Summary
Ilex cornuta (I. cornuta) is a traditional Chinese medicine (TCM) that has been used in clinical practice for hundreds of years. In order to provide more information about the chemical basis of its pharmacological effects, phytochemical investigation on the roots of I. cornuta was conducted in this study. The roots of the plant were firstly extracted with 95% EtOH, and then the crude was partitioned with petroleum ether, EtOAc and n-butyl alcohol. Different chromatographies were employed to isolate the crude step by step and the crude was further purified by semipreparative high performance liquid chromatography (HPLC). As a result, two new triterpenoid saponins (1, 2), together with 12 known compounds (3–14), were isolated from the roots of I. cornuta. Their structures were determined based on nuclear magnetic resonance (NMR), mass spectrum (MS) technologies, chemical reactions as well as gas chromatography (GC). Compounds 4, 6, 8, 11, 12 and 13 were isolated from this genus for the first time. The structures of compounds 1 and 2 were determined as 3β-O-α-D-xylopyranosyl-(1→3)-α-L-2-O-acetylarabinopyranosyl-(1→2)-β-D glucopyranosyl-23-hydroxyl-20α(H)-urs-12-en-28-oic acid 28-O-β-D-glucopyranosyl ester (1) and 3β-O-α-D-xylopyranosly-(1→3)-α-L-2-O-acetylarabinopyranosyl-(1→2)-β-Dglucopyranosyl- 19α,23-dihydroxyl-20α(H)-urs-12-en-28-oic acid 28-O-β-D-glucopyranosyl ester (2).
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References
Fan LL, Zhong C, Feng YL, et al. Chemical constituents in roots of Ilex cornuta. Chin Tradit Herb Drugs (Chinese), 2011,42(2):234–236
Chen Y, Li KS, Xie TG. Hypotensive action of the extract of Kudingcha dongqingye (Ilex kudingcha). Chin Tradit Herb Drugs (Chinese), 1995,26(5): 250–252
Zhou SX, Yao ZR, Li J, et al. Flavonoids from the leaves of Ilex cornuta. Chin J Nat Med (Chinese), 2012,10(2):84–87
Nishimura K, Miyase T, Noguchi H. Triterpenoid Saponins from Ilex kudincha. J Nat Prod, 1999,62(8): 1128–1133
Zuo WJ, Zeng YM, Hu Y, et al. A new triterpene saponin from the leaves of Ilex kudincha. Chin Chem Lett, 2009,20(11):1331–1334
Ouyang MA, Yang CR, Chen ZL, et al. Triterpenes and triterpenoid glycosides from the leaves of Ilex kudincha. Phytochemistry, 1996,41(3):871–877
Li WL, Wu JL, Ren BR, et al. Chemical constituents of Chinese holly (Ilex cornuta Lindl. ex Paxt.). Zhiwu Ziyuan Yu Huanjing Xuebao (Chinese), 2003,12(2):1–5
Wang WL, Zhou X, Liu YL, et al. Two new 20α±(H)-ursane-type triterpenoids from Ilex cornuta and their cytotoxic activities. J Asian Nat Prod Res, 2014,16(2):175–180
Wu T, Li Y, Tang QJ, et al. Two unusual minor 18, 19-seco-ursane glycosides from leaves of Ilex cornuta. Food Chem, 2008,111(1):78–82
Li WL, Wu JL, Ren BR, et al. Pharmacological action of 3 compounds isolated from Ilex cornuta Lindl. ex Paxt. for angiocardiopathy. Zhiwu Ziyuan Yu Huanjing Xuebao (Chinese), 2003,12(3):6–10
Li SS, Zhao JP, Liu YL, et al. New triterpenoid saponins from Ilex cornuta and their protective effects against H2O2-induced myocardial cell injury. J Agric Food Chem (Chinese), 2014,62(2):488–496
Andrade FDPD, Piacente S, Pizza C, et al. Studies on the constituents of a Brazilian folk infusion, isolation and structure elucidation of new triterpene saponins from Ilex amara leaves. J Agric Food Chem, 2002,50(2):255–261
Wang JZ, Ye LM, Chen XB. A new C27-steroidal glycoside from Ophiopogon japonicus. Chin Chem Lett (Chinese), 2008,19(1):82–84
Pei YH, Hua Hm, Li ZL, et al. Application of nuclear magnetic resonance to the determination of the configuration of glycoside bond. Acta Pharm Sinica, 2011,46(2):127–131
Patra A, Chaudhuri SK, Panda SK. Betulin-3-caffeate from Quercus suber, 13C-NMR spectra of some lupenes. J Nat Prod, 1988,51(2):217–220
Li JJ, Yang J, Lv F, et al. Chemical constituents from the stems of Celastrus orbiculatus. Chin J Nat Med, 2012,10(4):279–283
Nishimura K, Fukuda T, Miyase T, et al. Activityguided isolation of triterpenoid acyl CoA cholesteryl acyl transferase (ACAT) inhibitors from Ilex kudincha. J Nat Prod, 1999,62(7):1061–1064
Cho JY, Kim CM, Lee HJ, et al. Caffeoyl triterpenes from pear (Pyrus pyrifolia Nakai) fruit peels and their antioxidative activities against oxidation of rat blood plasma. J Agric Food Chem, 2013,61(19):4563–4569
Liu JB, Zhang Y, Cui BS, et al. Chemical constituents from twigs of Myricaria bracteata. Chin Tradit Herb Drugs (Chinese), 2013,44(19):2661–2665
Lei T, Jiang HY, Hu Y, et al. Chemical Constituents of Parabarium huaitingii. Chin J Nat Med (Chinese), 2011,9(3):185–187
Zhu JH, Yu RM, Yang Y, et al. Two new compounds from transgenic Panax quinquefolium. Fitoterapia, 2010,81(5):339–342
Nan ZD, Zhao MB, Jiang Y, et al. Chemical constituents from stems of Cistanche deserticola cultured in Tarim desert. Chin J Chin Mater Med (Chinese), 2013,38(16):2665–2670
Jung K, Chin YW, Kim YC, et al. Potentially hepatoprotective glycolipid constituents of Lycium chinense fruits. Arch Pharm Res, 2005,28(12):1381–1385
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This study was supported by the National Natural Science Foundation of China (No. 81470157), the Natural Science Foundation of Hubei Province of China (No. 2017CFB650) and Wuhan Science and Technology Project (No. 2017060201010215).
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Zhan, Hx., Li, J., Ruan, Hl. et al. Two New Ursane-type Triterpenoid Glycosides from Ilex Cornuta. CURR MED SCI 38, 976–981 (2018). https://doi.org/10.1007/s11596-018-1972-4
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DOI: https://doi.org/10.1007/s11596-018-1972-4