Peonidin: Difference between revisions

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{{chembox
{{DISPLAYTITLE:Peonidin}}
| Verifiedfields = changed
{{Infobox chemical
| verifiedrevid = 400272599
| name = Peonidin
|ImageFile=Peonidin.png
| image = Peonidin.png
|ImageSize=200px
| image_size = 250px
|IUPACName=2-(4-Hydroxy-3-methoxyphenyl)chromenylium-3,5,7-triol
| image_alt = Chemical structure of Peonidin
|OtherNames=
| IUPAC_name = 3,5,7-Trihydroxy-2-(4-hydroxy-3-methoxyphenyl)chromenylium
|Section1={{Chembox Identifiers
| other_names = Peonidin chloride
|  CASNo_Ref = {{cascite|correct|??}}
| CAS_number = 134-01-0
| CASNo=134-01-0
| molecular_formula = C<sub>16</sub>H<sub>13</sub>O<sub>6</sub>
| PubChem=441773
| molar_mass = 301.27 g/mol
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 75314
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 589665
| ChEMBL2 = 1277324
|  SMILES=COC1=C(C=CC(=C1)C2=C(C=C3C (=CC(=CC3=[O+]2)O)O)O)O
  }}
|Section2={{Chembox Properties
|  Formula = C<sub>16</sub>H<sub>13</sub>O<sub>6</sub><sup>+</sup>
| MolarMass = 301.27 g/mol
|  ExactMass = 301.071213
|  Appearance=
|  Density=
|  MeltingPt=
|  BoilingPt=
|  Solubility=
  }}
|Section3={{Chembox Hazards
|  MainHazards=
|  FlashPt=
|  Autoignition=
  }}
}}
}}
[[Image:Paeonia officinalis officinalis0.jpg|thumb|right|200px|The generic garden peony.]]
== Introduction ==
'''Peonidin''' is a naturally occurring O-methylated anthocyanidin primarily known for its role as a plant pigment. It exhibits an appealing range of colors, notably purplish-red hues in flowers such as peonies and roses, from which it derives its name. It also imparts color to some blue flowers like the morning glory (''Ipomoea tricolor Cav cv''). Beyond its aesthetic contributions, peonidin has gathered interest for its potential health benefits and uses in food coloring due to its color stability across different pH levels.


=== Chemical Structure and Color Alteration ===
==Introduction==
Peonidin, like other anthocyanidins, has a highly conjugated chemical structure, which refers to alternating single and double bonds within the molecule. This structure is what enables peonidin to absorb and reflect specific wavelengths of light, thereby exhibiting color<ref>He, J., & Giusti, M. M. (2010). Anthocyanins: Natural colorants with health-promoting properties. Annual Review of Food Science and Technology, 1, 163-187.</ref>. The extent of conjugation changes with alterations in pH, which in turn, changes the color of peonidin:
'''Peonidin''' is an [[anthocyanidin]], a type of [[flavonoid]] pigment that is responsible for the red, purple, and blue colors in many [[fruits]] and [[flowers]]. It is a naturally occurring compound found in various [[plant]] species, including [[grapes]], [[blueberries]], and [[cranberries]]. Peonidin is known for its potential [[antioxidant]] properties and its role in [[human health]].


* At pH 2.0, peonidin exhibits a cherry red color.
==Chemical Structure==
* At pH 3.0, it transitions to a strong yellowish pink.
Peonidin is a [[glycoside]] derivative of [[cyanidin]], characterized by the presence of a methoxy group at the 3' position of the B-ring. Its chemical structure is defined by the molecular formula C<sub>16</sub>H<sub>13</sub>O<sub>6</sub>, and it is commonly found in the form of its chloride salt. The presence of hydroxyl and methoxy groups contributes to its solubility and stability in aqueous solutions.
* At pH 5.0, it turns grape red-purple.
* At pH 8.0, peonidin becomes deep blue.


Unlike many anthocyanidins, peonidin retains its color stability even at higher pH levels, a trait that has been capitalized upon in isolating it as a blue colorant from the "Heavenly Blue" morning glory.
==Biosynthesis==
Peonidin is synthesized in plants through the [[phenylpropanoid pathway]], which involves the conversion of [[phenylalanine]] to [[cinnamic acid]], followed by a series of enzymatic reactions leading to the formation of anthocyanidins. The specific methylation of cyanidin to form peonidin is catalyzed by the enzyme [[O-methyltransferase]].


