矮陀陀中一个新的脂肪酸苷类化合物

doi:10.6023/cjoc202310019

有机化学 ›› 2024, Vol. 44 ›› Issue (4): 1348-1356.DOI: 10.6023/cjoc202310019 上一篇下一篇

研究简报

矮陀陀中一个新的脂肪酸苷类化合物

刘培源^a^,^b, 韦玉璐^b, 宋静茹^b, 颜小捷^b, 卢凤来^b, 陈月圆^b, 羊学荣^b^,^*(), 李典鹏^b^,^c^,^*()

a 桂林医学院药学院广西桂林 541004
b 广西壮族自治区中国科学院广西植物研究所广西植物功能物质与资源持续利用重点实验室广西桂林 541006
c 广西中医药大学中药壮瑶药创新药物教育部工程研究中心广西南宁 530200

收稿日期:2023-10-22 修回日期:2023-11-28 发布日期:2023-12-15
基金资助:
广西自然科学基金(2020GXNSFBA297055); 广西科技基础条件与人才计划(桂科AA21196009); 国家重点研发项目(2022YFD1600302); 国家自然科学基金(U20A2004); 广西科学院基础研究基金(CQZ-C-1901); 桂林创新平台与人才计划(20210102-3); 广东省重点领域研究发展计划(2020B1111110003)

A New Fatty Acid Glycoside Compound in Munronia Pinnata

Peiyuan Liu^a^,^b, Yulu Wei^b, Jingru Song^b, Xiaojie Yan^b, Fenglai Lu^b, Yueyuan Cheng^b, Xuerong Yang^b(), Dianpeng Li^b^,^c()

a School of Pharmacy, Guilin Medical University, Guilin, Guangxi 541004
b Guangxi Key Laboratory of Plant Functional Phytochemicals and Sustainable Utilization, Guangxi Institute of Botany, Guangxi Zhuang Autonomous Region and Chinese Academy Sciences, Guilin, Guangxi 541006
c Engineering Research Center of Innovative Traditional Chinese, Zhuang and Yao Materia Medica, Ministry of Education, Guangxi University of Chinese Medicine, Nanning, Guangxi 530200

Received:2023-10-22 Revised:2023-11-28 Published:2023-12-15
Contact: * E-mail: yxrxl@sina.cn; ldp@gxib.cn
Supported by:
Natural Science Foundation of Guangxi(2020GXNSFBA297055); Guangxi Science and Technology Base and Talent Project (Guike AA21196009); National Key Research and Development Program(2022YFD1600302); National Natural Science Foundation of China(U20A2004); Basic Research Fund of Guangxi Academy of Sciences(CQZ-C-1901); Guilin Innovation Platform and Talent Plan(20210102-3); Key Area Research and Development Program of Guangdong Province(2020B1111110003)

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摘要/Abstract

采用多种色谱分离技术对楝科(Meliaceae)地黄连属(Munronia)羽状地黄连(Munronia pinnata W. Theobald)(矮陀陀)的地上部分进行化学成分研究, 从其95%乙醇部分中分离得到10个化合物, 并通过MS、IR、1D-和2D-NMR等谱学手段和量子化学计算方法等技术手段对其结构进行了鉴定, 分别为矮陀陀脂肪酸苷A (1)、2-[6-O-((2E)-6R-羟基-2,6-二甲基-2,7-辛二烯基)-β-D-吡喃葡萄糖基]-2-甲基乳酸氧苷(2)、山奈酚-3-O-(6''-O-反式对香豆酰基)-β-D-吡喃葡萄糖苷(3)、栗苷A (4)、山奈酚-3-O-(6''-O-顺式对香豆酰基)-β-D-吡喃葡萄糖苷(5)、金色酰胺醇酯(6)、布卢门醇A (7)、蚱蜢酮(8)、curcusinol (9)和黑麦草素内脂(10). 其中化合物1为新化合物, 化合物2的NMR数据为首次报道. 生物活性筛查显示化合物1在160 μmol/L的浓度下对HCT116、A549、HepG2、MCF7和MDAMB等肿瘤细胞均无细胞毒性作用.

