(2S)-Prenylflavanones and taraxerane triterpenoids from Mallotus mollissimus. (August 2017)

• Record Type: Journal Article
• Authors: Phan, Minh Giang; Vu, Minh Trang; Kawakami, Susumu; Otsuka, Hideaki
• Is Part Of: Biochemical systematics and ecology. Volume 73(2017)
• Page Start: 22
• Page End: 25
• Publication Date: 2017-08
• Subjects: Mallotus mollissimus -- Euphorbiaceae -- Taraxerane -- (2S)-Prenylflavanone; Chemotaxonomy -- Periodicals; Biochemical variation -- Periodicals; Ecology -- Periodicals; Biochemistry -- Periodicals; Ecology -- Periodicals; Chimiotaxinomie -- Périodiques; Variation biochimique -- Périodiques; Écologie -- Périodiques; 578.012
• DOI: 10.1016/j.bse.2017.05.004
• Languages: English
• ISSNs: 0305-1978

Abstract

Abstract: Three prenylflavanones, (2 S )-5, 7-dihydroxy-4′-methoxy-8-(3″, 3″-dimethylallyl)flavanone (3 ), (2 S )-5, 4′-dihydroxy-7-methoxy-6-(3″, 3″-dimethylallyl)flavanone (6 ), 8-prenylnaringenin (11 ), and a new epimeric pair (2″ S /2″ R )-(2 S )-5, 7-dihydroxy-4′-methoxy-6-(2″-hydroxy-3″-methylbut-3″-enyl)flavanones (4a/4b ) were isolated together with taraxerone, taraxerol, epitaraxerol, β -sitosterol, oleanolic acid, 1- O -docosanoyl glycerol, apigenin, and apigenin 7- O - β -D-glucopyranoside from the MeOH extract of the leaves of Mallotus mollissimus . The structures of the isolated compounds were determined on the basis of 1D/2D NMR and HR-MS spectroscopic data; the 2 S configuration of the prenylflavanones3, 4, and6 was deduced from CD spectroscopic data. The presence of three taraxerane triterpenoids reinforces the inclusion of M. mollissimus ( syn. Croton mollissimus ) in Mallotus genus. Among species of Mallotus the occurrence of the (2 S )-prenylflavanones3, 4, and6 is confined to M. mollissimus . Graphical abstract: Eleven compounds and a mixture of two new epimers4a /4b were isolated for the first time from the leaves of Mallotus mollissimus . The (2 S ) absolute configurations of prenylflavanones3, 6, and the epimeric pair4a /4b were determined by CD analysis. The presence of taraxerane triterpenoids reinforces the inclusion of M. mollissimus in Mallotus genus. Among species of Mallotus the occurrence of (2 S )-prenylflavanones3, 4a/4b, and6 is confined to M. mollissimus . Highlights: Eleven compounds and a mixture of two new epimers were isolated for the first time from the leaves of Mallotus mollissimus. The (2 S ) absolute configurations of prenylflavanones3, 6, and the epimeric pair4a /4b were determined by CD analysis. The presence of taraxerane triterpenoids reinforces the inclusion of M. mollissimus in Mallotus genus. Among the Mallotus species the occurrence of (2 S )-Prenylflavanones3, 4a/4b, and6 is confined to M. mollissimus.