Download PDF
Planta Med 2017; 83(09): 797-804
DOI: 10.1055/s-0042-123708
Natural Product Chemistry and Analytical Studies
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Triterpenoids with Antiplatelet Aggregation Activity from the Roots of Ilex pubescens

Qinglong Tan   *
1   School of Chinese Materia medica, Guangzhou University of Chinese Medicine, Guangzhou, China
3   Second affiliation hospital, Guangzhou University of Chinese Medicine, Guangzhou, China
,
Maosong Qiu   *
1   School of Chinese Materia medica, Guangzhou University of Chinese Medicine, Guangzhou, China
,
Di Cao
1   School of Chinese Materia medica, Guangzhou University of Chinese Medicine, Guangzhou, China
,
Tianqin Xiong
1   School of Chinese Materia medica, Guangzhou University of Chinese Medicine, Guangzhou, China
,
Lei Zhang
1   School of Chinese Materia medica, Guangzhou University of Chinese Medicine, Guangzhou, China
,
Lian Zhou
1   School of Chinese Materia medica, Guangzhou University of Chinese Medicine, Guangzhou, China
,
Li Rong
1   School of Chinese Materia medica, Guangzhou University of Chinese Medicine, Guangzhou, China
,
Jinsong Zhou
1   School of Chinese Materia medica, Guangzhou University of Chinese Medicine, Guangzhou, China
,
Jing Jin
2   School of Pharmaceutical Sciences, Sun Yat-Sen University, Guangzhou, China
,
Zhongxiang Zhao
1   School of Chinese Materia medica, Guangzhou University of Chinese Medicine, Guangzhou, China
› Author Affiliations
Further Information

Publication History

received 10 September 2016
revised 03 December 2016

accepted 08 December 2016

Publication Date:
22 December 2016 (online)

    Permissions and Reprints

Abstract

Two new triterpenes and five new triterpene saponins, named ilexpusons A–G (1–7), as well as eight known compounds were isolated from Ilex pubescens. The structures of the new compounds were established by a combination of chemical and spectroscopic methods, including HRESIMS, 1H-NMR, 13C-NMR, 1H-1H COSY, HSQC, HMBC, and NOESY. Additionally, the biological activity of compounds 1 – 15 against adenosine diphosphate-induced platelet aggregation in rabbit plasma was determined. Among the tested compounds, 1, 2, 5, 6, 8, 13, 14, and 15 exhibited significant inhibition of platelet aggregation in vitro.

Key words

Aquifoliaceae - Ilex pubescens - triterpenoids - ilexpusons A–G - antiplatelet aggregation

* Co-first authors.


Supporting Information

Spectroscopic data of compounds 1–7 and the dose-response curves of the active compounds are available as Supporting Information.

 

