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  1. Isoflavonoids
    1. Isoflavone Aglycones
    2. Acetoxy and Deuterated Isoflavones and Other Compounds
    3. Benzylated Isoflavones
    4. Isoflavone Glycosides
    5. Isoflavanones (Dihydroisoflavones)
    6. Isoflavans
    7. Pterocarpans
    8. Pterocarpenes (Anhydro/Dehydropterocarpans)
    9. Coumestans
    10. Rotenoids
    11. Desoxybenzoins
    12. Miscellaneous Compounds
  2. Phytoalexins and Other Antimicrobials
  3. Lignans
  4. Limonoids
  5. Soybean Isoflavones
    1. METABOLITES OF THE SOY ISOFLAVONES
    2. Daidzein Metabolites
    3. Genistein Metabolites
    4. Glycitein Metabolites
  6. Alkaloids
  7. Glucosinolates
  8. Flavonoids
    1. Flavone and Flavonol (3-Hydroxyflavone) Aglycones
    2. Flavone-O-Glycosides
    3. Flavone-O-Glucuronides
    4. Flavone-C-Glycosides
    5. Biflavones
    6. Aurones
    7. Biflavanones (linked 3,8”)
    8. Flavanones
    9. Dihydrochalcones
  9. Homoisoflavanones
  10. Xanthones

Isoflavonoids

Compounds marked * have one or more side-attachements derived by cyclisation of a prenyl group or groups. As the chemical description of these cyclic side-attachments is complicated, please enquire if more details are needed. Compounds in the following list are subdivided to show the particular isoflavonoid group to which they belong. Please note that the ring numbering system is not the same for all isoflavonoids. As a guide, the numbering of isoflavones, isoflavanones and isoflavans follows the well-established flavone convention, with the ring A carbons being numbered 5 to 8, and the ring B carbons numbered 2′ to 6′ . Carbons C-7 and C-4′ are the positions most often substituted. In pterocarpans and coumestans, carbon atoms in the ring equivalent to “A” of isoflavones are numbered 1 to 4 (clockwise, starting at bottom). Carbons in the ring equivalent to “B” of isoflavones are numbered 7 – 10 (clockwise, starting at top). In rotenoids, the C-7 of isoflavones becomes C-9 (anti-clockwise numbering from top), whilst C-4′ of isoflavones becomes C-3 (anti-clockwise numbering from bottom). For desoxybenzoins and alpha-methyldesoxybenzoins, the ring numbering system follows that widely used for the chalcone/dihydrochalcone group of flavonoids.

