白扁豆化学成分的分离与结构鉴定

Isolation and structural identification of chemical constituents from Dolichos lablab seeds

摘要

目的 对白扁豆的化学成分进行研究,以明确其物质基础。方法 综合利用多种色谱法对白扁豆体积分数70%乙醇提取物的化学成分进行分离纯化,并采用核磁共振波谱和质谱技术鉴定化合物结构。结果 从该提取物中分离鉴定了1个新化合物dolilabphenoside A₂(1)和6个已知化合物,分别为山奈酚-3-O-芸香糖苷(2)、山奈酚-3-O-洋槐糖苷(3)、山奈酚-3-O-芸香糖-7-O-葡萄糖苷(4)、山奈酚-3-O-{β-D-葡萄糖基-(1→2)-[α-L-鼠李糖基(1→6)-β-D-葡萄糖苷]}(5)、芦丁(6)和槲皮素-3-O-洋槐糖苷(7),化合物4~6为首次从扁豆属植物中分离得到。结论 这些发现拓展了人们对白扁豆植物化学成分的认识,为后续的药理学研究奠定了基础。

Abstract

Objective To investigate the chemical constituents of Dolichos lablab seeds to elucidate its material basis. Methods The chemical components of the 70% ethanol extract of D. lablab seeds were systematically isolated and purified using various chromatographic techniques. Structural identification of the obtained compounds was performed through nuclear magnetic resonance spectroscopy and mass spectrometry. Results Seven compounds were successfully isolated and characterized, including a novel compound, dolilabphenoside A₂ (1), as well as six known ones, nicotiflorin (2), kaempferol-3-robinobioside (3), kaempferol-3-O-rutinoside-7-O-glucoside (4), kaempferol-3-O-{β-D-glucopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranoside] (5), rutin (6), and quercetin 3-O-robibioside (7). Notably, compounds 4-6 were isolated from the genus Lablab for the first time. Conclusion These findings expand the understanding of the phytochemical composition of D. lablab seeds, providing a foundation for further pharmacological research.

关键词

白扁豆 / 化学成分 / 分离 / 结构鉴定

Key words

Dolichos lablab seeds / chemical constituent / isolation / structural identification

参考文献

[1] Chinese Pharmacopoeia Commission. Chinese Pharmacopoeia: Part 1 Chinese(中华人民共和国药典:一部)[M]. Beijing: China Medical Science and Technology Press, 2020.

[2] CHUN E, YOON S, PARVEEN A, et al. Alleviation of irritable bowel syndrome-like symptoms and control of gut and brain responses with oral administration of Dolichos lablab L. in a mouse model[J]. Nutrients, 2018, 10(10): 1475-1491.

[3] MOMIN M A M, HABIB M R, HASAN M R, et al. Anti-inflammatory, antioxidant and cytotoxicity potential of methanolic extract of two bangladeshi bean Lablab purpureus (l) sweet white and purple[J]. Int J Pharm Sci Res, 2012, 3(3): 776-781.

[4] ZHANG W, LI F, CHENG J, et al. Saponins from Dolichos lablab seeds with anti-inflammatory activity[J]. Bioorg Chem, 2024, 151: 107692.

[5] ZHANG W, CHENG J, RUAN J, et al. Aromatic compounds from the seeds of Dolichos lablab L. with anti-inflammatory activity[J]. Fitoterapia, 2023, 171: 105694.

[6] ZHANG W, RUAN J, CHENG J, et al. In vitro anti-inflammatory terpenoid glycosides from the seeds of Dolichos lablab[J]. Molecules, 2025, 30(8): 1779.

[7] ZHANG Y, RUAN J, YANG D, et al. Isolation and absolute configuration determination of Danshensu derivatives from the areial part of Clerodendranthus spicatus[J]. Journal of Shenyang Pharmaceutical University(沈阳药科大学学报), 2024, 41(7): 900-905, 928.

[8] ZHANG Q, YANG D, SHI Z, et al. Isolation and structural identification of C-glycosyl flavonoids from the leaves of Ohwia caudata (Thunberg) H. Ohashi[J]. Journal of Shenyang Pharmaceutical University(沈阳药科大学学报), 2024, 41(9): 1180-1189.

[9] FAROKHI-FIROOZI H, RAHAVI M, PIRALI-HAMEDANI M, et al. Essential oil analysis and isolation of coumarins and flavonol glycosides of Ferula goangulata (Schltdl.) Boiss. fruits[J]. Pharm Sci, 2021, 27(1): 139-146.

[10] LEONG C N, TAKO M, HANASHIRO I, et al. Antioxidant flavonoid glycosides from the leaves of Ficus pumila L[J]. Food Chem, 2008, 109(2): 415-420.

[11] BUDZIANOWSKI J. Kaempferol glycosides from Hosta ventricosa[J]. Phytochemistry, 1990, 29(11): 3643-3647.

[12] WANG L, WEI H, WANG J, et al. Investigation of chemical constituents of Mongolia medicine Hostae Flos (II)[J]. Chinese Traditional and Herbal Drugs(中草药), 2019, 50(2): 330-335.

[13] SHI S Y, CUI H H, YIN Y Q, et al. Chemical constituents from Calystegia sepium[J]. Chinese Traditional and Herbal Drugs(中草药), 2019, 50(1): 36-41.

[14] ZHANG W, ZHOU G, XIE E, et al. Study on the flavonoid constituents from the leaves of Turpinia arguta[J]. China Journal of Chinese Materia Medica(中国中药杂志), 2009, 34(12): 1603-1604.

[15] SUN X, TAN Y, ZHOU F, et al. Research progress in the treatment of ulcerative colitis with phenolic acid compounds[J]. Zhongyiyao Daobao(中医药导报), 2022, 28(2): 123-126, 130.

[16] LI T, ZOU Q, MAO Z, et al. Therapeutic effect of flavonoids from Desmodium triflorum on an ulcerative colitis mouse model and the influence on intestinal flora[J]. Chinese Journal of Comparative Medicine(中国比较医学杂志), 2022, 32(4): 29-38.

[17] LIU J. Effect and mechanism of rutin in relieving colitis in mice on JAK2 signaling pathway(基于JAK2信号通路探索芦丁缓解小鼠结肠炎作用及相关机制)[D]. Dalian: Dalian Medical University, 2021.

基金资助

国家自然科学基金资助项目面上项目(82574549)