Glaucolide from Vernonia staehelinoides

Antiplasmodial hirsutinolides from Vernonia staehelinoides and their utilization towards a simplified pharmacophore

“…These substructures are known to possess varying biological activities. The 2(5H)-furanone moiety occurs in many natural products that exhibit biological activities ranging from antibiotic (Miao andAndersen, 1991 andDavidson andIreland, 1990), cytotoxic (Ortega et al, 2000, Bohlmann et al, 1982aand Bohlmann et al, 1982b and antitumor properties (Hung et al, 1990) to inhibition of cholesterol biosynthesis (Kuhnt et al, 1990). On the other hand the dihydrofuran-4-one moiety is known for its antitumoral activity (Smith et al, 1981, Kupchan et al, 1976and LeQuesne et al, 1978.…”

“…staehelinoides is reported to be used medicinally but no details have been specified (Watt and Breyer-Brandwyk, 1962). Previous phytochemical investigations of this plant revealed that the roots contain squalene, stigmasterol and sitosterol while the aerial parts afforded caryophyllene, α-humulene, germacrene D and the novel glaucolide, 3βhydroxy-stilpnotomentolide-8-O-(5-acetoxysenecioate) (Bohlmann et al, 1982a andBohlmann et al, 1982b).…”

Triterpenoids

“…63 The bis(orthoquinone) (88) has been synthesized as a possible synthetic precursor to q~a s s i n .~~ The inactive quassinoid chaparrin (89) has been converted into castelanone (90) in 16% overall yield; this is a compound with significant antileukaemic activity (Scheme l).65 A series of bis(brusatoly1) and brusatolyl esters has been synthesized and tested for antileukaemic a~t i v i t y .~~,~~ (91), isolated from AiZunthus altissimu (Simaroubaceae), has shown that the 12-hydroxyl group has the a configuration.68 Three minor components from the same source were each shown (by X-ray analysis) to have a novel skeleton. These were shinjudilactone (92), which is a 13( 12+ 1 la)ubeo-picrasane,69 shinjulactone B (93), which is a 1,2-seco-l-nor-6(5 10)~beo-picrasane,~~ and shinjulactone C (94), which has an unprecedented hexacyclic 9P-H ~keleton.~ Treatment of ailanthone (91) with sodium hydrogen carbonate in aqueous methanol gave shinjudilactone (92) together with the (2-13 epimer. Similarly, norquassin (95) gave norquassinic acid (96).…”

“…~~, ~~ X-Ray analysis of ailanthone (91), isolated from AiZunthus altissimu (Simaroubaceae), has shown that the 12-hydroxyl group has the a configuration.68 Three minor components from the same source were each shown (by X-ray analysis) to have a novel skeleton. These were shinjudilactone (92), which is a 13( 12+ 1 la)ubeo-picrasane,69 shinjulactone B (93), which is a 1,2-seco-l-nor-6(5 10)~beo-picrasane,~~ and shinjulactone C (94), which has an unprecedented hexacyclic 9P-H ~keleton.~ Treatment of ailanthone (91) with sodium hydrogen carbonate in aqueous methanol gave shinjudilactone (92) together with the (2-13 epimer. Similarly, norquassin (95) gave norquassinic acid (96).…”

Análise metabolômica aplicada à quimiotaxonomia de espécies do gênero <i>Vernonia sensu lato</i> (Vernonieae)

“…Dentre as lactonas sesquiterpênicas, foram relatados com maior frequência as pertencentes a classe dos glaucolidos e dos hirsutinolidos WALLMEYER;JAKUPOVIC, 1982;LOPES, 1991).…”