Zoanthamine-Type Alkaloids Derived from Cultured Zoanthus kuroshio with Therapeutic Potential Against Osteoporosis.

IF 3.3 2区生物学 Q2 CHEMISTRY, MEDICINAL

Journal of Natural Products Pub Date : 2025-06-09 DOI:10.1021/acs.jnatprod.5c00457

Ngoc-Thac Pham, Bo-Rong Peng, Huong-Giang Le, You-Song Cheng, Yun-Shiuan Chen, Thanh Hao Huynh, Lo-Yun Chen, Le Anh Tuan Nguyen, Dang T Nguyen, Yu-Chia Chang, Jui-Hsin Su, Mohamed El-Shazly, Mei-Hsien Lee, Kuei-Hung Lai

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引用次数: 0

Abstract

Extracts of the zoanthid from Zoanthus kuroshio (ZK) exhibited significant in vitro antiosteoporotic activity in MG-63 cells, prompting the use of Global Natural Products Social Molecular Networking (GNPS) to identify alkaloid-rich fractions. Subsequently, five new zoanthamine-type alkaloids, norzoabenzaldehyde (1), norzoazepanol (2), 3-acetoxynorzoanthaminone (3), 11-hydroxynorzoanthamide B (4), and 11-hydroxyzoanthamide B (5), were isolated. Structural elucidation was achieved by spectroscopic analyses, time-dependent density functional theory nuclear magnetic resonance (TDDFT-NMR) calculations, and electronic circular dichroism (ECD). The alkaloid 3-hydroxynorzoanthamine exhibited notable alkaline phosphatase activity and promoted mineralization, with an IC₅₀ value of 20 μM, underscoring its potential as a promising lead compound for the development of osteoporosis therapeutics.

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从培养的黑斑草中提取的抗骨质疏松的斑蝥素类生物碱。

黑斑马齿苋（Zoanthus kuroshio， ZK）提取物在MG-63细胞中表现出显著的体外抗骨质疏松活性，促使使用全球天然产物社会分子网络（Global Natural Products Social Molecular network， GNPS）鉴定其富含生物碱的部分。随后，分离得到了去甲氮杂甲醇(1)、去甲氮杂甲醇(2)、3-乙酰氧基去甲氮杂甲胺酮(3)、11-羟基去甲氮杂甲酰胺B(4)和11-羟基去甲氮杂酰胺B(5) 5种新的防甲胺类生物碱。通过光谱分析、时变密度泛函理论核磁共振（TDDFT-NMR）计算和电子圆二色性（ECD）实现了结构解析。生物碱3-羟基去甲氰胺具有显著的碱性磷酸酶活性和矿化促进作用，IC50值为20 μM，表明其有潜力成为开发骨质疏松症治疗药物的先导化合物。

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

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.