Mangiferin

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Mangiferin
Mangiferin.svg
Mangiferin 3D BS.png
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 are no confirmed anti-disease effects or prescription drugs approved, as of 2019. [9]

See also

Related Research Articles

<span class="mw-page-title-main">Mango</span> Species of fruit

A mango is an edible stone fruit produced by the tropical tree Mangifera indica. It originated from the region between northwestern Myanmar, Bangladesh, and northeastern India. M. indica has been cultivated in South and Southeast Asia since ancient times resulting in two types of modern mango cultivars: the "Indian type" and the "Southeast Asian type". Other species in the genus Mangifera also produce edible fruits that are also called "mangoes", the majority of which are found in the Malesian ecoregion.

<i>Mangifera</i> Genus of flowering plants in the cashew family

Mangifera is a genus of flowering plants in the cashew family, Anacardiaceae. It contains 64 species, with the best-known being the common mango. The center of diversity of the genus is in the Malesian ecoregion of Southeast Asia, particularly in Sumatra, Borneo, and the Malay Peninsula. They are generally canopy trees in lowland rainforests, reaching a height of 30–40 m (98–131 ft).

<span class="mw-page-title-main">Cocoa butter</span> Pale-yellow, edible fat extracted from the cocoa bean

Cocoa butter, also called theobroma oil, is a pale-yellow, edible fat extracted from the cocoa bean. It is used to make chocolate, as well as some ointments, toiletries, and pharmaceuticals. Cocoa butter has a cocoa flavor and aroma. Its melting point is slightly below human body temperature. It is an essential ingredient of chocolate and related confectionary products. Cocoa butter does not contain butter or other animal products; it is vegan.

<span class="mw-page-title-main">Alkylresorcinol</span> Class of chemical compounds

Alkylresorcinols (ARs), also known as resorcinolic lipids, are amphiphilic phenolic lipids characterised by a non-polar odd-numbered alkyl side chain with up to 27 carbon atoms attached to a polar resorcinol (1,3-dihydroxybenzene) ring.

<span class="mw-page-title-main">Xanthone</span> Chemical compound

Xanthone is an organic compound with the molecular formula C13H8O2. It is a white solid.

Camphene is a bicyclic organic compound. It is one of the most pervasive monoterpenes. As with other terpenes, it is insoluble in water, flammable, colorless, and has a pungent smell. It is a minor constituent of many essential oils such as turpentine, cypress oil, camphor oil, citronella oil, neroli, ginger oil, valerian, and mango. It is produced industrially by isomerization of the more common alpha-pinene using a solid acid catalyst such as titanium dioxide.

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>Mangifera odorata</i> Species of tree

Mangifera odorata, commonly known as kwini, huani, or Saipan mango, is a species of plant with edible fruit in the family Anacardiaceae. It is similar to the related mango but is characterized by a strong turpentine-like smell on the skin and fibrous flesh. It is native to tropical Southeast Asia, but its exact original native range is unknown because it is only known from cultivated specimens and is believed to be a hybrid of Mangifera indica and Mangifera foetida. It is grown throughout Southeast Asia, from peninsular Thailand, to Malaysia, Indonesia and the southern Philippines. It has also been occasionally cultivated in southern Vietnam and the Marianas Islands.

<i>Mangifera pajang</i> Species of flowering plant

Mangifera pajang, commonly known as wild mango, is a species of tree in the family Anacardiaceae. It is endemic to Borneo, where it is known by the various native names: buahbambangan, buah mawang and buah embang.

<i>Mangifera indica</i> Species of flowering plant in the cashew family Anacardiaceae

Mangifera indica, commonly known as mango, is an evergreen species of flowering plant in the family Anacardiaceae. It is a large fruit tree, capable of growing to a height of 30 metres. There are two distinct genetic populations in modern mangoes – the "Indian type" and the "Southeast Asian type".

<span class="mw-page-title-main">Isoquercetin</span> Chemical compound

Isoquercetin, isoquercitrin or isotrifoliin is a flavonoid, a type of chemical compound. It is the 3-O-glucoside of quercetin. Isoquercitrin can be isolated from various plant species including Mangifera indica (mango) and Rheum nobile. It is also present in the leaves of Annona squamosa, Camellia sinensis (tea). and Vestia foetida

<span class="mw-page-title-main">Tectorigenin</span> Chemical compound

Tectorigenin is an O-methylated isoflavone, a type of flavonoid. It ha been isolated from leopard lily, Algerian iris and East Asian arrowroot.

