Pentacyclic Triterpenoids from the Aerial Parts of Lantana camara (original) (raw)

2003, CHEMICAL & PHARMACEUTICAL BULLETIN

Lantana camara L. (Verbenaceae) is a hairy shrub, native to tropical America. Different parts of this plant are used for the treatment of various human ailments such as itches, cuts, ulcers, swellings, bilious fever, catarrh, eczema, tetanus, malaria, tumors and rheumatism. 1,2) Phytochemical studies carried out by different groups of workers on different parts of the plant have resulted in the isolation of various terpenoids, steroids and flavonoids. In the course of investigations on the constituents of the aerial parts of L. camara, three new pentacyclic triterpenoids namely camaryolic acid (1), methylcamaralate (2) and camangeloyl acid (3) were isolated. The structures of these constituents were elucidated as 3,25-epoxy-3a -methoxy-22b -[b ,b -dimethylacryloyloxy]urs-12-en-28-oic acid, methyl 22b-acetoxy-3,25-epoxy-3ahydroxy-urs-12-en-28-oate and 3,25-epoxy-3a-hydroxy-22b-[(Z)-2Ј-methyl-2Ј-butenoyloxy]-11-oxoolean-12-en-28-oic acid respectively on the basis of various 2D-NMR techniques including 1 H-1 H correlation spectroscopy (COSY), nuclear overhauser enhancement spectroscopy (NOESY), heteronuclear multiple quantum coherence (HMQC) and heteronuclear multiple bond connectivity (HMBC). In addition six known compounds b-sitosterol 3-O-b-D-glucopyranoside (4), 6) octadecanoic acid (5), 7) docosanoic acid (6), 8) palmitic acid (7), 9) camaric acid (8) 10) and lantanolic acid (9) 11) were isolated from this plant. This is the first report of the isolation of compound 4 from L. camara. Herein, we report the structural assignments of the three new triterpenoids.