Isoflavone Aglycones

Acicerone (6-hydroxy-7-methoxy-3′,4′-methylenedioxyisoflavone)
Afrormosin (6,4′-dimethoxy-7-hydroxyisoflavone; glycitein-4′-methyl ether)
Alfalone (6-hydroxy-7,4′-dimethoxyisoflavone)
Alpinumisoflavone*
Alpinumisoflavone-4′-methyl ether*
Alpinumisoflavone-5,4′-dimethyl ether*
Auriculatin*
Biochanin A (5,7,-dihydroxy-4′-methoxyisoflavone; genistein-4′-methyl ether)
Biochanin A-7-methyl ether (genistein-7-methyl ether)
Cabreuvin (7,3′,4′-Trimethoxyisoflavone; cladrin-7-methyl ether)
Calopogoniumisoflavone A*
Calopogoniumisoflavone B*
Calycosin (7,3′-dihydroxy-4′-methoxyisoflavone; 3′-hydroxyformononetin)
Cladrin (7-hydroxy-3′,4′-dimethoxyisoflavone)
Conrauinone A*
Conrauinone C (5-methoxy-7-hydroxy-4′-geranyloxyisoflavone)
Corylin*
Cuneatin-7-methyl ether (7,2′-dimethoxy-4′ 5′-methylenedioxyisoflavone)
Daidzein (7,4′-dihydroxyisoflavone)
Daidzein-7,4′-dimethyl ether
2,3-Dehydrokievitone (5,7,2′,4′-tetrahydroxy-8-prenylisoflavone)
Derrone-4′-methyl ether*
Desmethylglycitein (6,7,4′-trihydroxyisoflavone)
6,3′-Dihydroxydaidzein (6,7,3′,4′-tetrahydroxyisoflavone)
8,3′-Dihydroxydaidzein (7,8,3′,4′-tetrahydroxyisoflavone)
5,7-Dihydroxyisoflavone
7,2′-Dihydroxy-4′,5′-dimethoxyisoflavone
7,2′-Dihydroxy-4′,5′-methylenedioxyisoflavone (demethylcuneatin)
5,7-Dimethoxyisoflavone
6,7-Dimethoxy-2′,4′-dihydroxyisoflavone)
7,8-Dimethoxy-4′-hydroxyisoflavone (8-methoxyisoformononetin)
7,2′-Dimethoxy-4′-hydroxyisoflavone (2′-methoxyisoformononetin)
6,8-Diprenylgenistein (5,7,4′-trihydroxy-6,8-diprenylisoflavone)
6,3′-Diprenylgenistein (5,7,4′-trihydroxy-6,3′-diprenylisoflavone)
Erythrinin A (indicanine C)*
Formononetin (7-hydroxy-4′-methoxyisoflavone; daidzein-4′-methyl ether)
Fujikinetin (6-methoxy-7-hydroxy-3′,4′-methylenedioxyisoflavone)
Genistein (5,7,4′-trihydroxyisoflavone)
Genistein-5,4′-dimethyl ether (5-O-methylbiochanin A)
Genistein-5,7,4′- trimethyl ether)
Glycitein (6-methoxy-7,4′-dihydroxyisoflavone)
Glycitein-7-methyl ether
Glycitein-7,4′-dimethyl ether
2′-Hydroxybiochanin A (5,7,2′-trihydroxy-4′-methoxyisoflavone)
5′-Hydroxycalopogoniumisoflavone B
8-Hydroxydaidzein (7,8,4′-trihydroxyisoflavone)
8-Hydroxydaidzein-7,8,4′-trimethyl ether)
2′-Hydroxydaidzein (7,2′,4′-trihydroxyisoflavone)
3′-Hydroxydaidzein (7,3′,4′-trihydroxyisoflavone)
7-Hydroxy-2′,4′-dimethoxyisoflavone (2′-methoxyformononetin)
2′-Hydroxyformononetin (7,2′-dihydroxy-4′-methoxyisoflavone)
6-Hydroxygenistein (5,6,7,4′-tetrahydroxyisoflavone)
8-Hydroxygenistein (5,7,8,4′-tetrahydroxyisoflavone)
2′-Hydroxygenistein (5,7,2′,4′-tetrahydroxyisoflavone)
2′-Hydroxylupalbigenin (6,3′-diprenyl-2′-hydroxygenistein)
3′-Hydroxy-8-O-methylretusin (7,3′-dihydroxy-8,4′-dimethoxyisoflavone)
3′-Hydroxy-5′-prenylbiochanin A (5,7,3′-trihydroxy-4′-methoxy-5′-prenylisoflavone)
5-Hydroxypseudobaptigenin (5,7-dihydroxy-3′,4′-methylenedioxyisoflavone)
5-Hydroxy-7,8,4′-trimethoxyisoflavone
7-Hydroxy-2′,3′,4′-trimethoxyisoflavone
7-Hydroxy-2′,4′,5′-trimethoxyisoflavone
