猫儿屎DS37菌株次生代谢产物化学成分的研究
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摘要
目的研究猫儿屎Decaisnea insignis(Griff.) Hook.f.&Thomson DS37菌株次生代谢产物的化学成分。方法猫儿屎内生真菌固体发酵物石油醚-乙酸乙酯-甲醇提取物采用硅胶、Sephadex LH-20和重结晶进行分离纯化,根据理化性质及波谱数据鉴定所得化合物的结构。结果从中分离得到10个化合物,分别鉴定为交链孢酚甲醚(1)、交链孢酚(2)、7-羟基-4-甲氧基-5-甲基香豆素(3)、5, 5′-二甲基-4, 4′, 7, 7′-四甲氧基-8, 8′-双香豆素(4)、5, 5′-二甲基-7-羟基-4, 4′, 7′-三甲氧基-6, 8′-双香豆素(5)、leptosphaepin(6)、1, 3-二辛酰基-2-亚油酸甘油酯(7)、胡萝卜苷(8)、asperpyrone C(9)、asperpyrone D(10)。结论化合物3～9为首次从该发酵物中分离得到。
AIM To study the chemical constituents from the secondary metabolite of DS37 bacterial strain of Decaisnea insignis(Griff.) Hook.f. & Thomson.METHODS The petroleum ether-ethyl acetate-methanol extract from endophytic fungal solid fermentation of D. insignis was isolated and purified by silica,Sephadex LH-20 and recrystallization,then the structures of obtained compounds were identified by physicochemical properties and spectral data.RESULTS Ten compounds were isolated and identified as alternariol methyl ether(1), alternariol(2), 7-hydroxy-4-methoxy-5-methylcoumrin(3), 5,5′-dimethy-4,4′,7,7′-tetramethoxy-8,8′-bicoumarin(4), 5,5′-dimethy-7-hydroxy-4,4′,7′-trimethoxy-6,8′-bicoumarin(5), leptosphaepin(6), 1,3-dicapryloyl-2-linoleoylglycerol(7), daucosterol(8), asperpyrone C(9), asperpyrone D(10).CONCLUSION Compounds 3-9 are isolated from this fermentation for the first time.
AIM To study the chemical constituents from the secondary metabolite of DS37 bacterial strain of Decaisnea insignis(Griff.) Hook.f. & Thomson.METHODS The petroleum ether-ethyl acetate-methanol extract from endophytic fungal solid fermentation of D. insignis was isolated and purified by silica,Sephadex LH-20 and recrystallization,then the structures of obtained compounds were identified by physicochemical properties and spectral data.RESULTS Ten compounds were isolated and identified as alternariol methyl ether(1), alternariol(2), 7-hydroxy-4-methoxy-5-methylcoumrin(3), 5,5′-dimethy-4,4′,7,7′-tetramethoxy-8,8′-bicoumarin(4), 5,5′-dimethy-7-hydroxy-4,4′,7′-trimethoxy-6,8′-bicoumarin(5), leptosphaepin(6), 1,3-dicapryloyl-2-linoleoylglycerol(7), daucosterol(8), asperpyrone C(9), asperpyrone D(10).CONCLUSION Compounds 3-9 are isolated from this fermentation for the first time.
引文
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[9] 王晓龙, 李守婷, 文春南, 等. 怀山药内生真菌厚孢镰刀菌的次生代谢产物研究[J]. 中草药, 2015, 46(7): 966-969.
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[12] Koohei N, Hideyuki S, Shoichi N, et al. Isolation and structures of novel bicoumarins, desertorins A, B, and C, from Emericella desertorum[J]. J Chin Chem Soc, 1987, 8: 1735-1738.
[13] 赵丽艳, 左伟, 付琪镔, 等. 绒白乳菇子实体的化学成分研究[J]. 中草药, 2010, 41(10): 1604-1608.
[14] Anand S, Arun K, Raman C, et al. Isolation and characterization of 1,3-dicapryloyl-2-linoleoylglycerol:A novel triglyceride from berries of Hippophae rhamnoides[J]. Chem Pharm Bull(Tokyo), 2005, 53(8): 1021-1024.