<i>Asplenium montanum</i> Species of fern in the family Aspleniaceae

Asplenium montanum, commonly known as the mountain spleenwort, is a small fern endemic to the eastern United States. It is found primarily in the Appalachian Mountains from Vermont to Alabama, with a few isolated populations in the Ozarks and in the Ohio Valley. It grows in small crevices in sandstone cliffs with highly acid soil, where it is usually the only vascular plant occupying that ecological niche. It can be recognized by its tufts of dark blue-green, highly divided leaves. The species was first described in 1810 by the botanist Carl Ludwig Willdenow. No subspecies have been described, although a discolored and highly dissected form was reported from the Shawangunk Mountains in 1974. Asplenium montanum is a diploid member of the "Appalachian Asplenium complex," a group of spleenwort species and hybrids which have formed by reticulate evolution. Members of the complex descended from A. montanum are among the few other vascular plants that can tolerate its typical habitat.

<i>Asplenium bradleyi</i> Species of fern in the family Aspleniaceae

Asplenium bradleyi, commonly known as Bradley's spleenwort or cliff spleenwort, is a rare epipetric fern of east-central North America. Named after Professor Frank Howe Bradley, who first collected it in Tennessee, it may be found infrequently throughout much of the Appalachian Mountains, the Ozarks, and the Ouachita Mountains, growing in small crevices on exposed sandstone cliffs. The species originated as a hybrid between mountain spleenwort and ebony spleenwort ; A. bradleyi originated when that sterile diploid hybrid underwent chromosome doubling to become a fertile tetraploid, a phenomenon known as allopolyploidy. Studies indicate that the present population of Bradley's spleenwort arose from several independent doublings of sterile diploid hybrids. A. bradleyi can also form sterile hybrids with several other spleenworts.

<span class="mw-page-title-main">Irilone</span> Chemical compound

Irilone is an isoflavone, a type of flavonoid. It can be found in Trifolium pratense, in Iris unguicularis and in Iris germanica.

Kaempferol 7-<i>O</i>-glucoside Chemical compound

Kaempferol 7-O-glucoside is a flavonol glucoside. It can be found in Smilax china, and in the fern Asplenium rhizophyllum, and its hybrid descendants, as part of a complex with caffeic acid.

<i>Iris unguicularis</i> Species of flowering plant

Iris unguicularis, the Algerian iris, is a rhizomatous flowering plant in the genus Iris, native to Greece, Turkey, Western Syria, and Tunisia. It grows to 30 centimetres (12 in), with grassy evergreen leaves, producing pale lilac or purple flowers with a central band of yellow on the falls. The flowers appear in winter and early spring. They are fragrant, with pronounced perianth tubes up to 20 cm (7.9 in) long.

<i>Fusarium mangiferae</i> Species of fungus

Fusarium mangiferae is a fungal plant pathogen that infects mango trees. Its aerial mycelium is white and floccose. Conidiophores on aerial mycelium originating erect and prostrate from substrate; they are sympodially branched bearing mono and polyphialides. Polyphialides have 2–5 conidiogenous openings. Phialides on the aerial conidiophores mono- and polyphialidic. Sterile hyphae are absent. Microconidia are variable in shape, obovoid conidia are the most abundant type, oval to allantoid conidia occurring occasionally. Microconidia mostly 0-septate with 1-septate conidia occurring less abundantly. Sporodochia are present. Macroconidia are long and slender, usually 3–5 septate. Chlamydospores are absent.

<span class="mw-page-title-main">Deoxygedunin</span> Chemical compound

Deoxygedunin, or 14,15-deoxygedunin, is a tetranortriterpenoid isolated from the Indian neem tree a plant that has been in traditional Indian medicine since ancient times as a remedy for various ailments.

Deporaus marginatus, commonly known as the mango leaf-cutting weevil, is a species of leaf weevil in the beetle family Attelabidae. It is a light tan colour with black elytra, and is found in tropical Asia where it is a pest of mango.

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. 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.