NCBI Taxonomy: 64578

Cotylelobium (ncbi_taxid: 64578)

found 40 associated metabolites at genus taxonomy rank level.

Ancestor: Dipterocarpoideae

Child Taxonomies: Cotylelobium malayanum, Cotylelobium burckii, Cotylelobium lanceolatum, Cotylelobium melanoxylon, Cotylelobium scabriusculum

4-Hydroxybenzoic acid

4-hydroxybenzoic acid

C7H6O3 (138.0317)


4-Hydroxybenzoic acid, also known as p-hydroxybenzoate or 4-carboxyphenol, belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups. 4-Hydroxybenzoic acid is a white crystalline solid that is slightly soluble in water and chloroform but more soluble in polar organic solvents such as alcohols and acetone. It is a nutty and phenolic tasting compound. 4-Hydroxybenzoic acid exists in all living species, ranging from bacteria to plants to humans. 4-Hydroxybenzoic acid can be found naturally in coconut. It is one of the main catechins metabolites found in humans after consumption of green tea infusions. It is also found in wine, in vanilla, in A√ßa√≠ oil, obtained from the fruit of the a√ßa√≠ palm (Euterpe oleracea), at relatively high concetrations (892¬±52 mg/kg). It is also found in cloudy olive oil and in the edible mushroom Russula virescens. It has been detected in red huckleberries, rabbiteye blueberries, and corianders and in a lower concentration in olives, red raspberries, and almonds. In humans, 4-hydroxybenzoic acid is involved in ubiquinone biosynthesis. In particular, the enzyme 4-hydroxybenzoate polyprenyltransferase uses a polyprenyl diphosphate and 4-hydroxybenzoate to produce diphosphate and 4-hydroxy-3-polyprenylbenzoate. This enzyme participates in ubiquinone biosynthesis. 4-Hydroxybenzoic acid can be biosynthesized by the enzyme Chorismate lyase. Chorismate lyase is an enzyme that transforms chorismate into 4-hydroxybenzoate and pyruvate. This enzyme catalyses the first step in ubiquinone biosynthesis in Escherichia coli and other Gram-negative bacteria. 4-Hydroxybenzoate is an intermediate in many enzyme-mediated reactions in microbes. For instance, the enzyme 4-hydroxybenzaldehyde dehydrogenase uses 4-hydroxybenzaldehyde, NAD+ and H2O to produce 4-hydroxybenzoate, NADH and H+. This enzyme participates in toluene and xylene degradation in bacteria such as Pseudomonas mendocina. 4-hydroxybenzaldehyde dehydrogenase is also found in carrots. The enzyme 4-hydroxybenzoate 1-hydroxylase transforms 4-hydroxybenzoate, NAD(P)H, 2 H+ and O2 into hydroquinone, NAD(P)+, H2O and CO2. This enzyme participates in 2,4-dichlorobenzoate degradation and is found in Candida parapsilosis. The enzyme 4-hydroxybenzoate 3-monooxygenase transforms 4-hydroxybenzoate, NADPH, H+ and O2 into protocatechuate, NADP+ and H2O. This enzyme participates in benzoate degradation via hydroxylation and 2,4-dichlorobenzoate degradation and is found in Pseudomonas putida and Pseudomonas fluorescens. 4-Hydroxybenzoic acid is a popular antioxidant in part because of its low toxicity. 4-Hydroxybenzoic acid has estrogenic activity both in vitro and in vivo (PMID 9417843). Isolated from many plants, free and combined. Alkyl esters of 4-hydroxybenzoic acid (see below) are used as food and cosmetic preservatives, mainly in their Na salt form, which makes them more water soluble. They are active at low concentrations and more pH-independent than the commonly used Benzoic acid DVN38-Z and 2,4-Hexadienoic acid GMZ10-P. The taste is more detectable than for those preservatives. Effectiveness increases with chain length of the alcohol, but for some microorganisms this reduces cell permeability and thus counteracts the increased efficiency. 4-Hydroxybenzoic acid is found in many foods, some of which are chicory, corn, rye, and black huckleberry. 4-hydroxybenzoic acid is a monohydroxybenzoic acid that is benzoic acid carrying a hydroxy substituent at C-4 of the benzene ring. It has a role as a plant metabolite and an algal metabolite. It is a conjugate acid of a 4-hydroxybenzoate. 4-Hydroxybenzoic acid is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). See also: Vaccinium myrtillus Leaf (part of); Galium aparine whole (part of); Menyanthes trifoliata leaf (part of) ... View More ... A monohydroxybenzoic acid that is benzoic acid carrying a hydroxy substituent at C-4 of the benzene ring. 4-Hydroxybenzoic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=99-96-7 (retrieved 2024-07-01) (CAS RN: 99-96-7). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). 4-Hydroxybenzoic acid, a phenolic derivative of benzoic acid, could inhibit most gram-positive and some gram-negative bacteria, with an IC50 of 160 μg/mL. 4-Hydroxybenzoic acid, a phenolic derivative of benzoic acid, could inhibit most gram-positive and some gram-negative bacteria, with an IC50 of 160 μg/mL.

