Oxyresveratrol

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Oxyresveratrol

IUPAC name 4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,3-diol
Other names 2,3',4,5'-Tetrahydroxy-trans-stilbene
Identifiers
CAS number	29700-22-9
PubChem	5281717
	Jmol-3D images	Image 1
SMILES C1=CC(=C(C=C1O)O)C=CC2=CC(=CC(=C2)O)O
InChI InChI=1S/C14H12O4/c15-11-4-3-10(14(18)8-11)2-1-9-5-12(16)7-13(17)6-9/h1-8,15-18H/b2-1+ Key: PDHAOJSHSJQANO-OWOJBTEDSA-N
Properties
Molecular formula	C₁₄H₁₂O₄
Molar mass	244.24 g/mol
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Oxyresveratrol is a stilbenoid. It is found in the heartwood of Artocarpus lakoocha and in the traditional drug 'Puag-Haad' made from it.^[1] It is also the aglycone of mulberroside A, a compound found in Morus alba, the white mulberry.^[2]

Oxyresveratrol is a potent tyrosinase inhibitor.^[2]

References

↑ Maneechai, S; Likhitwitayawuid, K; Sritularak, B; Palanuvej, C; Ruangrungsi, N; Sirisa-Ard, P (2009). "Quantitative analysis of oxyresveratrol content in Artocarpus lakoocha and 'Puag-Haad'". Medical principles and practice : international journal of the Kuwait University, Health Science Centre 18 (3): 223–7. doi:10.1159/000204354. PMID 19349726.
↑ 2.0 2.1 Kim, JK; Kim, M; Cho, SG; Kim, MK; Kim, SW; Lim, YH (2010). "Biotransformation of mulberroside a from Morus alba results in enhancement of tyrosinase inhibition". Journal of industrial microbiology & biotechnology 37 (6): 631–7. doi:10.1007/s10295-010-0722-9. PMID 20411402.

Stilbenoids and their glycosides

Aglycones

Dihydroxylated

Trihydroxylated

Resveratrol

Tetrahydroxylated

O-methylated

4-Methoxyresveratrol Gnetucleistol D (2-methoxyoxyresveratrol) Gnetucleistol E (3-methoxy-isorhapontigenin) Isorhapontigenin (3,4',5-trihydroxy-3'-methoxystilbene) Pterostilbene Rhapontigenin (3,3',5-trihydroxy-4'-methoxystilbene)

Combretastatins:	Combretastatin A-1 Combretastatin A-4

carboxylated

Hydrangeic acid

other acetylations

3,5-Dihydroxy-4-isopropyl-trans-stilbene

Glycosides

Astringin (Piceatannol 3-O-glucoside)
Foeniculoside I, II, III and IV
Isorhapontin (Isorhapontigenin glucoside)
Mulberroside A (Oxyresveratrol diglucoside)

of resveratrol	Piceid (trans-Resveratrol-3-O-glucoside) trans-Resveratrol-3-O-glucuronide Resveratroloside (trans-resveratrol-4'-O-beta-D-glucopyranoside)

of rhapontigenin	Rhapontigenin 3-O-rutinoside 4'-Methoxy-(E)-resveratrol 3-O-rutinoside Rhaponticin (Rhapontigenin glucoside)

Oligomeric forms

Ampelopsin C, E and H
Amurensin A, B, G and H
Balanocarpol
Carasinol B
Dibalanocarpol
Diptoindonesin C
Diptoindonesin F
Flexuosol A
Gnetin H
Hemsleyanol D
Isohopeaphenol
Kobophenol A
Laetevirenol A, B, C, D and E
Malibatol A and B
Suffruticosol A and B
Vaticanol C
Viniferal
E-ω-viniferin
Z-ω-viniferin

Tetramers:

Laetevirenol F and G

of resveratrol

Dimers	Amurensin A and H Ampelopsin A B D and F δ-viniferin ε-viniferin Leachinol F Pallidol Parthenocissin A Quadrangularin A Restrytisol A B and C

Trimers	α-viniferin Amurensin C D and G Malaysianol A Miyabenol C Resviniferin A and B trans-diptoindonesin B

Tetramers	Amurensin E F and K Gnetuhainin R (isorhapontigenin tetramer) Hopeaphenol Vaticanol B Vitisin A B and C β-viniferin (cyclic resveratrol tetramer)

Pentamers	Amurensin E and F

Higher polymers	γ-viniferin

Oligomeric forms
glycosides or conjugates

Diptoindonesin A
Laevifonol (an ε-viniferin-ascorbic acid hybrid compound)
Laevifoside (O-glucoside of ampelopsin A)

Synthetic

Stilbenoid drugs

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