Diterpenoids from Turraeanthus mannii

Abstract

Three new compounds, 15-acetoxy-12-hydroxy-16-methyl-labda-8(17),13E-diene (1), ent-labda-8(17),13-dien-15,16-olid-19-oic acid methyl ester (2), and 12-hydroxy-labda-8(17),13-dien-15,16-olide (3), together with two known compounds, 19-acetoxy-ent-labda-8(17),13-dien-15,16-olide (4), and 16-acetoxy-12,15-epoxy-15ß-hydroxy-labda-8(17),13(16)-diene (5) were isolated from the stem bark of Turraeanthus mannii (Meliaceae). The structures of compounds 1 - 3 were elucidated by analysis of the spectroscopic data. The crude methanol extract and compound 5 exhibited weak antibacterial and antifungal activity.

Key words

Turraeanthus mannii - Meliaceae - antibacterial activity - antifungal activity - diterpenes - labdanes

References

• 1 Letouzey R. Manuel de botanique forestier. Afrique Tropicale, Tome 2B. Familles (2eme partie). Nogent-sur-Marne; Centre Technique Forestier Tropical 1972.
• 2 Données Statistiques des Produits Non-Ligneux au Cameroun: Available at http://www.fao.org/DOCREP/003/X6699F02.htm . Accessed in 2006.
• 3 Bevan C WL, Ekong D EU, Halsall T G, Toft P. The structure of turraeanthin, an oxygenated tetracyclic triterpene monoacetate. J Chem Soc (C) 1967: 820-8.
• 4 Vardamides J C, Dongmo A B, Meyer M, Ndom J C, Azebaze A GB, Zounda M RS. et al . Alkaloids from the stem bark of Turraeanthus africanus (Meliaceae).  Chem Pharm Bull. 2006;  54 1034-6.
• 5 Tane P, Akam M T, Tsopmo A, Ndi P C, Sterner O. Two labdane diterpenoids and a seco-tetranortriterpenoid from Turraeanthus africanus .  Phytochemistry. 2004;  65 3083-7.
• 6 Tatsimo S JN, Tane P, Srinivas P V, Sondengam B L, Melissa J, Okunji O C. et al . Novel antimicrobial diterpenoids from Turraeanthus africanus .  Planta Med. 2005;  71 1145-51.
• 7 Zdero C, Bohlmann F, King R M. Ent-labdanes, manoyloxide and helipterol derivatives from Chrysocephalum ambiguum .  Phytochemistry. 1992;  31 1631-8.
• 8 Tayman F S, Atsu Barku V Y, Opoku-Boahen Y, Seifert K, Grote D. Isolation of ent-labdane (+)-12,15-epoxylabda-8(17),12,14-trien-16-yl acetate from the seeds of Turraeanthus africanus and its cytostatic/effect on the growth of cancer cells in vitro .  Chem Nat Comp. 2006;  42 46-8.
• 9 Sethi A, Khare A, Khare M P. A labdane diterpene and its glycoside from Melodinus monogynus .  Phytochemistry. 1988;  27 2255-9.
• 10 Ahmed M, Ahmed A A. Terpenoids from Conyza stricta .  Phytochemistry. 1990;  29 2715-6.
• 11 Barrero A F, Herrador M M, Arteaga P, Rosas-Romero A, Arteaga J F. Antioxidant activity of diterpenes and polyphenols from Ophryosporus heptanthus .  J Agric Food Chem. 2006;  54 2537-42.
• 12 Zdero C, Bohlmann F. Macrolide diterpenes and other ent-labdanes from Corymbium villosum .  Phytochemistry. 1988;  27 227-31.
• 13 Cangiano T, Della Greca M, Fiorentino A, Isidori M, Monaco P, Zarrelli A. Lactone diterpenes from the aquqtic plant Potamogeton natans .  Phytochemistry. 2001;  56 469-73.
• 14 O’Mathúna P D, Doskotch R W. Five new labdane diterpenes from Amphiachyris amoena .  J Nat Prod. 1994;  57 1382-90.
• 15 Zdero C, Ahmed A A, Bohlmann F, Mungai G M. Diterpenes and sesquiterpene xylosides from east African Conyza species.  Phytochemistry. 1990;  29 3167-72.