A novel limonoid from the seeds of Chisocheton siamensis

Abstract

Analysis of an acetone/hexane (1:1) extract of the seeds of Chisocheton siamensis led to the isolation of a novel limonoid, chisosiamensin (1), along with five known limonoids, dysobinin (2), azadiradione (3), mohinin (4), epoxyazadiradione (5), and 6α -acetoxyepoxyazadiradione (6). Their structures were characterized by spectroscopic methods, including UV, IR, NMR, and MS. All isolated limonoids were reported for the first time as secondary metabolites of C. siamensis.Résumé : L'analyse d'un extrait par un mélange acétone-hexane (1:1) de graines de Chisocheton siamensis a permis d'extraire un nouveau limonoîde, la chisosiamensine (1), aux côtés de cinq limonoïdes connus, la dysobinine (2), l'azadiradione (3), la mohinine (4), l'époxyazadiradione (5) et la 6α -acétoxyépoxyazadiradione (6). On a caractérisé leurs structures par des méthodes spectroscopiques, incluant l'UV, l'IR, la RMN et la SM. Tous les limonoïdes isolés ont été identifiés pour la première fois comme métabolites secondaires du C. siamensis.

Cytotoxic Steroids From The Stembak of Chisocheton celebicus KOORD

“…The genus Chisocheton, belong to family Meliaceae, consisting more than 50 plants and distributes in Nepal, India, Myanmar, China, Thailand, Indonesia, Malaysia, and Papua New Guinea (Vossen and Umali, 2002). Previous investigation of chemical constituents on Chisocheton plants had reported contain sesquiterpenoids (Phongmaykin et al, 2008), dammarane-type triterpenoids (Phongmaykin et al, 2008;Inada et al, 1993), lanostane-type triterpenoid (Katja et al, 2017a), tirucallane-type triterpenoids (Zhang et al, 2012) apo-tirucallane-type triterpenoids (Zhang et al, 2012;Yang et al, 2011), euphane-type triterpenoids (Supratman et al, 2019); limonoids (Maneerat et al, 2008;Laphookhieo et al, 2008;Mohamad et al, 2009;Yang et al, 2009;Najmuldeen et al, 2011;Wong et al, 2011;Nurlelasari et al, 2017;Supriatno et al, 2018), steroids (Najmuldeen et al, 2011) and phenolics (Inada et al, 1993).…”

Cytototoxic constituents from the bark of Chisocheton cumingianus (Meliaceae)

“…Previous phytochemical studies on Chisocheton plants reported the presence of compounds with interesting biological activities including sesquiterpenoids [2], dammarane-type triterpenoids [2,3], tirucallane-type triterpenoids [4], apo-tirucallane-type triterpenoids [4,5], limonoids [6][7][8][9][10][11], steroids [10], and phenolics [3].…”

Senyawa Disobinin yang Bersifat Antimalaria dari Biji Tumbuhan Chisocheton Macrophyllus (Meliaceae)

“…Proton metin pada δH 2,84 dan 7,40 (H-17) saling terjodoh dua ikatan ( 2 J) dengan karbon metilen pada C-16 (δC 33,6) dan karbon kuarterner pada C-13 (δC 47,9) dan C-20 (δC 125,5) menyarankan posisi gugus furan terikat pada C-17. Perbandingan data NMR disobinin dengan senyawa limonoid yang ditemukan pada C. siamensis (Laphookhieo et al, 2008) menunjukkan kesesuaian yang tinggi, sehingga dengan demikian diidentifikasikan sebagai disobinin. Senyawa disobinin diuji aktivitas antimalaria terhadap P. falciparum galur 3D7 dengan nilai 0,001-0,01µg/mL.…”