Antiplasmodial Activity of Labdanes from Aframomum latifolium and Aframomum sceptrum

 

 Buy Article Permissions and Reprints

Abstract

Bioguided fractionation of extracts of Aframomum latifolium and A. sceptrum (Zingiberaceae) resulted in isolation of (+)-(S)-nerolidol and seven labdanes, coronarin B, galanal A and B, galanolactone, (E)-8β,17-epoxylabd-12-ene-15,16-dial, (+)-(E)-labda-8(17), 12-diene-15,16-dial and its diethyl acetal, the latter being presumably an isolation artefact. The labdanes show a modest in vitro activity against a chloroquine-sensitive Plasmodium falciparum strain.

References

• 1 Abbiw D K. Useful Plants of Ghana. Kew, Richmond, Surrey; Royal Botanical Garden, Kew 1990
  Google Scholar
• 2 Iwu M M. Handbook on African Medicinal Plants. Boca Roton; CRC Press, Inc 1993
  Google Scholar
• 3 Escoubas P, Lajide L, Mizutani J. Termite antifeedant activity in Aframomum melegueta .  Phytochemistry. 1995;  40 1097-9
  CrossrefPubMedGoogle Scholar
• 4 Kimbu S F, Sondengam L B, Njimi T K, Akinniyi J A, Connolly J D. The structure of a labdane dialdehyde from Aframomom daniellii (Zingiberaceae). Journal of the Chemical Society Perkin Transaction 1 1979: 1303-4
  Google Scholar
• 5 Adegoke G O, Rao L M, Shankaracharya N B. A comparison of the essential oils of Aframomom daniellii (Hook. F.) K. Schum. and Amomum subulatum Roxb.  Flavour and Fragrance Journal. 1998;  13 349-52
  CrossrefPubMedGoogle Scholar
• 6 Ayafor J F, Tchuendem M HK, Nyasse B, Tillequin F, Anke H. Aframodial and other bioactive diterpenoids from Aframomum species.  Pure and Applied Chemistry . 1994;  66 2327-30
  PubMedGoogle Scholar
• 7 Morita H, Itokawa H. Cytotoxic and antifungal diterpenes from the seeds of Alpinia galanga .  Planta Medica. 1988;  54 117-20
  PubMedGoogle Scholar
• 8 Parmar V P, Jain S C, Gupta S, Talwar S, Rajwanshi V K, Kumar R, Azim A, Malhotra S, Kumar N, Jain R, Sharma N K, Tyagi O D, Lawrie S J, Errington W, Howarth O W, Olsen C E, Singh S K, Wengel J. Polyphenols and alkaloids from Piper species.  Phytochemistry. 1998;  49 1069-78
  CrossrefPubMedGoogle Scholar
• 9 Dittmer D C, Discordia R P, Zhang Y, Murphy C K, Kumar A, Pepito A S, Wang Y. A tellurium transposition route of allylic alcohols: Overcoming some limitations of the Sharpless-Katsuki asymmetric epoxidation.  Journal of Organic Chemistry. 1993;  58 718-31
  CrossrefPubMedGoogle Scholar
• 10 Itokawa H, Morita H, Katou I, Takeya K, Cavalheiro A J, De Oliveira R CB, Ishige M, Motidome M. Cytotoxic diterpenes from the rhizomes of Hedychium coronarium .  Planta Medica. 1988;  54 311-5
  PubMedGoogle Scholar
• 11 Itokawa H, Morita M, Mihanshi S. Labdane and bisnorlabdane type diterpenes from Alpinia speciosa K. Schum.  Chemical and Pharmaceutical Bulletin. 1980;  28 3452-3
  PubMedGoogle Scholar
• 12 Klayman D L. Qinghaosu (artemisinin): an antimalarial drug from China.  Science. 1985;  228 1045-55
  PubMedGoogle Scholar
• 13 Posner G H. Antimalarial peroxides in the qinghaosu (artemisinin) and yingzhaosu families.  Expert Opinion on Therapeutic Patents. 1998;  8 1487-93
  CrossrefPubMedGoogle Scholar
• 14 Jung M, Ko I, Lee S, Choi S J, Youn B H, Kim S K. A concise synthesis and in vitro cytotoxicity of new labdane diterpenes.  Bioorganic and Medicinal Chemistry Letters. 1998;  8 3295-8
  PubMedGoogle Scholar
• 15 Ziegler H, Stærk D, Christensen J, Hviid L, Hägerstrand H, Jaroszewski J W. In vitro Plasmodium falciparum drug-sensitivity assay: Inhibition of parasite growth by incorporation of stomatocytogenic amphiphiles into the erythrocyte membrane. Antimicrobial Agents and Chemotherapy, in press. 
  Google Scholar

Dr. Søren Brøgger Christensen

Department of Medicinal Chemistry

Royal Danish School of Pharmacy

Universitetsparken 2

DK-2100 Copenhagen

Denmark

Email: sbc@dfh.dk

Fax: +45 3530 6040