关键词: 楝科, 矮陀陀, 矮陀陀脂肪酸苷A, 结构鉴定

The chemical constituents of the aerial parts of Munronia pinnata W. Theobald were investigated by using chro- matographic techniques. Ten compounds were isolated from the 95% ethanol extract of Munronia pinnata. Their structures were identified as munrofatty A (1), 2-[[6-O-((2E)-6R-hydroxy-2,6-dimethyl-2,7-octadienoyl)-β-D-glucopyranosyl]oxy]-2- methylpropanoic acid (2), kaempferol-3-O-(6-O-trans-p-coumaroyl)-β-D-glucopyranoside (3), castanoside A (4), kaempferol- 3-O-(6''-O-cis-pcoumaroyl)-β-D-glucopyranoside (5), aurantiamide acetate (6), blumenol A (7), grasshopper ketone (8), curcusinol (9) and loliolide (10) through detailed analyses of various technical means, including MS, IR, 1D- and 2D-NMR spectroscopic methods, quantum calculation methods and other technical means. Compound 1 is a new compound, while NMR data of compound 2 are presented for the first time. Compound 1 was evaluated for cytotoxicity against HCT116, A549, HepG2, MCF7 and MDAMB cells, and was non-toxic to the tested cells at a concentration of 160 μmol/L.

Key words: meliaceae, Munronia pinnata, munrofatty A, structural identification

引用此文

刘培源, 韦玉璐, 宋静茹, 颜小捷, 卢凤来, 陈月圆, 羊学荣, 李典鹏. 矮陀陀中一个新的脂肪酸苷类化合物[J]. 有机化学, 2024, 44(4): 1348-1356.

Peiyuan Liu, Yulu Wei, Jingru Song, Xiaojie Yan, Fenglai Lu, Yueyuan Cheng, Xuerong Yang, Dianpeng Li. A New Fatty Acid Glycoside Compound in Munronia Pinnata[J]. Chinese Journal of Organic Chemistry, 2024, 44(4): 1348-1356.

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No.	1			2
No.	δ_C (type)	δ_H (J in Hz)		δ_C (type)	δ_H (J in Hz)
1 2 3 4 5 6 7 8 9 10 11 12 1' 2' 3' 4' 5' 6' 1'' 2'' 3'' 4''	169.9 (C) 125.9 (C) 140.5 (CH) 143.3 (CH) 128.6 (CH) 38.1 (CH₂) 40.1 (CH) 71.9 (CH) 40.6 (CH₂) 175.2 (CH) 12.6 (CH₃) 14.1 (CH₃) 99.9 (CH) 71.8 (CH) 78.3 (CH) 75.3 (CH) 75.5 (CH) 65.2 (CH₂) 179.0 (C) 80.4 (C) 24.6 (CH₃) 26.9 (CH₃)	— — 7.22 (d, J=11.3 Hz) 6.13 (dd, J=14.9, 11.3 Hz) 6.42~6.52 (m) 2.05~2.14 (m) 2.37~2.43 (m) 1.66~1.74 (m) 3.99 (dt, J=4.4, 4.1 Hz) 2.43~2.49 (m) — 1.92 (s) 0.93 (s) 4.55 (d, J=7.8 Hz) 3.28~3.30 (m) 3.41 (dd, J=9.0, 9.0 Hz) 3.25~3.28 (m) 3.52 (ddd, J=9.6, 7.3, 2.1 Hz) 4.18 (dd, J=11.8, 7.3 Hz) 4.48 (dd, J=11.8, 2.1 Hz) — — 1.51 (s) 1.46 (s)		169.5 (C) 128.4 (C) 144.4 (CH) 24.5 (CH₂) 41.8 (CH₂) 73.6 (C) 146.0 (CH) 112.4 (CH₂) 12.4 (CH₃) 27.8 (CH₃) — — 99.9 (CH) 71.8 (CH) 78.3 (CH) 75.3 (CH) 75.5 (CH) 65.2 (CH₂) 179.5 (C) 80.2 (C) 27.0 (CH₃) 24.6 (CH₃)	— — 6.81 (tq, J=7.7, 1.4 Hz) 2.16~2.32 (m) 1.57~1.63 (m) — 5.92 (dd, J=17.3, 10.8 Hz) 5.06 (dd, J=10.8, 1.5 Hz) 5.23 (dd, J=17.3, 1.5 Hz) 1.82 (s) 1.28 (s) — — 4.54 (d, J=7.8 Hz) 3.24~3.30 (m) 3.37~3.43 (m) 3.24~3.30 (m) 3.51 (ddd, J=9.5, 7.2, 2.1 Hz) 4.16 (dd, J=11.8, 7.3 Hz) 4.45 (dd, J=11.8, 2.1 Hz) — — 1.50 (s) 1.46 (s)