  • References

  • 1 Jiangsu New Medical College. Dictionary of Chinese Materia medica. Shanghai: Shanghai Scientific and Technological Press; 1977: 441
    Google Scholar
  • 2 Feng F, Zhu MX, Xie N, Liu WY, Chen DJ, You QD. Two new triterpenoid saponins from the root of Ilex pubescens . J Asian Nat Prod Res 2008; 10: 71-75
    CrossrefPubMedGoogle Scholar
  • 3 Jiang ZH, Wang JR, Li M, Liu ZQ, Chau KY, Zhao C, Liu L. Hemiterpene glucosides with anti-platelet aggregation activities from Ilex pubescens . J Nat Prod 2005; 68: 397-399
    PubMedGoogle Scholar
  • 4 Li L, Feng LS, He YX. Cytotoxic triterpenesaponins from Ilex pubescens . J Asian Nat Prod Res 2014; 16: 830-835
    CrossrefPubMedGoogle Scholar
  • 5 Li L, He YX, Gou ML, Dai C. Three new triterpenoid saponins from Ilex pubescens . J Asian Nat Prod Res 2012; 14: 1169-1174
    CrossrefPubMedGoogle Scholar
  • 6 Qin WJ, Jiao ZY, Fan ZT, Chen BQ, Lin XY, Yao JX. A study on the chemical constituents of the leaves of the Ilex pubescens Hook et Arn var glaber Chang. III. Elucidation of the structure of glaberide I. A new lignan compound. Yao Xue Xue Bao 1980; 15: 669-673
    PubMedGoogle Scholar
  • 7 Wang JR, Zhou H, Jiang ZH, Liu L. Two new triterpene saponins from the anti-inflammatory saponin fraction of Ilex pubescens root. Chem Biodivers 2008; 5: 1369-1376
    CrossrefPubMedGoogle Scholar
  • 8 Wu T, Zhang QW, Zhang XQ, Liu G, Wang L, Jiang MM, Feng YF, Ye WC. Two new compounds from the roots of Ilex pubescens . Nat Prod Res 2012; 26: 1408-1412
    CrossrefPubMedGoogle Scholar
  • 9 Xing XD, Zhang Q, Feng F, Liu WY. Chemical constituents from stems of Ilex pubescens . Zhong Yao Cai 2012; 35: 1429-1431
    PubMedGoogle Scholar
  • 10 Yang X, Ding Y, Sun ZH, Zhang DM. Studies on chemical constituents from Ilex pubescens . J Asian Nat Prod Res 2006; 8: 505-510
    CrossrefPubMedGoogle Scholar
  • 11 Yang X, Ding Y, Zhang DM. Studies on lignin glycosides in root from Ilex pubescens . Zhongguo Zhong Yao Za Zhi 2007; 13: 1303-1305
    PubMedGoogle Scholar
  • 12 Zhang CX, Lin CZ, Xiong TQ, Zhu CC, Yang JY, Zhao ZX. New triterpene saponins from the root of Ilex pubescens . Fitoterapia 2010; 81: 788-792
    CrossrefPubMedGoogle Scholar
  • 13 Zhou Y, Chai XY, Zeng KW, Zhang JY, Li N, Jiang Y, Tu PF. Ilexpublesnins C–M, eleven new triterpene saponins from the roots of Ilex pubescens . Planta Med 2013; 79: 70-77
    Article in Thieme ConnectPubMedGoogle Scholar
  • 14 Zhou Y, Zeng KW, Zhang JY, Li N, Chai XY, Jiang Y, Tu PF. Triterpene saponins from the roots of Ilex pubescens . Fitoterapia 2014; 97: 98-104
    CrossrefPubMedGoogle Scholar
  • 15 Zhou YB, Wang JH, Li XM, Fu XC, Yan Z, Zeng YM, Li X. Studies on the chemical constituents of Ilex pubescens . J Asian Nat Prod Res 2008; 10: 827-831
    CrossrefPubMedGoogle Scholar
  • 16 Zhou ZL, Feng ZC, Fu CY, Zeng L. A new triterpene saponin from the roots of Ilex pubescens . Nat Prod Res 2013; 27: 1343-1347
    CrossrefPubMedGoogle Scholar
  • 17 Wu P, Gao H, Li ZH, Liu ZQ. Two new triterpene saponins from the roots of Ilex pubescens . Phytochem Lett 2015; 12: 17-21
    CrossrefPubMedGoogle Scholar
  • 18 Qin WJ, Jiao ZY, Fan ZT, Chen BQ, Lin XY, Yao JX. Studies on chemical constituents from the leaves of Ilex pubescens . Acta Pharm Sin 1980; 11: 199
    PubMedGoogle Scholar
  • 19 Wu SX, Zhang EP, Wu PH. A clinical trial with Ilex pubescens as a radiosensitizer to nasopharyngeal carcinoma (I). Chin J Cancer 1992; 11: 56-59
