Xanthonoid

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Mangiferin, a xanthonoid found in mangoes Mangiferin.svg
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 2,4,6-trihydroxybenzophenone. This intermediate is subsequently converted by a benzophenone 3′-hydroxylase, a cytochrome P450 monooxygenase, leading to the formation of 2,3′,4,6-tetrahydroxybenzophenone. [1]

Some examples are tomentonone, zeyloxanthonone and calozeyloxanthone isolated from the bark of Calophyllum tomentosum , [2] apetalinone A, B, C and D from Calophyllum apetalum , [3] gaudichaudione A, B, C, D, E, F, G, H, gaudichaudiic acid A, B, C, D, E, morellic acid and forbesione from Garcinia gaudichaudii , [4] methylswertianin and bellidifolin from Swertia punicea [5] or psorospermin obtained from Psorospermum febrifugum . [6] Cassiaxanthone can be found in Cassia reticulata . [7]

Cytotoxic xanthones (gambogin, morellin dimethyl acetal, isomoreollin B, moreollic acid, gambogenic acid, gambogenin, isogambogenin, desoxygambogenin, gambogenin dimethyl acetal, gambogellic acid, gambogic acid, isomorellin, morellic acid, desoxymorellin and hanburin) can be isolated from the dry latex of Garcinia hanburyi (gamboge tree). [8]

Related Research Articles

<i>Garcinia</i> Genus of flowering plants

Garcinia is a genus of flowering plants in the family Clusiaceae native to Asia, America, Australia, tropical and southern Africa, and Polynesia. The number of species is disputed; the Kew Gardens recognise up to 400. Commonly, the plants in this genus are called saptrees, mangosteens, garcinias, or monkey fruit.

Xanthone Chemical compound

Xanthone is an organic compound with the molecular formula O[C6H4]2CO. It is a white solid.

Mangostin Chemical compound

Mangostin is a natural xanthonoid, a type of organic compound isolated from various parts of the mangosteen tree. It is a yellow crystalline solid with a xanthone core structure. Mangostin and a variety of other xanthonoids from mangosteen have been investigated for biological properties including antioxidant, anti-bacterial, anti-inflammatory, and anticancer activities.

Malvin Chemical compound

Malvin is a naturally occurring chemical of the anthocyanin family.

Neoflavonoids are a class of polyphenolic compounds. While flavonoids have the 2-phenylchromen-4-one backbone, neoflavonoids have the 4-phenylchromen backbone with no hydroxyl group substitution at position 2.

<i>Garcinia morella</i> Species of flowering plant

Garcinia morella is a species of tree in the family Clusiaceae found in India, and Sri Lanka.

<i>Hypericum androsaemum</i> Species of flowering plant in the St Johns wort family Hypericaceae

Hypericum androsaemum, also referred to as Tutsan, Shrubby St. John's Wort, or sweet-amber, is a flowering plant in the family Hypericaceae. It is a perennial shrub reaching up to 70 cm in height, native to open woods and hillsides in Eurasia.

Neohesperidose Chemical compound

Neohesperidose is the disaccharide which is present in some flavonoids. It can be found in species of Typha.

Mangiferin Chemical compound

Mangiferin is a xanthonoid. This molecule is a glucoside of norathyriol.

Benzoyl-CoA Chemical compound

Benzoyl-CoA is a molecule implied in the activity of the different enzymes 4-hydroxybenzoyl-CoA reductase, benzoyl-CoA reductase, benzoyl-CoA 3-monooxygenase, benzoate-CoA ligase, 2alpha-hydroxytaxane 2-O-benzoyltransferase, anthranilate N-benzoyltransferase, biphenyl synthase, glycine N-benzoyltransferase, ornithine N-benzoyltransferase and phenylglyoxylate dehydrogenase (acylating).

Psoralea plicata is a herb species in the genus Psoralea found in Pakistan.

<i>Garcinia hanburyi</i> Species of flowering plant

Garcinia hanburyi is a plant species in the genus Garcinia, the gamboge trees.

Swertia punicea is a plant species in the genus Swertia.

Violdelphin Chemical compound

Violdelphin is an anthocyanin, a plant pigment, has been found in the purplish blue flower of Aconitum chinense, in the blue flowers in the genus Campanula and in the blue flowers of Delphinium hybridum. It is a flavenoid natural product, incorporating two p-hydroxy benzoic acid residues, one rutinoside and two glucosides associated with a delphinidin.

Lunularin Chemical compound

Lunularin is a dihydrostilbenoid found in common celery. It has also been found in the roots of Hydrangea macrophylla.

<i>Hypericum mysorense</i> Species of flowering plant

Hypericum mysorense is a species of flowering plant in the Hypericaceae family. It is primarily found at high elevations in the Western Ghats of India and the mountains of Sri Lanka, but was also reported from Socoro by Isaac Bayley Balfour in the 19th century. It was studied to improve understanding of endosperm formation in Hypericum, and the identification of a number of xanthone derivatives from this species contributed to the chemotaxonomic description of subfamily Hypericoideae.

<i>Hypericum ericoides</i> Species of flowering plant in the St Johns wort family Hypericaceae

Hypericum ericoides is a dwarf shrub in the flowering plant family Hypericaceae, section Coridium. It is found in eastern and southeastern Spain, Morocco, and Tunisia. Its preferred habitat is fissures in calcareous rocks in warm, sunny places, from 200 to 2,000 meters above sea level (MASL).

<i>Ploiarium</i> Genus of woody plants

Ploiarium is a genus of three species of woody plants in the family Bonnetiaceae. It is native to tropical forests and peat swamp forests in Southeast Asia including southern Indochina, Malay Peninsula, Sumatra, and Borneo. Species are generally slow growing with irregular flowering and fruiting cycles. Colonization of plants by arbuscular mycorrhizal fungi is known to improve growth and biomass.

Garcinia forbesii, commonly known as the rose kandis or just kandis, is a small to medium sized tree in the family Clusiaceae or Guttiferae. The specific epithet (forbesii) honors Scottish naturalist Henry Ogg Forbes.

<i>Garcinia pseudoguttifera</i> Species of tree

Garcinia pseudoguttifera, known as the mo'onia tree in its native range, is a species of flowering tree in the family Clusiaceae or Guttiferae.

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