Discovery of Naphthol Tetramers from Endolichenic Fungus Daldinia childiae 047219 Based on MS/MS Molecular Networking

IF 3.3 2区生物学 Q2 CHEMISTRY, MEDICINAL Journal of Natural Products Pub Date : 2023-08-17 DOI:10.1021/acs.jnatprod.3c00468

Jaekyeong Kim, Mei Tong He, Jae-Seoun Hur, Jin Woo Lee, Kyo Bin Kang, Ki Sung Kang and Sang Hee Shim*,

引用次数: 0

Abstract

Feature-based molecular networking analysis suggested the presence of naphthol tetramers in Daldinia childae 047219, the same species but a different strain from one used previously for the discovery of naphthol trimers promoting adiponectin synthesis. The new tetramers were composed of 5-methoxy-4-naphthol, each of which was connected to one another in various positions. Targeted isolation afforded six previously unreported naphthol tetramers (1–6) together with 13 known polyketides (7–19) including naphthol monomers, dimers, and trimers. Structures of the isolated compounds were established by using NMR and mass spectroscopic analysis. Nodulisporin A (13), nodulisporin B (14), and 1,1′,3′,3″-ternaphthalene-5,5′,5″-trimethoxy-4,4′,4″-triol (16) demonstrated anti-inflammatory activities against NO production, but the new compounds were less active.

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基于MS/MS分子网络的内生真菌Daldinia chilae 047219中萘酚四聚体的发现

基于特征的分子网络分析表明，在Daldinia childae 047219中存在萘酚四聚体，这与先前发现促进脂联素合成的萘酚三聚体的菌株相同，但不同。新的四聚体由5-甲氧基-4-萘酚组成，每个四聚体在不同的位置上相互连接。靶向分离得到6个以前未报道的萘酚四聚体(1-6)和13个已知的聚酮(7-19)，包括萘酚单体、二聚体和三聚体。通过核磁共振和质谱分析确定了分离化合物的结构。结核孢素A(13)、结核孢素B(14)和1,1 '，3 '，3″-对萘-5,5 '，5″-三甲氧基-4,4 '，4″-三醇(16)具有抗炎活性，但新化合物活性较低。

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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.