   

epsilon-Viniferin

5-[6-hydroxy-2-(4-hydroxyphenyl)-4-[(Z)-2-(4-hydroxyphenyl)ethenyl]-2,3-dihydro-1-benzofuran-3-yl]benzene-1,3-diol

C28H22O6 (454.1416)


(7E,7R,8R)-epsilon-Viniferin is found in alcoholic beverages. (7E,7R,8R)-epsilon-Viniferin is isolated from leaves of wine grape (Vitis vinifera) infected with Botrytis cinere

   

trans-Piceid

(2S,3R,4S,5S,6R)-2-{3-hydroxy-5-[(E)-2-(4-hydroxyphenyl)ethenyl]phenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C20H22O8 (390.1315)


trans-Piceid is found in alcoholic beverages. trans-Piceid is present in grapeskins and red wine. It is isolated from Polygonum cuspidatum (Japanese knotweed).Piceid is a stilbenoid glucoside and is a major resveratrol derivative in grape juices (E/Z)-Polydatin ((E/Z)-Piceid) is a monocrystalline compound originally isolated from the root and rhizome of Polygonum cuspidatum. (E/Z)-Polydatin has anti-platelet aggregation, anti-oxidative action of low-density lipoprotein (LDL), cardioprotective activity, anti-inflammatory and immune-regulating functions[1]. (E/Z)-Polydatin ((E/Z)-Piceid) is a monocrystalline compound originally isolated from the root and rhizome of Polygonum cuspidatum. (E/Z)-Polydatin has anti-platelet aggregation, anti-oxidative action of low-density lipoprotein (LDL), cardioprotective activity, anti-inflammatory and immune-regulating functions[1]. (E/Z)-Polydatin ((E/Z)-Piceid) is a monocrystalline compound originally isolated from the root and rhizome of Polygonum cuspidatum. (E/Z)-Polydatin has anti-platelet aggregation, anti-oxidative action of low-density lipoprotein (LDL), cardioprotective activity, anti-inflammatory and immune-regulating functions[1]. Polydatin (Piceid), extracted from the roots of Reynoutria japonica, a widely used traditional Chinese remedies, possesses anti-inflammatory activity in several experimental models. Polydatin (Piceid) inhibits G6PD and induces oxidative and ER stresses. Polydatin (Piceid), extracted from the roots of Reynoutria japonica, a widely used traditional Chinese remedies, possesses anti-inflammatory activity in several experimental models. Polydatin (Piceid) inhibits G6PD and induces oxidative and ER stresses. Polydatin (Standard) is the analytical standard of Polydatin. This product is intended for research and analytical applications. Polydatin (Piceid), extracted from the roots of Reynoutria japonica, a widely used traditional Chinese remedies, possesses anti-inflammatory activity in several experimental models. Polydatin (Piceid) inhibits G6PD and induces oxidative and ER stresses.

