Quadrangularin A

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Quadrangularin A

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
PubChem	5318096
ChemSpider	4476724
Jmol-3D images	Image 1
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
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
Properties
Molecular formula	C₂₈H₂₂O₆
Molar mass	454.47 g/mol
Except where noted otherwise, 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

Dihydroxylated

Trihydroxylated

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

other acetylations

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)

Tetramers:

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

Synthetic

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