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Idaein

From Wikipedia, the free encyclopedia
Idaein
Structure of ideain chloride
Names
IUPAC name
(2S,4S,5R)-2-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromenylium-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol;chloride
Other names
Ideain, cyanidin 3-O-galactoside, Cy3Gal
Identifiers
3D model (JSmol)
ChemSpider
KEGG
UNII
  • InChI=1S/C21H20O11.ClH/c22-7-16-17(27)18(28)19(29)21(32-16)31-15-6-10-12(25)4-9(23)5-14(10)30-20(15)8-1-2-11(24)13(26)3-8;/h1-6,16-19,21-22,27-29H,7H2,(H3-,23,24,25,26);1H/t16?,17-,18-,19?,21+;/m0./s1
    Key: YTMNONATNXDQJF-DJBUQWCWSA-N
  • C1=CC(=C(C=C1C2=C(C=C3C(=CC(=CC3=[O+]2)O)O)OC4C(C(C(C(O4)CO)O)O)O)O)O.[Cl-]
Properties
C21H21ClO11 (chloride), C21H21O11+ (cation)
Molar mass 484.83 g/mol (chloride), 449.38 g/mol (cation)
UV-vis (λmax) 528 nm (in methanol)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Idaein, also known as ideain, cyanidin 3-O-galactoside, or Cy3Gal, is a type of anthocyanin, a class of plant pigment compounds.

Natural occurrences

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Idaein is the main anthocyanin compound in lingonberries (Vaccinium vitis-idaea),[1][2] and the name of the compound is derived from the Latin name of the plant.[1][3] It is also present as one of the many anthocyanins compounds found in bilberries (Vaccinium myrtillus)[4] and cranberries (Vaccinium macrocarpon).[5]

Idaein is the main anthocyanin in red-skinned or red-fleshed (for example Weirouge[6] or Surprise) apple varieties.[7][8][9] It is also found in Chinese hawthorn fruits (Crataegus spp.).[10] It is also the pigment in the copper beech (cultivar of Fagus sylvatica), that was identified in 1932.[11]

Quintinia serrata, the tawheowheo, a species of evergreen trees endemic to New Zealand, has different patterns of anthocyanins (cyanidin 3-O-glucoside and cyanidin 3-O-galactoside) in its leaves to protect the shade-adapted chloroplasts from direct sunlight.[12]

References

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  1. 1 2 Willstätter, Richard; Mallison, Heinrich (1915). "Untersuchungen über die Anthocyane. III. Über den Farbstoff der Preiselbeere" [Studies on anthocyanins. III. On the pigment of lingonberries]. Justus Liebigs Annalen der Chemie. 408 (1): 15–41. doi:10.1002/jlac.19154080103.
  2. ↑ Lehtonen, Henna-Maria; Rantala, Milla; Suomela, Jukka-Pekka; Viitanen, Matti; Kallio, Heikki (2009). "Urinary excretion of the main anthocyanin in lingonberry (Vaccinium vitis-idaea), cyanidin 3-O-galactoside, and its metabolites". Journal of Agricultural and Food Chemistry. 57 (10): 4447–4451. doi:10.1021/jf900894k.
  3. ↑ Grove, Kathryn E.; Robinson, Robert (1931). "An anthocyanin of Oxycoccus macrocarpus Pers". Biochemical Journal. 25 (5): 1706–1711. doi:10.1042/bj0251706. PMC 1260798. PMID 16744736.
  4. ↑ Baj, A; Bombardelli, E; Gabetta, B; Martinelli, EM (1983). "Qualitative and quantitative evaluation of Vaccinium myrtillus anthocyanins by high-resolution gas chromatography and high-performance liquid chromatography". Journal of Chromatography A. 279: 365–372. doi:10.1016/S0021-9673(01)93636-2.
  5. ↑ Ohnishi, Ryoko; Ito, Hideyuki; Kasajima, Naoki; Kaneda, Miyuki; Kariyama, Reiko; Kumon, Hiromi; Hatano, Tsutomu; Yoshida, Takashi (2006). "Urinary excretion of anthocyanins in humans after cranberry juice ingestion". Bioscience, Biotechnology, and Biochemistry. 70 (7): 1681–1687. doi:10.1271/bbb.60023.
  6. ↑ Sadilova, E; Stintzing, FC; Carle, R (2012). "Chemical quality parameters and anthocyanin pattern of red-fleshed Weirouge apples". Journal of Applied Botany and Food Quality. 80 (1): 82–87. doi:10.5073/JABFQ.2006.080.012.
  7. ↑ Würdig, Juliane; Flachowsky, Henryk; Höfer, Monika; Peil, Andreas; Eldin Ali, Mohammed Ali Mohammed Saad; Hanke, Magda-Viola (2014). "Phenotypic and genetic analysis of the German Malus Germplasm Collection in terms of type 1 and type 2 red-fleshed apples". Gene. 544 (2): 198–207. doi:10.1016/j.gene.2014.04.045. PMID 24768720.
  8. ↑ Sato, Hideto; Otagaki, Shungo; Saelai, Parichat; Kondo, Satoru; Shiratake, Katsuhiro; Matsumoto, Shogo (2017). "Varietal differences in phenolic compounds metabolism of type 2 red-fleshed apples" (PDF). Scientia Horticulturae. 219: 1–9. Bibcode:2017ScHor.219....1S. doi:10.1016/j.scienta.2017.02.041.
  9. ↑ Liang, Zhongxin; Liang, Hongrui; Guo, Yizhan; Yang, Dong (2021). "Cyanidin 3-O-galactoside: A natural compound with multiple health benefits". International Journal of Molecular Sciences. 22 (5): 2261. doi:10.3390/ijms22052261. PMC 7956414. PMID 33668383.
  10. ↑ Liu, Pengzhan; Kallio, Heikki; Lü, Deguo; Zhou, Chuansheng; Yang, Baoru (2011). "Quantitative analysis of phenolic compounds in Chinese hawthorn (Crataegus spp.) fruits by high performance liquid chromatography–electrospray ionisation mass spectrometry". Food Chemistry. 127 (3): 1370–1377. doi:10.1016/j.foodchem.2011.01.103.
  11. ↑ Robinson, R; Smith, H (1955). "Anthocyanins of the leaf of the copper beech (Fagus sylvatica) and the fruit of the cultivated strawberry (Fragaria virginiana)". Nature. 175 (4458): 634. doi:10.1038/175634a0.
  12. ↑ Gould, Kevin S; Markham, Kenneth R; Smith, Richard H; Goris, Jessica J (2000). "Functional role of anthocyanins in the leaves of Quintinia serrata A. Cunn". Journal of Experimental Botany. 51 (347): 1107–1115. doi:10.1093/jexbot/51.347.1107.
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