No.	1			2
No.	δ_C (type)	δ_H (J in Hz)		δ_C (type)	δ_H (J in Hz)
1 2 3 4 5 6 7 8 9 10 11 12 1' 2' 3' 4' 5' 6' 1'' 2'' 3'' 4''	169.9 (C) 125.9 (C) 140.5 (CH) 143.3 (CH) 128.6 (CH) 38.1 (CH₂) 40.1 (CH) 71.9 (CH) 40.6 (CH₂) 175.2 (CH) 12.6 (CH₃) 14.1 (CH₃) 99.9 (CH) 71.8 (CH) 78.3 (CH) 75.3 (CH) 75.5 (CH) 65.2 (CH₂) 179.0 (C) 80.4 (C) 24.6 (CH₃) 26.9 (CH₃)	— — 7.22 (d, J=11.3 Hz) 6.13 (dd, J=14.9, 11.3 Hz) 6.42~6.52 (m) 2.05~2.14 (m) 2.37~2.43 (m) 1.66~1.74 (m) 3.99 (dt, J=4.4, 4.1 Hz) 2.43~2.49 (m) — 1.92 (s) 0.93 (s) 4.55 (d, J=7.8 Hz) 3.28~3.30 (m) 3.41 (dd, J=9.0, 9.0 Hz) 3.25~3.28 (m) 3.52 (ddd, J=9.6, 7.3, 2.1 Hz) 4.18 (dd, J=11.8, 7.3 Hz) 4.48 (dd, J=11.8, 2.1 Hz) — — 1.51 (s) 1.46 (s)		169.5 (C) 128.4 (C) 144.4 (CH) 24.5 (CH₂) 41.8 (CH₂) 73.6 (C) 146.0 (CH) 112.4 (CH₂) 12.4 (CH₃) 27.8 (CH₃) — — 99.9 (CH) 71.8 (CH) 78.3 (CH) 75.3 (CH) 75.5 (CH) 65.2 (CH₂) 179.5 (C) 80.2 (C) 27.0 (CH₃) 24.6 (CH₃)	— — 6.81 (tq, J=7.7, 1.4 Hz) 2.16~2.32 (m) 1.57~1.63 (m) — 5.92 (dd, J=17.3, 10.8 Hz) 5.06 (dd, J=10.8, 1.5 Hz) 5.23 (dd, J=17.3, 1.5 Hz) 1.82 (s) 1.28 (s) — — 4.54 (d, J=7.8 Hz) 3.24~3.30 (m) 3.37~3.43 (m) 3.24~3.30 (m) 3.51 (ddd, J=9.5, 7.2, 2.1 Hz) 4.16 (dd, J=11.8, 7.3 Hz) 4.45 (dd, J=11.8, 2.1 Hz) — — 1.50 (s) 1.46 (s)

矮陀陀中一个新的脂肪酸苷类化合物

A New Fatty Acid Glycoside Compound in Munronia Pinnata

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