New Cytotoxic Triterpene Acids from Aboveground Parts of Manihot esculenta from the Suriname Rainforest

Abstract

Two novel triterpene acids, esculentoic acid A (1) and B (2) as well as the seven known compounds 3 - 9 were isolated from an EtOAc extract of leaves, stems, and twigs of Manihot esculenta by bioassay-guided fractionation for cytotoxic activity. The structures of the two new compounds were established as 3α-hydroxytaraxer-14-en-29-oic acid (1) and 3-oxotaraxer-14-en-29-oic acid (2) on the basis of 1D and 2D NMR spectroscopic data interpretation and chemical conversions. The two new compounds 1 and 2 showed moderate cytotoxicity against the A2780 human ovarian cancer cell line.

References

• 1 This manuscript is part 13 of our series ”Biodiversity Conservation and Drug Discovery in S uriname”. For part 12, see: Chaturvedula VSP, Schilling JK, Wisse JH, Miller JS, Evans R, Kingston DGI A new cytotoxic limonoid from Odontadenia macrantha from the Suriname rainforest. Mag. Reson. Chem 2003 71: 139-42
• 2 Prakash C VS, Hoch J M, Kingston D GI. Structure and stereochemistry of new cytotoxic clerodane diterpenoids from the bark of Casearia lucida from the Madagascar rainforest.  J. Nat. Prod.. 2002;  65 100-7
• 3 Raja K CM. Cyanoglucosides in cassava (Manihot esculenta Crantz) - occurrence, impact and degradation.  Trends Carbohyd. Chem.. 1999;  5 25-35
• 4 Sakai T, Nakagawa Y. Diterpenic stress metabolites from cassava roots.  Phytochemistry. 1988;  27 3769-79
• 5 Corbett R E, Cumming S D. Lichens and Fungi Part X. 14α-Taraxarane.  J. Chem. Soc. Perkin Trans.. 1972;  I 2827-9
• 6 Josef M F, Antje F, Johann L. Triterpenoids from gum mastic, the resin of Pistacia lentiscus .  Phytochemistry. 1991;  30 3709-12
• 7 Chatterjee A, Mukharjee R, Srimany S K, Bhattacharjee S. Isolation of lupenone from Cassia siamea .  J. Indian Chem. Soc.. 1966;  43 63-4
• 8 Anjaria J V, Mankad B N, Gulati O D. Isolation of stigmasterol and tocopherols from Leptadenia reticulata by a short-cut method.  Indian J. Pharm.. 1974;  36 148-9
• 9 Atta-ur-Rahman , Sultana N, Akhter F, Nighat F, Choudhary M I. Phytochemical studies on Adhatoda vasica nees . Nat. Prod. Letters 1997 10: 249-56
• 10 Chen T K, Ales D C, Baenziger N C, Weimer D F. Antirepellent triterpenoids from Cordia alliodora .  J. Org. Chem.. 1983;  48 3525-31
• 11 Rogers C B, Subramony G. The structure of imberic acid, a 1α-hydroxy pentacyclic triterpenoid from Combretum imberbe .  Phytochemistry. 1988;  27 531-3
• 12 Muhammad I, El Sayed K A, Mossa J S, Al-Said M S, El-Feraly F S, Clark A M, Hufford C D, Oh S, Mayer A MS. Bioactive 12-oleane triterpene and secotriterpene acids from Maytenus undata .  J. Nat. Prod.. 2000;  63 605-10
• 13 Kaneda N, Pezzuto J M, Kinghorn D A, Farnsworth N R, Santisuk T, Tuchinda P, Udchachon J, Reutrakul V. New multiflorane-type triterpenoid acids from Sandoricum indicum .  J. Nat. Prod.. 2001;  64 1243-5
• 14 Sakuri N, Yaguchi Y, Inoue T. Triterpenoids from Myrica rubra .  Phytochemistry. 1987;  26 217-9
• 15 McBrien K D, Bery R L, Lewes S E, Nedderman K M, Bursuker I, Huang S, Klehr S E, Leet J E. Rackicidins, new cytotoxic lipopeptides from Micromonospora sp. fermentation, isolation and characterization.  J. Antibiotics. 1995;  48 1446-52