Ichthynone (6-methoxyjamaicin)*
Ipriflavone (7-isopropyloxyisoflavone)
Iriskashmirianin (5,3′-dimethoxy-4′-hydroxy-6,7-methylenedioxyisoflavone)
Isodaidzein (7,3′-dihydroxyisoflavone)
Isoformononetin (7-methoxy-4′-hydroxyisoflavone; daidzein-7-methyl ether)
Isoglabrone*
Iso-osajin*
Iso-osajin-4′-methyl ether*
Isopomiferin*
Isopomiferin-3′,4′-dimethyl ether*
Jamaicin*
Kakkatin (6,4′-dihydroxy-7-methoxyisoflavone)
Kwakhurin (7,2′,4′-trihydroxy-5′-methoxy-6′-prenylisoflavone)
Licoisoflavone A (5,7,2′,4′-tetrahydroxy-3′-prenylisoflavone)
Luteone (5,7,2′,4′-tetrahydroxy-6-prenylisoflavone)
Lupalbigenin (6,3′-diprenylgenistein)
Lupinisoflavone A*
Lupinisoflavone D*
Lupiwighteone (5,7,4′-trihydroxy-8-prenylisoflavone; 8-prenylgenistein)
2′-Methoxybiochanin A (5,7-dihydroxy-2′,4′-dimethoxyisoflavone)
5′-Methoxycalopogoniumisoflavone B
2′-Methoxydaidzein (7,4′-dihydroxy-2′-methoxyisoflavone)
3′-Methoxydaidzein (7,4′-dihydroxy-3′-methoxyisoflavone)
5-Methoxydurmillone*
7-Methoxyisoflavone
4′-Methoxyisoflavone
7-Methoxy-5-hydroxyisoflavone
5-O-Methylbiochanin A (5,4′-dimethoxy-7-hydroxyisoflavone)
7,8-Methylenedioxy-4′-methoxyisoflavone
8-O-Methylretusin (7-hydroxy-8,4′-dimethoxyisoflavone; 8-methoxyformononetin)
Milldurone (6,7,2′-trimethoxy-4′,5′-methylenedioxyisoflavone)
Neobavaisoflavone (7-hydroxy-4′-prenyloxyisoflavone)
Orobol (5,7,3′,4′-tetrahydroxyisoflavone)
Orobol-7-methyl ether (santal)
Orobol-3′-methyl ether
Orobol-4′-methyl ether (pratensein)
Orobol-7,3′-dimethyl ether
Orobol-7,4′-dimethylether
Orobol-3′,4′-dimethyl ether
Orobol-7,3′,4′-trimethyl ether
Orobol-5,7,3′,4′-tetramethyl ether
Osajin*
Osajin-4′-methyl ether*
6,7,2′,3′,4′-Pentamethoxyisoflavone
Piscerythrone (5,7,2′,4′-tetrahydroxy-5′-methoxy-3′-prenylisoflavone)
Piscidone (5,7,3′,4′-tetrahydroxy-5′-methoxy-2′-prenylisoflavone)
Podospicatin (5,7,2′-trihydroxy-6,5′-dimethoxyisoflavone)
Pomiferin*
Pomiferin-3′,4′-dimethyl ether*
Pratensein (5,7,3′-trihydroxy-4′-methoxyisoflavone)
6′-Prenylpiscidone (5,7,3′,4′-tetrahydroxy-5′-methoxy-2′,6′-diprenylisoflavone)
Prunetin (5,4′-dihydroxy-7-methoxyisoflavone; genistein-7-methyl ether)
Pseudobaptigenin (7-hydroxy-3′,4′-methylenedioxyisoflavone),
Pseudobaptigenin-7-methyl ether
3′-Prenylbiochanin A (5,7-dihydroxy-4′-methoxy-3′-prenylisoflavone)
6-Prenyl-3′-methoxydaidzein (7,4′-dihydroxy-3′-methoxy-6-prenylisoflavone)
Retusin (7,8-dihydroxy-4′-methoxyisoflavone)
Retusin-7,8-dimethyl ether
Robustigenin (5-hydroxy-7,2′,4’5′-tetramethoxyisoflavone)
Santal (7-methoxy-5,3′,4′-trihydroxyisoflavone; orobol-7-methyl ether)
5,7,8,4′-Tetramethoxyisoflavone
Tectorigenin (5,7,4′-trihydroxy-6-methoxyisoflavone)
Teralin (7,4′-dihydroxy-2′-methoxyisoflavone; 2′-methoxydaidzein)
Texasin (6,7-dihydroxy-4′-methoxyisoflavone)
7,2′,4′-Trihydroxyisoflavone (2′-hydroxydaidzein)
7,2′,4′-Trimethoxyisoflavone
5,6,7-Trimethoxy-3′,4′-methylenedioxyisoflavone
Warangalone (scandenone)*
Wighteone (5,7,4′-trihydroxy-6-prenylisoflavone; 6-prenylgenistein)

