Sorbicillinoids with anti-inflammatory activity from the mangrove sediment-derived fungus Trichoderma reesei SCSIO 41705

IF 2.5 3区医学 Q3 CHEMISTRY, MEDICINAL

Fitoterapia Pub Date : 2025-04-30 DOI:10.1016/j.fitote.2025.106580

Lin-Fang Zhong , Qing-Hui Zou , Xu-Meng Ren , Juan Ling , Shu-Hua Qi

{"title":"Sorbicillinoids with anti-inflammatory activity from the mangrove sediment-derived fungus Trichoderma reesei SCSIO 41705","authors":"Lin-Fang Zhong , Qing-Hui Zou , Xu-Meng Ren , Juan Ling , Shu-Hua Qi","doi":"10.1016/j.fitote.2025.106580","DOIUrl":null,"url":null,"abstract":"<div><div>Thirteen new sorbicillinoids including trichosorbicilloid A (1), 12-epi- trichosorbicilloid A (2), trichosorbicilloids B − C (3–4), 24-hydroxy-12-epi-trichobisvertinol D (5), 15,24-dihydroxy-12-epi-trichobisvertinol D (6), 15,24-dihydroxy-13,14-tetrahydro-12-epi-trichobisvertinol D (7), 15-hydroxy-13,14-tetrahydro-12-epi-trichobisvertinol D (8), 24-hydroxy-trichobisvertinol D (9), 15,24-hydroxy-trichobisvertinol D (10), 13,20-dihydroxy-trichodermolide (11), 20-hydroxy-13-trichodermolide acid (12), and trichosorbicilloid D (13) were isolated from the mangrove sediment-derived fungus Trichoderma reesei SCSIO 41705. Their structures were determined by extensive spectroscopic analysis, and their absolute configurations were established by quantum chemical calculations of electronic circular dichroism (ECD) spectra or comparison of experimental ECD spectra. Compounds 1 and 2 possess a novel cagelike polycyclic skeleton with a unique 5/5/5/5/6 ring system. Compound 3 was the first example of hybrid sorbicillinoid fused vertinolide with a 3-propyl-1H-indole unit by Michael-addition. Compounds 5–13 as dimeric sorbicillinoids have different sorbyl side chains. Biologically, compounds 3, 11 and 13 showed potent anti-inflammatory activity by inhibiting the LPS-induced NO production in RAW 264.7 cells. A preliminary structure-anti-inflammatory activity relationship of sorbicillinoids was also discussed.</div></div>","PeriodicalId":12147,"journal":{"name":"Fitoterapia","volume":"183 ","pages":"Article 106580"},"PeriodicalIF":2.5000,"publicationDate":"2025-04-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Fitoterapia","FirstCategoryId":"3","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0367326X25002059","RegionNum":3,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, MEDICINAL","Score":null,"Total":0}

引用次数: 0

Abstract

Thirteen new sorbicillinoids including trichosorbicilloid A (1), 12-epi- trichosorbicilloid A (2), trichosorbicilloids B − C (3–4), 24-hydroxy-12-epi-trichobisvertinol D (5), 15,24-dihydroxy-12-epi-trichobisvertinol D (6), 15,24-dihydroxy-13,14-tetrahydro-12-epi-trichobisvertinol D (7), 15-hydroxy-13,14-tetrahydro-12-epi-trichobisvertinol D (8), 24-hydroxy-trichobisvertinol D (9), 15,24-hydroxy-trichobisvertinol D (10), 13,20-dihydroxy-trichodermolide (11), 20-hydroxy-13-trichodermolide acid (12), and trichosorbicilloid D (13) were isolated from the mangrove sediment-derived fungus Trichoderma reesei SCSIO 41705. Their structures were determined by extensive spectroscopic analysis, and their absolute configurations were established by quantum chemical calculations of electronic circular dichroism (ECD) spectra or comparison of experimental ECD spectra. Compounds 1 and 2 possess a novel cagelike polycyclic skeleton with a unique 5/5/5/5/6 ring system. Compound 3 was the first example of hybrid sorbicillinoid fused vertinolide with a 3-propyl-1H-indole unit by Michael-addition. Compounds 5–13 as dimeric sorbicillinoids have different sorbyl side chains. Biologically, compounds 3, 11 and 13 showed potent anti-inflammatory activity by inhibiting the LPS-induced NO production in RAW 264.7 cells. A preliminary structure-anti-inflammatory activity relationship of sorbicillinoids was also discussed.

Abstract Image

查看原文本刊更多论文

从红树林沉积物衍生的真菌里氏木霉（Trichoderma reesei） SCSIO 41705中提取具有抗炎活性的山梨脂素

13个新的sorbicillinoids包括(1)trichosorbicilloid 12-epi——trichosorbicilloid (2), trichosorbicilloids B−C (3 - 4), 24-hydroxy-12-epi-trichobisvertinol D(5), 15日24-dihydroxy-12-epi-trichobisvertinol D(6), 15日24-dihydroxy-13, 14-tetrahydro-12-epi-trichobisvertinol D (7), 15-hydroxy-13, 14-tetrahydro-12-epi-trichobisvertinol D (8), 24-hydroxy-trichobisvertinol D(9), 15日24-hydroxy-trichobisvertinol D(10), 13日20-dihydroxy-trichodermolide (11),20-羟基-13-trichodermolide acid（12）和trichosorbicillloid D（13）分别从红树林沉积真菌Trichoderma reesei SCSIO 41705中分离得到。通过广泛的光谱分析确定了它们的结构，并通过电子圆二色（ECD）光谱的量子化学计算或实验ECD光谱的比较确定了它们的绝对构型。化合物1和2具有新颖的笼状多环骨架，具有独特的5/5/5/5/6环体系。化合物3是第一个通过迈克尔加成法将山梨霉素类化合物与3-丙基- 1h -吲哚单元融合的杂化水杨酸酯。化合物5-13作为二聚山梨二烯酸具有不同的山梨基侧链。在生物学上，化合物3、11和13通过抑制lps诱导的RAW 264.7细胞NO的产生而显示出强大的抗炎活性。并初步探讨了山梨比酯类化合物的结构-抗炎活性关系。

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分钟内获得全文求助全文

来源期刊

Fitoterapia 医学-药学

CiteScore

5.80

自引率

2.90%

发文量

198

审稿时长

1.5 months

期刊介绍： Fitoterapia is a Journal dedicated to medicinal plants and to bioactive natural products of plant origin. It publishes original contributions in seven major areas: 1. Characterization of active ingredients of medicinal plants 2. Development of standardization method for bioactive plant extracts and natural products 3. Identification of bioactivity in plant extracts 4. Identification of targets and mechanism of activity of plant extracts 5. Production and genomic characterization of medicinal plants biomass 6. Chemistry and biochemistry of bioactive natural products of plant origin 7. Critical reviews of the historical, clinical and legal status of medicinal plants, and accounts on topical issues.