HDAC inhibitor SAHA triggers the production of previously undescribed sesquiterpenes and undergoes biotransformation by the fungus Robillarda sessilis from Verbena officinalis L.

IF 3.2 2区生物学 Q2 BIOCHEMISTRY & MOLECULAR BIOLOGY

Phytochemistry Pub Date : 2025-01-22 DOI:10.1016/j.phytochem.2025.114411

Liangxiu Liao , Junguo Huang , Tao Zhu , Shan Ran , Qingpei Liu , Wenjing Wang , Xiaolong Yang

{"title":"HDAC inhibitor SAHA triggers the production of previously undescribed sesquiterpenes and undergoes biotransformation by the fungus Robillarda sessilis from Verbena officinalis L.","authors":"Liangxiu Liao , Junguo Huang , Tao Zhu , Shan Ran , Qingpei Liu , Wenjing Wang , Xiaolong Yang","doi":"10.1016/j.phytochem.2025.114411","DOIUrl":null,"url":null,"abstract":"<div><div>Cultivation of the endophytic fungus <em>Robillarda sessilis</em> XL-308 with SAHA resulted in the discovery of two previously undescribed cyclonerane sesquiterpenes (<strong>1</strong> and <strong>2</strong>), one previously unreported norcadinane type sesquiterpene (<strong>3</strong>), and seven suberanilohydroxamic acid (SAHA) derivatives (<strong>4</strong>–<strong>10</strong>). The identification of previously undescribed compounds was confirmed through NMR spectroscopic analyses, quantum chemistry calculations, and single-crystal X-ray crystallography. Among them, compounds <strong>1</strong> and <strong>2</strong> were products of the silenced genome in XL-308 that activated by SAHA. Concurrently, SAHA underwent biotransformation because of its moderate toxicity towards this fungus. It was hypothesized that the hydroxamic acid group in SAHA triggering the self-defense mechanism of XL-308 and converting SAHA into a less toxic derivative <strong>5</strong>.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"233 ","pages":"Article 114411"},"PeriodicalIF":3.2000,"publicationDate":"2025-01-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Phytochemistry","FirstCategoryId":"99","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0031942225000342","RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"BIOCHEMISTRY & MOLECULAR BIOLOGY","Score":null,"Total":0}

引用次数: 0

Abstract

Cultivation of the endophytic fungus Robillarda sessilis XL-308 with SAHA resulted in the discovery of two previously undescribed cyclonerane sesquiterpenes (1 and 2), one previously unreported norcadinane type sesquiterpene (3), and seven suberanilohydroxamic acid (SAHA) derivatives (4–10). The identification of previously undescribed compounds was confirmed through NMR spectroscopic analyses, quantum chemistry calculations, and single-crystal X-ray crystallography. Among them, compounds 1 and 2 were products of the silenced genome in XL-308 that activated by SAHA. Concurrently, SAHA underwent biotransformation because of its moderate toxicity towards this fungus. It was hypothesized that the hydroxamic acid group in SAHA triggering the self-defense mechanism of XL-308 and converting SAHA into a less toxic derivative 5.

Abstract Image

查看原文本刊更多论文

通过用 SAHA 培养内生真菌 Robillarda sessilis XL-308，发现了两种以前未曾报道过的环戊烷类倍半萜（1 和 2）、一种以前未曾报道过的去甲丁烷类倍半萜（3）和七种亚伯兰羟肟酸（SAHA）衍生物（4-10）。通过核磁共振光谱分析、量子化学计算和单晶 X 射线晶体学研究，确认了以前未曾报道过的化合物。其中，化合物 1 和 2 是 XL-308 中被 SAHA 激活的沉默基因组的产物。同时，由于 SAHA 对该真菌具有中等毒性，因此会发生生物转化。据推测，SAHA 中的羟肟酸基团触发了 XL-308 的自我防御机制，并将 SAHA 转化为毒性较低的衍生物 5。

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

Phytochemistry 生物-植物科学

CiteScore

6.40

自引率

7.90%

发文量

443

审稿时长

39 days

期刊介绍： Phytochemistry is a leading international journal publishing studies of plant chemistry, biochemistry, molecular biology and genetics, structure and bioactivities of phytochemicals, including ''-omics'' and bioinformatics/computational biology approaches. Phytochemistry is a primary source for papers dealing with phytochemicals, especially reports concerning their biosynthesis, regulation, and biological properties both in planta and as bioactive principles. Articles are published online as soon as possible as Articles-in-Press and in 12 volumes per year. Occasional topic-focussed special issues are published composed of papers from invited authors.