目的 通过硫酸二乙酯化学诱变法从海绵共生真菌Emericella variecolor XSA-07-2中发现新颖活性次级代谢产物。方法 用硫酸二乙酯对菌株进行化学诱变,并通过化学指纹筛选,获得XSA-07-2突变株M8;采用硅胶、ODS、半制备HPLC等方法对菌株发酵提取物中的全新成分进行分离纯化,运用NMR、MS等现代波谱学方法鉴定化合物的结构。结果 从XSA-07-2的化学诱变突变株M8中发现了3个新颖的聚酮类化合物,化合物3具有抗氧化活性,DPPH清除率的IC50为(13.58±0.14) μg·mL-1。结论 利用硫酸二乙酯化学诱变可以刺激海绵共生真菌XSA-07-2的突变株产生新颖抗氧化活性聚酮化合物。
Abstract
OBJECTIVE To study the new bioactive secondary metabolites of diethyl sulfate chemical mutant strain of sponge-associated fungus Emericella variecolor XSA-07-2. METHODS Diethyl sulfate was used to make chemical mutagenesis of strain XSA-07-2, and one mutant strain M8 was chosen for large-scale fermentation to generate new secondary metabolites. The compounds were isolated and purified by chromatography on silica gel and ODS reversed-phase column and semi-preparative HPLC techniques. And their structures were identified by their physicochemical properties and NMR, MS data analysis. RESULTS Three new polyketides 1-3 were isolated from the extract of the solid fermentation culture of mutant strain M8. Compound 3 showed moderated antioxidant activity with IC50 of (13.58±0.14) μg·mL-1 by DPPH assay. CONCLUSION Diethyl sulfate chemical mutagenesis can stimulate sponge-associated fungus Emericella variecolor XSA-07-2 mutant strain M8 to produce new antioxidant polyketides.
关键词
海洋真菌 /
化学诱变 /
聚酮类化合物 /
抗氧化
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Key words
marine-derived fungi /
chemical mutagenesis /
polyketide /
antioxidant
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中图分类号：
R284
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参考文献
[1] BLUNT J W, COPP B R, KEYZER R A, et al. Marine natural products [J] . Nat Prod Rep, 2017, 34: 235-294.
[2] BLUNT J W, COPP B R, KEYZER R A, et al. Marine natural products [J] . Nat Prod Rep, 2016, 33: 382-431.
[3] BLUNT J W, COPP B R, KEYZER R A, et al. Marine natural products [J] . Nat Prod Rep, 2015, 32: 116-211.
[4] ZHANG Q H, TIAN L, YAN Z, et al.Chemical Constituents of a Marine Fungus Nigrospora sphaerica[J] . Chin Pharm J (中国药学杂志), 2014,49(1):26-29.
[5] WANG Y, LI Z L, BAI J, et al. Alkaloids from the Marine-Derived Fungus Aspergillus fumigatus YK-7 and Their Antitumor Activities[J] . Chin Pharm J(中国药学杂志), 2017,52(15):21-25.
[6] REN H, CAO X L, GU Q Q, et al. Antitumor Metabolites from Marine-Derived Fungus Gliocladium catenulatum T31[J] . Chin Pharm J( 中国药学杂志), 2010,45(22):1720-1723.
[7] MARTIN J F, LIRAS P. Evolutionary formation of gene clusters by reorganization: the meleagrin/roquefortine paradigm in different fungi [J] . Appl Microbiol Blot, 2016, 100(4):1579-1587.
[8] SLOT J C, HIBBETT D S. Horizontal transfer of a nitrate assimilation gene cluster and ecological transitions in fungi: a phylogenetic study [J] . PLoS One, 2007, 2(10):e1097.
[9] GROND S, PAPSTAVROU I, ZEECK A. Novel a-L-rhamnopyranosides from a singlestrain of streptomyces by supplement-induced biosynthetic steps [J] . Eur J Org Chem, 2002, 2002(19):3237-3242.
[10] CUETO M, JENSEN P R, KAUFFMAN C, et al. A new antibiotic produced by a marine fungus in response to bacterial challenge [J] . J Nat Prod, 2001, 64(11):1444-1446.
[11] SUN K L, ZHU G L, HAO J J, et al. Chemical-epigenetic method to enhance the chemodiversity of the marine algicolous fungus, Aspergillus terreus OUCMDZ-2739 [J] . Tetrahedron, 2017, 74(1):84-87.
[12] LIU W, WANG L P, SUN K L, et al. Diketopiperazine and diphenylether derivatives from marine algae-derived Aspergillus versicolor OUCMDZ-2738 by epigenetic activation [J] . Mar Drugs,2019,17(1):6.
[13] LONG H L, CHENG Z B, HUANG W, et al. Diasteltoxins A-C, asteltoxin-based dimmers from a mutant of the sponge-associated emericella variecolor fungus [J] . Org Lett, 2016,18:4678-4681.
[14] WU Q, WU C M, LONG H L, et al. Varioxiranols A-G and 19-O-methyl-22-methoxypre shamixanthone, PKS and hybrid PKS-derived metabolites from a sponge-associated Emericella variecolor Fungus [J] . J Nat Prod, 2015,78(10):2461-2470.
[15] MENSOR L L, MENEZES F S, LEITAO G G, et al. Screening of Brazilian plant extracts for antioxidant activity by use of DPPH free radical method [J] . Phytother Res,2001, 15(2):127-130.
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脚注
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基金
国家自然科学基金项目资助(81803423,21502004);浙江省自然科学基金青年基金项目资助(LQ18D060005);北京自然科学基金项目资助(7182086)
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