Todasinoid A, a New Eremophilane-type Sesquiterpene from the Plant Toddalia asiatica

IF 1.5 4区生物学 Q3 CHEMISTRY, APPLIED

Records of Natural Products Pub Date : 2022-08-30 DOI:10.25135/rnp.356.2206.2486

T. Lin, Lijing Cai, Mengying Zhang, Jie He

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引用次数: 0

Abstract

: A new sesquiterpene, named todasinoid A ( 1 ), together with eight known compounds ( 2 − 9 ) were isolated from the roots of Toddalia asiatica . The gross structure of todasinoid A were established by analyses of the NMR and HRESIMS data. A comparison of the experimental ECD spectrum of 1 with the calculated ECD spectra for a model compound ( 1a ) resolved the absolute configuration of 1 . The known compounds were identified to be bullatantriol ( 2 ), aculeatin ( 3 ), 6-(3-ethoxy-2-hydroxy-3-methylbutyl)-5,7-dimethoxy-2H-1-benzopyran-2-one ( 4 ), trans -N-p-coumaroyltyramine ( 5 ), feruloyltyramine ( 6 ), − sitosterol ( 7 ), sitosterol D -glucoside( 8 ), 7 α -hydroxysitosterol ( 9 ) by comparing the NMR data and specific rotations with reported data in literature. Compound 1 is an eremophilane-type sesquiterpenoid containing a mercaptolactate side-chain that is rarely found in nature. Compounds 2 , 5 , and 9 were isolated from this plant for the first time. Bioassay study revealed that compound 5 exhibited inhibitory effects against  -glucosidase with an IC 50 of 320  M, being more active than the positive control acarbose.

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Todasinoid A:一种新的茶树属倍半萜类化合物

:从亚洲龙舌(Toddalia asiatica)的根中分离到一个新的倍半萜，命名为todasinoid A(1)，并分离到8个已知化合物(2 ~ 9)。通过NMR和HRESIMS数据分析，确定了todasinoid A的总体结构。将模型化合物(1a)的实验ECD光谱1与计算ECD光谱进行比较，可以分辨出1的绝对构型。通过NMR数据和特定旋光度与文献数据的比较，确定了已知化合物为:bullatantriol(2)、aculeatin(3)、6-(3-乙氧基-2-羟基-3-甲基丁基)-5,7-二甲氧基- 2h -1-苯并吡喃-2-one(4)、反式- n-对- coumaroyylyramine(5)、阿魏酰乙胺(6)、-谷甾醇(7)、谷甾醇D -葡萄糖苷(8)、7 α -羟基谷甾醇(9)。化合物1是一种含有巯基乳酸侧链的芥子酸型倍半萜类化合物，在自然界中很少发现。其中化合物2、5、9为首次从该植物中分离得到。生物测定结果表明，化合物5对-葡萄糖苷酶具有抑制作用，ic50为320M，活性高于阳性对照阿卡波糖。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Records of Natural Products 生物-医药化学

CiteScore

3.10

自引率

26.30%

发文量

审稿时长

4 months

期刊介绍： Records of Natural Products is a journal of natural product chemistry. Reviews, book reviews, research papers and short reports are considered on the substances of plants, microbes and animals. Discussions on the structure elucidation, synthesis of naturally occurring compounds and biological activity of natural compounds and plant extracts, biosynthesis of natural products and essential oils of aromatic plants as well as chemotaxonomy in the field of plants are welcomed in the journal. All published research articles in Records of Natural Products have undergone rigorous peer review, based on initial editor screening and anonymized refereeing by expert referees.