| 摘要: |
| 从采自青岛近海的红藻多管藻(Polysiphonia urceolata)中分离到一株毛壳霉属真菌球毛壳菌(Chaetomium globosum.)，对其发酵代谢产物的化学成分进行了研究。采用溶剂提取、分配，硅胶柱层析、葡聚糖凝胶柱层析以及制备薄层层析等技术已分离获得6个单体化合物，通过一维、二维超导核磁共振技术、质谱技术等鉴定了其中4个化合物的结构，均为苯甲醛类衍生物，分别为2-(1-庚烯基)-3、6-二羟基-5-(3-甲基-2-丁烯基)苯甲醛(Ⅰ)、2-庚基-3、6-二羟基-5-(3-甲基-2-丁烯基)苯甲醛(Ⅱ)、2-(3、5-庚二烯基)-3、6-二羟基-5-(3-甲基-2-丁烯基)苯甲醛(Ⅲ)、2-(1、3、5-庚三烯基)-3、6-二羟基-5-(3-甲基-2-丁烯基)苯甲醛(Ⅳ)。 |
| 关键词: 海藻 多管藻 内生真菌 次生代谢产物 苯甲醛类衍生物 |
| DOI： |
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| 基金项目:国家自然科学基金资助项目,30530080号;山东省科技发展计划资助项目,2006GG2205023号 |
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| BENZALDEHYDES FROM AN ENDOPHYTIC FUNGUS CHAETOMIUM GLOBOSUM SEPARATED FROM MARINE RED ALGA POLYSIPHONIA URCE OLAT A |
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WANG Song1,2, ZHANG Yi1,2, LI Xiao-Ming1, WANG Bin-Gui1
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1.Institute of Oceanology,Chinese Academy of Sciences,Qingdao,266071;2.Graduate School of Chinese Academy of Sciences,Beijing,100039
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| Abstract: |
| Marine microorganisms have become an important source of biologically active secondary metabolites, among them marine fungi is one of them for the discovery of structurally unique natural marine products with anticipated biomedical potential. Recently, many biologically active metabolites have been discovered and reported from marine algal-derived endophytic fungi. This paper describes the isolation and structural determination of four benzaldehyde derivatives from Chaetomium globosum, a marine algal derived endophytic fungus.
The endophytic fungus Chaetomium globosum was originally separated from marine red alga Polysiphonia urceolate Grev that was collected in the coast of Qingdao, China. The liquid medium was incubated at room temperature for 40 days. The mycelium and filtrate were extracted with methanol and EtOAc respectively. Crude extracts were evaporated from mycelium and filtrate respectively under reduced pressure at 40°C. The two extracts were assayed against P-338 and A-549 cell lines and each showed significant bioactivity. Since the HPLC profiles of the two extracts were nearly identical, they were combined before further separation. Initial chromatographic separation of the extracts was performed on silica gel (200-300 mesh, Qingdao Haiyang Chemical Inc., China) column chromatography (CC) with a gradient solvent system from 3% acetone/petroleum ether to 100% acetone. The fractions were monitored by inspection of thin layer chromatography (TLC). Fractions l2-l5 were combined and were further chromatographied on silica gel using an EtOAc/petroleum ether gradient system to give a subfraction containing 4 compounds shown below, which was further purified over Sephadex LH-20 (Merck, Darmstadt, Germany) using chloroform/MeOH (1:1) as solvent system. Four benzaldehyde derivatives were finally isolated and purified.
The chemical structures of the 4 secondary metabolites were spectroscopically analyzed with IR (Nicolet Impact 400 FT-IR Spectrophotometer), EIMS (Autospec 3000), and lD and 2D NMR (Bruker 500 MHZ spectrometer) spectral data. They were determined as:
(I) 2-(l -heptenyl)-3, 6-dihydroxy-5-(3-methyl-2-butenyl) benzaldehyde;
(II) 2-heptyl-3, 6-dihydroxy-5-(3-methyl-2-butenyl) benzaldehyde;
(III) 2-(3, 5-heptadienyl)-3, 6-dihydroxy-5-(3-methyl-2-butenyl) benzaldehyde;
(IV) 2-(l, 3, 5-heptatrienyl)-3, 6-dihydroxy-5-(3-methyl-2-butenyl) benzaldehyde.
Although a series of benzaldehyde derivatives have been isolated from terrestrial fungi such as from Aspergillus sp., these 4 compounds were isolated from marine-derived fungus for the first time. |
| Key words: Marine algae, Polysiphonia urceolate, Endophytic fungus, Secondary metabolites, Benzaldehyde derivatives |
