Planta Med 2012; 78(15): 1702-1705
DOI: 10.1055/s-0032-1315209
Natural Product Chemistry
Letters
Georg Thieme Verlag KG Stuttgart · New York

Antiviral Triterpenoid Saponins from the Roots of Ilex asprella

Min Zhou
1   State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, Peopleʼs Republic of China
2   Graduate University of Chinese Academy of Sciences, Beijing, Peopleʼs Republic of China
,
Min Xu
1   State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, Peopleʼs Republic of China
,
Xiao-Xia Ma
1   State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, Peopleʼs Republic of China
4   Current address: Yunnan College of Traditional Chinese Medicine, Kunming, Peopleʼs Republic of China
,
Kai Zheng
3   Guangzhou Jinan Biomedicine Research & Development Center, Guangzhou, Peopleʼs Republic of China
,
Ke Yang
3   Guangzhou Jinan Biomedicine Research & Development Center, Guangzhou, Peopleʼs Republic of China
,
Chong-Ren Yang
1   State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, Peopleʼs Republic of China
,
Yi-Fei Wang
3   Guangzhou Jinan Biomedicine Research & Development Center, Guangzhou, Peopleʼs Republic of China
,
Ying-Jun Zhang
1   State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, Peopleʼs Republic of China
› Author Affiliations
Further Information

Publication History

received 12 June 2012
revised 09 July 2012

accepted 16 July 2012

Publication Date:
13 August 2012 (online)

Abstract

Two new sulfur-containing triterpenoid saponins, asprellanosides A (1) and B (2), were isolated from the roots of Ilex asprella, together with 10 known compounds (312). An in vitro anti-HSV-1 activity test of the isolates (14, 67, and 912) showed that only asprellanoside A (1) and oblonganoside H (6) exhibited anti-HSV-1 activity with TIC values of 0.14 and 0.18 mM, respectively.

These authors contributed equally to this paper.


