Chromene Dimers from Cultures of Basidiomycete Panus similis.

IF 3.6 2区 生物学 Q2 CHEMISTRY, MEDICINAL Journal of Natural Products Pub Date : 2025-03-28 Epub Date: 2025-02-26 DOI:10.1021/acs.jnatprod.4c01475
Somporn Palasarn, Prattana Tanyapanyachon, Vanicha Vichai, Phongeun Sysouphanthong, Kevin D Hyde, Nattika Saengkrit, Masahiko Isaka
{"title":"Chromene Dimers from Cultures of Basidiomycete <i>Panus similis</i>.","authors":"Somporn Palasarn, Prattana Tanyapanyachon, Vanicha Vichai, Phongeun Sysouphanthong, Kevin D Hyde, Nattika Saengkrit, Masahiko Isaka","doi":"10.1021/acs.jnatprod.4c01475","DOIUrl":null,"url":null,"abstract":"<p><p>Four chromene dimers, panusimilins A-D (<b>1</b>-<b>4</b>) (racemic mixtures), and two previously undescribed chromanes (<b>5a</b>/<b>5b</b> and <b>6a</b>/<b>6b</b>) were isolated from cultures of basidiomycete <i>Panus similis</i> TBRC-BCC 52578. Interestingly, synthetic compounds closely related to panusimilins A-C (<b>1</b>-<b>3</b>) were previously reported, which were produced by Lewis acid promoted dimerization of a plant-derived chromene, precocene II. In the present study, panusimilins were isolated from the culture broth extract of the fungus <i>P. similis</i>. The chromane monomers were shown to be a non-racemic mixture of enantiomers, and their absolute configurations were elucidated by conversion to Mosher ester derivatives. The isolated compounds were evaluated for their cytotoxic activities. Among them, 2,2-dimethyl-3,4,6-trihydroxychromane (<b>6a</b>/<b>6b</b>) showed selective activity to NCI-H187 cells (IC<sub>50</sub> 9.1 μM). On the other hand, panusimilin B (<b>2</b>) exhibited antioxidant activity in the DPPH radical scavenging assay (IC<sub>50</sub> 66 μM).</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"777-784"},"PeriodicalIF":3.6000,"publicationDate":"2025-03-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Natural Products ","FirstCategoryId":"99","ListUrlMain":"https://doi.org/10.1021/acs.jnatprod.4c01475","RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2025/2/26 0:00:00","PubModel":"Epub","JCR":"Q2","JCRName":"CHEMISTRY, MEDICINAL","Score":null,"Total":0}
引用次数: 0

Abstract

Four chromene dimers, panusimilins A-D (1-4) (racemic mixtures), and two previously undescribed chromanes (5a/5b and 6a/6b) were isolated from cultures of basidiomycete Panus similis TBRC-BCC 52578. Interestingly, synthetic compounds closely related to panusimilins A-C (1-3) were previously reported, which were produced by Lewis acid promoted dimerization of a plant-derived chromene, precocene II. In the present study, panusimilins were isolated from the culture broth extract of the fungus P. similis. The chromane monomers were shown to be a non-racemic mixture of enantiomers, and their absolute configurations were elucidated by conversion to Mosher ester derivatives. The isolated compounds were evaluated for their cytotoxic activities. Among them, 2,2-dimethyl-3,4,6-trihydroxychromane (6a/6b) showed selective activity to NCI-H187 cells (IC50 9.1 μM). On the other hand, panusimilin B (2) exhibited antioxidant activity in the DPPH radical scavenging assay (IC50 66 μM).

查看原文
分享 分享
微信好友 朋友圈 QQ好友 复制链接
本刊更多论文
相似担子菌培养物中铬二聚体的研究。
从担子菌Panus similis TBRC-BCC 52578培养物中分离到四种铬二聚体,panussimilins A-D(1-4)(消旋混合物)和两种先前描述过的铬(5a/5b和6a/6b)。有趣的是,以前已经报道了与panusimilins a - c(1-3)密切相关的合成化合物,这些化合物是由Lewis酸促进植物来源的色素precoceni二聚化产生的。在本研究中,从真菌P. similis的培养液中分离出泛菌素。铬单体是对映体的非外消旋混合物,它们的绝对构型通过转化为Mosher酯衍生物得到了证实。对分离得到的化合物进行了细胞毒活性评价。其中2,2-二甲基-3,4,6-三羟基铬胺(6a/6b)对NCI-H187细胞具有选择性活性(IC50为9.1 μM)。另一方面,panusimilin B(2)在DPPH自由基清除实验中显示出抗氧化活性(IC50 66 μM)。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
求助全文
约1分钟内获得全文 去求助
来源期刊
CiteScore
9.10
自引率
5.90%
发文量
294
审稿时长
2.3 months
期刊介绍: The Journal of Natural Products invites and publishes papers that make substantial and scholarly contributions to the area of natural products research. Contributions may relate to the chemistry and/or biochemistry of naturally occurring compounds or the biology of living systems from which they are obtained. Specifically, there may be articles that describe secondary metabolites of microorganisms, including antibiotics and mycotoxins; physiologically active compounds from terrestrial and marine plants and animals; biochemical studies, including biosynthesis and microbiological transformations; fermentation and plant tissue culture; the isolation, structure elucidation, and chemical synthesis of novel compounds from nature; and the pharmacology of compounds of natural origin. When new compounds are reported, manuscripts describing their biological activity are much preferred. Specifically, there may be articles that describe secondary metabolites of microorganisms, including antibiotics and mycotoxins; physiologically active compounds from terrestrial and marine plants and animals; biochemical studies, including biosynthesis and microbiological transformations; fermentation and plant tissue culture; the isolation, structure elucidation, and chemical synthesis of novel compounds from nature; and the pharmacology of compounds of natural origin.
期刊最新文献
α-Helical Peptides Encoded in Collagen Exhibit Antimicrobial Activity with Low Cytotoxicity. Discovery of Enantiomeric Monoterpene-Coumarins with Neuroprotective Activities from the Rhizomes of Luvunga scandens. Discovery, Isolation, and Bactericidal Activity of a Cyclotide from Spigelia anthelmia L. (Loganiaceae). The Terpenoid Alkaloids of Colobognath Millipedes: Insights into Structural Diversity and Function. Dihydro-α-Pyrone Antibiotics from a Soil-Derived Fungus Talaromyces sp. G23.
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
现在去查看 取消
×
提示
确定
0
微信
客服QQ
Book学术公众号 扫码关注我们
反馈
×
意见反馈
请填写您的意见或建议
请填写您的手机或邮箱
已复制链接
已复制链接
快去分享给好友吧!
我知道了
×
扫码分享
扫码分享
Book学术官方微信
Book学术文献互助
Book学术文献互助群
群 号:604180095
Book学术
文献互助 智能选刊 最新文献 互助须知 联系我们:info@booksci.cn
Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。
Copyright © 2023 Book学术 All rights reserved.
ghs 京公网安备 11010802042870号 京ICP备2023020795号-1