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{{short description|Red anthocyanidin pigment found in certain flowers and fruits}}
{{chembox
{{chembox
| Verifiedfields = changed
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 409412023
| verifiedrevid = 409412023
| ImageFile=pelargonidin.svg
| ImageFile=pelargonidin.svg
| ImageSize=200px
| ImageSize=200px
| IUPACName=2-(4-Hydroxyphenyl)chromenylium-3,5,7-triol
| IUPACName=3,4′,5,7-Tetrahydroxyflavylium
| SystematicName=3,5,7-Trihydroxy-2-(4-hydroxyphenyl)-1λ<sup>4</sup>-benzopyran-4-ylium
| OtherNames=
| OtherNames=
|Section1={{Chembox Identifiers
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo_Ref = {{cascite|correct|??}}
| CASNo=134-04-3
| CASNo=134-04-3
| UNII_Ref = {{fdacite|correct|FDA}}
⚫
| PubChem=440832
| UNII = DFL6200791
⚫
| PubChem=440832
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 25863
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 1197905
| ChEMBL = 1197905
| SMILES=C1=CC(=CC=C1C2=C(C=C3C (=CC(=CC3=[O+]2)O)O)O)O
| SMILES = C1=CC(=CC=C1C2=C(C=C3C(=CC(=CC3=[O+]2)O)O)O)O
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 389676
| 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
| InChIKey = XVFMGWDSJLBXDZ-IKLDFBCSAF
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = XVFMGWDSJLBXDZ-UHFFFAOYSA-O

| KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG = C05904
}}
}}
|Section2={{Chembox Properties
|Section2={{Chembox Properties
| Formula = C<sub>15</sub>H<sub>11</sub>O<sub>5</sub><sup>+</sup>
| Formula = C<sub>15</sub>H<sub>11</sub>O<sub>5</sub><sup>+</sup>
| MolarMass = 271.24 g/mol
| MolarMass = 271.24 g/mol
| Appearance=
| ExactMass = 271.060648 u
| Appearance=
| Density=
| Density=
| MeltingPt=
| MeltingPt=
| BoilingPt=
| BoilingPt=
| Solubility=
| Solubility=
}}
}}
|Section3={{Chembox Hazards
|Section3={{Chembox Hazards
| MainHazards=
| MainHazards=
| FlashPt=
| FlashPt=
| AutoignitionPt =
| Autoignition=
}}
}}
}}
}}
'''Pelargonidin''' is an [[anthocyanidin]], a type of plant pigment producing a characteristic orange color used in food and industrial dyes.<ref>{{cite patent
'''Pelargonidin''' is an [[anthocyanidin]], a type of plant pigment. Like all anthocyanins, it is an [[antioxidant]]. It produces a characteristic orange color, and can be found in red [[geranium]]s, and ripe [[Raspberry|raspberries]] and [[Strawberry|strawberries]], as well as [[Blueberry|blueberries]], [[Blackberry|blackberries]], [[plum]]s and [[Cranberry|cranberries]] and [[pomegranate]]s. It is present in large amounts in [[kidney bean]]s.<ref>LZ Lin, JM Harnly, MS Pastor-Corrales, DL Luthria. The polyphenolic profiles of common bean (Phaseolus vulgaris L.). Food Chemistry, 2008.</ref>
| country = US
| number = 6,767,999
| status = granted
| title = Anthocyantin coloring agent and method for the production thereof from organic matter
| pubdate = Nov 01, 2001
| gdate = July 27, 2004
| fdate = Dec 21, 2001
| pridate = Apr 26, 2000
| inventor = Smirnov, Vitaly; Sidorov, Viktor; Smirnova, Valentina
| url = http://patft.uspto.gov/netacgi/nph-Parser?Sect1=PTO2&Sect2=HITOFF&u=%2Fnetahtml%2FPTO%2Fsearch-adv.htm&r=1&p=1&f=G&l=50&d=PTXT&S1=pelargonidin.ABTX.&OS=abst/pelargonidin&RS=ABST/pelargonidin
}}</ref>

== Natural occurrences ==
=== Presence in flowers ===
Pelargonidin can be found in red [[geranium]]s (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 [[Rose]]s (Rosa) obtain their color from this phytochemical. <ref>{{Cite journal|title=Determination of Flavonoids and Carotenoids and Their Contributions to Various Colors of Rose Cultivars (Rosa spp.)|year=2019|last1=Huihua|first1=Wan|last2=Chao|first2=Yu|last3=Yu|first3=Han|last4=Xuelian|first4=Guo|journal=Frontiers in Plant Science|volume=10|pages=123|doi=10.3389/fpls.2019.00123|pmid=30809238|pmc=6379320|doi-access=free}}</ref>