[15] 赵庆春, 付艳辉, 郭涛, 等. 葫蔓藤中非生物碱类化学成分的分离与鉴定[J]. 沈阳药科大学学报, 2007, 24(10): 619-622.
[16] Akiyama K, Teraguchi S, Hamasaki Y, et al. New dimeric naphthopyrones from Aspergillus niger[J]. J Nat Prod, 2003, 66(1): 136-139.
[17] Zhan J, Gunaherath G, Wijeratne E, et al. Asperpyrone D and other metabolites of the plant-associated fungal strain Aspergillus tubingensis[J]. Phytochemistry, 2007, 68(3): 368-372.
[2] 薛长勇, 郑子新, 张荣欣, 等. 高脂肪、蔗糖膳食致肥胖的作用机理研究[J]. 营养学报, 1999, 21(1): 42-47.
[3] 王鹏飞, 马养民, 孔阳. 猫儿屎内生真菌分离鉴定及抑菌活性研究[J]. 广东农业科学, 2013, 40(13): 85-87.
[4] An C Y, Li X M, Li C S, et al. Aniquinazolines A-D, four new quinazolinone alkaloids from marine-derived endophytic fungus Aspergillus nidulans[J]. Mar Drugs, 2013, 11(7): 2682-2694.
[5] Liang X R, Miao F P, Song Y P, et al. Trichocitrin, a new fusicoccane diterpene from the marine brown alga-endophytic fungus Trichoderma citrinoviride cf-27[J]. Nat Prod Res, 2016, 30(14): 1605-1610.
[6] Zhao J L, Yan M, Shan T J, et al. Antimicrobial metabolites from the endophytic fungus Pichia guilliermondii isolated from Paris polyphylla var. yunnanensis[J]. Molecules, 2010, 15(11): 7961-7070.
[7] Kjer J, Wray V, Edradaebel R, et al. Xanalteric acids I and II and related phenolic compounds from an endophytic Alternaria sp. isolated from the mangrove plant Sonneratia alba[J]. J Nat Prod, 2009, 72(11): 2053-2057.
[8] Tan N, Tao Y W, Pan J H, et al. Isolation, structure elucidation, and mutagenicity of four alternariol derivatives produced by the mangrove endophytic fungus No.2240[J]. Chem Nat Com, 2008, 44(3): 296-300.
[9] 王晓龙, 李守婷, 文春南, 等. 怀山药内生真菌厚孢镰刀菌的次生代谢产物研究[J]. 中草药, 2015, 46(7): 966-969.
[10] Wolfgang H, Michael M. Regio and stereoselective intermolecular oxidative phenol coupling in kotanin biosynthesis by Aspergillus Niger[J]. Chem Bio Chem, 2007, 8(5): 521-529.
[11] Tepaske M, Gloer J, Wicklow D, et al. Isolation of bicoumarin derivative having anti-insectan activity from the sclerotia[J]. J Nat Prod, 1992, 55(8): 1080-1086.
[12] Koohei N, Hideyuki S, Shoichi N, et al. Isolation and structures of novel bicoumarins, desertorins A, B, and C, from Emericella desertorum[J]. J Chin Chem Soc, 1987, 8: 1735-1738.
[13] 赵丽艳, 左伟, 付琪镔, 等. 绒白乳菇子实体的化学成分研究[J]. 中草药, 2010, 41(10): 1604-1608.
[14] Anand S, Arun K, Raman C, et al. Isolation and characterization of 1,3-dicapryloyl-2-linoleoylglycerol:A novel triglyceride from berries of Hippophae rhamnoides[J]. Chem Pharm Bull(Tokyo), 2005, 53(8): 1021-1024.
[15] 赵庆春, 付艳辉, 郭涛, 等. 葫蔓藤中非生物碱类化学成分的分离与鉴定[J]. 沈阳药科大学学报, 2007, 24(10): 619-622.
[16] Akiyama K, Teraguchi S, Hamasaki Y, et al. New dimeric naphthopyrones from Aspergillus niger[J]. J Nat Prod, 2003, 66(1): 136-139.
[17] Zhan J, Gunaherath G, Wijeratne E, et al. Asperpyrone D and other metabolites of the plant-associated fungal strain Aspergillus tubingensis[J]. Phytochemistry, 2007, 68(3): 368-372.