Planta Med 2010; 76(7): 726-728
DOI: 10.1055/s-0029-1240656
Natural Product Chemistry
Letters
© Georg Thieme Verlag KG Stuttgart · New York

Bioactive Diterpenes from the Aerial Parts of Anisochilus harmandii

Ratsami Lekphrom1 , Somdej Kanokmedhakul1 , Kwanjai Kanokmedhakul1
  • 1Natural Products Research Unit, Department of Chemistry and Center for Innovation in Chemistry, Faculty of Science, Khon Kaen University, Khon Kaen, Thailand
Further Information

Publication History

received June 29, 2009 revised October 29, 2009

accepted November 3, 2009

Publication Date:
30 November 2009 (online)

Abstract

Two new diterpenes, 4-epi-triptobenzene L (1) and 12-O-deacetyl-6-O-acetyl-19- acetyloxycoleon Q (2), as well as eight known diterpenes (310) were isolated from the aerial parts of Anisochilus hamandii. Structures of the isolated compounds were identified from spectroscopic evidence. Compounds 1, 2, 5, and 10 exhibited antiplasmodial activity against Plasmodium falciparum (IC50 4.70, 2.90, 3.03, and 7.20 µg/mL, respectively), while 3, 5, and 7 showed antimycobacterial activity against Mycobacterium tuberculosis (MIC 50 µg/mL). In addition, only 10 showed strong cytotoxicity against NCI-H187 cells (IC50 4.43 µg/mL).

References

  • 1 Xi-wen L, Hedge I C. Lamiaceae. Flora of China, Vol. 17. Beijing; Science Press 1994: 268
  • 2 Suddee S, Paton A J, Parnell J. A taxonomic revision of tribe Ocimeae dumort (Lamiaceae) in continental South East Asia II. Plectranthinae.  Kew Bulletin. 2004;  59 379-387
  • 3 Subramanian S, Nair A G R. Flavonoids of the leaves of Mentha spicata and Anisochilus carnosus.  Phytochemistry. 1972;  11 452-453
  • 4 Ramani V A, Arunachalam T, Antony T V, Amaladasan M. A phytochemical analysis of the medicinal plant: Anisochillus carnosus.  Asian J Chem. 2002;  14 247-254
  • 5 Smitinand T. Thai plant names, revised edition. Bangkok; Prachachon Co. Limited 2001: 36
  • 6 Carvalho M G, Rumjanex V M, Lopes M J S, Carvalho A G. Diterpenes from Pinus.  Phytochemistry. 1998;  38 1101-1105
  • 7 Tanaka R, Ohtsu H, Matsunaga S. Abietane diterpene acids and other constituents from the leaves of Larix kaempferi.  Phytochemistry. 1997;  46 1051-1057
  • 8 Matloubi-Moghadam F, Ruedi P, Eugster C. Neue Coleone und Royleanone aus Coleus somaliensis (S. Moore).  Helv Chim Acta. 1984;  67 201-208
  • 9 Duan H, Takaishi Y, Momota H, Ohmono Y, Taki T, Jia Y, Li D. Immunosuppressive diterpenoids from Tripterygium wilfordii.  J Nat Prod. 1999;  62 1522-1525
  • 10 Ruedi P, Schmid M J, Prewo R, Bieri J H, Eugster H C. 37. Spirocoleone: Synthese und Charakterisierung von vier diastereomeren Spiro (methylcyclopropan)-Substrukturen; Revision der Konfiguration an C (12) und C (15) von Coleon P und Derivaten sowie von Coleon-Z-Derivaten; Röntgenstrukturanalysen von Lanugon J und weiteren Spirocoleonen.  Helv Chim Acta. 1983;  66 429-449
  • 11 Miyase T, Yoshizaki F, Kabengele N T, Ruedi P, Eugster C H. Struktur von 13 Diterpenen (Coleonen) aus Blattdrüsen von Solenostemon sylvticus und Coleus garckeanus (Labiatae).  Helv Chim Acta. 1979;  62 2374-2383
  • 12 Targer W, Jensen J B. Human malaria parasites in continuous culture.  Science. 1976;  193 673-675
  • 13 Desjardins R E, Canfield C J, Haynes J D, Chulay J D. Quantitative assessment of antimalarial activity in vitro by a semiautomated microdilution technique.  Antimicrob Agents Chemother. 1979;  16 710-718
  • 14 Collins L, Franzblau S G. Microplate alamar blue assay versus BACTEC 460 system for high-throughput screening of compounds against Mycobacterium tuberculosis and Mycobacterium avium.  Antimicrob Agents Chemother. 1997;  4 1004-1009
  • 15 Skehan P, Storeng R, Scudiero D, Monks A, McMahon J, Vistica D, Warren J T, Bokesch H, Kenney S, Boyd M R. New colorimetric cytotoxicity assay for anticancer-drug screening.  J Natl Cancer Inst. 1990;  82 1107-1112

Assoc. Prof. Dr. Somdej Kanokmedhakul

Natural Products Research Unit
Department of Chemistry and Center for Innovation in Chemistry
Faculty of Science
Khon Kaen University

Friendship Street

Khon Kaen 40002

Thailand

Phone: + 66 43 20 22 22 41 ext. 12243, 123704

Fax: + 66 43 20 23 73

Email: somdej@kku.ac.th