52617-33-1Relevant academic research and scientific papers
CRYSTAL AND MOLECULAR STRUCTURE OF ISOGARCINOL
Krishnamurthy, N.,Ravindranath, B.
, p. 2233 - 2236 (1982)
The controversy with regard to the structures of the closely related polyisoprenylated phenolic compounds, garcinol, isogarcinol, camboginol, cambogin, xanthochymol and isoxanthochymol is cleared by X-ray crystallographic analisis of the naturally occurring isogarcinol.The unusual UV spectral characteristics of the chromophore of isogarcinol are discussed.
The guttiferones, HIV-inhibitory benzophenones from Symphonia globulifera, Garcinia livingstonei, Garcinia ovalifolia and Clusia rosea
Gustafson, Kirk R.,Blunt, John W.,Munro, Murray H. G.,Fuller, Richard W.,McKee, Tawnya C.,Cardellina II, John H.,McMahon, James B.,Cragg, Gordon M.,Boyd, Michael R.
, p. 10093 - 10102 (1992)
Extracts from species of the tropical plant genera Symphonia, Garcinia and Clusia (Guttiferae) have yielded a series of new polyisoprenylated benzophenone derivatives named guttiferones A-E (1-5). Structural assignments were based on detailed spectral analysis. These compounds inhibit the cytophatic effects of in vitro HIV infection.
Total synthesis and absolute configuration assignment of MRSA active garcinol and isogarcinol
Socolsky, Cecilia,Plietker, Bernd
, p. 3053 - 3061 (2015/02/05)
A short total synthesis of (±)-garcinol and (±)-isogarcinol, two endo-type B PPAPs with reported activity against methiciline resistant Staphylococcus aureus (MRSA), is presented. The separation of framework-constructing from framework-decorating steps and the application of two highly regio- and stereoselective Pd-catalysed allylations, that is, the Pd-catalysed decarboxylative Tsuji-Trost allylation and the diastereoselective Pd-catalysed allyl-allyl cross-coupling, are key elements that allowed the total synthesis to be accomplished within 13 steps starting from acetylacetone. After separation of the enantiomers the absolute configurations of the four natural products (i.e., (-)-garcinol, (+)-guttiferone E (i.e., ent-garcinol), (-)-isogarcinol, and (+)-isoxanthochymol (i.e., ent-isogarcinol)) were assigned based on ECD spectroscopy.
Xanthochymol and Isoxanthochymol, Two Novel Polyisoprenylated Benzophenones from Gracinia xanthochymus
Rao, A. V. Rama,Ventkatswamy, G.,Yemul, S. S.
, p. 627 - 633 (2007/10/02)
Two optically active polyprenylated benzophenone derivates, (+)-xanthochymol and (+)-isoxanthochymol have been isolated from the fruits of Gracinia xanthochymus (fam.: Guttiferae).Both these compounds possess the same molecular formula, C38H50O6, and have many common features.Xanthochymol has a free enolic hydroxyl group which forms a part of the chroman ring in isoxanthochymol.Chemical and spectral evidence clearly indicate that both these compounds are derived from maclurin (2,4,6,3',5'-pentahydroxybenzophenone) in which the acetate derived phloroglucinol ringbecomes the target of attack by five "active isoprene" groups.Although, a partial structure has been suggested, the final structure for (+)-isoxanthochymol (V) has been established by X-ray analysis.Spectral evidence including 13C NMR data leads to structure (VIII) for (+)-xanthochymol which has also been arrived at independently by Blount and Williams . (+)-Xanthochymol has been smoothly converted to (+)-isoxanthochymol by acid-catalysed reactions.Bronianone isolated earlier by Ollis et al., from G. hambroniana has the same basic skeleton as xanthochymol and can be represented as X instead of having a bicyclooctene system.