=== Commercial Use ===
==Sources==
Due to its unusual color stability, a cafeoyl-acylated buffered formulation of peonidin has been patented for utilization as a food coloring agent. This aspect of peonidin provides a natural alternative to synthetic food colorants, aligning with an increasing consumer demand for natural food additives<ref>Lila, M. A. (2004). Anthocyanins and human health: An in vitro investigative approach. Journal of Biomedicine and Biotechnology, 2004(5), 306-313.</ref>.
Peonidin is predominantly found in:
* [[Vitis vinifera]] (grapes)
* [[Vaccinium corymbosum]] (blueberries)
* [[Vaccinium macrocarpon]] (cranberries)
* [[Prunus cerasus]] (sour cherries)


== Health Implications ==
==Health Benefits==
Research has revealed that peonidin, along with other anthocyanidins, possesses potential inhibitory and apoptotic effects on cancer cells in vitro, notably against metastatic human breast cancer cells. However, a significant concern regarding the use of anthocyanidins for therapeutic purposes is their bioavailability. Despite showing promise in vitro, anthocyanidins are rapidly eliminated from the human body, which casts doubt on their efficacy in vivo<ref>Wang, L. S., & Stoner, G. D. (2008). Anthocyanins and their role in cancer prevention. Cancer letters, 269(2), 281-290.</ref>.
Peonidin has been studied for its potential health benefits, which include:


== Dietary Sources ==
===Antioxidant Activity===
The principal dietary source of peonidin is raw cranberries, providing 42 mg per 100 g of fruit. Other significant sources include:
Peonidin exhibits strong [[antioxidant]] properties, which help in neutralizing [[free radicals]] and reducing oxidative stress. This activity is crucial in preventing [[cellular damage]] and reducing the risk of [[chronic diseases]] such as [[cardiovascular disease]] and [[cancer]].


* Blueberries, plums, grapes, and cherries, ranging from 5 to 12 mg/100 g.
===Anti-inflammatory Effects===
* Purple-fleshed sweet potatoes, with certain cultivars containing up to 40 mg/100 g (cooked).
Studies suggest that peonidin may have [[anti-inflammatory]] effects by inhibiting the production of pro-inflammatory cytokines. This can be beneficial in managing conditions like [[arthritis]] and other inflammatory disorders.
* Raw black rice and black bananas.


Fresh fruits have been found to contain higher levels of peonidin compared to their frozen counterparts; for instance, frozen blueberries almost lack peonidin. This disparity underscores the general guideline that fresh fruits tend to be more nutritious and health-beneficial due to their higher content of phenolic compounds<ref>Wang, S. Y., & Lin, H. S. (2000). Antioxidant activity in fruits and leaves of blackberry, raspberry, and strawberry varies with cultivar and developmental stage. Journal of Agricultural and Food Chemistry, 48(2), 140-146.</ref>.
===Cardiovascular Health===
Peonidin may contribute to [[cardiovascular health]] by improving [[endothelial function]] and reducing [[blood pressure]]. Its antioxidant properties also help in preventing the oxidation of [[low-density lipoprotein]] (LDL) cholesterol, a key factor in the development of [[atherosclerosis]].


== Conclusion ==
==Potential Applications==
Peonidin's unique chemical structure not only imparts vibrant colors to various flora but also holds potential health benefits and commercial value as a natural food colorant. While its in vitro anti-cancer effects are promising, further research is needed to fully understand its bioavailability and efficacy in vivo. Nonetheless, the consumption of peonidin-rich fresh fruits aligns well with the broader nutritional advice favoring fresh over processed foods for better health outcomes.
Peonidin is being explored for its use in:
* [[Nutraceuticals]]: As a dietary supplement for its health-promoting properties.
* [[Food Industry]]: As a natural colorant due to its vibrant hue.
* [[Cosmetics]]: For its antioxidant properties in skin care products.


== References ==
==Research and Studies==
<references />
Ongoing research is focused on understanding the molecular mechanisms of peonidin's action in the human body, its bioavailability, and its potential therapeutic applications. Clinical trials are being conducted to evaluate its efficacy in disease prevention and management.


== References ==
==Conclusion==
<references />
Peonidin is a significant anthocyanidin with promising health benefits. Its role as an antioxidant and anti-inflammatory agent makes it a valuable compound in both the food and pharmaceutical industries. Further research is needed to fully elucidate its potential and applications.