=== Presence in food ===
Pelargonidin can be found in berries such as ripe [[Raspberry|raspberries]] and [[Strawberry|strawberries]], as well as [[Blueberry|blueberries]], [[Blackberry|blackberries]], [[Cranberry|cranberries]] but also in [[saskatoon berries]]<ref>{{Cite journal|doi=10.1300/J492v05n03_10|title=Compositional and Functional Properties of Saskatoon Berry and Blueberry|year=2005|last1=Mazza|first1=G.|journal=International Journal of Fruit Science|volume=5|issue=3|pages=101–120|s2cid=85691882|doi-access=free}}</ref> and [[chokeberries]]. It is also found in [[plum]]s and [[pomegranate]]s. Pelargonidin gives red [[radish|radishes]] their color.<ref name="NishioKitashiba2017">{{cite book|author=Takeshi Nishio|editor=Takeshi Nishio, Hiroyasu Kitashiba|title=The Radish Genome|url=https://books.google.com/books?id=8JQ4DwAAQBAJ&pg=PA70|date=4 October 2017|publisher=Springer|isbn=978-3-319-59253-4|page=4}}</ref>

It is present in large amounts in [[kidney bean]]s.<ref>{{Cite journal|doi=10.1016/j.foodchem.2007.08.038|title=The polyphenolic profiles of common bean (Phaseolus vulgaris L.)|year=2008|last1=Lin|first1=Long-Ze|last2=Harnly|first2=James M.|last3=Pastor-Corrales|first3=Marcial S.|last4=Luthria|first4=Devanand L.|journal=Food Chemistry|volume=107|pages=399–410|url=https://naldc-legacy.nal.usda.gov/naldc/download.xhtml?id=11587&content=PDF|pmc=4276374|pmid=25544796|issue=1}}</ref>


== Glycosides ==
== Glycosides ==
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. <ref>{{Cite journal |doi=10.1186/s12934-018-0951-6 |title=Engineering de novo anthocyanin production in Saccharomyces cerevisiae |year= 2018 |last1=Levisson |first1=Mark |last2=Patinios |first2=Constantinios |last3=Hein |first3=Sascha |last4=de Groot |first4=Phillip A. |journal=Microbial Cell Factories |volume=17 |issue=103|page=103 |pmid=29970082 |pmc=6029064 |doi-access=free }}</ref>
Acylated pelargonidin glycosides can be found in red-purple flowers of ''[[Ipomoea purpurea]]''.<ref>Acylated pelargonidin glycosides in red-purple flowers of Ipomoea purpurea. Saito N, Tatsuzawa F, Yokoi M, Kasahara K, Iida S, Shigihara A and Honda T, Phytochemistry, December 1996, volume 43, issue 6, pages 1365-1370, {{PMID|8987912}}</ref>
[[File:Pelargonidin 3-O-glucoside.svg|thumb|[[Pelargonidin 3-glucoside]].]]
However this glucosidation reduces its antioxidant activity,<ref>{{Cite journal|doi=10.1016/j.lwt.2021.111581|title=Glycosides changed the stability and antioxidant activity of pelargonidin|year=2021|last1=Li|first1=Wenfeng|last2=Gu|first2=Mengyuan|last3=Gong|first3=Pengling|last4=Wang|first4=Jinxia|journal=Lebensmittel-Wissenschaft & Technologie|volume=147|issue=3|page=111581|s2cid=235531625}}</ref> and changes the wavelength of max light absorbance from 520 nm to 516 nm. <ref>{{cite book |last=Gould|first=Kevin S.|date=2009|title=Anthocyanidins: Biosynthesis, Functions, and Applications|location=New York|publisher=Springer|page=286|isbn=978-0-387-77334-6}}</ref>

Acylated pelargonidin glycosides can be found in red-purple flowers of ''[[Ipomoea purpurea]]''.<ref>{{Cite journal|pmid=8987912|year=1996|last1=Saito|first1=N|last2=Tatsuzawa|first2=F|last3=Yokoi|first3=M|last4=Kasahara|first4=K|last5=Iida|first5=S|last6=Shigihara|first6=A|last7=Honda|first7=T|title=Acylated pelargonidin glycosides in red-purple flowers of Ipomoea purpurea|volume=43|issue=6|pages=1365–70|journal=Phytochemistry|doi=10.1016/s0031-9422(96)00501-8}}</ref>


== See also ==
== See also ==
Line 39: Line 80:
* [[List of compounds with carbon number 15]]
* [[List of compounds with carbon number 15]]


⚫
== References ==
⚫
{{reflist}}
== External links ==
== External links ==
{{commonscat|Pelargonidin}}
{{commonscat|Pelargonidin}}
* [http://www.ch.ic.ac.uk/wiki/index.php/It:Pelargonidin It:Pelargonidin:ChemWiki]


⚫
== References ==
⚫
{{reflist}}


{{Anthocyanins}}
{{Anthocyanins}}


[[Category:Anthocyanidins]]
[[Category:Anthocyanidins]]
[[Category:Phenolic compounds found in raspberries]]
[[Category:Resorcinols]]
[[Category:Resorcinols]]

{{Natural-phenol-stub}}

Latest revision as of 15:05, 3 December 2023

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 ?)

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

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]
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