Planta Med 2013; 79(11): 978-986
DOI: 10.1055/s-0032-1328650
Natural Product Chemistry
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Antiproliferative Triterpenoid Saponins from the Stem of Psychotria sp.

Cui-Xian Zhang*
1   School of Chinese Materia Medica, Guangzhou University of Chinese Medicine, Guangzhou, P. R. China
,
Dong-Mei Zhang*
2   Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University, Guangzhou, P. R. China
,
Min-Feng Chen
2   Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University, Guangzhou, P. R. China
,
Shan-Yue Guan
3   Instrumental Analysis & Research Center, Sun Yat-Sen University, Guangzhou, P. R. China
,
Jun-Hua Yao
3   Instrumental Analysis & Research Center, Sun Yat-Sen University, Guangzhou, P. R. China
,
Xi-Xin He
1   School of Chinese Materia Medica, Guangzhou University of Chinese Medicine, Guangzhou, P. R. China
,
Ling-Fang Lei
1   School of Chinese Materia Medica, Guangzhou University of Chinese Medicine, Guangzhou, P. R. China
,
Ying Zhong
1   School of Chinese Materia Medica, Guangzhou University of Chinese Medicine, Guangzhou, P. R. China
,
Zhi-Fang Wang
1   School of Chinese Materia Medica, Guangzhou University of Chinese Medicine, Guangzhou, P. R. China
,
Wen-Cai Ye
2   Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University, Guangzhou, P. R. China
› Author Affiliations
Further Information

Publication History

received 27 November 2012
revised 20 April 2013

accepted 12 May 2013

Publication Date:
26 June 2013 (online)

Abstract

Six new triterpenoid saponins, psychotrianosides A–F (16), and two known triterpenoid saponins, psychotrianoside G (7) and ardisianoside D (8), were isolated from Psychotria sp. Their structures were determined mainly by spectroscopic methods. The cytotoxic activities of 18 against five human cancer cell lines (MDA-MB-231, MCF-7, MCF-7/ADM, HepG2, and HepG2/ADM) are reported for the first time. Psychotrianoside C (3) showed the most potent antiproliferative activity among these saponins, and the IC50 value of 3 against MDA-MB-231 was 2.391 ± 0.161 µM. Compound 3 was also found to induce apoptosis.

* These authors contributed equally to this work.


Supporting Information

 
  • References

  • 1 Schultes RE, Raffauf RF editors. The healing forest. Portland: Dioscorides Press; 1990: 392
  • 2 Delectis Florae Reipublicae Popularis Sinicae Agendae Academiae Sinicae Edita. Flora Reipublicae Popularis Sinicae. Beijing: Science and Technology Press; 2004. 72. 47
  • 3 Guangdong Food and Drugs Administration. Standard of traditional Chinese medicine of Guangdong. Guangdong: Guangdong Science and Technology Press; 2004. 1. 12
  • 4 Solis P, Ravelo AG, Palenzuela JA, Gupta MP, González A, Phillipson JD. A quinoline alkaloid from Acanthosyris paulo-alvinii . Phytochemistry 1997; 44: 963-969
  • 5 Jannic V, Gueritte F, Laprevote O, Serani L, Martin MT, Sévenet T, Potier P. Pyrrolidinoindoline alkaloids from Psychotria oleoides and Psychotria lyciiflora . J Nat Prod 1999; 62: 838-843
  • 6 Murillo R, Castro V. Isolation of the alkaloid harmane from Psychotria suerrensis . Ing Cienc Quim 1998; 18: 61-62
  • 7 Verotta L, Pilati T, Tato M, Elisabetsky E, Amador TA, Nunes DS. Pyrrolidinoindoline alkaloids from Psychotria colorata . J Nat Prod 1998; 61: 392-396
  • 8 Beretz A, Roth-Georger A, Corre G, Kuballa B, Anton R, Cazenave JP. Polyindolinic alkaloids from Psychotria forsteriana. Potent inhibitors of the aggregation of human platelets. Planta Med 1985; 4: 300-303
  • 9 Hayashi T, Smith FT, Lee KH. Antitumor agents. 89. Psychorubrin, a new cytotoxic naphthoquinone from Psychotria rubra and its structure-activity relationships. J Med Chem 1987; 30: 2005-2008
  • 10 Solis PN, Langat C, Gupta MP, Kirby GC, Warhurst DC, Phillipson JD. Bioactive compounds from Psychotria camponutans . Planta Med 1995; 61: 62-65
  • 11 Lee KH, Lin YM, Wu TS, Zhang DC, Yamagishi T, Hayashi T, Hall IH, Chang JJ, Wu RY, Yang TH. The cytotoxic principles of Prunella vulgaris, Psychotria serpens, and Hyptis capitata: ursolic acid and related derivatives. Planta Med 1988; 54: 308-310
  • 12 Zhang CX, Peng GT, He XX, Lin CZ, Xiong TQ, Deng JW, Zhao ZX, Zhu CC. Chemical constituents of Psychotria sp. (I). Acta Sci Nat Univ Sunyatseni 2010; 49: 22-25
  • 13 Zhang CX, Peng GT, He XX, Zhu CC, Deng JW, Wei YL. Progress in chemical constituents and bioactivities of Psychotria . Nat Prod Res Devel 2011; 23: 571-576 581
  • 14 Guan XT, Jiang MT, Gong YM, Zhao TZ, Hong SH. Sapogenin and secondary glucosides of coral ardisia (Ardisia crenata). Zhongcaoyao 1987; 18: 338-341
  • 15 Chang XL, Li W, Jia ZH, Satou T, Fushiya S, Koike K. Biologically active triterpenoid saponins from Ardisia japonica . J Nat Prod 2007; 70: 179-187
  • 16 Jia ZH, Koike K, Ohmoto T, Ni MY. Triterpenoid saponins from Ardisia crenata . Phytochemistry 1994; 37: 1389-1396
  • 17 Ohtsuki T, Miyagawa T, Koyano T, Kowithayakorn T, Kawahara N, Goda Y, Ishibashi M. Acylated triterpenoid saponins from Schima noronhae and their cell growth inhibitory activity. J Nat Prod 2008; 71: 918-921
  • 18 Li HY, Ohmoto T, Ikeda K. Dianchinenosides A and B, two new saponins from Dianthus chinensis . J Nat Prod 1993; 56: 1065-1070
  • 19 Bock K, Lundt I, Pedersen C. Assignment of anomeric structure to carbohydrates through geminal 13C–H coupling constants. Tetrahedron Lett 1973; 13: 1037-1040
  • 20 Liang D, Hao ZY, Zhang GJ, Zhang QJ, Chen RY, Yu DQ. Cytotoxic triterpenoid saponins from Lysimachia clethroides . J Nat Prod 2011; 74: 2128-2136
  • 21 Kotwicka M, Jendraszak M, Jedrzejczak P. Phosphatidylserine membrane translocation in human spermatozoa: topography in membrane domains and relation to cell vitality. J Membr Biol 2011; 240: 165-170
  • 22 Yelamos J, Farres J, Llacuna L, Ampurdanés C, Martin-Caballero J. PARP-1 and PARP-2: new players in tumour development. Am J Cancer Res 2011; 1: 328-346
  • 23 Wu SB, Pang F, Wen Y, Zhang HF, Zhao Z, Hu JF. Antiproliferative and apoptotic activities of linear furocoumarins from Notopterygium incisum on cancer cell lines. Planta Med 2010; 76: 82-85