Peonidin: Difference between revisions

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'''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]].
| Verifiedfields = changed
| verifiedrevid = 400272599
|ImageFile=Peonidin.png
|ImageSize=200px
|IUPACName=2-(4-Hydroxy-3-methoxyphenyl)chromenylium-3,5,7-triol
|OtherNames=
|Section1={{Chembox Identifiers
|  CASNo_Ref = {{cascite|correct|??}}
| CASNo=134-01-0
|  PubChem=441773
| 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 ===
==Chemical Structure==
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 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 2.0, peonidin exhibits a cherry red color.
==Biosynthesis==
* At pH 3.0, it transitions to a strong yellowish pink.
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]].
* 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.
==Sources==
Peonidin is predominantly found in:
* [[Vitis vinifera]] (grapes)
* [[Vaccinium corymbosum]] (blueberries)
* [[Vaccinium macrocarpon]] (cranberries)
* [[Prunus cerasus]] (sour cherries)


=== Commercial Use ===
==Health Benefits==
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 has been studied for its potential health benefits, which include:


== Health Implications ==
===Antioxidant Activity===
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 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]].


== Dietary Sources ==
===Anti-inflammatory Effects===
The principal dietary source of peonidin is raw cranberries, providing 42 mg per 100 g of fruit. Other significant sources include:
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.


* Blueberries, plums, grapes, and cherries, ranging from 5 to 12 mg/100 g.
===Cardiovascular Health===
* Purple-fleshed sweet potatoes, with certain cultivars containing up to 40 mg/100 g (cooked).
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]].
* 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>.
==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.


== Conclusion ==
==Research and Studies==
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.
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 ==
==See Also==
<references />
* [[Anthocyanin]]
 
* [[Flavonoid]]
== References ==
* [[Antioxidant]]
<references />
{{stub}}
 
[[Category:Anthocyanidins]]
{{Anthocyanins}}
[[Category:Flavonoids]]
 
[[Category:Antioxidants]]
[[Category:Nutrition]]
[[Category:Phytochemicals]]
[[Category:O-Methylated anthocyanidins]]
== Peonidin ==
[[Category:Resorcinols]]{{food}} {{adapted}}
<gallery>
File:Peonidin.png|Peonidin
File:Paeonia_officinalis_officinalis0.jpg|Paeonia officinalis
</gallery>

Latest revision as of 21:15, 23 February 2025

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[edit]

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[edit]

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[edit]

Peonidin is predominantly found in:

Health Benefits[edit]

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

Antioxidant Activity[edit]

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[edit]

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[edit]

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[edit]

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[edit]

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.

See Also[edit]

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Peonidin[edit]

  • Peonidin
    Peonidin
  • Paeonia officinalis
    Paeonia officinalis
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