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Mangiferin

March 15, 2024

Mangiferin is a glucosylxanthone (xanthonoid). This molecule is a glucoside of norathyriol.

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
  • 4773-96-0 Y
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:6682 N
ChEMBL
  • ChEMBL455364 N
ChemSpider
  • 4444966 N
ECHA InfoCard 100.153.319
KEGG
  • C10077 N
  • 5281647
UNII
  • 1M84LD0UMD N
  • DTXSID60197263
  • 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
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).
N verify (what is YN ?)

Natural occurrences edit

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 edit

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]

See also edit

References edit

  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.
  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 (inactive 2024-02-17).{{cite journal}}: CS1 maint: DOI inactive as of February 2024 (link)
  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.
  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.

March 15, 2024
mangiferin, glucosylxanthone, xanthonoid, this, molecule, glucoside, norathyriol, namesiupac, name, glucopyranosyl, tetrahydroxy, xanthen, onesystematic, iupac, name, tetrahydroxy, trihydroxy, hydroxymethyl, oxan, xanthen, oneother, names, anhydro, tetrahydrox. Mangiferin is a glucosylxanthone xanthonoid This molecule is a glucoside of norathyriol Mangiferin NamesIUPAC name 2 b D Glucopyranosyl 1 3 6 7 tetrahydroxy 9H xanthen 9 oneSystematic 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 oneOther names 1S 1 5 Anhydro 1 1 3 6 7 tetrahydroxy 9 oxo 9H xanthen 2 yl D glucitolIdentifiersCAS Number 4773 96 0 Y3D model JSmol Interactive imageChEBI CHEBI 6682 NChEMBL ChEMBL455364 NChemSpider 4444966 NECHA InfoCard 100 153 319KEGG C10077 NPubChem CID 5281647UNII 1M84LD0UMD NCompTox Dashboard EPA DTXSID60197263InChI 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 NKey AEDDIBAIWPIIBD ZJKJAXBQSA N NInChI 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 s1Key AEDDIBAIWPIIBD ZJKJAXBQBFSMILES 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 OPropertiesChemical formula C 19H 18O 11Molar mass 422 342 g mol 1Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references Contents 1 Natural occurrences 2 Research 3 See also 4 ReferencesNatural occurrences editMangiferin 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 editPreliminary 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 See also editEuxanthic acidReferences edit K Gorter April 1922 Sur La Substance Mere 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 Wurtele 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 inactive 2024 02 17 a href Template Cite journal html title Template Cite journal cite journal a CS1 maint DOI inactive as of February 2024 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 amp 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 S2CID 31518535 Mangiferin CID 5281647 PubChem National Library of Medicine US National Institutes of Health 23 November 2019 Retrieved 24 November 2019 Retrieved from https en wikipedia org w index php title Mangiferin amp oldid 1212467512, wikipedia, wiki, book, books, library,

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