, and 1H, 13C, DEPT, HMQC, and HMBC NMR experiments. The most potent estrogenic activity of these isolated natural products in an estrogen receptor (ERα) competitive-binding assay was for 3, which exhibited an IC50 value of 80 μM, compared with 18 nM for the natural steroid 17β-estradiol. Results were interpreted via virtual docking of isolated compounds to an ERα crystal structure.     

Sesquiterpene chromones from Ferula fukanensis and their nitric oxide production inhibitory effects

Five new sesquiterpene chromone derivatives, fukanefurochromones A-E (1-5), were isolated from a 80% aqueous methanol extract of the roots of Ferula fukanensis. The structures were elucidated on the basis of spectroscopic evidence, especially heteronuclear multiple-bond connectivity (HMBC) and high-resolution MS. The sesquiterpene chromone derivatives inhibited nitric oxide (NO) production and inducible NO synthase (iNOS) gene expression by a murine macrophage-like cell line (RAW 264.7), which was activated by lipopolysaccharide (LPS) and recombinant mouse interferon-gamma (IFN-gamma).     

香豆素类化合物生物学活性研究进展

综述了近10年来香豆素类化合物有效成分及生物学活性的研究进展。香豆素是自然界很重要的一大类天然有机化合物,实验研究发现香豆素类化合物具有抗HIV、抗癌、降压、抗心律失常、抗骨质疏松、镇痛、平喘及抗菌等多方面生物学活性。因此,完善香豆素类化合物提取分离工艺,寻找有效的先导化合物,合成并筛选出高效低毒的香豆素类衍生物已成为药物研发工作的重要方向之一。     

Copacamphane,picrotoxane, and alloaromadendrane sesquiterpene glycosides and phenolic glycosides from Dendrobium moniliforme

Seven sesquiterpene glycosides with copacamphane, picrotoxane, and alloaromadendrane sesquiterpene aglyons along with three phenolic glycosides have been isolated from the stems of Dendrobium moniliforme. Among them, dendromonilisides A-D (1-4) were characterized as new compounds, and their structures were determined on the basis of spectral and chemical methods and by X-ray diffraction analysis. The six known compounds were identified as dendrosides A, C, and F, dendromoniliside E, vanilloloside, and acanthoside B. In a preliminary biological test procedure, compounds 1, 3, and vanilloloside were found to stimulate the proliferation of B cells and inhibit the proliferation of T cells in vitro.     

Sesquiterpene phenylpropanoids from Ferula fukanensis and their nitric oxide production inhibitory effects

Five new sesquiterpene phenylpropanoid derivatives, fukanedone A (1), fukanedone B (2), fukanedone C (3), fukanedone D (4), and fukanedone E (5), and a novel phenyl-oxo-acetate ester, fukaneketoester A (6), were isolated from a 80% aqueous methanol extract of the roots of Ferula fukanensis. The structures were elucidated on the basis of spectroscorpic evidence, especially heteronuclear multiple-bond connectivity (HMBC) and high-resolution MS. The sesquiterpene phenylpropanoid derivatives inhibited nitric oxide (NO) production and inducible NO synthase (iNOS) gene expression by a murine macrophage-like cell line (RAW 264.7), which was activated by lipopolysaccharide (LPS) and recombinant mouse interferon-gamma (IFN-gamma).     

An unusual sesquiterpene derivative from Ferula kuhistanica

An unusual new sesquiterpene derivative, kuhistaferone (1), was isolated from the fruits of the Uzbekistan medicinal plant Ferula kuhistanica. The structure of 1 was established on the basis of spectroscopic evidence. Compound 1 showed moderate cytotoxicity against the human colon tumor cell line HCT116.     

金粟兰属植物的化学成分和药理作用研究进展

金粟兰属植物在化学成分和药理作用方面的研究进展进行了综述。金粟兰属植物在民间是治疗肿疖、毒蛇咬伤和跌打损伤的良药，从金粟兰科金粟兰属植物共分离得到68个化合物，化学结构类型包括萜类、香豆素及香豆素苷类、酰胺、有机酸、甾体及甾体皂苷等，其中倍半萜烯类化合物51个。现代药理研究表明金粟兰属植物多具有抗菌、抗肿瘤、增强免疫等活性。目前尚有必要对该属植物的化学成分和药理作用进行深入研究以验证该属植物的民间疗效、探讨该属甚至该科的化学分类学及系统学位置等，从而更好地对其进行开发利用。     

Pelorol from the tropical marine sponge Dactylospongia elegans

From the dichloromethane solubles of the tropical marine sponge Dactylospongia elegans, a new aromatic substituted sesquiterpene, pelorol (1), and the known sesquiterpene, ilimaquinone (2), were isolated. The structures of 1 and 2 were deduced from their spectroscopic data. The biological activities of compounds 1 and 2 were assessed in a variety of bioassays, and both compounds were found to have weak antitrypanosomal and antiplasmodial effects.     

香豆素类化学成分的药理作用及毒性机制研究进展

香豆素是一类以苯骈α-吡喃酮为基本结构的芳香族天然产物,根据化学结构可分为简单香豆素、呋喃香豆素、吡喃香豆素和其他香豆素类。该类成分在自然界中分布广泛,现代药理和临床研究表明,中药中香豆素类化合物具有抗肿瘤、抗炎、抗骨质疏松等多种药理活性。然而随着研究的深入与临床的大量应用,中药中香豆素类化合物被发现可致肝脏、肾脏等损伤,其安全性亦引发广泛关注。对中药中香豆素类化学成分及其药理作用进行总结,着重阐述毒性成分（异）补骨脂素、甲氧基补骨脂素、（异）欧前胡素和白花丹醌等的毒性研究进展,以期为中药中香豆素类化合物的研究与合理使用提供科学指导与借鉴,提高含香豆素类成分中药临床用药的有效性与安全性。     

香豆素类化合物抗肿瘤作用研究进展

香豆素(coumarin)是一类具有苯并α吡喃酮母核天然产物的总称，通常依据α吡喃酮环上取代基的不同结合，将其分为简单、呋喃、吡喃和其他香豆素类化合物4种。实验研究发现香豆素类化合物具有抗HIV、抗癌、降压、抗心律失常、抗骨质疏松、镇痛、平喘及抗菌等多种生物活性，具有潜在的药用价值，其中抗肿瘤作用是一个研究热点。因此,研究开发更多天然植物香豆素成分，寻找有效的先导化合物, 完善香豆素类化合物的提取工艺,合成并筛选出高效低毒的香豆素类化合物及其衍生物已成为当今药物研究与开发工作的重中之重。