Mangiferin

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Mangiferin
Chemical structure of mangiferin Mangiferin.svg
Chemical structure of mangiferin
Chemical structure of mangiferin 3D Mangiferin 3D BS.png
Chemical structure of mangiferin 3D
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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.153.319 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
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 X mark.svgN
    Key: AEDDIBAIWPIIBD-ZJKJAXBQSA-N X mark.svgN
  • 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
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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Mangiferin is a glucosylxanthone (xanthonoid). This molecule is a glucoside of norathyriol.

Contents

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 Aspleniums. [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

  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. Bibcode:2008JAFC...56.5599B. doi:10.1021/jf800738r. PMID   18558692.
  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 .
  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. Bibcode:1971PChem..10.2117S. doi:10.1016/S0031-9422(00)97205-4.
  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. S2CID   31518535.
  9. ↑ "Mangiferin, CID 5281647". PubChem, National Library of Medicine, US National Institutes of Health. 23 November 2019. Retrieved 24 November 2019.
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