Idaein

Last updated
Idaein
Ideain Chloride.svg
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
PubChem CID
UNII
  • 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.

Contents

Natural occurrences

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 sun light. [12]

References

  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. ↑ Urinary Excretion of the Main Anthocyanin in Lingonberry (Vaccinium vitis-idaea), Cyanidin 3-O-Galactoside, and Its Metabolites. Henna-Maria Lehtonen, Milla Rantala, Jukka-Pekka Suomela, Matti Viitanen and Heikki Kallio, J. Agric. Food Chem., 2009, 57 (10), pages 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. ↑ Qualitative and quantitative evaluation of vaccinium myrtillus anthocyanins by high-resolution gas chromatography and high-performance liquid chromatography. A. Baj, E. Bombardelli, B. Gabetta and E.M. Martinelli, Journal of Chromatography A, Volume 279, 25 November 1983, Pages 365-372, doi : 10.1016/S0021-9673(01)93636-2
  5. ↑ Urinary Excretion of Anthocyanins in Humans after Cranberry Juice Ingestion. Ryoko Ohnishi, Hideyuki Ito, Naoki Kasajima, Miyuki Kaneda, Reiko Kariyama, Hiromi Kumon, Tsutomu Hatano and Takashi Yoshida, Bioscience, Biotechnology, and Biochemistry, 2006, Volume 70, Issue 7, pages 1681-1687, {{DOI:10.1271/bbb.60023}}
  6. ↑ Chemical quality parameters and anthocyanin pattern of red-fleshed Weirouge apples. E. Sadilova, F. C. Stintzing and R. Carle, Journal of Applied Botany and Food Quality, 2006, volume 80, pages 82-87 (link to abstract Archived 2016-09-21 at the Wayback Machine )
  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.
  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. ↑ Quantitative analysis of phenolic compounds in Chinese hawthorn (Crataegus spp.) fruits by high performance liquid chromatography–electrospray ionisation mass spectrometry. Pengzhan Liu, Heikki Kallio, Deguo Lü, Chuansheng Zhou, Baoru Yang, Food Chemistry, Volume 127, Issue 3, 1 August 2011, Pages 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. Bibcode:1955Natur.175..634R. doi: 10.1038/175634a0 .
  12. ↑ Functional role of anthocyanins in the leaves of Quintinia serrata A. Cunn. Kevin S. Gould, Kenneth R. Markham, Richard H. Smith and Jessica J. Goris, J. Exp. Bot., 2000, volume 51, issue 347, pages 1107-1115, doi : 10.1093/jexbot/51.347.1107
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