Xanthanoid chemical compound
Mangiferin
Names
IUPAC name
2-(β-D -Glucopyranosyl)-1,3,6,7-tetrahydroxy-9H -xanthen-9-one
Systematic IUPAC name
1,3,6,7-Tetrahydroxy-2-[(2S ,3R ,4R ,5S ,6R )-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-9H -xanthen-9-one
Other names
(1S )-1,5-Anhydro-1-(1,3,6,7-tetrahydroxy-9-oxo-9H -xanthen-2-yl)-D -glucitol
Identifiers
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
100.153.319
KEGG
UNII
InChI=1S/C19H18O11/c20-4-11-15(25)17(27)18(28)19(30-11)12-8(23)3-10-13(16(12)26)14(24)5-1-6(21)7(22)2-9(5)29-10/h1-3,11,15,17-23,25-28H,4H2/t11-,15-,17+,18-,19+/m1/s1
N Key: AEDDIBAIWPIIBD-ZJKJAXBQSA-N
N InChI=1/C19H18O11/c20-4-11-15(25)17(27)18(28)19(30-11)12-8(23)3-10-13(16(12)26)14(24)5-1-6(21)7(22)2-9(5)29-10/h1-3,11,15,17-23,25-28H,4H2/t11-,15-,17+,18-,19+/m1/s1
Key: AEDDIBAIWPIIBD-ZJKJAXBQBF
C1=C2C(=CC(=C1O)O)OC3=C(C2=O)C(=C(C(=C3)O)[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O
Properties
C 19 H 18 O 11
Molar mass
422.342 g·mol−1
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
Mangiferin is a glucosylxanthone (xanthonoid ). This molecule is a glucoside of norathyriol .
Natural occurrences
Mangiferin was first isolated from the leaves and bark of Mangifera indica (the mango tree).[ 1] It can also be extracted from mango peels and kernels,[ 2] [ 3] Iris unguicularis ,[ 4] Anemarrhena asphodeloides rhizomes[ 5] and Bombax ceiba leaves.[ 6] It is also found in the genera Salacia and Cyclopia , as well as in coffee leaves and some species of Crocus .
Among the group of Asplenium hybrids known as the "Appalachian Asplenium complex", mangiferin and isomangiferin are produced only by Asplenium montanum and its hybrid descendants. The distinctive gold-orange fluorescence of these compounds under ultraviolet light has been used to aid in the chromatographic identification of hybrid Asplenium s.[ 7]
Research
Preliminary research is conducted on the potential biological properties of mangiferin,[ 8] although there were no confirmed anti-disease effects or prescription drugs approved, as of 2019.[ 9]
See also
References
^ K. Gorter (April 1922). "Sur La Substance Mère du Jaune Indien ", Bulletin du Jardin botanique de Buitenzorg, (in French). Volume 4 Series 3 Issue 2: p. 260–267; [J.C.S. (20 April 1923). "The precursor of Indian-yellow ", Chemical Abstracts, (in English), Volume 17 Issue No. 8: p. 1472] – via archive.com
^ Barreto J.C.; Trevisan M.T.S.; Hull W.E.; Erben G.; De Brito E.S.; Pfundstein B.; Würtele G.; Spiegelhalder B.; Owen R.W. (2008). "Characterization and quantitation of polyphenolic compounds in bark, kernel, leaves, and peel of mango (Mangifera indica L.)". Journal of Agricultural and Food Chemistry . 56 (14): 5599–5610. doi :10.1021/jf800738r . PMID 18558692 .
^ Rajneet K Khurana, Rajneet K Khurana; Kaur, Ranjot; Lohan, Shikha; K Singh, Kamalinder; Singh, Bhupinder (2016). "Mangiferin: a promising anticancer bioactive" (PDF) . Pharmaceutical Patent Analyst . 5 (3): 169–181. doi :10.4155/ppa-2016-0003 . PMID 27088726 .
^ Atta-Ur-Rahman; Hareem, Sumaira; Iqbal Choudhary, Muhammad; Sener, Bilge; Abbaskhan, Ahmed; Siddiqui, Hina; Anjum, Shazia; Orhan, Ilkay; Gurbuz, Ilhan; Ayanoglu, Filiz (2010). "New and Known Constituents from Iris unguicularis and Their Antoioxidant Activity" . Heterocycles . 82 : 813. doi :10.3987/COM-10-S(E)6 .
^ Miura, T.; Ichiki, H.; Hashimoto, I.; Iwamoto, N.; Kato, M.; Kubo, M.; Ishihara, E.; Komatsu, Y.; Okada, M.; Ishida, T.; Tanigawa, K. (2001). "Antidiabetic Activity of a Xanthone Compound, Mangiferin". Phytomedicine . 8 (2): 85–87. doi :10.1078/0944-7113-00009 . PMID 11315760 .
^ Dar, A; Faizi, S; Naqvi, S; Roome, T; Zikr-Ur-Rehman, S; Ali, M; Firdous, S; Moin, S. T. (2005). "Analgesic and antioxidant activity of mangiferin and its derivatives: The structure activity relationship" . Biological & Pharmaceutical Bulletin . 28 (4): 596–600. doi :10.1248/bpb.28.596 . PMID 15802793 .
^ Smith, Dale M.; Harborne, Jeffrey B. (1971). "Xanthones in the Appalachian Asplenium complex". Phytochemistry . 10 (9): 2117–2119. Bibcode :1971PChem..10.2117S . doi :10.1016/S0031-9422(00)97205-4 .
^ Khare, Puja; Shanker, Karuna (10 September 2016). "Mangiferin: A review of sources and interventions for biological activities". BioFactors . 42 (5): 504–514. doi :10.1002/biof.1308 . ISSN 0951-6433 . PMID 27658353 . S2CID 31518535 .
^ "Mangiferin, CID 5281647" . PubChem, National Library of Medicine, US National Institutes of Health. 23 November 2019. Retrieved 24 November 2019 .
Aglycones
Apetalinone A , B , C and D
Bellidifolin
Calozeyloxanthone
Desoxygambogenin
Desoxymorellin
Euxanthone
Forbesione
Gambogellic acid
Gambogenic acid
Gambogenin
Gambogenin dimethyl acetal
Gambogic acid
Gambogin
Gaudichaudiic acid A , B , C , D and E
Gaudichaudione A , B , C , D , E , F , G and H
Hanburin
Isogambogenin
Isojacareubin
Isomorellin
Isomoreollin B
Methylswertianin
Morellic acid
Morellin dimethyl acetal
Moreollic acid
Norathyriol
Psorospermin
2,3′,4,6-tetrahydroxybenzophenone
Tomentonone
Zeyloxanthonone
Glycosides Acetylated Misc.