Multiple in vitro biological effects of phenolic compounds from Terminalia chebula var. tomentella

doi:10.1016/j.jep.2021.114135

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	Multiple in vitro biological effects of phenolic compounds from Terminalia chebula var. tomentella
	Zhang,Xiao-Rui ; Qiao,Yi-Jun ; Zhu,Hong-Tao ; Kong,Qing-Hua ; Wang,Dong; Yang,Chong-Ren ; Zhang,Ying-Jun
	2021
发表期刊	JOURNAL OF ETHNOPHARMACOLOGY
ISSN	0378-8741
卷号	275 页码:114135
摘要	Ethnopharmacological relevance: Terminalia chebula (TC), a well-known Indian Ayurvedic medicine introduced into China in the Sui and Tang Dynasties, has been recorded and used medicinally as Fructus Chebulae, together with its variety tomentella (TCT) in the Chinese Pharmacopoeia. They have been also used commonly for the treatment of diabetes mellitus by Tibetan medicine.Aim of the study: To investigate the main bioactive and therapeutic principles in the fruits of TCT, based on the extensive evaluation of their anti-inflammatory and hypoglycemic activities.Materials and methods: The TCT fresh fruits were analyzed by HPLC and separated further by column chromatography and preparative HPLC. The isolated compounds were identified by extensive spectroscopic analyses, including 1D/2D NMR, MS, UV, IR and ECD. Anti-inflammatory activity was evaluated by inhibition of NO production in RAW264.7 cells. The specific iNOS (PDB ID: 3E7G) structure was prepared by Discovery Studio 4.0, and the molecular docking simulation was performed on GOLD (version 5.2.2). Hypoglycemic activity was measured using the substrate solution of 4-nitrophenyl-alpha-D-glucopyranoside enzyme and buffer solution.Results: The HPLC analysis method of polyphenols in the fruits of TCT was established, and 13 main chromatographic peaks were identified, including six hydrolyzable tannins (2, 4-7, 10-11), three simple phenols (12-14), and one oleanane pentacyclic triterpene, arjungenin. Extensive chromatographic separation of TCT fresh fruits yielded 14 compounds, including one new natural hydrolyzable tannin, 2,3-(S)-HHDP-6-O-galloyl-Dglucose (1). The known compounds were identified as 10 hydrolyzable tannins (2-11) and three simple phenols (12-14). Compounds 10 (IC50 = 36.43 +/- 0.21 mu M), 11 (IC50 = 42.28 +/- 0.09 mu M) displayed stronger NO inhibitory activity than the positive control L-NMMA (IC50 = 42.34 +/- 0.66 mu M), while 2, 4, and 9 showed moderate inhibitory activity against NO production. Further molecular docking simulation of specific iNOS on 10 and 11, as well as five previously isolated lignans 15-19 showed that there were no obvious rules between docking results and the in vitro NO inhibitory activity for hydrolyzable tannins (10 and 11), while the mechanism of anti-inflammatory activity for lignans was related to the substitution of conjugated aldehyde groups. Moreover, most of the hydrolyzable tannins (1-2, 4-5, 9-11) and simple phenol (12) displayed stronger inhibitory effects on alpha-glucosidase than the positive control, quercetin (IC50 = 6.118 +/- 0.071 mu M), with IC50 values ranging from 0.079 to 16.494 mu M. Among these bioactive isolates, the hydrolyzable tannins 2, 4-5, and 9-11, and simple phenol 12 are major chemical components in TCT fruit. Conclusions: The results showed that lignans and hydrolyzed tannins are the main active ingredients of TCT fruits, responsible for the traditional treatment of sore throat and cough. Moreover, hydrolyzed tannins and simple phenolic compounds with potential hypoglycemic activity are closely related to the ethno-pharmacological uses of TCT fruits on diabetes in Tibetan medicine.
关键词	Terminalia chebula var tomentella Combretaceae Fructus Chebulae Hydrolyzed tannins Simple phenolic compounds Anti-inflammation Anti-diabetes NITRIC-OXIDE ANTIOXIDANT TANNINS CONSTITUENTS VALIDATION ALGORITHM ESTERS FRUITS
DOI	10.1016/j.jep.2021.114135
WOS记录号	WOS:000657648900002
引用统计	被引频次：9[WOS] [WOS记录] [WOS相关记录]
文献类型	期刊论文
条目标识符	http://ir.kib.ac.cn/handle/151853/73041
专题	中国科学院昆明植物研究所
作者单位	1.[Zhang, Xiao-Rui 2.Qiao, Yi-Jun 3.Zhu, Hong-Tao 4.Kong, Qing-Hua 5.Wang, Dong 6.Yang, Chong-Ren 7.Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650201, Yunnan, Peoples R China 8.Univ Chinese Acad Sci, Beijing 100049, Peoples R China 9.Chinese Acad Sci, Kunming Inst Bot, Yunnan Key Lab Nat Med Chem, Kunming 650201, Yunnan, Peoples R China
推荐引用方式 GB/T 7714	Zhang,Xiao-Rui,Qiao,Yi-Jun,Zhu,Hong-Tao,et al. Multiple in vitro biological effects of phenolic compounds from Terminalia chebula var. tomentella[J]. JOURNAL OF ETHNOPHARMACOLOGY,2021,275:114135.
APA	Zhang,Xiao-Rui.,Qiao,Yi-Jun.,Zhu,Hong-Tao.,Kong,Qing-Hua.,Wang,Dong.,...&Zhang,Ying-Jun.(2021).Multiple in vitro biological effects of phenolic compounds from Terminalia chebula var. tomentella.JOURNAL OF ETHNOPHARMACOLOGY,275,114135.
MLA	Zhang,Xiao-Rui,et al."Multiple in vitro biological effects of phenolic compounds from Terminalia chebula var. tomentella".JOURNAL OF ETHNOPHARMACOLOGY 275(2021):114135.

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