Triterpenes from Garcia parviflora. Cytotoxic evaluation of natural and semisynthetic friedelanes.
Three new friedelane-type triterpenes, 1,2-dehydro-2,3-secofriedelan-3-oic acid (1), 1β-hydroxyfriedelin (2), and 3β-hydroxyfriedelan-23-oic acid (3), and the known compounds friedelin-3,4-lactone (4), acetyl aleuritolic acid (5), 4-hydroxy-5-propionyl-1,3-di-O-methylpyrogallol, elemicin, and (-)-syringaresinol were isolated from the leaves of Garcia parviflora. The structures of 1-3 were elucidated by spectroscopic methods, including 1D and 2D NMR, HREIMS, X-ray, and CD analysis. Some derivatives of 2 (6-14) were prepared via oxidation, reduction, and esterification. The natural triterpenes and the semisynthetic friedelane derivatives were tested for cytotoxic activity against human cancer cell lines U251, PC-3, K562, HCT-15, MCF-7, and SKLU-1. Compound 5 was cytotoxic against U251 cells.
Reyes
Blanca M
BM
Instituto de Química, Universidad Nacional Autónoma de México, Ciudad Universitaria, Circuito Exterior, Coyoacán 04510, México DF.
Ramírez-Apan
María Teresa
MT
Toscano
Rubén A
RA
Delgado
Guillermo
G
D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D004354:Drug Screening Assays, Antitumor; D019665:Euphorbiaceae / Q000737:chemistry*; D005260:Female; D006801:Humans; D020014:K562 Cells; D008297:Male; D008800:Mexico; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D018515:Plant Leaves / Q000737:chemistry; D013237:Stereoisomerism; D014315:Triterpenes / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*
C554262:1,2-dehydro-2,3-secofriedelan-3-oic acid; C554263:1beta-hydroxyfriedelin; C554264:3beta-hydroxyfriedelan-23-oic acid; D000972:Antineoplastic Agents, Phytogenic; D014315:Triterpenes; C421805:friedelane