{{Anthocyanins}}
==References==
* [1] Andersen, Ø. M., & Jordheim, M. (2006). The Anthocyanins. In: Andersen, Ø. M., & Markham, K. R. (Eds.), Flavonoids: Chemistry, Biochemistry and Applications. CRC Press.
* [2] He, J., & Giusti, M. M. (2010). Anthocyanins: Natural Colorants with Health-Promoting Properties. Annual Review of Food Science and Technology, 1, 163-187.


[[Category:Nutrition]]
==See Also==
[[Category:O-Methylated anthocyanidins]]
* [[Anthocyanin]]
[[Category:Resorcinols]]{{food}} {{adapted}}
* [[Flavonoid]]
* [[Antioxidant]]
 
[[Category:Anthocyanidins]]
[[Category:Flavonoids]]
[[Category:Antioxidants]]
[[Category:Phytochemicals]]

Revision as of 02:10, 2 January 2025


Peonidin
Peonidin.png
Identifiers
CAS Number
PubChem CID
ChemSpider ID
UNII
ChEBI
ChEMBL
Properties
Chemical Formula
Molar Mass 301.27 g/mol
Appearance
Density
Melting Point
Boiling Point
Hazards
GHS Pictograms [[File:|50px]]
GHS Signal Word
GHS Hazard Statements
NFPA 704 [[File:|50px]]
References

Introduction

Peonidin is an anthocyanidin, a type of flavonoid pigment that is responsible for the red, purple, and blue colors in many fruits and flowers. It is a naturally occurring compound found in various plant species, including grapes, blueberries, and cranberries. Peonidin is known for its potential antioxidant properties and its role in human health.

Chemical Structure

Peonidin is a glycoside derivative of cyanidin, characterized by the presence of a methoxy group at the 3' position of the B-ring. Its chemical structure is defined by the molecular formula C16H13O6, and it is commonly found in the form of its chloride salt. The presence of hydroxyl and methoxy groups contributes to its solubility and stability in aqueous solutions.

Biosynthesis

Peonidin is synthesized in plants through the phenylpropanoid pathway, which involves the conversion of phenylalanine to cinnamic acid, followed by a series of enzymatic reactions leading to the formation of anthocyanidins. The specific methylation of cyanidin to form peonidin is catalyzed by the enzyme O-methyltransferase.

Sources

Peonidin is predominantly found in:

Health Benefits

Peonidin has been studied for its potential health benefits, which include:

Antioxidant Activity

Peonidin exhibits strong antioxidant properties, which help in neutralizing free radicals and reducing oxidative stress. This activity is crucial in preventing cellular damage and reducing the risk of chronic diseases such as cardiovascular disease and cancer.

Anti-inflammatory Effects

Studies suggest that peonidin may have anti-inflammatory effects by inhibiting the production of pro-inflammatory cytokines. This can be beneficial in managing conditions like arthritis and other inflammatory disorders.

Cardiovascular Health

Peonidin may contribute to cardiovascular health by improving endothelial function and reducing blood pressure. Its antioxidant properties also help in preventing the oxidation of low-density lipoprotein (LDL) cholesterol, a key factor in the development of atherosclerosis.

Potential Applications

Peonidin is being explored for its use in:

  • Nutraceuticals: As a dietary supplement for its health-promoting properties.
  • Food Industry: As a natural colorant due to its vibrant hue.
  • Cosmetics: For its antioxidant properties in skin care products.

Research and Studies

Ongoing research is focused on understanding the molecular mechanisms of peonidin's action in the human body, its bioavailability, and its potential therapeutic applications. Clinical trials are being conducted to evaluate its efficacy in disease prevention and management.

Conclusion

Peonidin is a significant anthocyanidin with promising health benefits. Its role as an antioxidant and anti-inflammatory agent makes it a valuable compound in both the food and pharmaceutical industries. Further research is needed to fully elucidate its potential and applications.

References

  • [1] Andersen, Ø. M., & Jordheim, M. (2006). The Anthocyanins. In: Andersen, Ø. M., & Markham, K. R. (Eds.), Flavonoids: Chemistry, Biochemistry and Applications. CRC Press.
  • [2] He, J., & Giusti, M. M. (2010). Anthocyanins: Natural Colorants with Health-Promoting Properties. Annual Review of Food Science and Technology, 1, 163-187.

See Also

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