flavanol ,IUPAC, some chemical related flavanol moiety,biological sources, uses

1. Central University of Punjab
A Central University Established by an Act of Parliament
Under Guidance
Dr. Priyanka Sharma
Presented by
Akanksha Raghuvanshi
Department of pharmaceutical sciences and natural products
FLAVANOID:FLAVANOL
presentation

2. Flavan-3-ols are structurally diverse and include a range of
compounds, such as
catechin,
epicatechin gallate,
epigallocatechin,
epigallocatechin gallate,
proanthocyanidins,
theaflavins,
thearubigins
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2
3
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5
6
7
8
2
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3`
4`
1
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5`
6`
2
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3`
1
`
IUPAC name: 3-hydroxy-2-phenylchromen
Flavanols
2

3. Flavan-2-phenyl-3,4-dihydro-2H-chromen-3-ol skeleton
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2
3
4
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7
8
3`
4`
5`
6`
2`
3`
1`
2-phenyl
Flavan
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4. Flavan-2-phenyl-3,4-dihydro-2H-chromen-3-ol skeleton
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2
3
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7
8
2`
3`
4`
1` 5`
6`
2`
3`
1`
H
H
H
Flavan
4
H

5. Flavan-2-phenyl-3,4-dihydro-2H-chromen-3-ol skeleton
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2
3
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7
8
2`
3`
4`
1` 5`
6`
2`
3`
1`
H
H
H
Flavan
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H

6. IUPAC name:(2R,3S)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-
2H-chromene-3,5,7-triol
Catechin
Biological source:-Mimosa catechu (Acacia catechu L.f)
(-)-epicatechin (2R,3R)
(+)-epicatechin (2S,3S)
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3
2
3
2
3
Antioxidant Properties
vasodilation (relaxation of blood vessels)
Anti-Inflammatory
Weight Management
Neuroprotective Effects
4`
3`
2
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1
`
5
7
3`
6

7. Gallocatechol
Biological source:-Green tea from Camellia
sinensis leaves
IUPAC name:2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-
chromene-3,5,7-triol
Epicatechin gallate
IUPAC name: (2R,3R)-3′,4′,5,7-Tetrahydroxyflavan-3-yl 3,4,5-
trihydroxybenzoate
5
7
4`
3`
Biological source :1.Camellia sinensis
2.Fagopyrum esculentum, family
Polygonaceae
3.Vitis vinifera
Anti-Obesity Effects
Antimicrobial Activity
Liver Protection
Antioxidant Properties
Anti-Inflammatory
Neuroprotective Effects
Gastrointestinal Health
Liver Protection
Anti-Inflammatory
Neuroprotective Effects
Diabetes Management
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1
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3`
4`
5`
3
5
7
3
4
5
7

8. Epigallocatechin gallate
IUPAC name:(2R,3R)-3′,4′,5,5′,7-Pentahydroxyflavan-3-
yl 3,4,5-trihydroxybenzoate
5
7
4`
3`
5`
Biological source : Camellia sinensis
Camellia taliensis
Afzelechin
IUPAC name: (2R,3S)-2-(4-hydroxyphenyl)-3,4-
dihydro-2H-chromene-3,5,7-triol
Biological source : Bergenia ligulata
antioxidative
Antiinflammatory
Antitumor
Antiallergic Effects
Antimicrobial Activity
Antioxidant Activity
Anti-Inflammatory Effects
4
5
3
4`
8

9. Biological source : Acacia mearnsii
Acacia baileyana
Fisetinidol
IUPAC name: (2R,3S)-Flavan-3,3′,4′,7-tetrol
Guibourtinidol
IUPAC name(2R,3S)-Flavan-3,4′,7-triol
Biological source : Cassia abbreviata
anti-resorptive effects (interfare bone remodelling) Not have much study over this molecule
Not have much study over this molecule
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10. IUPAC name: (2R,3S)-Flavan-3,3′,4′,7,8-pentol
Biological source : Prosopis juliflora
Mesquitol, with its pyrogallol-type A-ring, is more susceptible
to quinone formation
IUPAC name: (2R,3S)-Flavan-3,3′,4′,5′,7-pentol
Biological source;Stryphnodendron adstringens
Mesquitol Robinetinidol
Not have much study over this molecule Not have much study over this molecule
Control/reduce cholestrol
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References
1. https://www.sciencedirect.com/topics/pharmacology-toxicology-and-pharmaceutical-science/flavanols
2. https://en.wikipedia.org/wiki/Flavan-3-ol
3. Del Río D, Rodríguez Mateos A, Spencer JP, Tognolini M, Borges G, Crozier A (May 2013). "Dietary
(poly)phenolics in human health: structures, bioavailability, and evidence of protective effects against chronic
diseases". Antioxidants & Redox Signaling. 18 (14): 1818–
1892. doi:10.1089/ars.2012.4581. PMC 3619154. PMID 22794138.