Malayanines A and B, two novel limonoids from Chisocheton erythrocarpus Hiern

Advances in Chemistry and Bioactivity of the Genus Chisocheton Blume

“…Phytochemical investigation of C. ceramicus bark afforded various classes of limonoids including highly modified structures of phragmalins and mexicanolides. Based on the published biogenetic pathways toward the formation of various limonoids, a plausible biogenetic pathway ( Scheme ) is proposed in this review toward the formation of mexicanolides and phragmalins of C. ceramicus from ring D ‐ seco ‐limonoid gedunin ( 51 ) . The phragmalin class limonoids reported by Najmuldeen et al .…”

“…were isolated from C. erythrocarpus bark collected from Hutan Simpan Terenas of Kedah, a northern state of Peninsular Malaysia . However, when the same plant part was collected from Johor, the most southern state of Malaysia, two new limonoids, malayanine A ( 54 ) and malayanine B ( 55 ), were isolated . Erythrocarpines were also present in the extract; thus, a biogenetic pathway from erythrocarpine A ( 30 ) to malayanine A ( 54 ) and malayanine B ( 55 ) was proposed, where it was suggested that erythrocarpine A ( 30 ) might give rise to malayanine A ( 54 ) through C(29)–C(1) bridge formation and C(1)–C(2) bond cleavage, whereas a C(29)–C(1) bridge formation and C(10)–C(1) bond cleavage by oxygen radical‐mediated coupling leads to malayanine B ( 55 ).…”

“…Plausible biogenetic pathway for the formation of mexicanolide, phragmalin, and mexicanolide‐derived A , B ‐ seco limonoids in Chisocheton .…”

“…Possibly, these compounds derive from phragmalin class limonoids. However, the absence of phragmalins in C. erythrocarpus or in Trichilia connaroides , which produces trichiliton A, a limonoid similar to that of chisomicine A ( 53 ) suggests that mexicanolides act as the precursor toward the formation of aforementioned molecules . Based on the previously proposed biosynthetic pathways, mexicanolides undergo a photoinitiated Norrish II reaction for the production of phragmalins and related limonoids .…”

A New Lignan Derivative, Lasiocarpone, from The Stembark of Chisocheton iasiocarpus (Meliaceae)

“…The Chisocheton plant genera as a second largest plant of Meliaceae family, consisting of 50 plants and widely distributed in the tropics. Previous phytochemical studies of this genera have produced some compounds with interesting biological activity, such as anti-plasmodial 1 limonoid 2 , cytotoxic limonoid 3 , and anti-inflammatory limonoids 4 , NO production inhibitory activity limonoids 5 , cell growth inhibitory activity limonoids 6 , anti-inflammatory protolimonoids 7 , cytotoxic triterpenoid 8 and cytotoxic tetranortriterpenoid 9 .…”