Piceid

Last updated
Piceid
Piceid.svg
Trans-piceid
Names
IUPAC name
3-Hydroxy-5-[(E)-2-(4-hydroxyphenyl)ethen-1-yl]phenyl β-D-glucopyranoside
Systematic IUPAC name
(2S,3R,4S,5S,6R)-2-{3-Hydroxy-5-[(E)-2-(4-hydroxyphenyl)ethen-1-yl]phenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol
Other names
Polydatin
Resveratrol 3-β-mono-D-glucoside
cis-Piceid
trans-Piceid
3,5,4'-Trihydroxystilbene-3-O-β-D-glucopyranoside
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.208.708 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C20H22O8/c21-10-16-17(24)18(25)19(26)20(28-16)27-15-8-12(7-14(23)9-15)2-1-11-3-5-13(22)6-4-11/h1-9,16-26H,10H2/b2-1+/t16-,17-,18+,19-,20-/m1/s1 X mark.svgN
    Key: HSTZMXCBWJGKHG-CUYWLFDKSA-N X mark.svgN
  • InChI=1/C20H22O8/c21-10-16-17(24)18(25)19(26)20(28-16)27-15-8-12(7-14(23)9-15)2-1-11-3-5-13(22)6-4-11/h1-9,16-26H,10H2/b2-1+/t16-,17-,18+,19-,20-/m1/s1
    Key: HSTZMXCBWJGKHG-CUYWLFDKBI
  • OC1=CC(/C=C/C3=CC=C(O)C=C3)=CC(O[C@H]2[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O2)=C1
Properties
C20H22O8
Molar mass 390.388 g·mol−1
AppearanceWhite powder
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Piceid is a stilbenoid glucoside and is a major resveratrol derivative in grape juices. [1] It can be found in the bark of Picea sitchensis . [2] It can also be isolated from Reynoutria japonica (syn. Fallopia japonica), [3] the Japanese knotweed (syn. Polygonum cuspidatum).

Resveratrol can be produced from piceid via the mold Aspergillus oryzae . [3] as the fungus produces a potent beta-glucosidase. [4]

trans-Piceid is the glucoside formed with trans-resveratrol, while cis-piceid is formed with cis-resveratrol.

trans-Resveratrol-3-O-glucuronide is one of the two metabolites of trans-piceid in rat. [5]

Resveratrol glucoside from transgenic alfalfa prevents aberrant crypt foci in mice. [6]

See also

Related Research Articles

<span class="mw-page-title-main">Resveratrol</span> Organic compound

Resveratrol (3,5,4′-trihydroxy-trans-stilbene) is a stilbenoid, a type of natural phenol, and a phytoalexin produced by several plants in response to injury or when the plant is under attack by pathogens, such as bacteria or fungi. Sources of resveratrol in food include the skin of grapes, blueberries, raspberries, mulberries, and peanuts.

<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>Aspergillus oryzae</i> Filamentous fungus

Aspergillus oryzae, also known as kōji mold, is a filamentous fungus used in East Asia to saccharify rice, sweet potato, and barley in the making of alcoholic beverages such as sake and shōchū, and also to ferment soybeans for making soy sauce and miso. However, in the production of fermented foods of soybeans such as soy sauce and miso, Aspergillus sojae is sometimes used instead of A. oryzae. Incidentally, in China and Korea, the fungi used for fermented foods for a long time in the production of traditional alcoholic beverages were not A. oryzae but fungi belonging to Rhizopus and Mucor. A. oryzae is also used for the production of rice vinegars. Barley kōji (麦麹) or rice kōji (米麹) are made by fermenting the grains with A. oryzae hyphae.

<span class="mw-page-title-main">Phytase</span> Class of enzymes

A phytase is any type of phosphatase enzyme that catalyzes the hydrolysis of phytic acid – an indigestible, organic form of phosphorus that is found in many plant tissues, especially in grains and oil seeds – and releases a usable form of inorganic phosphorus. While phytases have been found to occur in animals, plants, fungi and bacteria, phytases have been most commonly detected and characterized from fungi.

<span class="mw-page-title-main">Alpha-glucosidase</span> Enzyme

α-Glucosidase is a glucosidase located in the brush border of the small intestine that acts upon α(1→4) bonds:

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

Emodin (6-methyl-1,3,8-trihydroxyanthraquinone) is a chemical compound, of the anthraquinone family, that can be isolated from rhubarb, buckthorn, and Japanese knotweed. Emodin is particularly abundant in the roots of the Chinese rhubarb, knotweed and knotgrass as well as Hawaii ‘au‘auko‘i cassia seeds or coffee weed. It is specifically isolated from Rheum palmatum L. It is also produced by many species of fungi, including members of the genera Aspergillus, Pyrenochaeta, and Pestalotiopsis, inter alia. The common name is derived from Rheum emodi, a taxonomic synonym of Rheum australe, and synonyms include emodol, frangula emodin, rheum emodin, 3-methyl-1,6,8-trihydroxyanthraquinone, Schüttgelb (Schuttgelb), and Persian Berry Lake.