   

Viniferin

5-[6-hydroxy-2-(4-hydroxyphenyl)-4-[2-(4-hydroxyphenyl)ethenyl]-2,3-dihydro-1-benzofuran-3-yl]benzene-1,3-diol

C28H22O6 (454.1416)


   

trans-Piceid

(2S,3R,4S,5S,6R)-2-[3-hydroxy-5-[(E)-2-(4-hydroxyphenyl)vinyl]phenoxy]-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol

C20H22O8 (390.1315)


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, a nephroprotective agent and a geroprotector. It is a stilbenoid, a polyphenol, a beta-D-glucoside and a monosaccharide derivative. It is functionally related to a trans-resveratrol. 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. Polydatin is a natural product found in Vitis rupestris, Vitis labrusca, and other organisms with data available. trans-Piceid is found in alcoholic beverages. trans-Piceid is present in grapeskins and red wine. It is isolated from Polygonum cuspidatum (Japanese knotweed).Piceid is a stilbenoid glucoside and is a major resveratrol derivative in grape juices A stilbenoid that is trans-resveratrol substituted at position 3 by a beta-D-glucosyl residue. (E/Z)-Polydatin ((E/Z)-Piceid) is a monocrystalline compound originally isolated from the root and rhizome of Polygonum cuspidatum. (E/Z)-Polydatin has anti-platelet aggregation, anti-oxidative action of low-density lipoprotein (LDL), cardioprotective activity, anti-inflammatory and immune-regulating functions[1]. (E/Z)-Polydatin ((E/Z)-Piceid) is a monocrystalline compound originally isolated from the root and rhizome of Polygonum cuspidatum. (E/Z)-Polydatin has anti-platelet aggregation, anti-oxidative action of low-density lipoprotein (LDL), cardioprotective activity, anti-inflammatory and immune-regulating functions[1]. (E/Z)-Polydatin ((E/Z)-Piceid) is a monocrystalline compound originally isolated from the root and rhizome of Polygonum cuspidatum. (E/Z)-Polydatin has anti-platelet aggregation, anti-oxidative action of low-density lipoprotein (LDL), cardioprotective activity, anti-inflammatory and immune-regulating functions[1]. Polydatin (Piceid), extracted from the roots of Reynoutria japonica, a widely used traditional Chinese remedies, possesses anti-inflammatory activity in several experimental models. Polydatin (Piceid) inhibits G6PD and induces oxidative and ER stresses. Polydatin (Piceid), extracted from the roots of Reynoutria japonica, a widely used traditional Chinese remedies, possesses anti-inflammatory activity in several experimental models. Polydatin (Piceid) inhibits G6PD and induces oxidative and ER stresses. Polydatin (Standard) is the analytical standard of Polydatin. This product is intended for research and analytical applications. Polydatin (Piceid), extracted from the roots of Reynoutria japonica, a widely used traditional Chinese remedies, possesses anti-inflammatory activity in several experimental models. Polydatin (Piceid) inhibits G6PD and induces oxidative and ER stresses.

   

Lyoniresinol

(1S,2R,3R)-1,2,3,4-Tetrahydro-7-hydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)-6,8-dimethoxy-2,3-naphthalenedimethanol; (+)-Lyoniresinol; Lyoniresinol, (+)-

C22H28O8 (420.1784)


(+)-lyoniresinol is a lignan that is tetralin substituted by a 4-hydroxy-3,5-dimethoxy group at position 4, hydroxymethyl groups at positions 2 and 3, methoxy groups at positions 5 and 7 and a hydroxy group at position 6. Isolated from Machilus robusta and Sinocalamus affinis, it exhibits antineoplastic activity. It has a role as a metabolite and an antineoplastic agent. It is a dimethoxybenzene, a lignan, a primary alcohol, a polyphenol and a member of tetralins. (+)-Lyoniresinol is a natural product found in Salacia chinensis, Litsea coreana, and other organisms with data available. A lignan that is tetralin substituted by a 4-hydroxy-3,5-dimethoxy group at position 4, hydroxymethyl groups at positions 2 and 3, methoxy groups at positions 5 and 7 and a hydroxy group at position 6. Isolated from Machilus robusta and Sinocalamus affinis, it exhibits antineoplastic activity.

