Analgesic Grayanane-Derived Diterpenoids from the Flowers of Rhododendron molle.

IF 3.6 2区生物学 Q2 CHEMISTRY, MEDICINAL Journal of Natural Products Pub Date : 2025-03-28 Epub Date: 2025-03-11 DOI:10.1021/acs.jnatprod.4c01303

Yang Song, Hui-Min Yan, Bing Chai, Zhao-Xin Zhang, Fang-Fei Li, Qin-Yan Shi, Hai-Qiang Wang, Yong Li, Shi-Shan Yu

引用次数: 0

Abstract

Ten new grayanane-derived diterpenoids, rhodomollein LVII-LXVI (1-10), along with the known compound rhodomollein XLIII (11), were isolated from the flowers of Rhododendron molle. Their structures were elucidated by detailed spectroscopic analysis, X-ray diffraction crystallography, and ECD calculations. Rhodomollein LVII-LIX (1-3) are the first-discovered 3-O-(E)-p-coumaroylquinic acid, nicotinic acid, and 2-furoic acid derivatives of grayanane diterpenoids, respectively. In an acetic acid-induced writhing test, compounds 1 and 3 demonstrated significant antinociceptive effects with writhing inhibition rates of 77.2% and 71.5%, respectively, at a dose of 0.2 mg/kg. Compound 1 was found to be twice as potent as morphine, exhibiting significantly lower toxicity (LD₅₀ = 130.90 mg/kg, i.p.) compared to rhodojaponin VI (LD₅₀ = 1.79 mg/kg, i.p.).

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从杜鹃花中提取的具有镇痛作用的灰杉烷类二萜。

从杜鹃（Rhododendron molle）花中分离得到10个新的灰色烷类二萜类化合物rhodomollein LVII-LXVI（1-10）和已知化合物rhodomollein XLIII（11）。它们的结构通过详细的光谱分析、x射线衍射晶体学和ECD计算得以阐明。Rhodomollein LVII-LIX（1-3）分别是第一个发现的3-O-(E)-对香豆酰奎宁酸、烟酸和2-呋喃酸的灰色烷二萜衍生物。在醋酸诱导扭体实验中，化合物1和3在0.2 mg/kg剂量下表现出明显的抗扭体抑制作用，扭体抑制率分别为77.2%和71.5%。化合物1的效价是吗啡的两倍，毒性（LD50 = 130.90 mg/kg, i.p）明显低于红参素VI （LD50 = 1.79 mg/kg, i.p）。

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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.