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Planta Med 2015; 81(01): 56-61
DOI: 10.1055/s-0034-1383369
Natural Product Chemistry
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Minor Valepotriates from Valeriana jatamansi and Their Cytotoxicity against Metastatic Prostate Cancer Cells

Sheng Lin
1   Department of Natural Product Chemistry, School of Pharmacy, Second Military Medical University, Shanghai, P. R. China.
2   State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, P. R. China
,
Peng Fu
1   Department of Natural Product Chemistry, School of Pharmacy, Second Military Medical University, Shanghai, P. R. China.
3   Department of Pharmacy, Changhai Hospital, Second Military Medical University, Shanghai, P. R. China
,
Tao Chen
4   Longgang Central Hospital, ENT hospital of Longgang Central Hospital, Otolaryngology Institute of Shenzhen University, Otolaryngology Institute of Shenzhen, Shenzhen, Guangdong, P. R. China
,
Ji Ye
1   Department of Natural Product Chemistry, School of Pharmacy, Second Military Medical University, Shanghai, P. R. China.
,
Yong-Qing Su
1   Department of Natural Product Chemistry, School of Pharmacy, Second Military Medical University, Shanghai, P. R. China.
,
Xian-Wen Yang
1   Department of Natural Product Chemistry, School of Pharmacy, Second Military Medical University, Shanghai, P. R. China.
,
Zhong-Xiao Zhang
1   Department of Natural Product Chemistry, School of Pharmacy, Second Military Medical University, Shanghai, P. R. China.
,
Wei-Dong Zhang
1   Department of Natural Product Chemistry, School of Pharmacy, Second Military Medical University, Shanghai, P. R. China.
› Author Affiliations
Further Information

Publication History

received 10 June 2014
revised 16 October 2014

accepted 28 October 2014

Publication Date:
03 December 2014 (online)

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Abstract

Ten new valepotriates, jatamanvaltrates P–Y (1–10) and a known one, nardostachin (11), have been isolated from the whole plants of Valeriana jatamansi. The structures of the new compounds were determined by detailed spectroscopic data analysis. The isolated compounds were evaluated for cytotoxic activity against PC-3M cells, and a structure-activity relationship was examined for all the valepotriates isolated from V. jatamansi. The results highlighted the structure-activity relationship importance of the C-3–C-4 double bond, the oxirane ring, and the 10-chlorine in the valepotriates.

Key words

Valerianaceae - Valeriana jatamansi - Valepotriates - cytotoxicity - structure-activity relationship - metastatic prostate cancer cells

Supporting Information

 

  • References

  • 1 Bounthanh C, Bergmann C, Beck JP, Haag-Berrurier M, Anton R. Valepotriates, a new class of cytotoxic and antitumor agents. Planta Med 1981; 41: 21-28
    Article in Thieme ConnectPubMedGoogle Scholar
  • 2 Lin S, Shen YH, Li HL, Yang XW, Chen T, Lu LH, Huang ZS, Liu RH, Xu XK, Zhang WD, Wang H. Acylated iridoids with cytotoxicity from Valeriana jatamansi . J Nat Prod 2009; 72: 650-655
    CrossrefPubMedGoogle Scholar
  • 3 Lin S, Chen T, Liu XH, Shen YH, Li HL, Shan L, Liu RH, Xu XK, Zhang WD, Wang H. Iridoids and lignans from Valeriana jatamansi . J Nat Prod 2010; 73: 632-638
    CrossrefPubMedGoogle Scholar
  • 4 Lin S, Shen YH, Zhang ZX, Li HL, Shan L, Liu RH, Xu XK, Zhang WD. Revision of the Structures of 1, 5-Dihydroxy-3, 8-epoxyvalechlorine, Volvaltrate B, and Valeriotetrate C from Valeriana jatamansi and V. officinalis . J Nat Prod 2010; 73: 1723-1726
    CrossrefPubMedGoogle Scholar
  • 5 Lin S, Zhang ZX, Chen T, Ye J, Dai WX, Shan L, Su J, Shen YH, Li HL, Liu RH, Xu XK, Wang H, Zhang WD. Characterization of chlorinated valepotriates from Valeriana jatamansi . Phytochemistry 2013; 85: 185-193
    CrossrefPubMedGoogle Scholar
  • 6 Zhang WD, Su J, Lin S, Shan L, Liu RH, Li HL, Xu XK. The application of iridoids for preparing human ovarian cancer therapeutic drug. Chinese Patent ZL201010126582.X; 2012.
    PubMedGoogle Scholar
  • 7 Li XG, Chen T, Lin S, Zhao J, Chen PZ, Ba Q, Guo H, Liu YL, Li JQ, Chu RA, Shan L, Zhang WD, Wang H. Valeriana jatamansi constituent IVHD-valtrate as a novel therapeutic agent to human ovarian cancer: in vitro and in vivo activities and mechanisms. Curr Cancer Drug Tar 2013; 13: 472-483
    CrossrefPubMedGoogle Scholar
  • 8 Gränicher F, Christen P, Kamalaprija P, Burger U. An iridoid diester from Valeriana officinalis var. sambucifolia hairy roots. Phytochemistry 1995; 38: 103-105
    CrossrefPubMedGoogle Scholar
  • 9 Bagchi A, Oshima Y, Hikino H. Iridoids of Randia ruiziana . Planta Med 1988; 44: 87-88
    Article in Thieme ConnectPubMedGoogle Scholar
  • 10 Xu YM, McLaughlin SP, Gunatilaka AAL. Sorbifolivaltrates A–D, diene valepotriates from Valeriana sorbifolia . J Nat Prod 2007; 70: 2045-2048
    CrossrefPubMedGoogle Scholar