   

Epsilon-Viniferin

1,3-BENZENEDIOL, 5-(2,3-DIHYDRO-6-HYDROXY-2-(4-HYDROXYPHENYL)-4-(2-(4-HYDROXYPHENYL)ETHENYL)-3-BENZOFURANYL)-, (2R-(2.ALPHA.,3.BETA.,4(E)))-

C28H22O6 (454.1416)


(-)-trans-epsilon-viniferin is a stilbenoid that is the (-)-trans-stereoisomer of epsilon-viniferin, obtained by cyclodimerisation of trans-resveratrol. It has a role as a metabolite. It is a member of 1-benzofurans, a polyphenol and a stilbenoid. It is functionally related to a trans-resveratrol. It is an enantiomer of a (+)-trans-epsilon-viniferin. Epsilon-viniferin is a natural product found in Dipterocarpus grandiflorus, Dipterocarpus hasseltii, and other organisms with data available. A stilbenoid that is the (-)-trans-stereoisomer of epsilon-viniferin, obtained by cyclodimerisation of trans-resveratrol.

   

4-hydroxybenzoate

4-Hydroxybenzoic acid

C7H6O3 (138.0317)


4-Hydroxybenzoic acid, a phenolic derivative of benzoic acid, could inhibit most gram-positive and some gram-negative bacteria, with an IC50 of 160 μg/mL. 4-Hydroxybenzoic acid, a phenolic derivative of benzoic acid, could inhibit most gram-positive and some gram-negative bacteria, with an IC50 of 160 μg/mL.

   

p-Hydroxybenzoic acid

p-Hydroxybenzoic acid

C7H6O3 (138.0317)


4-Hydroxybenzoic acid, a phenolic derivative of benzoic acid, could inhibit most gram-positive and some gram-negative bacteria, with an IC50 of 160 μg/mL. 4-Hydroxybenzoic acid, a phenolic derivative of benzoic acid, could inhibit most gram-positive and some gram-negative bacteria, with an IC50 of 160 μg/mL.

   

piceid

(2S,3R,4S,5S,6R)-2-[3-hydroxy-5-[(E)-2-(4-hydroxyphenyl)vinyl]phenoxy]-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol

C20H22O8 (390.1315)


Origin: Plant, Glucosides, Stilbenes (E/Z)-Polydatin ((E/Z)-Piceid) is a monocrystalline compound originally isolated from the root and rhizome of Polygonum cuspidatum. (E/Z)-Polydatin has anti-platelet aggregation, anti-oxidative action of low-density lipoprotein (LDL), cardioprotective activity, anti-inflammatory and immune-regulating functions[1]. (E/Z)-Polydatin ((E/Z)-Piceid) is a monocrystalline compound originally isolated from the root and rhizome of Polygonum cuspidatum. (E/Z)-Polydatin has anti-platelet aggregation, anti-oxidative action of low-density lipoprotein (LDL), cardioprotective activity, anti-inflammatory and immune-regulating functions[1]. (E/Z)-Polydatin ((E/Z)-Piceid) is a monocrystalline compound originally isolated from the root and rhizome of Polygonum cuspidatum. (E/Z)-Polydatin has anti-platelet aggregation, anti-oxidative action of low-density lipoprotein (LDL), cardioprotective activity, anti-inflammatory and immune-regulating functions[1]. Polydatin (Piceid), extracted from the roots of Reynoutria japonica, a widely used traditional Chinese remedies, possesses anti-inflammatory activity in several experimental models. Polydatin (Piceid) inhibits G6PD and induces oxidative and ER stresses. Polydatin (Piceid), extracted from the roots of Reynoutria japonica, a widely used traditional Chinese remedies, possesses anti-inflammatory activity in several experimental models. Polydatin (Piceid) inhibits G6PD and induces oxidative and ER stresses. Polydatin (Standard) is the analytical standard of Polydatin. This product is intended for research and analytical applications. Polydatin (Piceid), extracted from the roots of Reynoutria japonica, a widely used traditional Chinese remedies, possesses anti-inflammatory activity in several experimental models. Polydatin (Piceid) inhibits G6PD and induces oxidative and ER stresses.

   

Epsilon-viniferin

Epsilon-viniferin

C28H22O6 (454.1416)


Annotation level-1

   

Ampelopsin B

Ampelopsin B

C28H22O6 (454.1416)


A heterotetracyclic stilbenoid that is a homodimer obtained by cyclodimerisation of resveratrol.

   

Cis-epsilon-viniferin

(Z)-epsilon-Viniferin

C28H22O6 (454.1416)


Isolated from wine grapes. cis-epsilon-Viniferin is found in fruits.

