Bina Shaheen SIDDIQUI, Syed Kashif ALI, Syed Tariq ALI, Fayyaz AHMED

Pregnane steroids from the heartwood of Azadirachta indica

The heartwood of Azadirachta indica (Meliaceae) yielded a new steroid (2a, 3b, 4b-trihydroxypregnan-16-one) and 2 known steroids (2b, 3b, 4b-trihydroxypregnan-16-one and 2a, 3a, 4b-trihydroxypregnan-16-one). Their structures were elucidated through spectral studies including 2D NMR (COSY, NOESY, J-resolved, HMQC, HMBC) experiments.

Anahtar Kelimeler:

Azadirachta indica, Meliaceae, heartwood, steroids, 2a, 3b, 4b-trihydroxypregnan-16-one, 2b, 3b, 4b -trihydroxypregnan-16-one, 2a, 3a, 4b-trihydroxypregnan-16-one.

Pregnane steroids from the heartwood of Azadirachta indica

Keywords:

Azadirachta indica, Meliaceae, heartwood, steroids, 2a, 3b, 4b-trihydroxypregnan-16-one, 2b, 3b, 4b -trihydroxypregnan-16-one, 2a, 3a, 4b-trihydroxypregnan-16-one.,

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OAc O H R = ββββ-OH, R1 = α αα R = R1 = ββββ-OH R = R1=αα-OH αααα-OH Figure. Compounds isolated from Azadirachta indica. Acetylation of 1 To a solution 1 (10 mg) in pyridine (0.5 mL) was added Ac2O (1 mL) and the mixture was left overnight at room temperature. The mixture was poured over crushed ice and extracted with EtOAc. After the usual workup of the EtOAc phase and puriŞcation by TLC (silica gel, CHCl3) the triacetyl derivative, 2α , 3 β , β - triacetoxypregnan-16-one (1a) (3.8 mg) was obtained as an amorphous powder. IR νmax(CHCl3): 1742
(C=O), 1725 (br., ester carbonyls) cm−1; EIMS m/z : 476 [M+].1H-NMR (400MHz, CDCl3): δ 5.32 (1H, dd, J =4.0, 3.3 Hz, H-4), 5.28 (1H, br. m, H-2), 4.90 (1H, dd, J = 11.1, 4.0 Hz, H-3), 2.06, 2.00, 1.95 (each 3H, s, 3 x OAc).
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