Antitubercular Cassane Furanoditerpenoids from the Roots of Caesalpinia pulcherrima

Abstract

Activity-guided fractionation of a root extract of Caesalpinia pulcherrima led to the isolation of two cassane-furanoditerpenoids, 6β-benzoyl-7β-hydroxyvouacapen-5α-ol (1) and 6β-cinnamoyl-7β-hydroxyvouacapen-5α-ol (2). Compound 2 showed strong antitubercular activity with a minimum inhibitory concentration (MIC) of 6.25 μg/mL, whereas the benzoyl analogue (1) was less active (MIC 25 μg/mL). Both compounds expressed moderate cytotoxic activity towards KB (human oral carcinonoid cancer), BC (human breast cancer) and NCl-H187 (small cell lung cancer) cell lines.

References

• 1 Small P M, Schecter G F, Goodman P C, Sande M A, Chaisson R E, Hopewell P C. Treatment of tuberculosis in patients with advanced human immunodeficiency virus infection.  New Engl J Med. 1991;  324 289-94
• 2 Bradford W Z, Martin J N, Reingold A L, Schecter G F, Hopewell P C, Small P M. The changing epidemiology of acquired drug-resistant tuberculosis in San Francisco, USA.  Lancet. 1996;  348 928-31
• 3 Lotschert W, Beese G. Collins Guide to Tropical plants. London; Collins 1983: p. 45
• 4 Jain S K, DeFilipps R A. Medicinal Plants of India. Reference Publications Michigan; 1991: pp. 210-1
• 5 Wutthithammaweach W. Encyclopedia of herbs: compilation of Thai pharmaceuticals. 1st edn Bangkok; Odion store 1997: p. 488
• 6 Ragasa C Y, Hofilena J G, Rideout J A. New furanoid diterpenes from Caesalpinia pulcherrima .  J Nat Prod. 2002;  65 1107-10
• 7 Mcpherson D D, Che C T, Cordell G A, Soejarto D D, Pezzuto J M, Fong H HS. Diterpenoids from Caesalpinia pulcherrima .  Phytochemistry. 1986;  25 167-70
• 8 Che C T, McPherson D D, Cordell G A, Fong H HS. Pulcherralpin, a new diterpene ester from Caesalpinia pulcherrima .  J Nat Prod. 1986;  49 561-9
• 9 Patil A D, Freyer A J, Webb R L, Zuber G, Reichwein R, Bean M F. et al . Pulcherrimins A - D, novel diterpene dibenzoates from Caesalpinia pulcherrima with selective activity against DNA repair-defiant yeast mutants.  Tetrahedron. 1997;  53 1593-7
• 10 Jiang R W, Ma S C, He Z D, Huang X S, But P P, Wang H. et al . Molecular structures and antiviral activities of naturally occurring and modified cassane furanoditerpenoids and friedelane triterpenoids from Caesalpinia minax .  Bioorg Med Chem. 2002;  10 2161-70
• 11 Oh S R, Kim D S, Lee I S, Jung K Y, Lee J J, Lee H K. Anticomplementary activity of constituents from the heartwood of Caesalpinia sappan .  Planta Med. 1998;  64 456-8
• 12 Choi S Y, Yang K M, Jeon S D, Kim J H, Khil L Y, Chang T S. et al . Brazilin modulates immune function mainly by augmenting T cell activity in halothane administered mice.  Planta Med. 1997;  63 405-8
• 13 Bacchi E M, Sertie J A, Villa N, Katz H. Antiulcer action and toxicity of Styrax camporum and Caesalpinia ferrea .  Planta Med. 1995;  61 204-7
• 14 Bacchi E M, Sertie J A. Antiulcer action of Styrax camporum and Caesalpinia ferrea in rats.  Planta Med. 1994;  60 118-20
• 15 Hikino H, Taguchi T, Fujimura H, Hiramatsu Y. Anti-inflammatory principles of Caesalpinia sappan wood and of Haematoxylon campechianum wood.  Planta Med. 1977;  31 214-20
• 16 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 .  Antimicrobial Agents and Chemotherapy. 1997;  41 1004-9
• 17 Skehan P, Storeng R, Scudiero D, Monks A, McMahon J, Vistica D. et al . New colorimetric cytotoxicity assay for anticancer-drug screening.  Journal of National Cancer Institute. 1990;  82 1107-12