Acetoxy and Deuterated Isoflavones and Other Compounds

Deutero-2′-hydroxyformononetin (D at C-2 on non-aromatic C-ring)
Formononetin-7-acetate
Isopterofuran acetate (acetate derivative of a furanoid phytoalexin)
Deutero-maackiain (D at C-6a on non-aromatic B-ring)
Deutero-maackiain (2 x D at C-6 and D at C-11a on non-aromatic ring B)
Maackian-3-acetate
Deutero-medicarpin (2 x D at C-6 on non-aromatic B-ring)
Medicarpin-3-acetate
Deutero-medicarpin-3-acetate (2 x D at C-6 on non-aromatic B-ring)
Vignafuran acetate (acetate derivative of furanoid phytoalexin)

Benzylated Isoflavones

Unusual benzylated isoflavones for analytical use or bio-test purposes.

7-Benzyloxy-2′,4′-dimethoxyisoflavone
7-Benzyloxy-3′,4′-dimethoxyisoflavone
7-Benzyloxy-2′,3′,4′-trimethoxyisoflavone
7-Benzyloxy-2′,4′,5′-trimethoxyisoflavone
7-Benzyloxy-4′-methoxyisoflavone (formononetin-7-benzyl ether)
2′-Benzyloxy-7,4′-dimethoxyisoflavone
7,8-Dibenzyloxy-4′-methoxyisoflavone
7,2′-Dibenzyloxy-8,4′-dimethoxyisoflavone
7,2′-Dibenzyloxy-3′,4′-dimethoxyisoflavone
7,2′-Dibenzyloxy-4′,5′-methylenedioxyisoflavone
7,2′-Dibenzyloxy-4′-methoxyisoflavone
7,3′-Dibenzyloxy-4′-methoxyisoflavone (calycosin-7,3′-dibenzyl ether)
7,8,2′,4′-Tetrabenzyloxyisoflavone
7,2′,4′-Tribenzyloxyisoflavone
7,2′,4′-Tribenzyloxy-8-methoxyisoflavone

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Isoflavone Glycosides
6”-O-Acetyldaidzin
6”-O-Acetylgenistin
6”-O-Acetylglycitin
Cladrin-7-O-glucoside
Daidzin (daidzein-7-O-glucoside)
Daidzein-7,4′-di-O-glucoside
Formononetin-7-O-gentiobioside
7-Hydroxyisoflavone-7-O-glucoside
Genistin (genistein-7-O-glucoside)
Genistein-7,4′-di-O-glucoside
Glycitin (glycitein-7-O-glucoside)
Isogenistin (genistein-4′-O-glucoside)
6”-O-Malonyldaidzin
6”-O-Malonylgenistin
6”-O-Malonylglycitin
Ononin (formononetin-7-O-glucoside)
Orobol-7-glucoside (oroboside)
Pratensein-7-glucoside (pratensin)
4′-O-prenyloxy-4′-demethylcalopogoniumisoflavone A*
Prunitrin (prunetin-7-O-glucoside)
Pseudobaptisin (pseudobaptigenin-7-rhamnoglucoside)
Puerarin (daidzein-8-C-glucoside)
Rothindin (pseudobaptigenin-7-O-glucoside)
Sissotrin (biochanin A-7-O-glucoside)
Sphaerobioside (genistein-7-rhamnoglucoside)
Tectoridin (tectorigenin-7-O-glucoside)
Texasin-7-O-glucoside
Wistin (afrormosin-7-O-glucoside)

