Constituents from leaves of Macaranga hemsleyana

IF 4.7 4区 医学 Q1 CHEMISTRY, MEDICINAL
Joseph Sakah Kaunda , Jia Liu , Yaojun Xu , Yuansi Chen , Chenfang Yue , Xingjie Zhang , Ruihan Zhang , Muhammad Amin , Weilie Xiao , Hongliang Li , Xiaoli Li
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Abstract

Objective

To study constituents of the leaves of Macaranga hemsleyana, and evaluate their inhibitory effects against NOD-like receptor thermal protein domain associated protein 3 (NLRP3) inflammasome activation, and antiproliferative activity.

Methods

The constituents were isolated and purified by column chromatography on MCI gel CHP20P/P120, silica gel, Sephadex LH-20, and HPLC. The structures of compounds were determined by 1D, 2D NMR, and HR-ESI-MS data. The inhibitory effect of compounds on inflammasome activation was determined by lactate dehydrogenase (LDH) procedure. The antiproliferative activity was evaluated using MTT assay.

Results

The study led to the isolation of 23 compounds, including one new compound, identified as (2Z)-3-[4-(β-D-glucopyranosyloxy)-2′-hydroxy-5′-methoxyphenyl]-2-propenoic acid (1), together with 22 known compounds recognized as 1,4-dihydro-4-oxo-3-pyridinecarbonitrile (2), methyl 4-methoxynicotinate (3), 4-methoxynicotinonitrile (4), 1-(3-O-β-D-glucopyranosyl-4,5-dihydroxyphenyl)-ethanone (5), neoisoastilbin (6), isoastilbin (7), aromadendrin (8), neoastilbin (9), astilbin (10), quercitrin (11), neoschaftoside (12), apigenin 6,8-bis-C-α-L-arabinoside (13), vitexin (14), bergenin (15), scopoletin (16), glucopyranoside salicyl (17), koaburside (18), benzyl β-D-glucoside (19), icariside B5 (20), roseoside (21), loliolide (22), and adenosine (23). The tested compounds did not show LDH inhibition nor antiproliferative activity.

Conclusion

Compound 1 was a new glycoside. Compounds 2 and 3 were obtained for the first time from natural source. The 22 known compounds constituted of alkaloids (24, 23), phenolics (5, 15, 17, 18), flavonoids (614), coumarin (16), benzyl glycoside (19), and norsesquiterpenes (2022). All the compounds, 123, were revealed from M. hemsleyana for the first time. This is the initial uncovering of molecules 110, 12, 13, 1719, and 23 from the genus Macaranga. The isolated compounds, 11, 1416, and 2022 established taxonomic classification of M. hemsleyana in Euphorbiaceae family. Flavonoids were outstanding as chemosystematic markers of Macaranga genus.

金刚鹦鹉叶的成分
目的 研究Macaranga hemsleyana叶中的成分,并评估其对NOD样受体热蛋白域相关蛋白3(NLRP3)炎性体激活的抑制作用和抗增殖活性。通过一维、二维 NMR 和 HR-ESI-MS 数据确定了化合物的结构。乳酸脱氢酶(LDH)法测定了化合物对炎症小体活化的抑制作用。抗增殖活性采用 MTT 法进行评估。结果这项研究分离出 23 种化合物,其中包括一种新化合物,即 (2Z)-3-[4-(β-D-Glucopyranosyloxy)-2′-hydroxy-5′-methoxyphenyl]-2-propenoic acid (1)、以及 22 种已知化合物,如 1,4-二氢-4-氧代-3-吡啶甲腈(2)、4-甲氧基烟酸甲酯(3)、4-甲氧基烟腈(4)、1-(3-O-β-D-吡喃葡萄糖基-4、5-二羟基苯基)-乙酮 (5)、新异黄芪素 (6)、异黄芪素 (7)、芳香腺苷 (8)、新黄芪素 (9)、黄芪素 (10)、槲皮素 (11)、新槲皮苷 (12)、芹菜素 6,8-双-C-α-L-阿拉伯糖苷 (13)、槲皮素(11)、新槲皮苷(12)、芹菜素 6,8-双-C-α-L-阿拉伯糖苷(13)、荆芥苷(14)、小檗苷(15)、莨菪亭(16)、水杨酸葡萄糖苷(17)、葵苷(18)、苄基 β-D-葡萄糖苷(19)、冰片苷 B5(20)、玫瑰苷(21)、萝莉苷(22)和腺苷(23)。结论化合物 1 是一种新的苷类化合物。结论化合物 1 是一种新的糖苷,化合物 2 和 3 是首次从天然来源获得的。已知的 22 种化合物包括生物碱(2-4、23)、酚类(5、15、17、18)、黄酮类(6-14)、香豆素(16)、苄基糖苷(19)和后四萜类(20-22)。所有化合物(1-23)都是首次从 M. hemsleyana 中发现。这是首次从马缨丹属植物中发现 1-10、12、13、17-19 和 23 号分子。分离出的化合物 11、14-16 和 20-22 确立了大戟科 M. hemsleyana 的分类。黄酮类化合物是 Macaranga 属的化学系统标记。
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
Chinese Herbal Medicines
Chinese Herbal Medicines CHEMISTRY, MEDICINAL-
CiteScore
4.40
自引率
5.30%
发文量
629
审稿时长
10 weeks
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