{"title":"与天麻相关的内生青霉 YUD17006 的多重氧化多酮化合物","authors":"","doi":"10.1016/S1875-5364(24)60724-7","DOIUrl":null,"url":null,"abstract":"<div><div>Three novel, highly oxygenated polyketides, multioketides A−C (<strong>1</strong>−<strong>3</strong>), and three previously described multioxidized aromatic polyketides (<strong>4−6</strong>), were isolated from an endophytic <em>Penicillium</em> sp. YUD17006 associated with <em>Gastrodia elata</em>. Their chemical structures were elucidated using extensive spectroscopic data, electronic circular dichroism calculations, and single X-ray diffraction analysis. All metabolites were characterized by a typical <em>α</em>,<em>β</em>-unsaturated ketone fragment and exhibited a high degree of oxidation. Multioketides A and B were identified as a pair of epimers featuring a rare dihydroisobenzofuranone core. Multioketide C possessed a novel 5/6/6/6 heterotetracyclic chemical architecture with unusual 1,4-dioxin functionalities. Plausible biosynthetic pathways for <strong>1−6</strong> were proposed. Additionally, compound <strong>3</strong> demonstrated weak inhibitory activities against both acetylcholinesterase and protein tyrosine phosphatase 1B.</div></div>","PeriodicalId":10002,"journal":{"name":"Chinese Journal of Natural Medicines","volume":null,"pages":null},"PeriodicalIF":4.0000,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Multioxidized polyketides from an endophytic Penicillium sp. YUD17006 associated with Gastrodia elata\",\"authors\":\"\",\"doi\":\"10.1016/S1875-5364(24)60724-7\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>Three novel, highly oxygenated polyketides, multioketides A−C (<strong>1</strong>−<strong>3</strong>), and three previously described multioxidized aromatic polyketides (<strong>4−6</strong>), were isolated from an endophytic <em>Penicillium</em> sp. YUD17006 associated with <em>Gastrodia elata</em>. Their chemical structures were elucidated using extensive spectroscopic data, electronic circular dichroism calculations, and single X-ray diffraction analysis. All metabolites were characterized by a typical <em>α</em>,<em>β</em>-unsaturated ketone fragment and exhibited a high degree of oxidation. Multioketides A and B were identified as a pair of epimers featuring a rare dihydroisobenzofuranone core. Multioketide C possessed a novel 5/6/6/6 heterotetracyclic chemical architecture with unusual 1,4-dioxin functionalities. Plausible biosynthetic pathways for <strong>1−6</strong> were proposed. Additionally, compound <strong>3</strong> demonstrated weak inhibitory activities against both acetylcholinesterase and protein tyrosine phosphatase 1B.</div></div>\",\"PeriodicalId\":10002,\"journal\":{\"name\":\"Chinese Journal of Natural Medicines\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":4.0000,\"publicationDate\":\"2024-11-01\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Chinese Journal of Natural Medicines\",\"FirstCategoryId\":\"3\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S1875536424607247\",\"RegionNum\":2,\"RegionCategory\":\"医学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"INTEGRATIVE & COMPLEMENTARY MEDICINE\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Chinese Journal of Natural Medicines","FirstCategoryId":"3","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S1875536424607247","RegionNum":2,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"INTEGRATIVE & COMPLEMENTARY MEDICINE","Score":null,"Total":0}
引用次数: 0
摘要
从与 Gastrodia elata 相关的内生青霉 YUD17006 中分离出了三种新型高含氧多酮苷,多酮苷 A-C (1-3),以及之前描述过的三种多氧化芳香族多酮苷 (4-6)。通过大量光谱数据、电子圆二色性计算和单 X 射线衍射分析,阐明了它们的化学结构。所有代谢物都具有典型的 α、β-不饱和酮片段,并表现出高度氧化性。经鉴定,多酮类化合物 A 和 B 是一对具有罕见二氢异苯并呋喃酮核心的表聚物。多酮类化合物 C 具有新颖的 5/6/6/6 杂四环化学结构和不寻常的 1,4-二恶英官能团。提出了 1-6 的合理生物合成途径。此外,化合物 3 对乙酰胆碱酯酶和蛋白酪氨酸磷酸酶 1B 都有微弱的抑制活性。
Multioxidized polyketides from an endophytic Penicillium sp. YUD17006 associated with Gastrodia elata
Three novel, highly oxygenated polyketides, multioketides A−C (1−3), and three previously described multioxidized aromatic polyketides (4−6), were isolated from an endophytic Penicillium sp. YUD17006 associated with Gastrodia elata. Their chemical structures were elucidated using extensive spectroscopic data, electronic circular dichroism calculations, and single X-ray diffraction analysis. All metabolites were characterized by a typical α,β-unsaturated ketone fragment and exhibited a high degree of oxidation. Multioketides A and B were identified as a pair of epimers featuring a rare dihydroisobenzofuranone core. Multioketide C possessed a novel 5/6/6/6 heterotetracyclic chemical architecture with unusual 1,4-dioxin functionalities. Plausible biosynthetic pathways for 1−6 were proposed. Additionally, compound 3 demonstrated weak inhibitory activities against both acetylcholinesterase and protein tyrosine phosphatase 1B.
期刊介绍:
The Chinese Journal of Natural Medicines (CJNM), founded and sponsored in May 2003 by China Pharmaceutical University and the Chinese Pharmaceutical Association, is devoted to communication among pharmaceutical and medical scientists interested in the advancement of Traditional Chinese Medicines (TCM). CJNM publishes articles relating to a broad spectrum of bioactive natural products, leading compounds and medicines derived from Traditional Chinese Medicines (TCM).
Topics covered by the journal are: Resources of Traditional Chinese Medicines; Interaction and complexity of prescription; Natural Products Chemistry (including structure modification, semi-and total synthesis, bio-transformation); Pharmacology of natural products and prescription (including pharmacokinetics and toxicology); Pharmaceutics and Analytical Methods of natural products.