Isoflavanones (Dihydroisoflavones)
Cajanol (5,4′-dihydroxy-7,2′-dimethoxyisoflavanone)
Dalbergioidin (5,7,2′,4′-tetrahydroxyisoflavanone)
Dihydrocalopogoniumisoflavone A*
Dihydrodaidzein (7,4′-dihydroxyisoflavanone)
Dihydrodaidzein dimethyl ether
Dihydroformononetin (7-hydroxy-4′-methoxyisoflavanone)
Dihydrobiochanin A (5,7-dihydroxy-4′-methoxyisoflavanone)
Dihydrogenistein (5,7,4′-trihydroxyisoflavanone)
Dihydroisoformononetin (7-methoxy-4′-hydroxyisoflavanone)
Dihydrojamaicin*
Dihydroprunetin (5,4′dihydroxy-7-methoxyisoflavanone)
Ferreirin (5,7,2′-trihydroxy-4′-methoxyisoflavanone)
Homoferreirin (5,7-dihydroxy-2′,4′-dimethoxyisoflavanone)
Kievitone (5,7,2′,4′-tetrahydroxy-8-prenylisoflavanone)

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Isoflavans
Arvensan (7,2′-dimethoxy-4′-hydroxyisoflavan)
cis/trans-7,4′-Dihydroxyisoflavan-4-ol (tetrahydrodaidzein)
(-)-S-Equol (7,4′-dihydroxyisoflavan (optically active)
Equol (racaemic)
Equol-7-methyl ether
Equol-4′-methyl ether
Equol-7,4′-dimethyl ether
Isoequol (7,3′-dihydroxyisoflavan)
Isomucronulatol (7,2′-dihydroxy-3′,4′-dimethoxyisoflavan)
Isosativan (7,4′-dimethoxy-2′-hydroxyisoflavan)
Lotisoflavan (5,7-dimethoxy-2′,4′-dihydroxyisoflavan)
Mucronulatol (7,3′-dihydroxy-2′,4′-dimethoxyisoflavan)
Phaseollinisoflavan*
Sativan (7-hydroxy-2′,4′-dimethoxyisoflavan)
Vestitol (7,2′-dihydroxy-4′-methoxyisoflavan)

Pterocarpans
Calopocarpin (2-prenyl-3,9-dihydroxypterocarpan)
Demethylmedicarpin (3,9-dihydroxypterocarpan)
2,8-Dihydroxy-3,9-dimethoxypterocarpan
2,8-Dihydroxy-3,9,10-trimethoxypterocarpan
2,10-Dihydroxy-3,4,8,9-tetramethoxypterocarpan
Edunol (3-hydroxy-8,9-methylenedioxy-2-prenylpterocarpan)
Erythrabyssin II (3,9-dihydroxy-2,10-diprenylpterocarpan; 2-prenylphaseollidin)
Erybraedin (3,9-dihydroxy-4,10-diprenylpterocarpan; 4-prenylphaseollidin)
Ficifolinol (3,9-dihydroxy-2,8-diprenylpterocarpan)
Folinin*
Glyceollin I
Homopterocarpin (3,9-dimethoxypterocarpan)
6a-Hydroxymaackiain (3,6a-dihydroxy-8,9-methylenedioxypterocarpan)
8-Hydroxy-3,4,9,10-tetramethoxypterocarpan
Isomedicarpin (3-methoxy-9-hydroxypterocarpan)
Isoneorautenol*
Maackiain (3-hydroxy-8,9-methylenedioxypterocarpan)
Medicarpin (3-hydroxy-9-methoxypterocarpan)
Neodulin (edulin)*
Neorautane*
Neorautenane*
Neorautenol*
Phaseollidin (3,9-dihydroxy-10-prenylpterocarpan)
Phaseollin*
Pterocarpin (3-methoxy-8,9-methylenedioxypterocarpan)
Trifolirhizin (maackiain-3-O-glucoside)
Tuberosin*

