虎杖苷, trans-piceid

trans-Resveratrol 3-O-b-D-glucuronide

3,4',5-Trihydroxystilbene-3-b-D-glucopyranoside is a natural compound that has been shown to have anti-inflammatory properties in animal studies. This compound binds to the sirtuin 1 enzyme, which regulates cellular metabolism and inflammation. The regulatory effects of this compound on type 2 diabetes and tumor growth are mediated by its ability to inhibit the activity of creatine phosphokinase, an enzyme that plays an important role in energy production and cell proliferation. 3,4',5-Trihydroxystilbene-3-b-D-glucopyranoside is also able to reverse the effects of malignant tumors induced by resveratrol. This compound is a natural source for compounds with anti-inflammatory potential.

3,4′-5-Trihydroxystilbene-3-β-D-glucopyranoside is a stilbene glucoside that has been found in V. vinifera and has diverse biological activities. It reduces the growth of SKOV3 ovarian cancer cell 3D aggregates in a concentration-dependent manner. 3,4′-5-Trihydroxystilbene-3-β-D-glucopyranoside (10 and 20 µg/ml) inhibits IL-17 production in activated peripheral blood mononuclear cells (PBMCs). It inhibits the loss of glutathione peroxidase 4 (GPX4) activity induced by the ferroptosis inducer hemin in Neuro2a neuroblastoma cells. 3,4′-5-Trihydroxystilbene-3-β-D-glucopyranoside (50 mg/kg) reduces escape latency in a rat model of vascular dementia induced by four-vessel occlusion (4-VO).

Piceid, also known as polydatin or trans-piceid, belongs to the class of organic compounds known as stilbene glycosides. Stilbene glycosides are compounds structurally characterized by the presence of a carbohydrate moiety glycosidically linked to the stilbene skeleton. Thus, piceid is considered to be an aromatic polyketide lipid molecule. Piceid exists as a solid and is considered to be practically insoluble (in water) and relatively neutral. Within the cell, piceid is primarily located in the cytoplasm. Piceid can be biosynthesized from trans-resveratrol. Outside of the human body, piceid can be found in a number of food items such as green vegetables, peanut, common grape, and fruits. This makes piceid a potential biomarker for the consumption of these food products.

Polydatin, or Piceid, is a natural precursor and glycoside form of resveratrol with a monocrystalline structure. While it is isolated from the bark of *Picea sitchensis* or *Polygonum cuspidatum*, polydatin may be detected in grape, peanut, hop cones, red wines, hop pellets, cocoa-containing products, chocolate products and many daily diets. Polydatin possesses anti-inflammatory, immunoregulatory, anti-oxidative and anti-tumor activities. It is shown to mediate a cytotoxic action on colorectal cancer cells by inducing cell arrest and apoptosis.

Trans-piceid is a stilbenoid that is trans-resveratrol substituted at position 3 by a beta-D-glucosyl residue. It has a role as a metabolite, a potassium channel modulator, an anti-arrhythmia drug, a hepatoprotective agent, an antioxidant and a nephroprotective agent. It is a stilbenoid, a polyphenol, a beta-D-glucoside and a monosaccharide derivative. It derives from a trans-resveratrol.

Title: Resveratrol

CAS Registry Number: 501-36-0

CAS Name: 5-[(1E)-2-(4-hydroxyphenyl)ethenyl]-1,3-benzenediol

Additional Names: trans-resveratrol; (E)-5-(p-hydroxystyryl)resorcinol; 3,4¢,5-stilbenetriol; 3,5,4¢-trihydroxystilbene

Molecular Formula: C14H12O3

Molecular Weight: 228.24

Percent Composition: C 73.67%, H 5.30%, O 21.03%

Literature References: Phytoalexin found in a variety of plants; active ingredient of Asian folk medicine "Kojo-Kon" which is the powdered root of the Japanese knotweed. Isoln from white hellebore and structure: M. Takaoka, J. Fac. Sci., Hokkaido Imp. Univ. Ser. 3 3, 1 (1940); C.A. 34, 7887 (1940); from fescue grass: R. G. Powell et al., Phytochemistry 35, 335 (1994). Isoln of monomers, oligomers, isomers and glucosides from wine: F. Mattivi et al., J. Agric. Food Chem. 43, 1820 (1995). GC-MS determn: D. M. Goldberg et al., J. Am. Enol. Viticult. 46, 159 (1995). Produced as stress metabolite in response to fungal infection or injury: G. H. Dai et al., Physiol. Mol. Plant Pathol. 46, 177 (1995); P. Jeandet et al., J. Phytopathol. 143, 135 (1995). Antiplatelet aggregating activity: A. A. E. Bertelli et al., Int. J. Tissue React. 17, 1 (1995); and implications in coronary heart disease: C. R. Pace-Asciak et al., Clin. Chim. Acta 235, 207 (1995).

Properties: Off-white powder from MeOH, mp 253-255°.

Melting point: mp 253-255°

Derivative Type: 3-b-mono-D-glucoside

CAS Registry Number: 65914-17-2

Additional Names: Polydatin; piceid

Molecular Formula: C20H22O8

Molecular Weight: 390.38

Percent Composition: C 61.53%, H 5.68%, O 32.79%

Literature References: Isoln from fresh root of Polygonum cuspidatum Sieb. & Zucc., Polygonaceae, and structure: Nonomura et al., Yakugaku Zasshi 83, 988 (1963).

Derivative Type: (Z)-Form

CAS Registry Number: 61434-67-1

Additional Names: cis-Resveratrol

Literature References: GC-MS determn in wine: D. M. Goldberg et al., J. Agric. Food Chem. 43, 1245 (1995).