N Berova, J Breinholt, G W Jensen, A Kjaer, L C Lo, K Nakanishi, R I Nielsen, C E Olsen, C Pedersen, C E Stidsen
{"title":"malonfungin:一种从镰刀菌中提取的抗真菌氨基丙酸。","authors":"N Berova, J Breinholt, G W Jensen, A Kjaer, L C Lo, K Nakanishi, R I Nielsen, C E Olsen, C Pedersen, C E Stidsen","doi":"10.3891/acta.chem.scand.48-0240","DOIUrl":null,"url":null,"abstract":"<p><p>In screening for antifungal metabolites, a novel compound, malonofungin, exhibiting growth inhibitory activity against Botrytis cinerea (grey mould), has been isolated from fermentations of Phaeoramularia fusimaculans CBS 616.87. Its structure is established as (E)-(3R,4S,5S)-5-acetoxy-2-amino-2-carboxy-3,4-dihydroxy-14-oxoicos++ +-6-enoic acid, representing an addition to the rare class of naturally occurring aminomalonic acids. 1H NMR data and extensive use of CD spectroscopy have been utilized to establish the absolute stereochemistry of malonofungin. The structural and biological relationship of malonofungin to previously reported fungal metabolites is discussed.</p>","PeriodicalId":76966,"journal":{"name":"Acta chemica Scandinavica (Copenhagen, Denmark : 1989)","volume":"48 3","pages":"240-51"},"PeriodicalIF":0.0000,"publicationDate":"1994-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"9","resultStr":"{\"title\":\"Malonofungin: an antifungal aminomalonic acid from Phaeoramularia fusimaculans.\",\"authors\":\"N Berova, J Breinholt, G W Jensen, A Kjaer, L C Lo, K Nakanishi, R I Nielsen, C E Olsen, C Pedersen, C E Stidsen\",\"doi\":\"10.3891/acta.chem.scand.48-0240\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p><p>In screening for antifungal metabolites, a novel compound, malonofungin, exhibiting growth inhibitory activity against Botrytis cinerea (grey mould), has been isolated from fermentations of Phaeoramularia fusimaculans CBS 616.87. Its structure is established as (E)-(3R,4S,5S)-5-acetoxy-2-amino-2-carboxy-3,4-dihydroxy-14-oxoicos++ +-6-enoic acid, representing an addition to the rare class of naturally occurring aminomalonic acids. 1H NMR data and extensive use of CD spectroscopy have been utilized to establish the absolute stereochemistry of malonofungin. The structural and biological relationship of malonofungin to previously reported fungal metabolites is discussed.</p>\",\"PeriodicalId\":76966,\"journal\":{\"name\":\"Acta chemica Scandinavica (Copenhagen, Denmark : 1989)\",\"volume\":\"48 3\",\"pages\":\"240-51\"},\"PeriodicalIF\":0.0000,\"publicationDate\":\"1994-03-01\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"9\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Acta chemica Scandinavica (Copenhagen, Denmark : 1989)\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://doi.org/10.3891/acta.chem.scand.48-0240\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"\",\"JCRName\":\"\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Acta chemica Scandinavica (Copenhagen, Denmark : 1989)","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.3891/acta.chem.scand.48-0240","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 9
摘要
在抗真菌代谢产物的筛选中,从fusimaculans Phaeoramularia CBS 616.87的发酵中分离到一种具有抑制灰霉菌生长活性的新化合物malonfungin。其结构确定为(E)-(3R,4S,5S)-5-乙酰氧基-2-氨基-2-羧基-3,4-二羟基-14-氧基++ +-6-烯酸,代表了天然存在的罕见氨基酸类的新成员。利用1H NMR数据和广泛使用的CD光谱建立了丙二醇的绝对立体化学。本文讨论了malonofungin与先前报道的真菌代谢产物的结构和生物学关系。
Malonofungin: an antifungal aminomalonic acid from Phaeoramularia fusimaculans.
In screening for antifungal metabolites, a novel compound, malonofungin, exhibiting growth inhibitory activity against Botrytis cinerea (grey mould), has been isolated from fermentations of Phaeoramularia fusimaculans CBS 616.87. Its structure is established as (E)-(3R,4S,5S)-5-acetoxy-2-amino-2-carboxy-3,4-dihydroxy-14-oxoicos++ +-6-enoic acid, representing an addition to the rare class of naturally occurring aminomalonic acids. 1H NMR data and extensive use of CD spectroscopy have been utilized to establish the absolute stereochemistry of malonofungin. The structural and biological relationship of malonofungin to previously reported fungal metabolites is discussed.