Pterocarpenes (Anhydro/Dehydropterocarpans)

Anhydromedicarpin (3-hydroxy-9-methoxypterocarp-6a-ene)
Anhydropisatin (3-methoxy-8,9-methylenedioxypterocarp-6a-ene)

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Coumestans
Coumestrol (3,9-dihydroxycoumestan)
Coumestrol-9-methyl ether (9-O-methylcoumestrol)
Coumestrol-3,9-dimethyl ether
9,10-Dihydroxycoumestan
9,10-Dimethoxycoumestan
Medicagol (3-hydroxy-8,9-methylenedioxycoumestan)
Trifoliol (3,7-dihydroxy-9-methoxycoumestan)

Rotenoids
Amorphigenin*
Amorphin*
Deguelin*
Dehydromillettone*
6-Hydroxysumatrol (villosin)*
10-Methoxydeguelin*
Millettone*
Millettosin**
Rotenone*
12a-Hydroxyrotenone*
Rotenonone*
Sumatrol*
Tephrosin*
Toxicarol*

Desoxybenzoins
Angolensin (2,4-dihydroxy-4′-methoxy-alpha-methyl desoxybenzoin)
Desmethylangolensin (2,4,4′-trihydroxy-alpha-methyldesoxybenzoin)
2,4-Dihydroxy-4′-methoxydesoxybenzoin (formononetin desoxybenzoin)
2,4-Dihydroxy-3′,4′-dimethoxydesoxybenzoin (cladrin desoxybenzoin)
2,4-dihydroxy-3′,4′-methylenedioxydesoxybenzoin (pseudobaptigenin desoxybenzoin)
6-Hydroxydesmethylangolensin (2,4,6,4′-tetrahydroxy-alpha-methyldesoxybenzoin)
2,4,6,4′-Tetrahydroxydesoxybenzoin (genistein desoxybenzoin)
2,4,4′-Trihydroxydesoxybenzoin (daidzein desoxybenzoin)
2,3,4,-Trihydroxy-4′-methoxydesoxybenzoin (retusin deoxybenzoin)
2,4,6-Trihydroxy-4′-methoxydesoxybenzoin (biochanin A desoxybenzoin)
2,4,6-Trihydroxy-3′,4′-methylenedioxydesoxybenzoin (5-hydroxypseudobaptigenin
desoxybenzoin)

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Miscellaneous Compounds
Bryacarpene-1 (3,8,9-trimethoxy-4,10-dihydroxypterocarpene)
Bryacarpene-2 (3,8,9-trimethoxy-10-hydroxypterocarpene)
7,4′-Dihydroxyisoflav-3-ene (dehydroequol)
Lupinalbin A (5,7,4′-trihydroxycoumaronochromone)
Lupinalbin B (5,7,4′-trihydroxy-6-prenylcoumaronochrome)
Robustic acid* (arylcoumarin)
Miroestrol* (unique structure, powerful phytoestrogen)

Phytoalexins and Other Antimicrobials
The isoflavonoids display a wide range of biological properties. Some, for example the pterocarpan maackiain, have anti-tumour properties, or function as anti-oxidants (e.g. the isoflavones desmethylglycitein and genistein). A few, like coumestrol and miroestrol are powerful phytoestrogens in their own right. Others, notably daidzein, formononetin, genistein and biochanin A are pro-estrogens capable of being converted to more active substances (such as equol) by intestinal microflora. Some of the rotenoids, especially rotenone and tephrosin, are potent insecticides and fish poisons. Research has also shown that certain isoflavonoids are strongly anti-microbial (especially antifungal), acting as defensive compounds, either pre-formed (e.g. the isoflavones luteone and wighteone) or post-infectional (various pterocarpans/isoflavans), in the tissues of many leguminous plants. These latter compounds are termed phytoalexins because in certain plants their formation only occurs as a defense response, a rough analogy being the production of antibodies by humans and other animals. Plantech (U.K.) is able to offer the widest available range of plant phytoalexins for analytical use and small scale biological testing. Our main products are listed below. Please enquire for compounds that are not listed.

