Isorhapontin

Last updated
Isorhapontin
Isorhapontin.svg
Names
IUPAC name
3-Hydroxy-5-[(1E)-2-(4-hydroxy-3-methoxyphenyl)ethen-1-yl]phenoxy β-D-glucopyranoside
Systematic IUPAC name
(2S,3R,4S,5S,6R)-2-{3-Hydroxy-5-[(1E)-2-(4-hydroxy-3-methoxyphenyl)ethen-1-yl]phenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol
Other names
Isorhapontigenin glucoside
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.230.305 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • 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
  • 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
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).

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]

Related Research Articles

<i>Picea abies</i> Species of plant

Picea abies, the Norway spruce or European spruce, is a species of spruce native to Northern, Central and Eastern Europe.

<i>Picea sitchensis</i> Species of large coniferous tree

Picea sitchensis, the Sitka spruce, is a large, coniferous, evergreen tree growing to almost 100 meters (330 ft) tall, with a trunk diameter at breast height that can exceed 5 m (16 ft). It is by far the largest species of spruce and the fifth-largest conifer in the world, and the third-tallest conifer species. The Sitka spruce is one of the few species documented to exceed 90 m (300 ft) in height. Its name is derived from the community of Sitka in southeast Alaska, where it is prevalent. Its range hugs the western coast of Canada and the US, continuing south into northernmost California.

<i>Lamium album</i> Species of flowering plant

Lamium album, commonly called white nettle or white dead-nettle, is a flowering plant in the family Lamiaceae. It is native throughout Europe and Asia, growing in a variety of habitats from open grassland to woodland, generally on moist, fertile soils.

<span class="mw-page-title-main">Malvin</span> Chemical compound

Malvin is a naturally occurring chemical of the anthocyanin family.

<span class="mw-page-title-main">Piceid</span> Chemical compound

Piceid is a stilbenoid glucoside and is a major resveratrol derivative in grape juices. It can be found in the bark of Picea sitchensis. It can also be isolated from Reynoutria japonica, the Japanese knotweed.

<span class="mw-page-title-main">Piceatannol</span> Chemical compound

Piceatannol is the organic compound with the formula ( 2C6H3)2CH)2. Classified as a stilbenoid and a phenol, it is a white solid, although samples often are yellow owing to impurities.

In enzymology, a sterol 3beta-glucosyltransferase is an enzyme that catalyzes the chemical reaction

<span class="mw-page-title-main">Daidzin</span> Chemical compound

Daidzin is a natural organic compound in the class of phytochemicals known as isoflavones. Daidzin can be found in Japanese plant kudzu and from soybean leaves.

<span class="mw-page-title-main">Ononin</span> Chemical compound

Ononin is an isoflavone glycoside, the 7-O-β-D-glucopyranoside of formononetin, which in turn is the 4'-O-methoxy derivative of the parent isoflavone daidzein.

<span class="mw-page-title-main">Prodelphinidin</span>

Prodelphinidin is a name for the polymeric tannins composed of gallocatechin. It yields delphinidin during depolymerisation under oxidative conditions.

<span class="mw-page-title-main">Syringetin</span> Chemical compound

Syringetin is an O-methylated flavonol, a type of flavonoid. It is found in red grape, in Lysimachia congestiflora and in Vaccinium uliginosum. It is one of the phenolic compounds present in wine.

<span class="mw-page-title-main">Xanthonoid</span> Class of phenolic chemical compounds

A xanthonoid is a chemical natural phenolic compound formed from the xanthone backbone. Many members of the Clusiaceae contain xanthonoids.

<span class="mw-page-title-main">Astringin</span> Chemical compound

Astringin is a stilbenoid, the 3-β-D-glucoside of piceatannol. It can be found in the bark of Picea sitchensis or Picea abies.

<span class="mw-page-title-main">Picein</span> Chemical compound

Picein is a phenolic compound found in mycorrhizal roots of Norway spruces. It is the glucoside of piceol.

<span class="mw-page-title-main">Piceol</span> Phenolic compound found in Norway spruces

Piceol is a phenolic compound found in the needles and in mycorrhizal roots of Norway spruces. Picein is the glucoside of piceol.

<span class="mw-page-title-main">Isorhapontigenin</span> Chemical compound

Isorhapontigenin is a tetrahydroxylated stilbenoid with a methoxy group. It is an isomer of rhapontigenin and an analog of resveratrol. It is found in the Chinese herb Gnetum cleistostachyum, in Gnetum parvifolium and in the seeds of the palm Aiphanes aculeata.

<span class="mw-page-title-main">Hypolaetin</span> Chemical compound

Hypolaetin is a flavone. It is the aglycone of hypolaetin 8-glucuronide, a compound found in the liverwort Marchantia berteroana. Hypolaetin 8-glucoside can be found in Sideritis leucantha.

<span class="mw-page-title-main">Skimmin</span> Chemical compound

Skimmin is a glucoside of umbelliferone.

4-Hydroxybenzoic acid 4-<i>O</i>-glucoside Chemical compound

4-Hydroxybenzoic acid 4-O-glucoside is a glucoside of p-hydroxybenzoic acid. It can be found in mycorrhizal and non-mycorrhizal roots of Norway spruces.

Catechin-5-<i>O</i>-glucoside Chemical compound

Catechin 5-O-glucoside is a flavanol glucoside. It can be found in rhubarb and in the bark of Rhaphiolepis umbellata. It can also be formed from (+)-catechin by plant-cultured cells of Eucalyptus perriniana.

References

  1. 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. PMID   24197010. S2CID   43504838.
  2. 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
  3. 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
  4. 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.