Anti-androgenic triterpenoids from the Brazilian medicinal plant, Cordia multispicata.
Compounds 1-6 were isolated from the AcOEt soluble fraction of leaves of the Brazilian medicinal plant, Cordia multispicata, and their structures were elucidated to be 3beta,25-epoxy-21beta-acetoxy-3alpha,22beta-dihydroxyurs-12-en-28-al (1), 3beta,25-epoxy-28-acetoxy-3alpha,21beta,22beta-trihydroxyurs-12-ene (2), 21beta-acetoxy-22beta-hydroxy-3-oxours-12-en-28-al (3), 28-acetoxy-6beta, 21beta,22beta-trihydroxy-3-oxours-12-ene (4), 21beta,22beta-dihydroxy-3-oxours-1 2-en-28-al (5) and 3beta,21beta,22beta-trihydroxyurs-I2-en-28-al (6), respectively, by means of spectral data, especially two dimensional NMR techniques. Triterpenes having the hemiketal structure at the A-ring, an acyloxy group at C-22 and/or ketone at C-3 showed potent anti-androgenic activity.
Kuroyanagi
M
M
School of Bioresources, Hiroshima Prefectural University, Shobara, Japan. kuroyang@bio.hiroshima-pu.ac.jp
Seki
T
T
Hayashi
T
T
Nagashima
Y
Y
Kawahara
N
N
Sekita
S
S
Satake
M
M
D013741:3-Oxo-5-alpha-Steroid 4-Dehydrogenase / Q000378:metabolism; D058891:5-alpha Reductase Inhibitors; D000726:Androgen Antagonists / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D001938:Brazil; D005419:Flavonoids / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D010936:Plant Extracts / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D010946:Plants, Medicinal / Q000737:chemistry*; D014315:Triterpenes / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*
D058891:5-alpha Reductase Inhibitors; D000726:Androgen Antagonists; D005419:Flavonoids; D010936:Plant Extracts; D014315:Triterpenes; D013741:3-Oxo-5-alpha-Steroid 4-Dehydrogenase