Transformed steroids—65

Sterols and Terpenoids from Melia azedarach

“…The IR spectrum showed absorption peaks at 3432 (OH), 1729 (CO), and 1631 cm −1 (CC), respectively. UV absorption at λ max 258 nm (log ε 3.79) was consistent with a five-membered α,β-unsaturated ketone chromophore . The signals at δ H 11.98 (2H, br s) in the 1 H NMR spectrum and corresponding signals at δ C 174.4 (s) and 172.5 (s) in the 13 C NMR spectrum indicated the presence of two carboxyl groups.…”

“…UV absorption at λ max 258 nm (log ε 3.79) was consistent with a five-membered R,β-unsaturated ketone chromophore. 6 The signals at δ H 11.98 (2H, br s) in the 1 H NMR spectrum and corresponding signals at δ C 174.4 (s) and 172.5 (s) in the 13 C NMR spectrum indicated the presence of two carboxyl groups. Signals of a ketone group (δ C 207.7, s) and a trisubstituted double bond (δ C 148.2, 129.0) were also presented.…”

“…Fifteen known compounds were also isolated and identified as meliastatin 3, kulonic acid, kulactone, , sendanolactone, , toosendanone A, dubione B, 24-methylenecycloartenone, meliavolin, 12β,20( S )-dihydroxydammar-24-en-3-one, dammarendiol II 3- O -caffeate, toosendanin, 1-tigloyl-3,20-diacetyl-11-methoxymeliacarpinin, 2β,3β,4β-trihydroxypregn-16-one, 3β-hydroxypregn-5,17(20)-dien-16-one, and 5α,8α-epidioxyergosta-6,22-dien-3β-ol by comparison of their physical and spectroscopic data with those published in the literature.…”

“…Fractionation of a 90% ethanol extract of M. azedarach bark by repetitive chromatographic separation yielded eight new compounds (1)(2)(3)(4)(5)(6)(7)(8). Compound 1 was obtained as colorless needles (MeOH) and possessed the molecular formula C 21 H 30 O 5 by HRESIMS, indicating seven degrees of unsaturation.…”

“…An EtOH extract of dried bark of M. azedarach (30 kg) was concentrated, and the aqueous solution was partitioned with EtOAc. The EtOAc extract (820 g) was subjected to silica gel CC eluted with CHCl 3 -Me 2 CO (from 1:0 to 0:1) to give seven fractions (1)(2)(3)(4)(5)(6)(7). Fraction 2 (80 g), subjected to silica gel CC eluted with petroleum ether-Me 2 CO from 20:1 to 8:1, gave four subfractions (2a-2d).…”