Spiro-meroterpenoids, Syzygioblanes D–H, Isolated from Indonesian Medicinal Plant Syzygium oblanceolatum

IF 3.6 2区生物学 Q2 CHEMISTRY, MEDICINAL

Journal of Natural Products Pub Date : 2024-12-13 DOI:10.1021/acs.jnatprod.4c0115410.1021/acs.jnatprod.4c01154

Nona Koga, Kaede Kawashima, Chihiro Ito, Tomoya Nishida, Shuichi Fukuyoshi, Yohei Saito, Katsunori Miyake, Saidanxia Amuti, Abdul Rahim, Ahmad Najib, Gemini Alam, Atsushi Mizokami, Nobuyuki Tanaka and Kyoko Nakagawa-Goto*,

{"title":"Spiro-meroterpenoids, Syzygioblanes D–H, Isolated from Indonesian Medicinal Plant Syzygium oblanceolatum","authors":"Nona Koga, Kaede Kawashima, Chihiro Ito, Tomoya Nishida, Shuichi Fukuyoshi, Yohei Saito, Katsunori Miyake, Saidanxia Amuti, Abdul Rahim, Ahmad Najib, Gemini Alam, Atsushi Mizokami, Nobuyuki Tanaka and Kyoko Nakagawa-Goto*, ","doi":"10.1021/acs.jnatprod.4c0115410.1021/acs.jnatprod.4c01154","DOIUrl":null,"url":null,"abstract":"Syzygioblanes A–C (1–3), isolated from the Indonesian traditional herbal medicine Syzygium oblanceolatum (S. oblanceolatum), are meroterpenoids with a spiro ring formed through a [4 + 2] cycloaddition of the flavanone desmethoxymatteucinol with cyclic sesquiterpenoids. Our ongoing phytochemical investigation of S. oblanceolatum resulted in the isolation of five additional spiro-meroterpenoids, syzygioblanes D–H (4–8), which are hybrids of the same flavanone with eudesmane/cadinane-type sesquiterpenoids. A possible biosynthetic pathway involves enzymatic dearomative hydroxylation of desmethoxymatteucinol followed by [4 + 2] cyclization of the resulting diene with a cyclic sesquiterpene containing an exocyclic methylene to form the unique spiro ring in the syzygioblane molecule. The isolated syzygioblanes F (6) and G (7) demonstrated collateral sensitivity by inhibiting the growth of multidrug-resistant tumor cell lines more than the related chemosensitive tumor cell lines.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":"87 12","pages":"2872–2880 2872–2880"},"PeriodicalIF":3.6000,"publicationDate":"2024-12-13","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://pubs.acs.org/doi/10.1021/acs.jnatprod.4c01154","RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, MEDICINAL","Score":null,"Total":0}

引用次数: 0

Abstract

Syzygioblanes A–C (1–3), isolated from the Indonesian traditional herbal medicine Syzygium oblanceolatum (S. oblanceolatum), are meroterpenoids with a spiro ring formed through a [4 + 2] cycloaddition of the flavanone desmethoxymatteucinol with cyclic sesquiterpenoids. Our ongoing phytochemical investigation of S. oblanceolatum resulted in the isolation of five additional spiro-meroterpenoids, syzygioblanes D–H (4–8), which are hybrids of the same flavanone with eudesmane/cadinane-type sesquiterpenoids. A possible biosynthetic pathway involves enzymatic dearomative hydroxylation of desmethoxymatteucinol followed by [4 + 2] cyclization of the resulting diene with a cyclic sesquiterpene containing an exocyclic methylene to form the unique spiro ring in the syzygioblane molecule. The isolated syzygioblanes F (6) and G (7) demonstrated collateral sensitivity by inhibiting the growth of multidrug-resistant tumor cell lines more than the related chemosensitive tumor cell lines.

Abstract Image

查看原文本刊更多论文

从印尼药用植物斜针叶桐中分离的螺粒萜类化合物，syzygioblane D-H

Syzygioblanes a - c（1-3）是从印度尼西亚传统草药Syzygium oblanceolatum （S. oblanceolatum）中分离出来的，是一种带有螺旋环的meroterpenoids，通过[4 + 2]环加成黄酮去甲氧基matteucinol与环状倍半萜形成螺旋环。我们正在进行的对斜针叶树的植物化学研究结果分离出另外5种螺-半萜类化合物，syzygioblanes D-H(4-8)，它们是同一种黄酮与菊酯类/苯甲酸类倍半萜类化合物的杂交产物。一种可能的生物合成途径包括酶促去甲氧基matteucinol的去芳香羟基化，然后用含有外环亚甲基的环倍半萜对所得到的二烯进行[4 + 2]环化，从而在syzygioblane分子中形成独特的螺旋环。分离的syzygioblane F(6)和G(7)通过抑制多药耐药肿瘤细胞系的生长而比相关的化学敏感肿瘤细胞系表现出侧支敏感性。

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

Journal of Natural Products 生物-药学

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.