Quadrangularin A

Quadrangularin A
Names

IUPAC name (1E,2R,3R)-2-(3,5-dihydroxyphenyl)-3-(4-hydroxyphenyl)-1-[(4-hydroxyphenyl)methylidene]-2,3-dihydroindene-4,6-diol
Other names (±)-Quadrangularin A
Identifiers
CAS Number	252557-25-8
ChEBI	CHEBI:76192
ChemSpider	4476724
Jmol interactive 3D	Image
PubChem	5318096
InChI InChI=1S/C28H22O6/c29-18-5-1-15(2-6-18)9-23-24-13-22(33)14-25(34)28(24)27(16-3-7-19(30)8-4-16)26(23)17-10-20(31)12-21(32)11-17/h1-14,26-27,29-34H/b23-9-/t26-,27+/m1/s1 Key: BIQMSWPBPAKGSE-PBSLAQMISA-N
SMILES C1=CC(=CC=C1C=C2C(C(C3=C(C=C(C=C23)O)O)C4=CC=C(C=C4)O)C5=CC(=CC(=C5)O)O)O
Properties
Chemical formula	C₂₈H₂₂O₆
Molar mass	454.47 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Quadrangularin A is an oligostilbene found in Cissus quadrangularis^[1] and in Parthenocissus laetevirens.^[2] It is a resveratrol dimer.

References

↑ Total Synthesis of (±)-Quadrangularin A. Wenling Li, Hao Li, Ying Li and Zijie Hou, Angewandte Chemie International Edition, Volume 45, Issue 45, page 7609-7611, doi:10.1002/anie.200603097
↑ Characterization of polyphenol compounds from the roots and stems of Parthenocissus laetevirens by high-performance liquid chromatography/tandem mass spectrometry. Juanjuan Chen, Shan He, Hui Mao, Cuirong Sun and Yuanjiang Pan, Rapid Commun. Mass Spectrom., 2009, volume 23, pages 737–744, doi:10.1002/rcm

Oligostilbenoids and their glycosides

Diptoindonesin C
Diptoindonesin F
Gnetin H
Hemsleyanol D
Isohopeaphenol
Laetevirenol A, B, C, D and E
Suffruticosol A and B
Viniferal
E-ω-viniferin
Z-ω-viniferin

Dimers

Diptoindonesin G
Jezonodione
B
Scirpusin A
Tibeticanol (piceatannol dimer)

Trimers

Amurensin B
Gnetin E
Gneyulin A
Johorenol A
Ampelopsin E
Vaticanol G

Tetramers:

Dibalanocarpol
Gnetin J (3"-hydroxygnetin E)
Gnetin K (3"-methoxygnetin E)
Gnetuhainin R (isorhapontigenin tetramer)
Laetevirenol F and G

Higher polymers
(five units or more)

Vaticanol D, H, I and J

Oligomeric forms
of resveratrol

Dimers	Amurensin A and H Ampelopsin A B D and F Balanocarpol Cyphostemmin A and B δ-viniferin ε-viniferin Gnetin A and C Leachinol F Malibatol A Pallidol Parthenocissin A Quadrangularin A Restrytisol A, B and C Vitisinol D

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

Tetramers	Ampelopsin H Amurensin K Caraphenol B Carasinol B Flexuosol A Hopeaphenol Kobophenol A Miyabenol A Vaticanol B and C Vaticaphenol A Vitisin A B and C β-viniferin (cyclic resveratrol tetramer)

Pentamers	Amurensin E and F

Hexamers	Chunganenol

Higher polymers	γ-viniferin Valeriaphenol A

Glycosides or conjugates

Diptoindonesin A (C-glucoside of ε-viniferin)
Foeniculoside I (glucoside of miyabenol C), II, III and IV
Laevifonol (an ε-viniferin-ascorbic acid hybrid compound)
Laevifoside (O-glucoside of ampelopsin A)

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