   

(+)-cis-epsilon-Viniferin

(+)-cis-epsilon-Viniferin

C28H22O6 (454.1416)


A stilbenoid that is the (+)-cis-stereoisomer of epsilon-viniferin, obtained by cyclodimerisation of cis-resveratrol.

   

(1r,2r,3r,9s,10s,17s)-3-[(2s,3s)-7-hydroxy-3-(3-hydroxy-5-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-5-yl]-2,9,17-tris(4-hydroxyphenyl)-8-oxapentacyclo[8.7.2.0⁴,¹⁸.0⁷,¹⁹.0¹¹,¹⁶]nonadeca-4,6,11,13,15,18-hexaene-5,13,15-triol

(1r,2r,3r,9s,10s,17s)-3-[(2s,3s)-7-hydroxy-3-(3-hydroxy-5-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-5-yl]-2,9,17-tris(4-hydroxyphenyl)-8-oxapentacyclo[8.7.2.0⁴,¹⁸.0⁷,¹⁹.0¹¹,¹⁶]nonadeca-4,6,11,13,15,18-hexaene-5,13,15-triol

C62H52O17 (1068.3204)


   

(1s,2r,3r,9r,10s,17s)-3-(3-hydroxy-5-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-2,9,17-tris(4-hydroxyphenyl)-8-oxapentacyclo[8.7.2.0⁴,¹⁸.0⁷,¹⁹.0¹¹,¹⁶]nonadeca-4,6,11,13,15,18-hexaene-5,13,15-triol

(1s,2r,3r,9r,10s,17s)-3-(3-hydroxy-5-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-2,9,17-tris(4-hydroxyphenyl)-8-oxapentacyclo[8.7.2.0⁴,¹⁸.0⁷,¹⁹.0¹¹,¹⁶]nonadeca-4,6,11,13,15,18-hexaene-5,13,15-triol

C48H42O14 (842.2574)


   

6-(3,5-dihydroxyphenyl)-7,11,19-tris(4-hydroxyphenyl)-8,18-dioxapentacyclo[11.6.1.0²,¹⁰.0⁵,⁹.0¹⁷,²⁰]icosa-2,4,9,11,13,15,17(20)-heptaene-4,15-diol

6-(3,5-dihydroxyphenyl)-7,11,19-tris(4-hydroxyphenyl)-8,18-dioxapentacyclo[11.6.1.0²,¹⁰.0⁵,⁹.0¹⁷,²⁰]icosa-2,4,9,11,13,15,17(20)-heptaene-4,15-diol

C42H30O9 (678.189)


   

(1s,2s,3r,4r,10r,11s)-4-[(2s,3s)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]-3,11-bis(4-hydroxyphenyl)hexacyclo[8.7.6.1²,⁵.0¹²,¹⁷.0¹⁸,²³.0⁹,²⁴]tetracosa-5,7,9(24),12,14,16,18,20,22-nonaene-6,8,14,19,21-pentol

(1s,2s,3r,4r,10r,11s)-4-[(2s,3s)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]-3,11-bis(4-hydroxyphenyl)hexacyclo[8.7.6.1²,⁵.0¹²,¹⁷.0¹⁸,²³.0⁹,²⁴]tetracosa-5,7,9(24),12,14,16,18,20,22-nonaene-6,8,14,19,21-pentol

C56H42O12 (906.2676)


   

(+)-ε-viniferin

(+)-ε-viniferin

C28H22O6 (454.1416)


   

(1s,2s,3s,9r,10r,17r)-3-(3,5-dihydroxyphenyl)-2,9,17-tris(4-hydroxyphenyl)-8-oxapentacyclo[8.7.2.0⁴,¹⁸.0⁷,¹⁹.0¹¹,¹⁶]nonadeca-4,6,11,13,15,18-hexaene-5,13,15-triol

(1s,2s,3s,9r,10r,17r)-3-(3,5-dihydroxyphenyl)-2,9,17-tris(4-hydroxyphenyl)-8-oxapentacyclo[8.7.2.0⁴,¹⁸.0⁷,¹⁹.0¹¹,¹⁶]nonadeca-4,6,11,13,15,18-hexaene-5,13,15-triol

C42H32O9 (680.2046)


   

