Four new diarylheptanoids and two new terpenoids from the fruits of Alpinia oxyphylla and their anti-inflammatory activities

IF 4 2区医学 Q1 INTEGRATIVE & COMPLEMENTARY MEDICINE

Chinese Journal of Natural Medicines Pub Date : 2024-10-01 DOI:10.1016/S1875-5364(24)60723-5

Jie DONG , Haibo LI , Mi ZHOU , Xinsheng YAO , Jianliang GENG , Yang YU

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引用次数: 0

Abstract

Four previously unreported diarylheptanoids (1a/1b−2a/2b), one undescribed sesquiterpenoid (8), one new diterpenoid (12), and twelve known analogs were isolated from the fruits of Alpinia oxyphylla. The structural elucidation of these compounds was achieved through a comprehensive analysis of spectroscopic data, single-crystal X-ray diffraction, electronic circular dichroism (ECD), and modified Mosher’s method. Enantiomeric mixtures (1a/1b, 2a/2b, 3a/3b, 4a/4b, and 5a/5b) were separated on a chiral column using acetonitrile-water mixtures as eluents. Among them, compounds 3a/3b and 4a/4b were isolated as optically pure enantiomers in the initial chiral separation. Furthermore, most of the isolates were evaluated for their inhibitory effects against the production of nitric oxide (NO) and interleukin-6 (IL-6) in lipopolysaccharide (LPS)-induced RAW264.7 macrophages. Interestingly, 2 and 4 showed significant inhibitory activities against NO production with IC₅₀ values of 33.65 and 9.88 μmol·L⁻¹ (hydrocortisone: IC₅₀ 34.26 μmol·L⁻¹), respectively. Additionally, they also partially reduced the secretion of IL-6.

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牛膝草果实中的四种新的二芳基庚酸类化合物和两种新的萜类化合物及其抗炎活性。

通过对光谱数据、单晶 X 射线衍射、电子圆二色性（ECD）和改良莫舍尔法的综合分析，从 Alpinia oxyphylla 果实中分离出了四种以前未报道过的二芳基庚烷类化合物（1a/1b-2a/2b）、一种未报道过的倍半萜类化合物（8）、一种新的二萜类化合物（12）和十二种已知的类似物。通过对光谱数据、单晶 X 射线衍射、电子圆二色性（ECD）和改进的莫舍尔法进行综合分析，这些化合物的结构得以阐明。以乙腈-水混合物为洗脱剂，在手性色谱柱上分离了对映体混合物（1a/1b、2a/2b、3a/3b、4a/4b 和 5a/5b）。其中，化合物 3a/3b 和 4a/4b 在初次手性分离中分离出光学纯对映体。此外，还评估了大部分分离物对脂多糖（LPS）诱导的 RAW264.7 巨噬细胞产生一氧化氮（NO）和白细胞介素-6（IL-6）的抑制作用。有趣的是，2 和 4 对一氧化氮的产生具有显著的抑制作用，IC50 值分别为 33.65 和 9.88 μmol-L-1（氢化可的松：IC50 为 34.26 μmol-L-1）。此外，它们还能部分减少 IL-6 的分泌。

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来源期刊

Chinese Journal of Natural Medicines INTEGRATIVE & COMPLEMENTARY MEDICINE-PHARMACOLOGY & PHARMACY

CiteScore

7.50

自引率

4.30%

发文量

2235

期刊介绍： The Chinese Journal of Natural Medicines (CJNM), founded and sponsored in May 2003 by China Pharmaceutical University and the Chinese Pharmaceutical Association, is devoted to communication among pharmaceutical and medical scientists interested in the advancement of Traditional Chinese Medicines (TCM). CJNM publishes articles relating to a broad spectrum of bioactive natural products, leading compounds and medicines derived from Traditional Chinese Medicines (TCM). Topics covered by the journal are: Resources of Traditional Chinese Medicines; Interaction and complexity of prescription; Natural Products Chemistry (including structure modification, semi-and total synthesis, bio-transformation); Pharmacology of natural products and prescription (including pharmacokinetics and toxicology); Pharmaceutics and Analytical Methods of natural products.