海洋真菌Metarhizium sp. P2100中一种具有特殊[4,4]双环壬烷骨架的倍半萜

IF 2.1 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron Pub Date : 2025-03-22 DOI:10.1016/j.tet.2025.134607

Zhong-Lian Ma , Zhi-Pu Yu , Ling Lv , Zhi-Qing Liu , Chang-Yun Wang , Guang-Shan Yao

{"title":"海洋真菌Metarhizium sp. P2100中一种具有特殊[4,4]双环壬烷骨架的倍半萜","authors":"Zhong-Lian Ma , Zhi-Pu Yu , Ling Lv , Zhi-Qing Liu , Chang-Yun Wang , Guang-Shan Yao","doi":"10.1016/j.tet.2025.134607","DOIUrl":null,"url":null,"abstract":"<div><div>An oxidized 5/5/6 tricyclic sesquiterpene with a new 6-isopropyl-1,2,9-trimethyl-spiro [4.4]nonane carbon skeleton, metarhizane A (<strong>1</strong>), was isolated from a rare marine derived fungus <em>Metarhizium</em> sp. P2100. Its structure and the absolute configurations were assigned by interpretation of a combination of spectroscopic data and X-ray diffraction. This is the first example with a spiro [4,4] nonane core among the sesquiterpene skeletons. A plausible biosynthetic pathway for metarhizane A (<strong>1</strong>) initiated from farnesyl diphosphate (FPP) was predicted and discussed. The above results suggested that this marine-derived fungus has the potential to produce novel skeletons.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"178 ","pages":"Article 134607"},"PeriodicalIF":2.1000,"publicationDate":"2025-03-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"A new sesquiterpene with a specialized [4,4] bicyclononane skeleton from the marine-derived fungus Metarhizium sp. P2100\",\"authors\":\"Zhong-Lian Ma , Zhi-Pu Yu , Ling Lv , Zhi-Qing Liu , Chang-Yun Wang , Guang-Shan Yao\",\"doi\":\"10.1016/j.tet.2025.134607\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>An oxidized 5/5/6 tricyclic sesquiterpene with a new 6-isopropyl-1,2,9-trimethyl-spiro [4.4]nonane carbon skeleton, metarhizane A (<strong>1</strong>), was isolated from a rare marine derived fungus <em>Metarhizium</em> sp. P2100. Its structure and the absolute configurations were assigned by interpretation of a combination of spectroscopic data and X-ray diffraction. This is the first example with a spiro [4,4] nonane core among the sesquiterpene skeletons. A plausible biosynthetic pathway for metarhizane A (<strong>1</strong>) initiated from farnesyl diphosphate (FPP) was predicted and discussed. The above results suggested that this marine-derived fungus has the potential to produce novel skeletons.</div></div>\",\"PeriodicalId\":437,\"journal\":{\"name\":\"Tetrahedron\",\"volume\":\"178 \",\"pages\":\"Article 134607\"},\"PeriodicalIF\":2.1000,\"publicationDate\":\"2025-03-22\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Tetrahedron\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S0040402025001632\",\"RegionNum\":3,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Tetrahedron","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0040402025001632","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}

引用次数: 0

摘要

摘要从一种罕见的海洋真菌Metarhizium sp. P2100中分离到一种具有6-异丙基-1,2,9-三甲基-螺[4.4]壬烷碳骨架的5/5/6三环倍半萜类化合物metarhizane a(1)。通过对光谱数据和x射线衍射相结合的解释，确定了它的结构和绝对构型。这是第一个在倍半萜骨架中具有螺旋[4,4]壬烷核的例子。预测并讨论了由二磷酸法尼酯（FPP）引发的metarhizane A(1)的生物合成途径。上述结果表明，这种海洋来源的真菌具有产生新型骨骼的潜力。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

A new sesquiterpene with a specialized [4,4] bicyclononane skeleton from the marine-derived fungus Metarhizium sp. P2100

查看原文本刊更多论文

A new sesquiterpene with a specialized [4,4] bicyclononane skeleton from the marine-derived fungus Metarhizium sp. P2100

An oxidized 5/5/6 tricyclic sesquiterpene with a new 6-isopropyl-1,2,9-trimethyl-spiro [4.4]nonane carbon skeleton, metarhizane A (1), was isolated from a rare marine derived fungus Metarhizium sp. P2100. Its structure and the absolute configurations were assigned by interpretation of a combination of spectroscopic data and X-ray diffraction. This is the first example with a spiro [4,4] nonane core among the sesquiterpene skeletons. A plausible biosynthetic pathway for metarhizane A (1) initiated from farnesyl diphosphate (FPP) was predicted and discussed. The above results suggested that this marine-derived fungus has the potential to produce novel skeletons.

求助全文

通过发布文献求助，成功后即可免费获取论文全文。去求助

来源期刊

Tetrahedron 化学-有机化学

CiteScore

3.90

自引率

4.80%

发文量

439

审稿时长

34 days

期刊介绍： Tetrahedron publishes full accounts of research having outstanding significance in the broad field of organic chemistry and its related disciplines, such as organic materials and bio-organic chemistry. Regular papers in Tetrahedron are expected to represent detailed accounts of an original study having substantially greater scope and details than that found in a communication, as published in Tetrahedron Letters. Tetrahedron also publishes thematic collections of papers as special issues and ''Reports'', commissioned in-depth reviews providing a comprehensive overview of a research area.