Dysobinin, a new tetranortriterpene from Dysoxylum binectariferum

A new havanensin-type limonoid from Chisocheton macrophyllus

“…Correlations between δ H 5.46 (H-6) and CH 3 -19 (δ H 1.28) with β-oriented, indicated that H-6 was β-oriented and acetyl group at C-6 is α-oriented. Furthermore, the optical rotation of 1, [ α] 27 D +122.5° (c 0.2, MeOH) is the same sign to those of previously reported dysobinin ( 6) ([α] 20 D + 150°) [17,18]. Therefore, the structure of 1 was elucidated as the new havanensin-type of limonoid derivative and named 16β-hydroxydysobinin.…”

“…These functionalities accounted for seven out of the twelve degrees of unsaturation, while the remaining five degrees of unsaturation corresponded to the pentacyclic limonoid structure [6,11,15,16]. The NMR spectra data of 1 resembled those of previously reported dysobinin [16,17], except for the appearance of oxygenated signals [δ H 4.49 (1H, t, J = 7.7 Hz), δ C 67.2], thus suggesting that 1 was a hydroxyl analog of dysobinin. Position of the hydroxyl group at C-16 was determined through the 1 H-1 H correlated spectroscopy ( 1 H-1 H COSY) and proton multiple bond connectivity (HMBC) experiments (Fig.…”

Dysobinin, a tetranortriterpenoid

“…Dysobinin was isolated from the alcoholic extract of the air-dried powdered fruits of Dysoxylum binecteriferum (Singh et al, 1976). Diffraction-quality crystals were obtained by slow evaporation from a methanol solution at room temperature.…”

“…Dysobinin is a tetranortriterpenoid belonging to the meliacin class of compounds and was isolated from Dysoxylum binecteriferum in around 2% yield (Singh et al, 1976). It is an example of a growing family of meliacins and is of chemotaxonomic importance as it is a 6-acetoxy derivative of azadirone occurring in Melia azadirachta, a plant of the same family.…”

Production of rohitukine in leaves and seeds ofDysoxylum binectariferum: An alternate renewable resource

“…Dysoxylum binectariferum is an evergreen tree native to India, China, and other parts of Asia. Other chemical compounds reported from the tree are 6,7-dihydroxy-1,14-meliacadien-3-one (6b,7a)-form, 6,7-DiAc, also known as dysobinin (Singh et al, 1976), and rohitukine N-oxide (Yang et al, 2004). Recently, 14 new dammarane-type triterpenoids were isolated from the bark of D. binectariferum (Yan et al, 2014).…”