(1r,2r,3r,9s,10s,17s)-3-(3,5-dihydroxyphenyl)-2,9,17-tris(4-hydroxyphenyl)-8-oxapentacyclo[8.7.2.0⁴,¹⁸.0⁷,¹⁹.0¹¹,¹⁶]nonadeca-4,6,11,13,15,18-hexaene-5,13,15-triol

(1r,2r,3r,9s,10s,17s)-3-(3,5-dihydroxyphenyl)-2,9,17-tris(4-hydroxyphenyl)-8-oxapentacyclo[8.7.2.0⁴,¹⁸.0⁷,¹⁹.0¹¹,¹⁶]nonadeca-4,6,11,13,15,18-hexaene-5,13,15-triol

C42H32O9 (680.2046)


   

(1s,8r,9r,16s)-8,16-bis(4-hydroxyphenyl)tetracyclo[7.6.1.0²,⁷.0¹⁰,¹⁵]hexadeca-2,4,6,10,12,14-hexaene-4,6,12,14-tetrol

(1s,8r,9r,16s)-8,16-bis(4-hydroxyphenyl)tetracyclo[7.6.1.0²,⁷.0¹⁰,¹⁵]hexadeca-2,4,6,10,12,14-hexaene-4,6,12,14-tetrol

C28H22O6 (454.1416)


   

(1r,2r,3s,4s,10r,11r)-4-(3,5-dihydroxyphenyl)-3,11-bis(4-hydroxyphenyl)hexacyclo[8.7.6.1²,⁵.0¹²,¹⁷.0¹⁸,²³.0⁹,²⁴]tetracosa-5,7,9(24),12,14,16,18,20,22-nonaene-6,8,14,19,21-pentol

(1r,2r,3s,4s,10r,11r)-4-(3,5-dihydroxyphenyl)-3,11-bis(4-hydroxyphenyl)hexacyclo[8.7.6.1²,⁵.0¹²,¹⁷.0¹⁸,²³.0⁹,²⁴]tetracosa-5,7,9(24),12,14,16,18,20,22-nonaene-6,8,14,19,21-pentol

C42H32O9 (680.2046)


   

(1r,8r,9s,16r)-8,16-bis(4-hydroxyphenyl)tetracyclo[7.6.1.0²,⁷.0¹⁰,¹⁵]hexadeca-2,4,6,10,12,14-hexaene-4,6,12,14-tetrol

(1r,8r,9s,16r)-8,16-bis(4-hydroxyphenyl)tetracyclo[7.6.1.0²,⁷.0¹⁰,¹⁵]hexadeca-2,4,6,10,12,14-hexaene-4,6,12,14-tetrol

C28H22O6 (454.1416)


   

(9s,10r,11s,12s)-12-(3,5-dihydroxyphenyl)-5,7,14,16-tetrahydroxy-9,11-bis(4-hydroxyphenyl)tetracyclo[8.6.1.0³,⁸.0¹³,¹⁷]heptadeca-1(17),3,5,7,13,15-hexaen-2-one

(9s,10r,11s,12s)-12-(3,5-dihydroxyphenyl)-5,7,14,16-tetrahydroxy-9,11-bis(4-hydroxyphenyl)tetracyclo[8.6.1.0³,⁸.0¹³,¹⁷]heptadeca-1(17),3,5,7,13,15-hexaen-2-one

C35H26O9 (590.1577)


   

12-(3,5-dihydroxyphenyl)-5,7,14,16-tetrahydroxy-9,11-bis(4-hydroxyphenyl)tetracyclo[8.6.1.0³,⁸.0¹³,¹⁷]heptadeca-1(17),3,5,7,13,15-hexaen-2-one

12-(3,5-dihydroxyphenyl)-5,7,14,16-tetrahydroxy-9,11-bis(4-hydroxyphenyl)tetracyclo[8.6.1.0³,⁸.0¹³,¹⁷]heptadeca-1(17),3,5,7,13,15-hexaen-2-one

C35H26O9 (590.1577)


   

(1r,2s,3s,9s,10s,17r)-3-(3-hydroxy-5-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-2,9,17-tris(4-hydroxyphenyl)-8-oxapentacyclo[8.7.2.0⁴,¹⁸.0⁷,¹⁹.0¹¹,¹⁶]nonadeca-4,6,11,13,15,18-hexaene-5,13,15-triol

