桂郁金化学成分及其生物活性研究

doi:10.16088/j.issn.1001-6600.2024112105

摘要/Abstract

摘要： 为探究桂郁金Curcuma kwangsiensis的化学成分及其生物活性,本文利用硅胶和半制备高效液相等传统与现代手段对桂郁金醇提取物进行分离纯化,通过现代波谱手段鉴定化合物的结构,并采用MTS法和Griess法分别检测化合物的抗肿瘤和抗炎活性。结果从桂郁金中分离得到18个化合物,分别鉴定为(3R,5S)-3,5-dihydroxy-1-(4,5-hydroxy-3-methoxy-phenyl)-7-(4-hydroxy-2-methoxy-phenyl)heptane(1)、5-((2S,4R,6S)-4-hydroxy-6-(4-hydroxy-3-methoxyphenethyl)-tetrahydro-2H-pyran-2-yl)-3-methoxybenzene-1,2-diol(2)、5-((2S,4S,6S)-4-hydroxy-6-(4-hydroxy-3-methoxyphenethyl)-tetrahydro-2H-pyran-2-yl)-3-methoxybenzene-1,2-diol(3)、broussonin B(4)、ellisinin A(5)、nyasol(6)、芫花素(7)、2,4-二叔丁基苯酚(8)、labda-8(17),13(14)-dien-15(16)-olide(9)、(E)-labda-8(17),12-dien-15,16-olide(10)、glutinol(11)、柠檬苦素(12)、β-谷甾醇(13)、豆甾醇(14)、胡萝卜苷(15)、小檗碱(16)、蔗糖(17)和棕榈酸(18),化合物1~12、16和17为首次从该植物中分离得到,化合物4~7,11,12,16首次从姜科植物中分离。抗肿瘤活性结果显示,化合物5对白血病HL-60、肺癌A549、肝癌HepG2、乳腺癌MDA-MB-231、结肠癌SW480细胞株的IC₅₀为5.11、44.82、12.27、28.82、15.78 μmol/L,化合物6对白血病HL-60和肝癌HepG2细胞的IC₅₀分别为20.30、35.74 μmol/L,化合物9对白血病HL-60细胞株的IC₅₀为34.24 μmol/L,化合物16对白血病HL-60、乳腺癌MDA-MB-231、结肠癌SW480细胞株的IC₅₀分别为6.31、30.57、31.39 μmol/L。抗炎活性结果表明,化合物9和16对LPS诱导的NO生成抑制活性的IC₅₀分别为45.76和44.67 μmol/L。本研究结果进一步丰富了桂郁金的化学成分库,为其后续的研究与开发利用奠定基础。

关键词: 桂郁金, 化学成分, 生物活性, 抗肿瘤, 抗炎

Abstract: To investigate the chemical constituents and biological activities of Curcuma kwangsiensis, the traditional and modern methods such as silica gel and semi-preparative high performance liquid chromatography were used to isolate and purify the ethanol extract of Curcuma kwangsiensis. Identification of the structure of compounds by modern spectroscopic means, and the anti-tumor and anti-inflammatory activities of the compounds were detected by MTS method and Griess method, respectively. A total of eighteen compounds were isolated from this plant and identified as(3R,5S)-3,5-dihydroxy-1-(4,5-hydroxy-3-methoxy-phenyl)-7-(4-hydroxy-2-methoxy-phenyl) heptane (1), 5-((2S,4R,6S)-4-hydroxy-6-(4-hydroxy-3-methoxyphenethyl)-tetrahydro-2H-pyran-2-yl)-3-methoxybenzene-1,2-diol (2), 5-((2S,4S,6S)-4-hydroxy-6-(4-hydroxy-3-methoxyphenethyl)-tetrahydro-2H-pyran-2-yl)-3-methoxybenzene-1,2-diol (3), broussonin B (4), ellisinin A (5), nyasol (6), genkwanin (7), 2,4-di-tert-butylphenol (8), labda-8(17)-,13(14)-dien-15(16)-olide (9),(E)-labda-8(17),12-dien-15,16-olide (10), glutinol (11), limonin (12), β-sitosterol (13), stigmasterol (14), daucosterol (15), berberine (16), sucrose (17) and palmitic acid (18). Compounds 1-12, 16, 17 were isolated from this plant for the first time, and compounds 4-7, 11, 12, 16 were isolated from Zingiberaceae for the first time. The results of antitumor activity showed that the IC₅₀ of compound 5 against leukemia HL-60, lung cancer A549, liver cancer HepG2, breast cancer MDA-MB-231 and colon cancer SW480 cell lines were 5.11, 44.82, 12.27, 28.82 and 15.78 μmol/L, respectively. The IC₅₀ of compound 6 on leukemia HL-60 and liver cancer HepG2 cells were 20.30 and 35.74 μmol/L, respectively. The IC₅₀ of compound 9 on leukemia HL-60 cells was 34.24 μmol/L, respectively. The IC₅₀ of compound 16 on leukemia HL-60, breast cancer MDA-MB-231 and colon cancer SW480 cells were 6.31, 30.57 and 31.39 μmol/L, respectively. The results of anti-inflammatory activity showed that the IC₅₀ values of compounds 9 and 16 against LPS-induced NO production were 45.76 and 44.67 μmol/L, respectively. The results of this study further enrich the chemical composition library of Curcuma kwangsiensis, and lay a foundation for its further research and development.

Key words: Curcuma kwangsiensis, chemical constituents, anti-tumo, biological activity, anti-inflammatory

中图分类号: R284

苏源丰, 李良波, 陈建桦, 张进燕, 卢羽玲, 蒙青爱, 何美英, 廖广凤, 卢汝梅. 桂郁金化学成分及其生物活性研究[J]. 广西师范大学学报（自然科学版）, 2025, 43(6): 152-161.

SU Yuanfeng, LI Liangbo, CHEN Jianhua, ZHANG Jinyan, LU Yuling, MENG Qingai, HE Meiying, LIAO Guangfeng, LU Rumei. Chemical Constituents and Biological Activities of Curcuma kwangsiensis[J]. Journal of Guangxi Normal University(Natural Science Edition), 2025, 43(6): 152-161.

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