Mangiferin

Mangiferin
Names
	IUPAC name (1S)-1,5-Anhydro-1-(1,3,6,7-tetrahydroxy-9-oxo-9H-xanthen-2-yl)-D-glucitol
Identifiers
CAS Number	4773-96-0 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:6682 ;
ChEMBL	ChEMBL455364 ;
ChemSpider	4444966 ;
ECHA InfoCard	100.153.319
KEGG	C10077 ;
PubChem CID	5281647;
UNII	1M84LD0UMD ;
CompTox Dashboard (EPA)	DTXSID60197263 ;
	InChI 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 Key: AEDDIBAIWPIIBD-ZJKJAXBQSA-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;
	SMILES 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
Chemical formula	C19H18O11
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).
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	Infobox references

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

Natural occurrences

Mangiferin was first isolated from the leaves and bark of Mangifera indica.[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.

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 Aspleniums.[7]

Research

Preliminary research is conducted on the potential biological properties of mangiferin,[8] although there are no confirmed anti-disease effects or prescription drugs approved, as of 2019.[9]

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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.CS1 maint: numeric names: authors list (link)
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. 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.
"Mangiferin, CID 5281647". PubChem, National Library of Medicine, US National Institutes of Health. 23 November 2019. Retrieved 24 November 2019.

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[1] 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

[2] 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.

[:0-3] 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.

[4] 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.CS1 maint: numeric names: authors list (link)

[Miura-5] 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.

[6] 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.

[7] Smith, Dale M.; Harborne, Jeffrey B. (1971). "Xanthones in the Appalachian Asplenium complex". Phytochemistry. 10 (9): 2117–2119. doi:10.1016/S0031-9422(00)97205-4.

[Khare-8] 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.

[pubchem-9] "Mangiferin, CID 5281647". PubChem, National Library of Medicine, US National Institutes of Health. 23 November 2019. Retrieved 24 November 2019.

Types of xanthonoids
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	Euxanthic acid Isomangiferin Mangiferin Mangostin-3,6-di-O-glucoside Wubangziside A Wubangziside B
Acetylated	Mangostin
Misc.	Indian yellow Gartanin 8-disoxygartanin Normangostin

Mangiferin

Natural occurrences

Research

See also

References