(1r,2s,3s,9s,10s,17r)-3-(3-hydroxy-5-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-2,9,17-tris(4-hydroxyphenyl)-8-oxapentacyclo[8.7.2.0⁴,¹⁸.0⁷,¹⁹.0¹¹,¹⁶]nonadeca-4,6,11,13,15,18-hexaene-5,13,15-triol

C48H42O14 (842.2574)


   

(1r,8r,16r)-8,16-bis(4-hydroxyphenyl)-15-oxatetracyclo[8.6.1.0²,⁷.0¹⁴,¹⁷]heptadeca-2,4,6,10,12,14(17)-hexaene-4,6,12-triol

(1r,8r,16r)-8,16-bis(4-hydroxyphenyl)-15-oxatetracyclo[8.6.1.0²,⁷.0¹⁴,¹⁷]heptadeca-2,4,6,10,12,14(17)-hexaene-4,6,12-triol

C28H22O6 (454.1416)


   

8-(4-hydroxy-3,5-dimethoxyphenyl)-6,7-bis(hydroxymethyl)-1,3-dimethoxy-5,6,7,8-tetrahydronaphthalen-2-ol

8-(4-hydroxy-3,5-dimethoxyphenyl)-6,7-bis(hydroxymethyl)-1,3-dimethoxy-5,6,7,8-tetrahydronaphthalen-2-ol

C22H28O8 (420.1784)


   

3-(3-hydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-2,9,17-tris(4-hydroxyphenyl)-8-oxapentacyclo[8.7.2.0⁴,¹⁸.0⁷,¹⁹.0¹¹,¹⁶]nonadeca-4,6,11,13,15,18-hexaene-5,13,15-triol

3-(3-hydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-2,9,17-tris(4-hydroxyphenyl)-8-oxapentacyclo[8.7.2.0⁴,¹⁸.0⁷,¹⁹.0¹¹,¹⁶]nonadeca-4,6,11,13,15,18-hexaene-5,13,15-triol

C48H42O14 (842.2574)


   

3-(3,5-dihydroxyphenyl)-2,9,17-tris(4-hydroxyphenyl)-8-oxapentacyclo[8.7.2.0⁴,¹⁸.0⁷,¹⁹.0¹¹,¹⁶]nonadeca-4,6,11,13,15,18-hexaene-5,13,15-triol

3-(3,5-dihydroxyphenyl)-2,9,17-tris(4-hydroxyphenyl)-8-oxapentacyclo[8.7.2.0⁴,¹⁸.0⁷,¹⁹.0¹¹,¹⁶]nonadeca-4,6,11,13,15,18-hexaene-5,13,15-triol

C42H32O9 (680.2046)


   

(1s,2r,3r,9s,10s,17s)-3-(3-hydroxy-5-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-2,9,17-tris(4-hydroxyphenyl)-8-oxapentacyclo[8.7.2.0⁴,¹⁸.0⁷,¹⁹.0¹¹,¹⁶]nonadeca-4,6,11,13,15,18-hexaene-5,13,15-triol

(1s,2r,3r,9s,10s,17s)-3-(3-hydroxy-5-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-2,9,17-tris(4-hydroxyphenyl)-8-oxapentacyclo[8.7.2.0⁴,¹⁸.0⁷,¹⁹.0¹¹,¹⁶]nonadeca-4,6,11,13,15,18-hexaene-5,13,15-triol

C48H42O14 (842.2574)


   

(1r,2r,3r,9s,10s,17s)-3-[(2r,3s)-3-(3,5-dihydroxyphenyl)-2-(4-hydroxyphenyl)-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzofuran-5-yl]-2,9,17-tris(4-hydroxyphenyl)-8-oxapentacyclo[8.7.2.0⁴,¹⁸.0⁷,¹⁹.0¹¹,¹⁶]nonadeca-4,6,11,13,15,18-hexaene-5,13,15-triol

(1r,2r,3r,9s,10s,17s)-3-[(2r,3s)-3-(3,5-dihydroxyphenyl)-2-(4-hydroxyphenyl)-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzofuran-5-yl]-2,9,17-tris(4-hydroxyphenyl)-8-oxapentacyclo[8.7.2.0⁴,¹⁸.0⁷,¹⁹.0¹¹,¹⁶]nonadeca-4,6,11,13,15,18-hexaene-5,13,15-triol

