Neohesperidose

Last updated
Neohesperidose
Neohesperidose.svg
Neohesperidose 3D BS.png
Names
IUPAC name
α-L-Rhamnopyranosyl-(1→2)-D-glucose
Systematic IUPAC name
(2R,3S,4R,5R)-3,4,5,6-Tetrahydroxy-2-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}hexanal
Other names
2-O-alpha-L-Rhamnopyranosyl-D-glucopyranose
2-O-alpha-L-Rhamnosyl-D-glucose
2-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranose
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.037.379 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
  • InChI=1S/C12H22O10/c1-3-5(14)7(16)9(18)12(20-3)22-10-8(17)6(15)4(2-13)21-11(10)19/h3-19H,2H2,1H3/t3-,4+,5-,6+,7+,8-,9+,10+,11+,12-/m0/s1 X mark.svgN
    Key: VSRVRBXGIRFARR-OUEGHFHCSA-N X mark.svgN
  • InChI=1/C12H22O10/c1-3-5(14)7(16)9(18)12(20-3)22-10-8(17)6(15)4(2-13)21-11(10)19/h3-19H,2H2,1H3/t3-,4+,5-,6+,7+,8-,9+,10+,11+,12-/m0/s1
    Key: VSRVRBXGIRFARR-OUEGHFHCBJ
  • O([C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O)[C@@H]2O[C@H]([C@H](O)[C@@H](O)[C@H]2O)C
Properties
C12H22O10
Molar mass 326.29 g/mol
Density 1.662 g/mL
Related compounds
Related compounds
Rhamnose
Glucose
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Neohesperidose is the disaccharide which is present in some flavonoids. It can be found in species of Typha . [1] [2]

Contents

Neohesperidosides

See also

Related Research Articles

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<span class="mw-page-title-main">Flavonoid</span> Class of plant and fungus secondary metabolites

Flavonoids are a class of polyphenolic secondary metabolites found in plants, and thus commonly consumed in the diets of humans.

<span class="mw-page-title-main">Anthocyanidin</span> Class of natural compounds

Anthocyanidins are common plant pigments, the aglycones of anthocyanins. They are based on the flavylium cation, an oxonium ion, with various groups substituted for its hydrogen atoms. They generally change color from red through purple, blue, and bluish green as a function of pH.

<i>Myrciaria dubia</i> Species of plant in the family Myrtaceae

Myrciaria dubia, commonly known as camu-camu, caçari, araçá-d'água, or camocamo, is a species of plant in the family Myrtaceae. It is a small bushy riverside tree from the Amazon rainforest in Peru and Brazil, which grows to a height of 3–5 m (9.8–16.4 ft) and bears a red/purple cherry-like fruit. It is a close relative of the false jaboticaba and the guavaberry or rumberry. As much as 2 to 3% of the fresh fruit by weight is vitamin C.

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Aristotelia chilensis, known as maqui or Chilean wineberry, is a tree species in the Elaeocarpaceae family native to South America in the Valdivian temperate forests of Chile and adjacent regions of southern Argentina. Limited numbers of these trees are cultivated in gardens for their small edible fruits. Wild-harvested fruits are commercially marketed.

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

Europinidin (Eu) is an O-methylated anthocyanidin. It is a water-soluble, bluish red plant dye. It is a rare O-methylated flavonoid, a derivative of delphinidin. It can be found in some species of Plumbago and Ceratostigma.

The pyranoanthocyanins are a type of pyranoflavonoids. They are chemical compounds formed in red wines by yeast during fermentation processes or during controlled oxygenation processes during the aging of wine. The different classes of pyranoanthocyanins are carboxypyranoanthocyanins, methylpyranoanthocyanins, pyranoanthocyanin-flavanols, pyranoanthocyanin-phenols, portisins, oxovitisins and pyranoanthocyanin dimers; their general structure includes an additional ring that may have different substituents linked directly at C-10.

<i>p</i>-Coumaroylated anthocyanin

p-Coumaroylated anthocyanins are a type of anthocyanins with a p-coumaric acid unit linked with a sugar to an anthocyanidin aglycone. 3-(6-p-Coumaroyl)glucosides are found in grape and wine. Cyanidin-3-O-(di-p-coumarylglucoside)-5-glucoside is found in dark opal basil. Red leaves of Perilla frutescens also accumulate cyanidin 3-(6-O-p-coumaroyl-β-D-glucoside)-5-(6-O-malonyl-β-D-glucoside).

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

Veronicastroside is a flavone, a type of flavonoid. It is the 7-O-neohesperidoside of luteolin. It can be found in Veronicastrum sibiricum var. japonicum and in Teucrium gnaphalodes.

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

Ideain, the cyanidin 3-O-galactoside, is an anthocyanin, a type of plant pigment.

<span class="mw-page-title-main">Basics of blue flower colouration</span>

Blue flower colour was always associated with something unusual and desired. Blue roses especially were assumed to be a dream that cannot be realised. Blue colour in flower petals is caused by anthocyanins, which are members of flavonoid class metabolites. We can diversify three main classes of anthocyanin pigments: cyaniding type responsible for red coloration, pelargonidin type responsible for orange colour and delphinidin type responsible for violet/blue flower and fruits coloration. The main difference in the structure of listed anthocyanins type is the number of hydroxyl groups in the B-ring of the anthocyanin. Nevertheless, in the monomeric state anthocyanins never show blue colour in the weak acidic and neutral pH. The mechanism of blue colour formation are very complicated in most cases, presence of delphinidin type pigments is not sufficient, great role play also the pH and the formation of complexes of anthocyanins with flavones and metal ions.

<i>Alkekengi</i> Species of edible flowering plant native to Eurasia

Alkekengi officinarum, the bladder cherry, Chinese lantern, Japanese-lantern, strawberry groundcherry, winter cherry, alchechengi berry, or Klabuster cherry is a species of flowering plant in the nightshade family Solanaceae. It is a close relative of the new world Calliphysalis carpenteri and a somewhat more distant relative to the members of the Physalis genus. This species is native to the regions covering Southern Europe to South Asia and Northeast Asia.

References

  1. Horowitz, R. M.; Gentili, Bruno (January 1963). "Flavonoids of citrus—VI: The structure of neohesperidose". Tetrahedron. 19 (5): 773–782. doi:10.1016/S0040-4020(01)99211-7.
  2. 1 2 3 Andersen, Oyvind M. (1989). "Delphinidin-3-neohesperidoside and cyanidin-3- neohesperidoside from receptacles of Podocarpus species". Phytochemistry. 28 (2): 495–497. Bibcode:1989PChem..28..495A. doi:10.1016/0031-9422(89)80039-1.
  3. Ismail, N.; Alam, M. (2001). "A novel cytotoxic flavonoid glycoside from Physalis angulata". Fitoterapia. 72 (6): 676–679. doi:10.1016/S0367-326X(01)00281-7.