Pelargonidin is an anthocyanidin, a type of plant pigment producing a characteristic orange color used in food and industrial dyes.[1]

Pelargonidin
Names
IUPAC name
3,4′,5,7-Tetrahydroxyflavylium
Systematic IUPAC name
3,5,7-Trihydroxy-2-(4-hydroxyphenyl)-1λ4-benzopyran-4-ylium
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
UNII
  • InChI=1S/C15H10O5/c16-9-3-1-8(2-4-9)15-13(19)7-11-12(18)5-10(17)6-14(11)20-15/h1-7H,(H3-,16,17,18,19)/p+1 ☒N
    Key: XVFMGWDSJLBXDZ-UHFFFAOYSA-O ☒N
  • InChI=1/C15H10O5/c16-9-3-1-8(2-4-9)15-13(19)7-11-12(18)5-10(17)6-14(11)20-15/h1-7H,(H3-,16,17,18,19)/p+1
    Key: XVFMGWDSJLBXDZ-IKLDFBCSAF
  • C1=CC(=CC=C1C2=C(C=C3C(=CC(=CC3=[O+]2)O)O)O)O
Properties
C15H11O5+
Molar mass 271.24 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Natural occurrences

edit

Presence in flowers

edit

Pelargonidin can be found in red geraniums (Geraniaceae). It is the predominant pigment causing the red coloration in the spathes of Philodendron (Araceae). The orange-coloured flowers of blue pimpernel (Anagallis monelli, Myrsinaceae) have a higher concentration of pelargonidin pigment. Red and Pink Roses (Rosa) obtain their color from this phytochemical. [2]

Presence in food

edit

Pelargonidin can be found in berries such as ripe raspberries and strawberries, as well as blueberries, blackberries, cranberries but also in saskatoon berries[3] and chokeberries. It is also found in plums and pomegranates. Pelargonidin gives red radishes their color.[4]

It is present in large amounts in kidney beans.[5]

Glycosides

edit

In many plant systems, Pelargonidin can be added to a glucose molecule to form Pelargonidin 3-glucoside (callistephin). This is done by the 3GT, anthocyanin 3-O-glucosyltransferase gene. [6]

 
Pelargonidin 3-glucoside.

However this glucosidation reduces its antioxidant activity,[7] and changes the wavelength of max light absorbance from 520 nm to 516 nm. [8]

Acylated pelargonidin glycosides can be found in red-purple flowers of Ipomoea purpurea.[9]

See also

edit

References

edit
  1. ^ US granted 6,767,999, Smirnov, Vitaly; Sidorov, Viktor; Smirnova, Valentina, "Anthocyantin coloring agent and method for the production thereof from organic matter", published Nov 01, 2001, issued July 27, 2004 
  2. ^ Huihua, Wan; Chao, Yu; Yu, Han; Xuelian, Guo (2019). "Determination of Flavonoids and Carotenoids and Their Contributions to Various Colors of Rose Cultivars (Rosa spp.)". Frontiers in Plant Science. 10: 123. doi:10.3389/fpls.2019.00123. PMC 6379320. PMID 30809238.
  3. ^ Mazza, G. (2005). "Compositional and Functional Properties of Saskatoon Berry and Blueberry". International Journal of Fruit Science. 5 (3): 101–120. doi:10.1300/J492v05n03_10. S2CID 85691882.
  4. ^ Takeshi Nishio (4 October 2017). Takeshi Nishio, Hiroyasu Kitashiba (ed.). The Radish Genome. Springer. p. 4. ISBN 978-3-319-59253-4.
  5. ^ Lin, Long-Ze; Harnly, James M.; Pastor-Corrales, Marcial S.; Luthria, Devanand L. (2008). "The polyphenolic profiles of common bean (Phaseolus vulgaris L.)". Food Chemistry. 107 (1): 399–410. doi:10.1016/j.foodchem.2007.08.038. PMC 4276374. PMID 25544796.
  6. ^ Levisson, Mark; Patinios, Constantinios; Hein, Sascha; de Groot, Phillip A. (2018). "Engineering de novo anthocyanin production in Saccharomyces cerevisiae". Microbial Cell Factories. 17 (103): 103. doi:10.1186/s12934-018-0951-6. PMC 6029064. PMID 29970082.
  7. ^ Li, Wenfeng; Gu, Mengyuan; Gong, Pengling; Wang, Jinxia (2021). "Glycosides changed the stability and antioxidant activity of pelargonidin". Lebensmittel-Wissenschaft & Technologie. 147 (3): 111581. doi:10.1016/j.lwt.2021.111581. S2CID 235531625.
  8. ^ Gould, Kevin S. (2009). Anthocyanidins: Biosynthesis, Functions, and Applications. New York: Springer. p. 286. ISBN 978-0-387-77334-6.
  9. ^ Saito, N; Tatsuzawa, F; Yokoi, M; Kasahara, K; Iida, S; Shigihara, A; Honda, T (1996). "Acylated pelargonidin glycosides in red-purple flowers of Ipomoea purpurea". Phytochemistry. 43 (6): 1365–70. doi:10.1016/s0031-9422(96)00501-8. PMID 8987912.
edit