海洋天然产物研究进展

2007年我国科学家在海洋天然产物领域进行了大量研究,发现了倍半萜、二萜、三萜、甾体、舍卤素的杂环化合物、含卤素的酚类化合物、环肽、生物碱等类型的化合物,并且对其抗菌、抗炎、细胞毒、清除自由基等生物活性进行了研究。本文按照海洋生物的种类和研究的侧重点,综述2007年我国在海洋天然产物领域内所取得的研究成果。     

069粗榧种子中的抗菌二萜

首次从粗榧(Cephalotaxus harringtonia)种子中分得到6个二萜成分，包括2个新的天然产物(1、2)，同时检测了其体外抗微生物活性。     

刺柳珊瑚Echinogorgia sp.中的三个神经酰胺

目的从刺柳珊瑚中寻找新化合物。方法采自南中国海域的刺柳珊瑚Echinogorgiasp.经色谱柱分离得到3个同系列的神经酰胺。结果通过波谱分析及化学转化等方法确定了其化学结构分别为(2S,3S,4R)-2-N-(1,3,4-三羟基-正二十烷基)-正十六碳酰胺(1)、(2S,3S,4R)-2-N-(1,3,4-三羟基-正二十烷基)-正十七碳酰胺(2)和(2S,3S,4R)-2-N-(1,3,4-三羟基-正二十烷基)-正十八碳酰胺(3)。结论 3个化合物均是首次从该物种中分离得到,其中化合物2是新化合物,命名为刺柳珊瑚酰胺(echinogoriamide)。     

中国海域柳珊瑚化学成分与生理活性研究

柳珊瑚一直是海洋天然产物研究的热点,从中分离得到的化合物包括甾醇类、萜类、含氮化合物类等多种类型,活性筛选实验表明,这些化合物普遍具有抗炎、抗菌、抗肿瘤和抗结核等多方面的生理活性。本文对2003年以来中国海域包括台湾海域柳珊瑚新的化学成分及其生理活性做一总结,为柳珊瑚的化学成分和活性研究提供参考。     

新天然化合物

本栏目选录了中国学者最新从天然产物中分离鉴定,且在中国期刊发表的新化合物,有的结构新颖,有的具有生物活性,本栏目对于候选药物发现、先导化合物的结构修饰与改造和天然有效活性成分的构效关系研究具有一定启发与借鉴作用。新天然化合物     

真菌来源杂萜类化合物的研究进展

杂萜类化合物是一类含有萜类骨架的杂合型天然产物,具有独特的结构和多样的生物活性,在抗菌、抗炎、抗肿瘤等方面均有所体现,成为天然产物领域的研究热点。笔者综述近5年真菌来源杂萜类化合物的研究进展,基于生源特征归纳了其化学结构和生物活性,将为新型杂萜类药物的开发提供有力支撑。     

日本珊瑚树中具有5,10-顺式结构关系和七元环结构的vibsane型二萜

从日本珊瑚树(Viburnum awabuki)叶中分离得到5个新化合物,为七元环结构的vibsane型二萜,它们在C-5和C-10位具有顺式结构关系。 干燥日本珊瑚树叶粉末(1.5kg),用甲醇室温浸泡1个月,将甲醇提取物蒸干,得到胶状提取物     

新天然化合物

本栏目选录了中国学者最新从天然产物中分离鉴定,且在中国期刊发表的新化合物,有的结构新颖,有的具有生物活性,本栏目对于候选药物发现、先导化合物的结构修饰与改造和天然有效活性成分的构效关系研究具有一定启发与借鉴作用。新天然化合物@李迩娜$中国药科大学!在读硕士研究生     

五味子科植物化学成分及生物活性研究取得可喜进展

中国科学院昆明植物研究所对若干种五味子科药用植物的化学成分和生物活性进行了系统的研究，并取得了新的进展。他们从云南、四川8种五味子科植物中分离鉴定了300余个化合物，包括近80个新化合物。已鉴定的化合物涉及木脂素、倍半萜、三萜、三萜苷、香豆素、黄酮、黄酮苷、甾醇和酚性成分等；新化合物类型包括三萜、木脂素和倍半萜等。除了得到前人报道的活性成分木脂素和三萜酸外，还首次发现了60余个结构新奇的、高氧化度且骨架重排的降三萜、二降三萜、三降三萜、五降三萜和八降三萜等11种新的骨架类型。其发现13个化合物具有明显抑制HIV的活性，具有显著抑制HIV活性的化合物有五味子素等3个，抑制作用最强的为五味子素。这为治疗艾滋病的药物提供了新的天然产物结构模式。     

