Isorhapontin

Isorhapontin
Names

IUPAC name (2S,3R,4S,5S,6R)-2-[3-hydroxy-5-[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Other names Isorhapontigenin glucoside
Identifiers
CAS Number	32727-29-0
ChemSpider	4445032
Jmol interactive 3D	Image
KEGG	C10266
PubChem	5281716
InChI InChI=1S/C21H24O9/c1-28-16-8-11(4-5-15(16)24)2-3-12-6-13(23)9-14(7-12)29-21-20(27)19(26)18(25)17(10-22)30-21/h2-9,17-27H,10H2,1H3/b3-2+/t17-,18-,19+,20-,21-/m1/s1 Key: KLPUXMNQDCUPNO-DXKBKAGUSA-N InChI=1/C21H24O9/c1-28-16-8-11(4-5-15(16)24)2-3-12-6-13(23)9-14(7-12)29-21-20(27)19(26)18(25)17(10-22)30-21/h2-9,17-27H,10H2,1H3/b3-2+/t17-,18-,19+,20-,21-/m1/s1 Key: KLPUXMNQDCUPNO-DXKBKAGUBI
SMILES COC1=C(C=CC(=C1)/C=C/C2=CC(=CC(=C2)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)O
Properties
Chemical formula	C₂₁H₂₄O₉
Molar mass	420.41 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Isorhapontin is a stilbenoid. It is the glucoside of isorhapontigenin. It can be found in mycorrhizal and non-mycorrhizal roots of Norway spruces (Picea abies),^[1] in the bark of Picea sitchensis^[2]^[3] or in white spruce (Picea glauca).^[4]

References

↑ Münzenberger, B; Heilemann, J; Strack, D; Kottke, I; Oberwinkler, F (1990). "Phenolics of mycorrhizas and non-mycorrhizal roots of Norway spruce". Planta 182 (1): 142–148. doi:10.1007/BF00239996.
↑ Stilbene glucosides in the bark of Picea sitchensis. Masakazu Aritomi, Dervilla M.X. Donnelly, Phytochemistry, Volume 15, Issue 12, 1976, Pages 2006–2008, doi:10.1016/S0031-9422(00)88881-0
↑ Astringin and isorhapontin distribution in Sitka spruce trees. Claudia D. Toscano Underwood and Raymond B. Pearce, Phytochemistry, Volume 30, Issue 7, 1991, Pages 2183–2189, doi:10.1016/0031-9422(91)83610-W
↑ Hammerbacher, A.; Ralph, S. G.; Bohlmann, J.; Fenning, T. M.; Gershenzon, J.; Schmidt, A. (2011). "Biosynthesis of the Major Tetrahydroxystilbenes in Spruce, Astringin and Isorhapontin, Proceeds via Resveratrol and is Enhanced by Fungal Infection". Plant Physiology 157 (2): 876–890. doi:10.1104/pp.111.181420. PMC 3192583. PMID 21865488.

Hydroxystilbenes and their glycosides (monomeric forms)

Dihydroxylated

Trihydroxylated

Resveratrol

Tetrahydroxylated

O-methylated

4-Methoxyresveratrol Gnetucleistol D (2-methoxyoxyresveratrol) Gnetucleistol E (3-methoxy-isorhapontigenin) Isorhapontigenin (3,4',5-trihydroxy-3'-methoxystilbene) Pinostilbene (3-methoxyresveratrol) Pterostilbene (3',5'-dimethoxyresveratrol) Rhapontigenin (piceatannol 4'-methyl ether)

Combretastatins	Combretastatin A-1 Combretastatin A-4

carboxylated

Hydrangeic acid

other acylations

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

Glycosides

Astringin (Piceatannol 3-O-glucoside)
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

oligostilbenoids

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