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Planta Med 2017; 83(01/02): 151-157
DOI: 10.1055/s-0042-109779
Natural Product Chemistry and Analytical Studies
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Intermedin A, a New Labdane Diterpene Isolated from Alpinia intermedia, Prolonged the Survival Time of P-388D1 Tumor-Bearing CDF1 Mice

Lih-Geeng Chen
1   Department of Microbiology, Immunology and Biopharmaceuticals, College of Life Sciences, National Chiayi University, Chiayi, Taiwan
,
Pei-Jung Su
2   Graduate Institute of Pharmacognosy Science, School of Pharmacy, Pharmacy of College, Taipei Medical University, Taipei, Taiwan
,
Po-Wei Tsai
3   School of Pharmacy, College of Pharmacy, Taipei Medical University, Taipei, Taiwan
,
Ling-Ling Yang
3   School of Pharmacy, College of Pharmacy, Taipei Medical University, Taipei, Taiwan
,
Ching-Chiung Wang
2   Graduate Institute of Pharmacognosy Science, School of Pharmacy, Pharmacy of College, Taipei Medical University, Taipei, Taiwan
3   School of Pharmacy, College of Pharmacy, Taipei Medical University, Taipei, Taiwan
4   Orthopedics Research Center, Taipei Medical University Hospital, Taipei, Taiwan
› Author Affiliations
Further Information

Publication History

received 01 November 2015
revised 15 May 2016

accepted 21 May 2016

Publication Date:
28 June 2016 (online)

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Abstract

Eight ethanolic extracts of indigenous Taiwanese plants of the genus Alpinia were tested for tumor cytotoxicity against AGS, Hep G2, HeLa, KB, and HL-60 cells. Among the 50 % and 95 % EtOH extracts of eight Alpinia species, the cytotoxic effects of Alpinia intermedia leaves were the strongest. When the leaf extract of A. intermedia was partitioned using n-hexane and aqueous solvents, the n-hexane layer showed a greater cytotoxic effect and could prolong the survival time of P-388D1 tumor-bearing CDF1 mice. Two new labdane diterpene derivatives, intermedin A (1) and intermedin B (2), and coronarin E (3) were isolated from the n-hexane layer of A. intermedia. Intermedin A induced apoptosis in HL-60 cells at 30 µg/mL and significantly prolonged the survival time of P-388D1 tumor-bearing CDF1 mice by 48.7 % at 20 mg/kg of body weight. We suggest that intermedin A is a major compound of A. intermedia and has a cytotoxic effect on HL-60 and P-388D1 cells.

Key words

Alpinia intermedia - Zingiberaceae - intermedin A - apoptosis - P-388D1 tumor-bearing CDF1 mice

Supporting Information

 

  • References

  • 1 Pezzuto JM. Plant-derived anticancer agents. Biochem Pharmacol 1997; 53: 121-133
    CrossrefPubMedGoogle Scholar
  • 2 Itokawa H, Morita H, Kobayashi T, Watanabew K, Iitaka Y. Novel sesquiterpenes from Alpinia intermedia Gagnep. Chem Pharm Bull (Tokyo) 1987; 35: 2860-2868
    CrossrefPubMedGoogle Scholar
  • 3 Tewari M, Quan LT, OʼRourke K, Desnoyers S, Zeng Z, Beidler DR, Poirier GG, Salvesen GS, Dixit VM. Yama/CPP32 beta, a mammalian homolog of CED-3, is a CrmA-inhibitable protease that cleaves the death substrate poly (ADP-ribose) polymerase. Cell 1995; 81: 801-809
    CrossrefPubMedGoogle Scholar
  • 4 Surh YJ. Molecular mechanisms of chemopreventive effects of selected dietary and medicinal phenolic substances. Mutat Res 1999; 428: 305-327
    CrossrefPubMedGoogle Scholar
  • 5 Chen L, He F. Difference of pharmacokinetics and pharmacodynamics in optics drugs. Chinese Journal of New Drugs and Clinical Remedies 2003; 22: 377-380
    PubMedGoogle Scholar
  • 6 Chen X, Li Y. Chiral drugs in the future. China Prescription Drug 2003; 8: 54-56
    PubMedGoogle Scholar
  • 7 Sampaio EP, Sarno EN, Galilly R, Cohn ZA, Kaplan G. Thalidomide selectively inhibits tumor necrosis factor α production by stimulated human monocytes. J Exp Med 1991; 173: 699-703
    CrossrefPubMedGoogle Scholar
  • 8 Raje N, Anderson K. Thalidomide – a revival story. New Engl J Med 1999; 341: 1606-1608
    CrossrefPubMedGoogle Scholar
  • 9 Peuckmann V, Fisch M, Bruera E. Potential novel uses of thalidomide: focus on palliative care. Drugs 2000; 60: 273-292
    CrossrefPubMedGoogle Scholar
  • 10 Grilo LS, Carrupt PA, Abriel H. Stereoselective inhibition of the hERG1 potassium channel. Front Pharmacol 2000; 1: 137
    PubMedGoogle Scholar
  • 11 Hedman A, Meijer DK. Stereoselective inhibition by the diastereomers quinidine and quinine of uptake of cardiac glycosides into isolated rat hepatocytes. J Pharm Sci 1998; 87: 457-461
    CrossrefPubMedGoogle Scholar
  • 12 Matsuda H, Morikawa T, Sakamoto Y, Toguchida I, Yoshikawa M. Labdane-type diterpenes with inhibitory effects on increase in vascular permeability and nitric oxide production from Hedychium coronarium . Bioorg Med Chem 2002; 10: 2527-2534
    CrossrefPubMedGoogle Scholar
  • 13 Sy LK, Brown GD. Labdane diterpenoids from Alpinia chinensis . J Nat Prod 1997; 60: 904-908
    CrossrefPubMedGoogle Scholar
  • 14 Bruggisser R, von Daeniken K, Jundt G, Schaffner W, Tullberg-Reinert H. Interference of plant extracts, phytoestrogens and antioxidants with the MTT tetrazolium assay. Planta Med 2002; 68: 445-448
    Article in Thieme ConnectPubMedGoogle Scholar
  • 15 Gong JP, Traganos F, Darzynkiewicz Z. A selective procedure for DNA extraction from apoptotic cells applicable for gel electrophoresis and flow cytometry. Anal Biochem 1994; 218: 314-319
    CrossrefPubMedGoogle Scholar
  • 16 Yang LL, Chang CC, Chen LG, Wang CC. Antitumor principle constituents of Myrica rubra var. acuminata . J Agric Food Chem 2003; 51: 2974-2979
    CrossrefPubMedGoogle Scholar