Phenylpropanoid and Iridoid Glucosides from the Whole Plant of Hemiphragma heterophyllum and Their alpha-Glucosidase Inhibitory Activities

Yan-Hong Li; Jia-Meng Dai; Cui Yang; Meng-Yuan Jiang; Yong Xiong; Yu-Kui Li; Hong-Rui Li; Kai Tian; Xiang-Zhong Huang

doi:10.1055/a-1081-7220

Planta Medica, Inhaltsverzeichnis

Planta Med 2020; 86(03): 205-211
DOI: 10.1055/a-1081-7220

Biological and Pharmacological Activity

Original Papers

Georg Thieme Verlag KG Stuttgart · New York

Phenylpropanoid and Iridoid Glucosides from the Whole Plant of Hemiphragma heterophyllum and Their alpha-Glucosidase Inhibitory Activities

Authors

Yan-Hong Li

Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission & Ministry of Education, Yunnan Minzu University, Kunming, Yunnan, P. R. China
Jia-Meng Dai

Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission & Ministry of Education, Yunnan Minzu University, Kunming, Yunnan, P. R. China
Cui Yang

Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission & Ministry of Education, Yunnan Minzu University, Kunming, Yunnan, P. R. China
Meng-Yuan Jiang

Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission & Ministry of Education, Yunnan Minzu University, Kunming, Yunnan, P. R. China
Yong Xiong

Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission & Ministry of Education, Yunnan Minzu University, Kunming, Yunnan, P. R. China
Yu-Kui Li

Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission & Ministry of Education, Yunnan Minzu University, Kunming, Yunnan, P. R. China
Hong-Rui Li

Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission & Ministry of Education, Yunnan Minzu University, Kunming, Yunnan, P. R. China
Kai Tian

Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission & Ministry of Education, Yunnan Minzu University, Kunming, Yunnan, P. R. China
Xiang-Zhong Huang

Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission & Ministry of Education, Yunnan Minzu University, Kunming, Yunnan, P. R. China

Abstract

Three phenylpropanoid glucosides (1 – 3) and one iridoid glucoside (11), together with eleven known glucosides, were isolated from the ethanol extract of the whole plant of Hemiphragma heterophyllum. Their structures were elucidated by means of 1D and 2D NMR spectroscopy, HRMS, and chemical methods. All compounds except 11 and 13 – 15 showed varying degrees of α-glucosidase inhibitory activity. Compounds 5, 9, and 12 were marginally active in the bioassay, while compounds 1 – 4, 6 – 8, and 10 exhibited appreciable inhibitory activity with an IC₅₀ value of 33.6 ~ 83.1 µM, which was much lower than that of the positive control acarbose (IC₅₀ = 310.8 µM).

Key words

Hemiphragma heterophyllum - Scrophulariaceae - phenylpropanoid glucosides - iridoid glucosides - α-glucosidase inhibitor activity