唇形科香茶菜属植物化学成分研究

目的 :综述我国近十年来对香茶菜属植物的化学成分及其活性的研究成果。方法 :查阅我国近十年来有关文献 ,对香茶菜属植物中新化学成分及其活性研究进行总结。结果和结论 :近十年来 ,在香茶菜属植物中共分得 2 3个新的化学成分 ,有三萜、甾醇、脂肪酸以及少量的黄酮、倍半萜、连烃甙等 ,但主要为二萜类化合物。研究证明该属植物的二萜类化合物具有广泛的生理活性 ,但对近年来发现的新化合物的活性研究还较少 ,应当结合药理实验对其作进一步的活性筛选及结构改造的研究。药理筛选发现许多二萜化合物具有细胞毒、抗肿瘤、抗炎活性作用。在研究中还发现该属植物除含二萜成分外 ,还富含三萜、甾醇、脂肪酸以及少量的黄酮、倍萜半、连烃甙等。从香茶菜属植物中分得 2 3个新化合物在分离鉴定新成分的同时进行简单的活性测试 ,同时结合药理实验对有活性作用的化合物进行进一步的研究 ,根据药理实验对某些化合物进行适当的结构改造 ,极有可能发展成为有希望的抗癌新药。     

Sesquiterpenoid metabolites with antiplasmodial activity from a Caribbean gorgonian coral, Eunicea sp

A chemical investigation of the Caribbean gorgonian octocoral Eunicea sp. collected along the northwest coast of Puerto Rico has afforded seven new secondary metabolites, 1-7, belonging to several types of sesquiterpenes, including elemane, eudesmane, and germacrane types, along with the known steroidal glycoside 8. Some of the new metabolites, 4-7, carry an unusual ester side chain at the C-6 position. The structures of all compounds, including their relative stereochemistry, were determined by combined spectroscopic methods. The present compounds exhibited a significant inhibitory effect upon the growth of the malarial parasite Plasmodium falciparum.     

Bioactive compounds from the gorgonian Briareum polyanthes. Correction of the structures of four asbestinane-type diterpenes

Our extended chemical investigation of the crude MeOH-CHCl3 extract of the gorgonian octocoral Briareum polyanthes from Puerto Rico has led to the isolation of three eunicellin-type diterpenoids, 1-3, along with five (4-8) diterpenoids of the asbestinane-type and one (9) of the briarane-type of polycyclized diterpenes. The structures and relative stereochemistry of the new compounds 1-9 were established on the basis of spectroscopic analysis (1H NMR, 13C NMR, HMQC, HMBC, NOESY). The biological activity of these compounds against pathogenic microbes responsible for various human infectious diseases was investigated. In addition, new data recorded for four known asbestinin diterpenes also isolated during this investigation and further analysis through chemical reactions have prompted us to revise our original structural assignments for these compounds.     

Bipinnatins K-Q, minor cembrane-type diterpenes from the West Indian Gorgonian Pseudopterogorgia kallos: isolation, structure assignment, and evaluation of biological activities

An extensive chemical study of the secondary metabolites found in the crude organic extract of the gorgonian octocoral Pseudopterogorgia kallos has led to the isolation of seven new cembranolides, bipinnatins K-Q ( 2- 8), and one known compound, bipinnatin E ( 9). The molecular structures of compounds 2- 8, many of which contain unusual structural features, were assigned mainly by 2D NMR spectroscopic methods and X-ray crystallographic analysis. The discovery of compounds 2- 8 may lend support to previously proposed mechanisms for the biosynthesis of recently isolated bioactive natural products from the same gorgonian specimen. The in vitro cytotoxicity of bipinnatins 4, 6, and 7 against the NCI tumor cells MCF breast cancer, NCI-H460 non-small cell lung cancer, and SF-268 CNS cancer was evaluated. However, only bipinnatin Q ( 6) displayed significant cytotoxic activity. Some of the compounds isolated proved to be inhibitors of acetylcholine receptors.     

