Dammarane-type triterpenes from the Brazilian medicinal plant Cordia multispicata.
From the Brazilian medicinal plant Carucaá (Cordia multispicata), oleanane- and ursane-type triterpenoids were previously reported as anti-androgenic constituents of the plant. In this study, purification of the polar elements of the EtOAc-soluble fraction of the plant revealed nine novel dammarane-type triterpenes, named cordianols A-I (1-9) along with the known compound cordialin A (10). The structures of these new compounds were elucidated by means of spectral methods including HRFABMS, (1)H NMR, (13)C NMR, and 2D NMR (HMQC, HMBC, NOESY). Absolute configuration at C-23 of compound 7 was determined by an excitone chirality method. Some of these new compounds revealed a hemiketal structure on the A ring and a hydroxylated or epoxidated 20(22)-(E)-ene side chain and showed weak anti-androgenic activity.
Kuroyanagi
Masanori
M
School of Bioresources, Hiroshima Prefectural University, 562 Nanatsuka, Shobara-shi, Hiroshima 727-0023, Japan. kuroyang@bio.hiroshima-pu.ac.jp
Kawahara
Nobuo
N
Sekita
Setsuko
S
Satake
Motoyoshi
M
Hayashi
Tatsuo
T
Takase
Yoichi
Y
Masuda
Kazuo
K
D001938:Brazil; D031213:Cordia / Q000737:chemistry*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010946:Plants, Medicinal / Q000737:chemistry*; D013237:Stereoisomerism; D014315:Triterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000097669:Dammaranes
D014315:Triterpenes; D000097669:Dammaranes