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Archive > Volume 16 Issue 3 > 2024,16(3):481-486. DOI:https://doi.org/10.1016/j.chmed.2023.03.006 Prev Next

山中平樹(shù)的化學(xué)成分研究

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Constituents from leaves of Macaranga hemsleyana

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    摘要:
    目的：研究山中平樹(shù)Macaranga hemsleyana的化學(xué)成分；對(duì)其抑制NLRP3炎癥小體和細(xì)胞增殖活性進(jìn)行評(píng)價(jià)。 方法：通過(guò)MCI，凝膠LH-20和硅膠柱色譜和HPLC等方法對(duì)山中平樹(shù)的化學(xué)成分進(jìn)行分離純化；借助1D, 2D NMR, 和 HR-ESI-MS等波譜數(shù)據(jù)對(duì)化學(xué)成分進(jìn)行鑒定；采用LDH法和MTT法進(jìn)行活性測(cè)試。 結(jié)果：從山中平樹(shù)中共分離得到23個(gè)化合物，包括1個(gè)新化合物(2Z)-3-[4-(β-D-glucopyranosyloxy)-2'-hydroxy-5'-methoxyphenyl]-2-propenoic acid (1), 和22個(gè)已知化合物，分別鑒定為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), adenosine (23). 所有測(cè)試的化合物均沒(méi)有顯示明顯的抑制LDH釋放和抑制細(xì)胞增殖活性。 結(jié)論：化合物1是一個(gè)新的糖苷，化合物2和3是首次獲得的天然產(chǎn)物。其他已知化合物包括生物堿(2?4, 23), 酚性成分 (5, 15, 17, 18), 黃酮 (6?14), 香豆素 (16), 酚苷 (19), 和降倍半萜(20?22)。所有化合物均為山中平樹(shù)中首次分到。化合物1?10, 12, 13, 17?19, 和 23 為血桐屬中首次分到。所有測(cè)試的化合物均沒(méi)有顯示明顯的抑制LDH釋放和抑制細(xì)胞增殖活性。

    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-(b-D-glucopyranosyloxy)-20-hydroxy-50-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-b-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-a-L-arabinoside (13), vitexin (14), bergenin (15), scopoletin (16), glucopyranoside salicyl (17), koaburside (18), benzyl b-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 (2–4, 23), phenolics (5, 15, 17, 18), flavonoids (6–14), coumarin (16), benzyl glycoside (19), and norsesquiterpenes (20–22). All the compounds, 1–23, were revealed from M. hemsleyana for the first time. This is the initial uncovering of molecules 1–10, 12, 13, 17–19, and 23 from the genus Macaranga. The isolated compounds, 11, 14–16, and 20–22 established taxonomic classification of M. hemsleyana in Euphorbiaceae family. Flavonoids were outstanding as chemosystematic markers of Macaranga genus.

    關(guān)鍵詞:
    抗增殖活性;化學(xué)分類;類黃酮;糖配體;山平中樹(shù);NLRP3炎性小體

    Keywords:


    Project Supported:
    This work was financially supported by the National Natural Science Foundation of China (No. 81860615, 82260682), and Project of Yunnan Characteristic Plant Screening and R&D Service CXO Platform (No. 2022YKZY001). Authors thank Advanced Analysis and Measurement Center of Yunnan University for the sample testing service.

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