    PubMedGoogle Scholar
  • 20 Gosmann G, Guillaume D, Taketa AT, Schenkel EP. Triterpenoid saponins from Ilex paraguariensis . J Nat Prod 1995; 58: 438-441
    CrossrefPubMedGoogle Scholar
  • 21 Muller K, Ziereis K, Paper DH. Ilex aquifolium: protection against enzymatic and non-enzymatic lipid peroxidation. Planta Med 1998; 64: 536-540
    Article in Thieme ConnectPubMedGoogle Scholar
  • 22 Ouyang MA, Liu YQ, Wang HQ, Yang CR. Triterpenoid saponins from Ilex latifolia . Phytochemistry 1998; 49: 2483-2486
    CrossrefPubMedGoogle Scholar
  • 23 Pezzuto de Andrade FD, Piacente S, Pizza C, Vilegas W. 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: 255-261
    CrossrefPubMedGoogle Scholar
  • 24 Taketa AT, Gnoatto SC, Gosmann G, Pires VS, Schenkel EP, Guillaume D. Triterpenoids from Brazilian Ilex species and their in vitro antitrypanosomal activity. J Nat Prod 2004; 67: 1697-1700
    CrossrefPubMedGoogle Scholar
  • 25 Taketa AT, Schmittmann-Schlager T, Guillaume D, Gosmann G, Schenkel EP. Triterpenoid glycosides and a triterpene from Ilex brevicuspis . Phytochemistry 2000; 53: 901-904
    CrossrefPubMedGoogle Scholar
  • 26 Tang L, Jiang Y, Chang HT, Zhao MB, Tu PF, Cui JR, Wang RQ. Triterpene saponins from the leaves of Ilex kudingcha . J Nat Prod 2005; 68: 1169-1174
    CrossrefPubMedGoogle Scholar
  • 27 Wang L, Cai Y, Zhang XQ, Fan CL, Zhang QW, Lai XP, Ye WC. New triterpenoid glycosides from the roots of Ilex asprella . Carbohydr Res 2012; 349: 39-43
    CrossrefPubMedGoogle Scholar
  • 28 Zhang AL, Ye Q, Li BG, Qi HY, Zhang GL. Phenolic and triterpene glycosides from the stems of Ilex litseaefolia . J Nat Prod 2005; 68: 1531-1535
    CrossrefPubMedGoogle Scholar
  • 29 Zhou M, Xu M, Ma XX, Zheng K, Yang K, Yang CR, Wang YF, Zhang YJ. Antiviral triterpenoid saponins from the roots of Ilex asprella . Planta Med 2012; 78: 1702-1705
    Article in Thieme ConnectPubMedGoogle Scholar
  • 30 Jiang YP, Li H, Pan XZ, Sun XG, Tang QF, Shao M. Chemical constituents from the roots of llex pubescens . Zhong Yao Cai 2013; 36: 1174-1178
    PubMedGoogle Scholar
  • 31 Melek FR, Miyase T, El-Gindl OD, Abdel-Khalik SM, Haggag MY. Saponins from Fagonia mollis . Phytochemistry 1996; 42: 1045-1047
    PubMedGoogle Scholar
  • 32 Zhao ZX, Jing J, Lin CZ, Xiong TQ, Luo HF, Qin CY, Zhu CC. Study on triterpenoid glycosides from roots of Ilex pubescens . China Pharmacist 2011; 5: 599-601
    PubMedGoogle Scholar
  • 33 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
    CrossrefPubMedGoogle Scholar
  • 34 Wang ZW, Wang JS, Luo J, Kong LY. α-Glucosidase inhibitory triterpenoids from the stem barks of Uncaria laevigata . Fitoterapia 2013; 90: 30-37
    CrossrefPubMedGoogle Scholar
  • 35 Hara S, Okabe H, Mihashi K. Separation of aldose enantiomers by gas-liquid chromatography. Chem Pharm Bull 1986; 34: 1843-1845
    CrossrefPubMedGoogle Scholar
  • 36 Li L, Shen YM, Yang XS, Zuo GY, Shen ZQ, Chen ZH, Hao XJ. Antiplatelet aggregation activity of diterpene alkaloids from Spiraea japonica . Eur J Pharmacol 2002; 449: 23-28
    CrossrefPubMedGoogle Scholar
  • 37 Wang Y, Wang J, Guo L, Gao X. Antiplatelet effects of qishen yiqi dropping pill in platelets aggregation in hyperlipidemic rabbits. Evid Based Complement Alternat Med 2012; 2012: 214-215
    PubMedGoogle Scholar
  • 38 Born GV, Cross MJ. The aggregation of blood platelets. J Physiol 1963; 168: 178-195
    CrossrefPubMedGoogle Scholar