C62H52O17 (1068.3204)


   

8,16-bis(4-hydroxyphenyl)tetracyclo[7.6.1.0²,⁷.0¹⁰,¹⁵]hexadeca-2,4,6,10,12,14-hexaene-4,6,12,14-tetrol

8,16-bis(4-hydroxyphenyl)tetracyclo[7.6.1.0²,⁷.0¹⁰,¹⁵]hexadeca-2,4,6,10,12,14-hexaene-4,6,12,14-tetrol

C28H22O6 (454.1416)


   

(1r,2r,3s,4r,10r,11r)-4-(3-hydroxy-5-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3,11-bis(4-hydroxyphenyl)hexacyclo[8.7.6.1²,⁵.0¹²,¹⁷.0¹⁸,²³.0⁹,²⁴]tetracosa-5,7,9(24),12,14,16,18,20,22-nonaene-6,8,14,19,21-pentol

(1r,2r,3s,4r,10r,11r)-4-(3-hydroxy-5-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3,11-bis(4-hydroxyphenyl)hexacyclo[8.7.6.1²,⁵.0¹²,¹⁷.0¹⁸,²³.0⁹,²⁴]tetracosa-5,7,9(24),12,14,16,18,20,22-nonaene-6,8,14,19,21-pentol

C48H42O14 (842.2574)


   

(1s,8r,9r,16r)-8,16-bis(4-hydroxyphenyl)tetracyclo[7.6.1.0²,⁷.0¹⁰,¹⁵]hexadeca-2,4,6,10,12,14-hexaene-4,6,12,14-tetrol

(1s,8r,9r,16r)-8,16-bis(4-hydroxyphenyl)tetracyclo[7.6.1.0²,⁷.0¹⁰,¹⁵]hexadeca-2,4,6,10,12,14-hexaene-4,6,12,14-tetrol

C28H22O6 (454.1416)


   

(1r,2r,3r,9s,10s,17s)-3-(3-hydroxy-5-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-2,9,17-tris(4-hydroxyphenyl)-8-oxapentacyclo[8.7.2.0⁴,¹⁸.0⁷,¹⁹.0¹¹,¹⁶]nonadeca-4,6,11,13,15,18-hexaene-5,13,15-triol

(1r,2r,3r,9s,10s,17s)-3-(3-hydroxy-5-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-2,9,17-tris(4-hydroxyphenyl)-8-oxapentacyclo[8.7.2.0⁴,¹⁸.0⁷,¹⁹.0¹¹,¹⁶]nonadeca-4,6,11,13,15,18-hexaene-5,13,15-triol

C48H42O14 (842.2574)


   

(1s,6r,7r,19s)-6-(3,5-dihydroxyphenyl)-7,11,19-tris(4-hydroxyphenyl)-8,18-dioxapentacyclo[11.6.1.0²,¹⁰.0⁵,⁹.0¹⁷,²⁰]icosa-2,4,9,11,13,15,17(20)-heptaene-4,15-diol

(1s,6r,7r,19s)-6-(3,5-dihydroxyphenyl)-7,11,19-tris(4-hydroxyphenyl)-8,18-dioxapentacyclo[11.6.1.0²,¹⁰.0⁵,⁹.0¹⁷,²⁰]icosa-2,4,9,11,13,15,17(20)-heptaene-4,15-diol

C42H30O9 (678.189)


   

(z)-ε-viniferin

(z)-ε-viniferin

C28H22O6 (454.1416)


   

(1r,2s,3s,9s,10s,17r)-3-(3,5-dihydroxyphenyl)-2,9,17-tris(4-hydroxyphenyl)-8-oxapentacyclo[8.7.2.0⁴,¹⁸.0⁷,¹⁹.0¹¹,¹⁶]nonadeca-4,6,11,13,15,18-hexaene-5,13,15-triol

(1r,2s,3s,9s,10s,17r)-3-(3,5-dihydroxyphenyl)-2,9,17-tris(4-hydroxyphenyl)-8-oxapentacyclo[8.7.2.0⁴,¹⁸.0⁷,¹⁹.0¹¹,¹⁶]nonadeca-4,6,11,13,15,18-hexaene-5,13,15-triol

C42H32O9 (680.2046)