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

IF 3.3 2区生物学 Q2 CHEMISTRY, MEDICINAL Journal of Natural Products Pub Date : 2024-12-13 DOI:10.1021/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, Kyoko Nakagawa-Goto

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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.

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从印度尼西亚传统草药连叶紫草（Syzygium oblanceolatum，S. oblanceolatum）中分离出的 Syzygioblanes A-C (1-3)是一种具有螺环的 meroterpenoids，通过黄酮 desmethoxymatteucinol 与环状倍半萜的 [4 + 2] 环加成形成。我们正在对 S. oblanceolatum 进行的植物化学研究分离出了另外五种螺萜类化合物，即 syzygioblanes D-H（4-8），它们是同一种黄烷酮与 eudesmane/cadinane-type倍半萜类化合物的杂交产物。一种可能的生物合成途径是对去甲氧基马脱苷醇进行酶促脱氧羟化，然后将生成的二烯与含有一个外环亚甲基的环状倍半萜进行[4 + 2]环化，形成syzygioblane分子中独特的螺环。分离出的syzygioblanes F (6) 和 G (7) 比相关的化疗敏感性肿瘤细胞株更能抑制耐多药肿瘤细胞株的生长，从而显示出其附带的敏感性。

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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.