{"title":"海洋真菌哈茨木霉ZN-4的吡咯烷类生物碱及聚酮衍生物","authors":"Chengzeng Zhou, Xunuo Li, Jiayu Pan, Yichao Ge, Xiaodan Wu, Bin Wu","doi":"10.1021/acs.joc.4c03114","DOIUrl":null,"url":null,"abstract":"Two unusual alkaloids with furanopyrrolidine skeleton, harzianopyrrolidones A–B (<b>1</b>–<b>2</b>), four new compounds, harzianopyridone B (<b>3</b>), harzianopyrone (<b>4</b>), (<i>R</i>)-1-(3,5-dihydroxy-4-methylphenyl)-1-hydroxyhept-5<i>E</i>-en-2-one (<b>5</b>), and harzianopyrrolidone C (<b>6</b>), together with two known compounds (<b>7</b>–<b>8</b>) were isolated from a marine-derived fungus <i>Trichoderma harzianum</i> ZN-4. Structures of the isolated compounds were elucidated based on their HRESIMS data, extensive NMR spectroscopic analyses, NMR calculation in combination with DP4+, ECD calculations, and a single-crystal X-ray diffraction experiment. New compounds <b>1</b>, <b>4,</b> and <b>5</b> exhibited potential cardiomyocyte protective activity at concentrations ranging from 5 to 20 μM. In addition, <b>7</b> showed moderate inhibitory activity against <i>Pestalotiopsis theae</i> with an MIC value of 25 μg/mL.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"23 1","pages":""},"PeriodicalIF":3.3000,"publicationDate":"2025-04-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Pyrrolidine Alkaloids and Polyketide Derivatives from the Marine-Derived Fungus Trichoderma harzianum ZN-4\",\"authors\":\"Chengzeng Zhou, Xunuo Li, Jiayu Pan, Yichao Ge, Xiaodan Wu, Bin Wu\",\"doi\":\"10.1021/acs.joc.4c03114\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"Two unusual alkaloids with furanopyrrolidine skeleton, harzianopyrrolidones A–B (<b>1</b>–<b>2</b>), four new compounds, harzianopyridone B (<b>3</b>), harzianopyrone (<b>4</b>), (<i>R</i>)-1-(3,5-dihydroxy-4-methylphenyl)-1-hydroxyhept-5<i>E</i>-en-2-one (<b>5</b>), and harzianopyrrolidone C (<b>6</b>), together with two known compounds (<b>7</b>–<b>8</b>) were isolated from a marine-derived fungus <i>Trichoderma harzianum</i> ZN-4. Structures of the isolated compounds were elucidated based on their HRESIMS data, extensive NMR spectroscopic analyses, NMR calculation in combination with DP4+, ECD calculations, and a single-crystal X-ray diffraction experiment. New compounds <b>1</b>, <b>4,</b> and <b>5</b> exhibited potential cardiomyocyte protective activity at concentrations ranging from 5 to 20 μM. In addition, <b>7</b> showed moderate inhibitory activity against <i>Pestalotiopsis theae</i> with an MIC value of 25 μg/mL.\",\"PeriodicalId\":57,\"journal\":{\"name\":\"Journal of Organic Chemistry\",\"volume\":\"23 1\",\"pages\":\"\"},\"PeriodicalIF\":3.3000,\"publicationDate\":\"2025-04-05\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Journal of Organic Chemistry\",\"FirstCategoryId\":\"1\",\"ListUrlMain\":\"https://doi.org/10.1021/acs.joc.4c03114\",\"RegionNum\":2,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Organic Chemistry","FirstCategoryId":"1","ListUrlMain":"https://doi.org/10.1021/acs.joc.4c03114","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
摘要
从海源真菌哈兹木霉ZN-4中分离得到2个具有呋喃吡啶骨架的不寻常生物碱,harzianopyrolidones a - B(1-2), 4个新化合物,harzianopyridone B (3), harzianopyrodone (4), (R)-1-(3,5-二羟基-4-甲基苯基)-1-羟基hept- 5e -en-2-one(5),和harzianopyrolidone C(6),以及2个已知化合物(7-8)。根据hremms数据、广泛的核磁共振光谱分析、结合DP4+的核磁共振计算、ECD计算和单晶x射线衍射实验,对分离化合物的结构进行了阐明。新化合物1、4和5在5 ~ 20 μM浓度范围内表现出潜在的心肌细胞保护活性。其中7个对拟盘多毛菌具有中等抑制活性,MIC值为25 μg/mL。
Pyrrolidine Alkaloids and Polyketide Derivatives from the Marine-Derived Fungus Trichoderma harzianum ZN-4
Two unusual alkaloids with furanopyrrolidine skeleton, harzianopyrrolidones A–B (1–2), four new compounds, harzianopyridone B (3), harzianopyrone (4), (R)-1-(3,5-dihydroxy-4-methylphenyl)-1-hydroxyhept-5E-en-2-one (5), and harzianopyrrolidone C (6), together with two known compounds (7–8) were isolated from a marine-derived fungus Trichoderma harzianum ZN-4. Structures of the isolated compounds were elucidated based on their HRESIMS data, extensive NMR spectroscopic analyses, NMR calculation in combination with DP4+, ECD calculations, and a single-crystal X-ray diffraction experiment. New compounds 1, 4, and 5 exhibited potential cardiomyocyte protective activity at concentrations ranging from 5 to 20 μM. In addition, 7 showed moderate inhibitory activity against Pestalotiopsis theae with an MIC value of 25 μg/mL.
期刊介绍:
Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.