血人參石油醚部位化學成分研究

王歡^1,2, 周謠^1,2, 張燦¹, 劉青³, 周萍³, 李金玉^1,2, 婁華勇^1,2, 潘衛東^1,2*

1. 貴州醫科大學省部共建藥用植物功效與利用國家重點實驗室/藥學院, 貴陽 550025;2.貴州省中國科學院天然產物化學重點實驗室,貴陽 550014;3. 貴陽德昌祥藥業有限公司,貴陽 550200

摘要:

為深入探究血人參中的活性物質成分,該文采用硅膠柱色譜、Sephadex LH-20柱色譜、半制備高效液相色譜以及重結晶等方法對血人參石油醚部位進行了系統分離純化,并利用現代波譜技術對分離得到的單體化合物進行結構鑒定。結果表明:從血人參石油醚部位共分離得到22個單體化合物,分別鑒定為β-谷甾酮(1)、豆甾烷3,6-二酮(2)、6β-羥基-豆甾-4-烯-3-酮(3)、(22E)-5α,8α-epidioxyergosta-6, 22-dien-3β-ol(4)、美迪紫檀素(5)、sativan(6)、2',4'-二羥基查爾酮(7)、6,7-dimethoxy-4-hydroxy-1-naphthoic acid(8)、對羥基苯甲酸乙酯(9)、2,4-二羥基苯甲酸乙酯(10)、(9E,11E)-13-oxo-9,11-ocatadecadienoic acid(11)、(9E,11E)-13-oxo-9,11-octadecadienoic acid methyl ester(12)、9-oxo-10E,12E-octadecadienoic acid methyl ester(13)、9-hydroxy-10E,12Z-octadecadienoic acid methyl ester(14)、pinellic acid(15)、9-oxo-10E,12E-octadecadienoic acid-(2S)-2,3-dihydroxypropyl ester(16)、β-谷甾醇(17)、白樺脂酸(18)、3β-hydroxyolean-12-en-11-one(19)、高麗槐素(20)、珊瑚菜素(21)、棕櫚酸(22)。其中,化合物1-3、7、11-16均為首次從豆科植物中分離得到,化合物1-16均為首次從木藍屬植物中分離得到,化合物1-16、18、19、21均為首次從血人參中分離得到。該研究結果進一步豐富了木藍屬植物血人參的化學結構類型,為該藥材的進一步開發利用奠定了科學基礎。

關鍵詞: 血人參, 木藍屬, 化學成分, 分離純化, 結構鑒定

DOI：10.11931/guihaia.gxzw202112044

分類號:Q946

文章編號:1000-3142(2023)01-0139-09

基金項目:國家自然科學基金(U1812403,32060100,32100322); 貴州省科技計劃項目(黔科合基礎-ZK [2021]一般534)。

Chemical constituents from petroleum ether part of roots of Indigofera stachyodes

WANG Huan^1,2, ZHOU Yao^1,2, ZHANG Can¹, LIU Qing³, ZHOU Ping³, LI Jinyu^1,2, LOU Huayong^1,2, PAN Weidong^1,2*

1. State Key Laboratory of Functions and Applications of Medicinal Plants/School of Pharmaceutial Sciences, Guizhou Medcial University, Guiyang 550025, China;2. Key Laboratory of Chemistry for Natural Product of Guizhou Province and Chinese Academy of Sciences, Guiyang 550014, China;3. Guiyang Dechangxiang Pharmaceutical Co., Ltd., Guiyang 550200, China

Abstract:

With the aim to investigate the active chemical constituents for the roots of Indigofera stachyodes, the petroleum ether part of this plant was separated and purified using silica gel column chromatography, Sephadex LH-20 column chromatography, semi-preparative high performance liquid chromatography, and recrystallization methods. The structures of obtained monomeric compounds were identified through modern spectral techniques by detail analysis of their electrospray ionization mass spectrometry, hydrogen and carbon nuclear magnetic resonance spectra data, as well as compared with the reported references. The results were as follows: twenty-two natural compounds were identified as β-sitostenone(1), stigmasta-3,6-di-one(2), 6β-hydroxystigmast-4-en-3-one(3),(22E)-5α,8α-epidioxyergosta-6,22-dien-3β-ol(4), medicarpin(5), sativan(6), 2',4'-dihydroxychaicone(7), 6,7-dimethoxy-4-hydroxy-1-naphthoic acid(8), p-hydroxybenzoic acid ethyl ester(9), 2,4-dihydroxybenzoic acid ethyl ester(10),(9E,11E)-13-oxo-9,11-ocatadecadienoic acid(11),(9E,11E)-13-oxo-9,11-octadecadienoic acid methyl ester(12), 9-oxo-10E,12E-octadecadienoic acid methyl ester(13), 9-hydroxy-10E,12Z-octadecadienoic acid methyl ester(14), pinellic acid(15)and 9-oxo-10E,12E-octadecadienoic acid-(2S)-2,3-dihydroxypropyl ester(16), β-sitosterol(17), betulinic acid(18), 3β-hydroxyolean-12-en-11-one(19), maackiain(20), phellopterin(21), palmitic acid(22). Of these compounds, ten compounds(compounds 1-3, 7, 11-16)were isolated from the Fabaceae for the first time; sixteen compounds(compounds 1-16)were obtained from Indigofera plant for the first time; at the same time, compounds 1-16, 18, 19, 21 were obtained from the roots of Indigofera stachyodes for the first time. Thus, the results of this research enrich the chemical structure types of roots of I. stachyodes, and afford a scientific foundation for its further rational use.

Key words: roots of Indigofera stachyodes, Indigofera, chemical constituents, isolation and purification, structural and identification