深圳大学学报理工版

红树植物内生真菌是新型天然产物先导药物的重要来源之一．为获得具有新颖结构的化合物，对两株红树内生真菌Phomopsissp.DHS11和AspergillusfumigatusJRJ111048的代谢产物进行研究．综合利用正/反相硅胶柱、SephadexLH20凝胶柱和HPLC高效液相色谱法，从发酵提取物中分离得到9种化合物，分别记为化合物1~9．利用高分辨电喷雾质谱（highresolutionelectrosprayionizationmassspectroscopy，HRESIMS）、核磁共振波谱（nuclearmagneticresonancespectroscopy，NMR）、旋光、紫外和红外光谱等技术，鉴定化合物1~9依次为norpestaphthalideC（1）、norpestaphthalideA（2-a）、norpestaphthalideB（2-b）、7-hydroxy-3-（2-hydroxy-propyl）-5-methyl-isochromen-1-one（3）、alternarosideB（4）、细胞松驰素B（5）、啤酒甾醇（6）、5-羟甲基糠醛（7）、N-（4-羟基苯乙基）-乙酰胺（8）和3，5-dihydroxybenzoicacid（9）．其中，化合物1为首次发现的新型苯并呋喃酮类化合物，化合物4是首次从Phomopsissp.属真菌中分离得到的脑苷脂类化合物．对化合物1~9进行体外免疫抑制、抗肿瘤和抗老年痴呆活性评价，结果表明，细胞松弛素类化合物5具有良好的免疫抑制活性．研究结果为深入挖掘红树植物内生真菌新型生物活性物质提供了参考．

Mangrove endophytic fungi are one of the important sources for discovering natural drug leads. In order to obtain natural compounds with novel structures, the metabolites of two mangrove endophytic fungi Phomopsis sp. DHS11 and Aspergillus fumigatus JRJ111048 were studied. As a result, nine compounds (1-9) were isolated from their fermentation extract by comprehensive silica gel, reverse phase silica gel, Sephadex LH20 column chromatography and high performance liquid chromatography (HPLC). The structures of these compounds were identified as norpestaphthalide C (1), norpestaphthalide A (2-a), norpestaphthalide B (2-b), 7-hydroxy-3-(2-hydroxy-propyl)-5-methyl-isochromen-1-one (3), alternaroside B (4), cytochalasin B (5), cerevisterol (6), 5-hydroxymethyl-furaldehyde (7), N-(4-hydroxyphenethyl) acetamide (8), 3, 5-dihydroxybenzoic acid (9) by using high resolution electrospray mass spectrometry (HRESIMS), nuclear magnetic resonance spectroscopy (NMR), optical rotation, ultraviolet, infrared spectroscopy techniques and comparing with reported data. Among them, compound 1 was a new benzofuranone-type natural compound discovered for the first time, and the compound 4 was a cerebroside-type natural product reported for the first time from Phomopsis sp. The immunosuppressive activity, antitumor activity and anti-Alzheimer's activity of compounds 1-9 were evaluated. The result showed that compound 5 displayed good immunosuppressive activity. The research results provide new clues for the in-depth exploration of new bioactive substances in mangrove endophytes.

引言
2 结果与讨论
3 结论

图1 化合物1～9的结构Fig. 1 Structures of 9 compounds

图2 化合物1的1H-1H COSY （粗线）、HMBC （单箭头）和ROESY （双箭头）相关Fig. 2 Key 1H-1H COSY (bold lines), HMBC (single arrows) and ROESY (double arrows) correlations of compound 1

表1 化合物1的1H-NMR（500 MHz）和13C-NMR（125 MHz）数据（DMSO-d6） Table 1 1H-NMR（500 MHz）and 13C-NMR（125 MHz） spectral data for compound 1 in DMSO-d6

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