Volltext

Referenzen

References
1 Flora of China Editorial Committee, Chinese Academy of Sciences. Flora of China, Vol. 67. Beijing: Science Press; 1979: 222-223
2 Logistic Department and Health Ministry of Kunming Military Region. Selected medicinal Plants of Yunnan. Kunming: Logistic Department and Health Ministry of Kunming Military Region Press; 1970: 668-669
3 Yang BL. Ethnic Yi herbal Medicine in China. Kunming: Yunnan Minorities Press; 2004: 512-513
4 Yang MF, Li YY, Li BG, Zhang GL. A new monoterpene glycoside from Hemiphragma heterophyllum . Acta Bot Sin 2004; 46: 1454-1457
5 Jin H, Mori A, Tanaka T, Kouno I, lshimaru K. A new phenylethanoid glycoside from Hemiphragma heterophyllum . Jpn Soc Food Chem 2006; 13: 83-86
6 Dai JM, Li YH, Pu XY, Yang C, Sun JX, Ruan R, Li XN, Tian K, Huang XZ. Chemical constituents from the whole herb of Hemiphragma heterophyllum . J Asian Nat Prod Res 2019; 21: 551-558
7 Tian L, Zhou JY. [Studies on chemical constituents from herb of Hemiphragma heterophyllum]. Chin J Chin Mater Med 2004; 29: 528-531
8 Ma WG, Li XC, Liu YQ, Li QS, Yang CR. Phenylpropanoid and iridoid glycosides from Hemiphragma heterophyllum . Acta Bot Yunnanica 1995; 17: 96-102
9 Lu Y, Dai JM, Li YH, Yang C, Tian K, Wang W, Yang Z, Ruan R, Huang XZ. Study on the flavonoids from Hemiphragma heterophyllum Wall. Chin J Ethnomed Ethnopharm 2017; 26: 21-24
10 de Souza TB, Brito KM, Silva NC, Rocha RP, de Sousa GF, Duarte LP, Coelho LF, Dias AL, Veloso MP, Carvalho DT, Dias DF. New eugenol glucoside-based derivative shows fungistatic and fungicidal activity against opportunistic Candida glabrata . Chem Biol Drug Des 2016; 87: 83-90
11 Jo Y, Kim M, Shin MH, Chung HY, Jung JH, Im KS. Antioxidative phenolics from the fresh leaves of Ternstroemia japonica . J Nat Prod 2006; 69: 1399-1403
12 Ersöz T, Taşdemir D, Çaliş İ. Phenylethanoid glycosides from Scutellaria galericulata . Turk J Chem 2002; 26: 465-471
13 Liu YG, Li X, Xiong DC, Yu B, Pu X, Ye XS. Synthetic phenylethanoid glycoside derivatives as potent neuroprotective agents. Eur J Med Chem 2015; 95: 313-323
14 Ashik M, Flowers MA, Karagianis G, Waterman PG. New phenolic glycosides from the stems and leaves of Casearia multinervosa . Nat Prod Res 2006; 20: 641-647
15 Ravn H, Nishibe S, Sasahara M, Bo LX. Phenolic compounds from Plantago asiatica . Phytochemistry 1990; 29: 3627-3631
16 Kikuchi M, Yamauch Y. Isolation and structure of new p-coumaroyl glycosides, osmanthuside A, B and C from the leaves of Osmanthus fragrans . J Pharmaceutical Soc Japan 1985; 105: 411-414
17 Miyase T, Ishino M, Akahori C, Ueno A, Ohkawa Y, Tanizawa H. Phenylethanoid glycosides from Plantago asiatica . Phytochemistry 1991; 30: 2015-2018
18 Wang H, Wu FH, Xiong F, Wu JJ, Zhang LY, Ye WC, Li P, Zhao SX. Iridoids from Neopicrorhiza scrophulariiflora and their hepatoprotective activities in vitro . Chem Pharm Bull 2006; 54: 1144-1149
19 Tasdemir D, Scapozza L, Zerbe O, Linden A, Çalis I, Sticher O. Iridoid glycosides of Leonurus persicus . J Nat Prod 1999; 62: 811-816
20 Machida K, Takehara E, Kobayashi H, Kikuchi M. Studies on the constituents of Gardenia species. III. New iridoid glycosides from the leaves of Gardenia jasminoides cv. fortuneana HARA. Chem Pharm Bull 2003; 51: 1417-1419
21 Ahmed B, Al-Rehaily AJ, Al-Howiriny TA, El-Sayed KA, Ahmad MS. Scropolioside-D₂ and harpagoside-B: two new iridoid glycosides from Scrophularia deserti and their antidiabetic and antiinflammatory activity. Biol Pharm Bull 2003; 26: 462-467
22 Van der Eycken E, De Bruyn A, Van der Eycken J, Callant P, Vandewalle M. Iridoids: The structure elucidation of specionin based on chemical evidence and ¹H NMR analysis. Tetrahedron 1986; 42: 5385-5396
23 Khan IA, Erdelmeier CA, Sticher O, Rali T. New phenolic glucosides from the leaves of Eurya tigang . J Nat Prod 1992; 55: 1270-1274
24 Furukawa M, Makino M, Ohkoshi E, Uchiyama T, Fujimoto Y. Terpenoids and phenethyl glucosides from Hyssopus cuspidatus (Labiatae). Phytochemistry 2011; 72: 2244-2252
25 Ishiura A, Kizu H, Tomimori T. On the constituents of the leaves of Scutellaria scandens Buch-Ham. ex D. Don. Jpn J Pharmacogn 1993; 47: 287-290
26 Hanhineva K, Soininen P, Anttonen MJ, Kokko H, Rogachev I, Aharoni A, Laatikainen R, Kärenlampi S. NMR and UPLC-qTOF-MS/MS characterisation of novel phenylethanol derivatives of phenylpropanoid glucosides from the leaves of strawberry (Fragaria × ananassa cv. Jonsok). Phytochem Anal 2009; 20: 353-364
27 Hou CC, Lin SJ, Cheng JT, Hsu FL. Bacopaside III, bacopasaponin G, and bacopasides A, B, and C from Bacopa monniera . J Nat Prod 2002; 65: 1759-1763
28 Sugiyama M, Kikuchi M. Study on the constituents of Osmanthus species. VI. Structures of phenylethanoid glycosides from the leaves of Osmanthus asiaticus Nakai. Chem Pharm Bull 1990; 38: 2953-2955
29 Kim MR, Lee SK, Kim CS, Kim KS, Moon DC. Phytochemical constituents of Carpesium macrocephalum F_R- et S_AV- . Arch Pharm Res 2004; 10: 1029-1033
30 He LY, Huang HJ. Chemical constituents of methanol portion of Illicium henryi . Chin J Chin Mater Med 2014; 39: 857-859
31 Chaudhuri RK, Sticher O. New iridoid glucosides and a lignan diglucoside from Globularia alypum L. Helv Chim Acta 1981; 64: 3-15
32 Sticher O, Meier B, Lehmann D, Swiatek L. Scrophulariosid, ein neues iridoidglucosid aus Scrophularia lateriflora . Planta Med 1980; 38: 246-254
33 Junior P. Iso-scrophulariosid, ein neues Iridoidgiucosid aus Penstemon eriantherus . Planta Med 1981; 43: 34-38
34 Li T, Zhang X, Song Y, Liu J. A microplate based screening method for α-glucosidase inhibitors. Chin J Clin Pharmacol 2005; 10: 1128-1134
35 Yang XW, Ma YL, He HP, Wang YH, Di YT, Zhou H, Li L, Hao XJ. Iridoid constituents of Tarenna attenuata . J Nat Prod 2006; 69: 971-974

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