Antimalarial Lanostane Dimers from Artificially Cultivated Fruiting Bodies of Ganoderma weberianum

IF 3.3 2区生物学 Q2 CHEMISTRY, MEDICINAL Journal of Natural Products Pub Date : 2023-10-10 DOI:10.1021/acs.jnatprod.3c00457

Panida Chinthanom, Vanicha Vichai, Pranee Rachtawee, Thitiya Boonpratuang and Masahiko Isaka*,

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Abstract

Investigation of cultivated fruiting bodies of Ganoderma weberianum led to the isolation of 11 previously unreported lanostane dimers, ganoweberianones C (3a), D (4a), E (5a), F (6a), G (7a), and H (8a) and isoganoweberianones A (1b), B (2b), D (4b), G (7b), and H (8b). Six new ganodermanontriol derivatives as three pairs of diastereomers (11/12, 13/14, and 15/16) and five new ganoweberianic acids (17–21) were also isolated. A method for semisynthesis of lanostane dimers by condensation of natural lanostanes was established, which was utilized in the structure elucidation and NMR data assignments of the undescribed natural lanostane dimers. Ganoweberianone D (4a) and isoganoweberianone D (4b) showed significant antimalarial activity against Plasmodium falciparum K1 (multidrug-resistant strain) with IC₅₀ values of 0.057 and 0.035 μM, respectively, whereas their cytotoxicity to Vero cells was weaker (IC₅₀ 8.1 and 19 μM, respectively).

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人工栽培网络灵芝果体中的抗疟Lanostane二聚体

对培养的网络灵芝子实体的研究导致分离出11种以前未报道的羊毛甾烷二聚体，即甘露糖内酯C（3a）、D（4a）、E（5a）、F（6a）、G（7a）和H（8a。还分离出6种新的甘露德甾体衍生物作为3对非对映异构体（11/12、13/14和15/16）和5种新的甘草酸（17-21）。建立了一种通过天然羊毛甾烷缩合半合成羊毛甾烷二聚体的方法，该方法用于未描述的天然羊毛甾烯二聚体结构阐明和NMR数据分配。Ganoweberianone D（4a）和异Ganoweberanione D（4b）对恶性疟原虫K1（耐多药菌株）表现出显著的抗疟活性，IC50值分别为0.057和0.035μM，而它们对Vero细胞的细胞毒性较弱（IC50分别为8.1和19μM）。

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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.