竹黄菌与竹红菌的化学成分及细胞毒活性比较研究
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摘要
为研究竹黄菌与竹红菌化学成分及细胞毒活性的差异,本研究通过高效液相色谱(HPLC)分析结合常规色谱方法,分离鉴定了两种真菌的6个相同成分,分别为3个主要成分竹红菌甲素(1)、竹红菌乙素(2)和竹红菌丙素(3),以及3,6,8-三羟基-1-甲基口山酮(7)、3,8-二羟基-6-甲氧基-1-甲基口山酮(8)和过氧麦角甾醇(9)。另外,从竹黄菌中还分离得到11,11′-二去氧沃替西林(5)、麦角甾-7,22E-二烯-3β,5α,6β-三醇(10)和麦角甾-7,22E-二烯-2β,3α,9α-三醇(11),并首次从竹红菌中分离得到竹红菌丁素(4)、灰黄霉素(6)、化合物7和8。活性筛选发现,化合物5对三株肿瘤细胞NCI-H1975、HepG2和MCF-7有很强细胞毒活性,化合物1有较强细胞毒活性,而化合物6活性较弱。
To investigate the differences of chemical composition and cytotoxic activity between two medicinal fungi,Shiraia bambusicola and Hypocrella bambusae,high performance liquid chromatography analysis and chromatographic separations were conducted.Six compounds were isolated from both fungi and characterized as hypocrellin A(1),hypocrellin B(2),hypocrellin C(3),3,6,8-trihydroxy-1-methylanthone(7),3,8-dihydroxy-6-methoxy-1-methylanthone(8) and ergosterol peroxide(9),respectively.In addition,11,11′-dideoxyverticillin(5),ergosta-7,22E-dien-3β,5α,6β-triol(10) and ergosta-7,22E-diene-2β,3α,9α-triol(11) were also obtained from S. bambusicola,while hypocrellin D(4),(+)-griseofulvin(6),compounds 7 and 8 were reported from H. bambusae for the first time.Compound 5 showed potent inhibitory activity against human lung adenocarcinoma cell(NCI-H1975),human carcinoma(HepG2) and human breast cancer cells(MCF-7).Compound 1 also showed significant inhibitory activity against the three cell lines.In contrast,the cytotoxic activity of compound 6 was relatively weak.
To investigate the differences of chemical composition and cytotoxic activity between two medicinal fungi,Shiraia bambusicola and Hypocrella bambusae,high performance liquid chromatography analysis and chromatographic separations were conducted.Six compounds were isolated from both fungi and characterized as hypocrellin A(1),hypocrellin B(2),hypocrellin C(3),3,6,8-trihydroxy-1-methylanthone(7),3,8-dihydroxy-6-methoxy-1-methylanthone(8) and ergosterol peroxide(9),respectively.In addition,11,11′-dideoxyverticillin(5),ergosta-7,22E-dien-3β,5α,6β-triol(10) and ergosta-7,22E-diene-2β,3α,9α-triol(11) were also obtained from S. bambusicola,while hypocrellin D(4),(+)-griseofulvin(6),compounds 7 and 8 were reported from H. bambusae for the first time.Compound 5 showed potent inhibitory activity against human lung adenocarcinoma cell(NCI-H1975),human carcinoma(HepG2) and human breast cancer cells(MCF-7).Compound 1 also showed significant inhibitory activity against the three cell lines.In contrast,the cytotoxic activity of compound 6 was relatively weak.
引文
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16 Fangkrathok N,Sripanidkulchai B,Umehara K,et al.Bioactive ergostanoids and a new polyhydroxyoctane from Lentinus polychrous mycelia and their inhibitory effects on E2-enhanced cell proliferation of T47D cells[J].Nat Prod Res,2013,27:1611-1619.
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2 Liang XH,Cai YJ,Liao XR,et al.The progress of research on medicinal fungus Shiraia bambusicola[J].J Food Sci Biotechnol(食品与生物技术学报),2008,27:21-26.
3 Long ZH,Yan XJ,Xu JA.Resources investigation on Shiraia bambusicola fungi from Zhejiang province[J].J Centr South Univ Forest Technol(中南林业科技大学学报),2009,29:166-170.
4 Lin HP,Huang XB,Mao SF,et al.Study on biological characters of wild Shiraia bambusicola[J].Chin Tradit Herb Drugs(中草药),2008,39:1407-1409.
5 Liu SZ,Zhao WM.Chemical constituents of medicinal fungus Shiraia bambusicola[J].Chin Tradit Herb Drugs(中草药),2010,41:1239-1242.
6 Liu W,Lu HJ,Zhang JC,et al.Primary study on the biological characteristics of Hypocrella bambusae producing red pigment[J].J Anhui Agri Sci(安徽农业科学),2008,36:412-412.
7 Ma GY,Khan SI,Jacob MR,et al.Antimicrobial and antileishmanial activities of hypocrellins A and B[J].Antimicrob Agents Chemother,2004,48:4450-4452.
8 Croce AC,Fasani E,Bottone MG,et al.Hypocrellin-B acetate as a fluorogenic substrate for enzyme-assisted cell photosensitization[J].Photochem Photobiol Sci,2011,10:1783-1790.
9 Kishi T,Tahara S,Taniguchi N,et al.New perylenequinones from Shiraia bambusicola[J].Planta Med,1991,57:376-379.
10 Fang LZ,Qing C,Shao HJ,et al.Hypocrellin D,a cytotoxic fungal pigment from fruiting bodies of the ascomycete Shiraia bambusicola[J].J Antibiot,2006,37:351-354.
11 Son BW,Jensen PR,Kauffman CA,et al.New cytotoxic epidithiodioxopiperazines related to verticillin A from a marine isolate of the fungus Penicillium[J].Nat Prod Lett,1999,13:213-222.
12 Sate Y,Oda T.Griseofulvin biosynthesis:New evidence of two acetate-dispositions in the ring A from 13C nuclear magnetic resonance studies[J].Tetrahedron Lett,1976,44:3971-3974.
13 Abdel-Lateff A,Klemke C,Gabriele M,et al.Two new xanthone derivatives from the algicolous marine fungus Wardomyces anomalus[J].J Nat Prod,2003,66:706-708.
14 Mutanyatta J,Matapa BG,Shushu DD,et al.Homoisoflavonoids and xanthones from the tubers of wild and in vitro regenerated Ledebouria graminifolia and cytotoxic activities of some of the homoisoflavonoids[J].Phytochemistry,2003,62:797-804.
15 Li GY,Li BG,Liu GY,et al.Sterol from Aspergillus ochraceus 43[J].Chin J Appl Environ Biol(应用与环境生物学报),2005,11:67-70.
16 Fangkrathok N,Sripanidkulchai B,Umehara K,et al.Bioactive ergostanoids and a new polyhydroxyoctane from Lentinus polychrous mycelia and their inhibitory effects on E2-enhanced cell proliferation of T47D cells[J].Nat Prod Res,2013,27:1611-1619.
17 Lee MK,Hung TM,Cuong TD,et al.Ergosta-7,22-diene-2β,3α,9α-triol from the fruit bodies of Ganoderma lucidum induces apoptosis in human myelocytic HL-60 cells[J].Phytother Res,2011,25:1579-1585.