<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.

<span class="mw-page-title-main">Phenolic content in wine</span> Wine chemistry

The phenolic content in wine refers to the phenolic compounds—natural phenol and polyphenols—in wine, which include a large group of several hundred chemical compounds that affect the taste, color and mouthfeel of wine. These compounds include phenolic acids, stilbenoids, flavonols, dihydroflavonols, anthocyanins, flavanol monomers (catechins) and flavanol polymers (proanthocyanidins). This large group of natural phenols can be broadly separated into two categories, flavonoids and non-flavonoids. Flavonoids include the anthocyanins and tannins which contribute to the color and mouthfeel of the wine. The non-flavonoids include the stilbenoids such as resveratrol and phenolic acids such as benzoic, caffeic and cinnamic acids.

Aberrant crypt foci (ACF) are clusters of abnormal tube-like glands in the lining of the colon and rectum. Aberrant crypt foci form before colorectal polyps and are one of the earliest changes seen in the colon that may lead to cancer. ACF are, as opposed to normal epithelial cells, apoptosis resistant. When looking for aberrant crypt foci with microscopy, methylene blue is used as a staining agent. The resulting figure is fairly easy to detect under the microscope at low magnification (x40).

<i>epsilon</i>-Viniferin Chemical compound

ε-Viniferin is a naturally occurring phenol, belonging to the stilbenoids family. It is a resveratrol dimer.

<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">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.

<i>trans</i>-Resveratrol-3-<i>O</i>-glucuronide Chemical compound

trans-Resveratrol-3-O-glucuronide is a metabolite of resveratrol and trans-resveratrol-3-O-glucoside (piceid).

<i>delta</i>-Viniferin Chemical compound

δ-Viniferin is a resveratrol dehydrodimer. It is an isomer of epsilon-viniferin. It can be isolated from stressed grapevine leaves. It is also found in plant cell cultures and wine. It can also be found in Rheum maximowiczii.

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

Miyabenol C is a stilbenoid. It is a resveratrol trimer. It is found in Vitis vinifera (grape), in Foeniculi fructus, in Caragana sinica.

<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">Liquiritin</span> Chemical compound

Liquiritin is the 4'-O-glucoside of the flavanone liquiritigenin. Liquiritin is one of flavone compounds derived from licorice.

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

Isorhapontin is a stilbenoid. It is the glucoside of isorhapontigenin. It can be found in mycorrhizal and non-mycorrhizal roots of Norway spruces, in the bark of Picea sitchensis or in white spruce.

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

Oligostilbenoids are oligomeric forms of stilbenoids. Some molecules are large enough to be considered polyphenols and constitute a class of tannins.

Gliflozins are a class of drugs in the treatment of type 2 diabetes (T2D). They act by inhibiting sodium/glucose cotransporter 2 (SGLT-2), and are therefore also called SGLT-2 inhibitors. The efficacy of the drug is dependent on renal excretion and prevents glucose from going into blood circulation by promoting glucosuria. The mechanism of action is insulin independent.

References

  1. Romero-Pérez, A. I.; Ibern-Gómez, M.; Lamuela-Raventós, R. M.; De La Torre-Boronat, M. C. (1999). "Piceid, the Major Resveratrol Derivative in Grape Juices". Journal of Agricultural and Food Chemistry. 47 (4): 1533–1536. doi:10.1021/jf981024g. PMID   10564012.
  2. Aritomi, M.; Donnelly, D. M. X. (1976). "Stilbene glucosides in the bark of Picea sitchensis". Phytochemistry. 15 (12): 2006. doi:10.1016/S0031-9422(00)88881-0.
  3. 1 2 Wang, H.; Liu, L.; Guo, Y. -X.; Dong, Y. -S.; Zhang, D. -J.; Xiu, Z. -L. (2007). "Biotransformation of piceid in Polygonum cuspidatum to resveratrol by Aspergillus oryzae". Applied Microbiology and Biotechnology. 75 (4): 763–768. doi:10.1007/s00253-007-0874-3. PMID   17333175.
  4. Zhang, Chunzhi; Li, Dai; Yu, Hongshan; Zhang, Bo; Jin, Fengxie (2007). "Purification and characterization of piceid-β-d-glucosidase from Aspergillus oryzae". Process Biochemistry. 42: 83–88. doi:10.1016/j.procbio.2006.07.019.
  5. Zhou, M.; Chen, X.; Zhong, D. (2007). "Simultaneous determination of trans-resveratrol-3-O-glucoside and its two metabolites in rat plasma using liquid chromatography with ultraviolet detection". Journal of Chromatography B. 854 (1–2): 219–223. doi:10.1016/j.jchromb.2007.04.025. PMID   17500049.
  6. RKineman, B. D.; Brummer, E. C.; Paiva, N. L.; Birt, D. F. (2010). "Resveratrol from Transgenic Alfalfa for Prevention of Aberrant Crypt Foci in Mice". Nutrition and Cancer. 62 (3): 351–361. doi:10.1080/01635580903407213. PMID   20358473.