New metabolites from the West Indian sea feather Pseudopterogorgia bipinnata

Two diterpenes, a novel seco-furanocembranolide (3) and the highly oxygenated cembranolide bipinnatolide K (4), have been isolated from the West Indian gorgonian octocoral Pseudopterogorgia bipinnata. The chemical structures of these compounds were determined by 1D and 2D NMR spectroscopy in combination with IR, UV, and HRFABMS analyses.     

Caucanolides A-F, unusual antiplasmodial constituents from a colombian collection of the gorgonian coral Pseudopterogorgia bipinnata

Six new diterpenoids, caucanolides A-F (1-6), have been isolated from extracts of the gorgonian octocoral Pseudopterogorgia bipinnata collected near the Colombian Southwestern Caribbean Sea. The structures of 1-6 were elucidated by comprehensive analysis of spectroscopic data. The caucanolides showed in vitro antiplasmodial activity against the malaria parasite, Plasmodium falciparum. In addition to possessing structures based on novel carbon skeletons, one of these metabolites, caucanolide B (2), constitutes the only example from nature of a secondary metabolite possessing the N(1),N(1)-dimethyl-N(2)-acylformamidine functionality.     

Marine soft corals of the genus Pseudopterogorgia: a resource for novel anti-inflammatory diterpenoids

This paper is a brief review of the diterpenoid chemistry of gorgonian corals of the genus Pseudopterogorgia. Previously described compounds and several new diterpenoids are presented in the context of their potential utilization in the development of anti-inflammatory and analgesic drugs.     

New terpenoid constituents from Eunicea pinta

The secondary metabolite composition of the gorgonian octocoral Eunicea pinta from San Andrés Island, Colombia, is described for the first time. This investigation has resulted in the isolation of eight new gamma-cembranolide-type diterpenes, namely, compounds 3-10, and a new saponin, 13, possessing a pregnene-derived aglycon. In addition, two previously known alpha-methylene-gamma-lactone cembranolides, euniolide (1) and succinolide (2), were also isolated. Their structures were determined on the basis of the results of spectroscopic analysis, X-ray diffraction analysis, and chemical conversions. The discovery of cembranolides 3-10 has prompted us to conclude that the structures proposed earlier for several uprolide-type cembranolides need revision and that a minor stereochemical correction is also in order for succinolide. Cytotoxicity of compounds 3, 4, and 13 toward various cancer cell lines and results of an antimycobacterial screening for 2, 4, and 13 also are described.     

Serrulatane diterpenes with antimycobacterial activity isolated from the West Indian sea whip Pseudopterogorgia elisabethae

Two new antimycobacterial serrulatane diterpenes, erogorgiaene (3) and 7-hydroxyerogorgiaene (4), and a novel C(40) bisditerpene (5), have been isolated from the West Indian gorgonian octocoral Pseudopterogorgia elisabethae. The structures of compounds 3-5 were determined by spectral (1D and 2D NMR, IR, UV, and HREIMS) analysis.     

Elisabatins A and B: new amphilectane-type diterpenes from the West Indian sea whip Pseudopterogorgia elisabethae.

A chemical study of the hexane extracts of the gorgonian octocoral Pseudopterogorgia elisabethae collected in San Andrés Island, Colombia, led to the isolation of two highly conjugated amphilectane-type diterpenes, compounds 1 and 2. Their structures were established by spectroscopic studies, which included 2D NMR correlation methods, IR, UV, and accurate mass measurements (HREIMS).     

Sequestered chemistry of the Arminacean nudibranch Leminda millecra in Algoa Bay, South Africa

Extracts of the endemic nudibranch Leminda millecra collected in Algoa Bay, South Africa, yielded four known metabolites, millecrones A (1) and B (2), isofuranodiene (5), and (+)-8-hydroxycalamenene (9), and nine new compounds, algoafuran (7), cubebenone (8), and a series of seven triprenylquinones and hydroquinones (21-27). A subsequent GC-MS survey of extracts of 21 of L. millecra's possible octocoral prey species in Algoa Bay identified the soft coral Alcyonium fauri as the source of 1 and the gorgonian Leptogorgia palma as the species producing 2 and 8.