Xanthonoid

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Mangiferin, a xanthonoid found in mangoes

A xanthonoid is a chemical natural phenolic compound formed from the xanthone backbone. Many members of the Clusiaceae contain xanthonoids.

Xanthonoid biosynthesis in cell cultures of Hypericum androsaemum involves the presence of a benzophenone synthase condensing a molecule of benzoyl-CoA with three malonyl-CoA yielding to . This intermediate is subsequently converted by a , a cytochrome P450 monooxygenase, leading to the formation of .[1]

Some examples are , and isolated from the bark of Calophyllum tomentosum,[2] , , and from ,[3] , , , , , , , , , , , , , and from Garcinia gaudichaudii,[4] and from Swertia punicea[5] or obtained from Psorospermum febrifugum.[6] can be found in Cassia reticulata.[7]

Cytotoxic xanthones (, , , , , , , , , , gambogic acid, , morellic acid, and ) can be isolated from the dry latex of Garcinia hanburyi (gamboge tree).[8]

References[]

  1. ^ Alternative pathways of xanthone biosynthesis in cell cultures of Hypericum androsaemum L. Werner Schmidt and Ludger Beerhues, FEBS Letters, Volume 420, Issues 2-3, 29 December 1997, Pages 143-146, doi:10.1016/S0014-5793(97)01507-X
  2. ^ Tomentonone, a new xanthonoid from the stem bark of Calophyllum tomentosum. Banerji A., Deshpande A. D., Prabhu B. R. and Padmanava P., Journal of natural products, 1994, vol. 57, no3, pp. 396-399
  3. ^ Prenylated xanthonoids from Calophyllum apetalum. Munekazu Iinuma, Tetsuro Ito, Hideki Tosa, Toshiyuki Tanaka, Ryoko Miyake and Veliah Chelladurai, Phytochemistry, Volume 46, Issue 8, December 1997, Pages 1423-1429, doi:10.1016/S0031-9422(97)00507-4
  4. ^ Novel cytotoxic polyprenylated xanthonoids from Garcinia gaudichaudii (Guttiferae). Shu-Geng Cao, Valerie H. L. Sng, Xiao-Hua Wu, a, Keng-Yeow Sim, B. H. K. Tan, J. T. Pereira and S. H. Goh, Tetrahedron, Volume 54, Issue 36, 3 September 1998, Pages 10915-10924, doi:10.1016/S0040-4020(98)00644-9
  5. ^ Anti-diabetic effect of methylswertianin and bellidifolin from Swertia punicea Hemsl. and its potential mechanism. L.-Y. Tian, X. Bai, X.-H. Chen, J.-B. Fang, S.-H. Liu and J.-C. Chen, Phytomedicine, Volume 17, Issue 7, June 2010, Pages 533-539, doi:10.1016/j.phymed.2009.10.007
  6. ^ Psorospermin, A New Antileukemic Xanthone From Psorospermum febrifugum. Kupchan S. Morris, Streelman David R. and Sneden Albert T., Journal of Natural Products, Volume 43, issue 2 (1980), p. 296-301. doi:10.1021/np50008a010
  7. ^ Cassiaxanthone, a hydroxyxanthone dicarboxylic acid from Cassia species. M. S. R. Nair, T. C. McMorris and Marjorie Anchel, Phytochemistry, Volume 9, Issue 5, May 1970, Pages 1153-1155, doi:10.1016/S0031-9422(00)85246-2
  8. ^ Cytotoxic xanthones from Garcinia hanburyi. Jun Asano, Kazuhiro Chiba, Masahiro Tada and Takao Yoshii, Phytochemistry, Volume 41, Issue 3, February 1996, Pages 815-820, doi:10.1016/0031-9422(95)00682-6
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