Supporting Information

 
  • References

  • 1 Qi YD, Ren YF. Advances of research on the roots of Ilex asprella . Asia-Pacific Tradit Med 2009; 5: 29-32
  • 2 Zhu WQ, Yan GH, Li PB. Experimental studies on anti-inflammatory activity of the water extract from Radix et Caulis llicis asprellae. J Guangdong College Pharm 2007; 23: 304-307
  • 3 Zhu WQ, Liu HS, Yan GH, Li PB. Anti-viral activity of the water extract from Radix et Caulis llicis asprellae. J Trop Med 2007; 7: 555-557
  • 4 Kashiwada Y, Zhang DC, Chen YP, Cheng CM, Chen HT, Chang HC, Chang JJ, Lee KH. Antitumor agents, 145. Cytotoxic asprellic acid A and acid C and asprellic acid B. new p-coumaroyl triterpenes, from Ilex asprella . J Nat Prod 1993; 56: 2077-2082
  • 5 Li MH, Du SJ, Yu SJ. Studies on the chemical constituents of the root of roughhaired holly (Ilex asprella). Chin Tradit Herb Drugs 1997; 28: 454-456
  • 6 Wang HL, Wu LJ, Lei Y, Zhou SX, Tu PF. Chemical constituents of the leaves of Ilex asprella . J Shenyang Pharm Univ 2009; 26: 279-281
  • 7 Cai Y, Zhang QW, Li ZJ, Fan CL, Wang L, Zhang XQ, Ye WC. Chemical constituents from roots of Ilex asprella . Chin Tradit Herb Drugs 2010; 41: 1426-1429
  • 8 Liu Q, Wang YF, Chen RJ, Zhang MY, Yang CR, Zhang YJ. Anti-coxsackie virus B3 norsesquiterpenoids from the roots of Phyllanthus emblica . J Nat Prod 2009; 72: 969-972
  • 9 Wang YF, Wang XY, Ren Z, Qian CW, Li YC, Kaio K, Wang QD, Zhang Y, Zheng LY, Jiang JH, Yang CR, Liu Q, Zhang YJ. Phyllaemblicin B inhibits coxsackie virus B3 induced apoptosis and myocarditis. Antiviral Res 2009; 84: 150-158
  • 10 Tian LW, Pei Y, Zhang YJ, Wang YF, Yang CR. 7-O-methylkaempferol and -quercetin glycosides from the whole plant of Nervilia fordii . J Nat Prod 2009; 72: 1057-1060
  • 11 Xiang YF, Ju HQ, Li S, Zhang YJ, Yang CR, Wang YF. Effects of 1,2,4,6-tetra-O-galloyl-beta-D-glucose from P. emblica on HBsAg and HBeAg secretion in HepG2.2.15 cell culture. Virol Sin 2010; 25: 375-380
  • 12 Ren Z, Zhang CH, Wang LJ, Cui YX, Qi RB, Yang CR, Zhang YJ, Wei XY, Lu DX, Wang YF. In vitro anti-viral activity of the total alkaloids from Tripterygium hypoglaucum against herpes simplex virus type 1. Virol Sin 2010; 25: 107-114
  • 13 Pei Y, Xiang YF, Chen JN, Lu CH, Hao J, Du Q, Lai CC, Qu C, Li S, Ju HQ, Ren Z, Liu QY, Xiong S, Qian CW, Zeng FL, Zhang PZ, Yang CR, Zhang YJ, Xu J, Kitazato K, Wang YF. Pentagalloylglucose downregulates cofilin1 and inhibits HSV-1 infection. Antiviral Res 2011; 89: 98-108
  • 14 Pei Y, Chen ZP, Ju HQ, Komatsu M, Ji YH, Liu G, Guo CW, Zhang YJ, Yang CR, Wang YF, Kitazato K. Autophagy is involved in anti-viral activity of pentagalloylglucose (PGG) against herpes simplex virus type 1 infection in vitro . Biochem Biophys Res Commun 2011; 405: 186-191
  • 15 Liu G, Xiong S, Xiang YF, Guo CW, Ge F, Yang CR, Zhang YJ, Wang YF, Kitazato K. Antiviral activity and possible mechanisms of action of pentagalloylglucose (PGG) against influenza A virus. Arch Virol 2011; 156: 1359-1369
  • 16 Pei Y, Du Q, Liao PY, Chen ZP, Wang D, Yang CR, Kitazato K, Wang YF, Zhang YJ. Notoginsenoside ST-4 inhibits virus penetration of herpes simplex virus in vitro . J Asian Nat Prod Res 2011; 13: 498-504
  • 17 Ju HQ, Wang SY, Pei Y, Xiang YF, Li S, Zhang YJ, Yang CR, Wang YF. In vitro study on the anti-HSV-1 and HBV activities of extracts from the fruit of Eucalyptus maidenii . Zhong Yao Cai 2011; 34: 242-245
  • 18 Wu ZJ, Ouyang MA, Wang CZ, Zhang ZK, Shen JG. Anti-tobacco mosaic virus (TMV) triterpenoid saponins from the leaves of Ilex oblonga . J Agric Food Chem 2007; 55: 1712-1717
  • 19 Sasmakov SA, Putieva ZM, Kachala VV, Saatov Z, Shashkov AS. Triterpene glycosides of Zygophyllum eichwaldii. II. Structure of zygoeichwaloside I. Chem Nat Compd 2001; 37: 347-350
  • 20 Li Y, Wu T, Cheng ZH, Wang ZT. New triterpene saponins and flavonol glycosides from the leaves of Ilex cornuta . Chin J Chem 2006; 24: 577-579
  • 21 Ouyang MA, Wang HQ, Liu YQ, Yang CR. Triterpenoid saponins from the leaves of Ilex latifolia . Phytochemisty 1997; 45: 1501-1505
  • 22 Hidaka K, Ito M, Matsuda Y, Kohda H, Yamasaki K, Yamahara J, Chisaka T, Kawakami Y, Sato T, Kagei K. New triterpene saponins from Ilex pubescens . Chem Pharm Bull 1987; 35: 524-529
  • 23 Yosioka I, Sugawara T, Ohsuka A, Kitagawa I. Soil bacterial hydrolysis leading to genuine aglycone. III. The structures of glycosides and genuine aglycone of Sanguisorbae Radix. Chem Pharm Bull 1971; 19: 1700-1707
  • 24 Hidaka K, Ito M, Matsuda Y, Kohda H, Yamasaki K, Yamahara J. A triterpene and saponin from roots of Ilex pubescens . Phytochemistry 1987; 26: 2023-2027
  • 25 Nakanishi T, Terai H, Nasu M, Miura I, Yoneda K. Two triterpenoid glycosides from leaves of Ilex cornuta . Phytochemistry 1982; 21: 1373-1377
  • 26 Wang HB, Mayer R, Rucker G, Neugebauer M. Bisepoxylignan glycosides from Stauntonia hexaphylla . Phytochemistry 1993; 34: 1621-1624
  • 27 Tsukamoto H, Hisada S, Nishibe S. Lignans from bark of the Olea plants. II. Chem Pharm Bull 1985; 33: 1232-1241
  • 28 Takeda Y, Mima C, Masuda T, Hirata E, Takushi A, Otsuka H. Glochidioboside, a glucoside of (7S,8R)-dihydrodehydrodiconiferyl alcohol from leaves of Glochidion obovatum . Phytochemistry 1998; 49: 2137-2139