Methyl Oxygenated friedooleananes from elaeodendron species

Abstract

This work describes the studies on several angular melnyl oxygenated friecoolearnanes which were isolated from two Sri Lanka Elueodendron species, E. glaucum ana E. balae (Celastraceae). The oceourrence and chemistry or angular methyl oxygenated oleananes and friedooleananes is surveyed. Two new methyl oxygenated D:A-friedooleananes, «3,26=dioxo=D: A~triedooleanan-25—01 and 25,28=-dihydroxy- D:A-fricdooleanans3-one along with eight known D:A~ friedooleananes were isolated from the stem bark of E. glaucum. Another methyl oxygenatec D:A—friedooleanarie , 28,29-dihydroxy-D: A~friedooleanen=3-one was isolated from the stem bark of E. balae. The benzene extract of the root bark or bk. bealas contained e new metnyl oxygenated Dibefriedooleanane, <formula> together with olean<formula> pristimerin, tingenone, <formula> and a new triterpene quinone=methide, 3,21—dihydroxy~24,29-dinor~D: A~friedooleans= 2,5,7,9(11),10(1)=pentene=2,22~dione. The ethyl acetate extract of the root vark of E. balae contained (—)=3,3",5,5',7=pentahydroxy=4*=me thoxy 2,3-cis-flavene, 4*°,5,7~trihydroxy=(~)-epicatecnin <formula> 4-O'-me thyl-(-)-epigallocatechin and a new Jeucoanthocyanidir. whose structure was postulated on the basis of its 1H NMR NMR spectral data. The first two flavonoids were 1d in the methaiol extract of the stem bark of MPP osether with the sugar alcohol aulcitol which o found in the methanol extract of the root bark 1e salie species. The thesis also includes a short chapter on ‘the uments used to assign the 13g NMR signals of four \-friedooleananols, one D:A=friedooleananal and two <formula> Amfriedooleanan=3—ones.