Arvensan (isoflavan)
Cajanol (isoflavanone)
Calopocarpin (pterocarpan)
Demethylmedicarpin (pterocarpan)
Glyceollin I (pterocarpan)
Isomedicarpin (pterocarpan)
Isomucronulatol (isoflavan)
Lotisoflavan (isoflavan)
Luteone (isoflavone, pre-formed)
Maackiain (pterocarpan)
Medicarpin (perocarpan)
Phaseollidin (pterocarpan
Phaseollin (pterocarpan)
Phaseollinisoflavan (isoflavan)
Pisatin (pterocarpan)
Sativan (isoflavan)
Tuberosin (pterocarpan)
Vestitol (isoflavan)
Wighteone (isoflavone, pre-formed)
Other phytoalexins (please enquire for specific needs)

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Lignans

In recent years, the lignans have come to prominence because of their ability to act in humans as powerful anti-oxidants scavenging free radicals which, amongst other things, are known to damage internal tissues (a factor involved in the development of some diseases) and cause skin to age prematurely. Like isoflavones such as daidzein and genistein, some plant lignans (or their metabolites) are also known to bind competitively to estrogen(oestrogen)-receptor sites in breast and prostrate tissues thus blocking the potential cancer-promoting/inducing effects of estrogenic compounds produced naturally in the human body. The lignan podophyllotoxin from the rhizomes of various American species of Podophyllum (e.g. P. peltatum) is a pharmacological precursor of the anti-cancer drug etoposide. Flax seeds (Linum sp.) are probably the most important source of lignan phytoestrogens in the human diet, the main compounds being secoisolariciresinol and secoisolariciresinol diglucoside. High quantities of the related phytoestrogen, matairesinol, are also found in flax. Numerous “alternative medicines/health products” containing flax lignans are marketed in the Western world. In the body, secoisolariciresinol diglucoside is hydrolysed to give the aglycone secoisolaricresinol, and both this and matairesinol are then metabolised by intestinal(enteric) bacteria to give two other estrogenic compounds, enterodiol (from secoisolariciresinol) and enterolactone (from matairesinol). Apart from flax seeds, lignans also occur in sesame seed (pinoresinol and sesamin), and in rye bran (syringaresinol, pinoresinol and laricresinol) and wheat bran (hydroxymatairesinol). The curious names of some of these compounds indicate both their structure and original source. Matairesinol, for example, simply means a phenolic compound (hence the “ol” part of the name”) derived from resin of the matai tree (a New Zealand species). Pinoresinol comes originally from pine resin, syringaresinol from the bark of lilac (Syringa sp.) and so on.

(-)-Alpha-Conidendrin
Arctigenin
Arctigenin gentiobioside
Arctiin
Asarinin
4′-Demethylpodophyllotoxin
4′-Demethylpodorhizol
Dibenzylmatairesinol
Enterodiol
Enterolactone
Epi-podophyllotoxin
Fargesin
(-)-Hydroxymatairesinol
Hypophyllanthin
Isodesoxypodophyllotoxin
(+)-Isolariciresinol
(+)-Lariciresinol
(-)-Maculatin (matairesinol dimethyl ether)
(-)-Matairesinol
(+/-)-Matairesinol
Matairesinoside
(-)-Nortrachelogenin
Phillyrin
Phyllanthin
Picropodophyllin
Picrodesoxypodophyllin
Pinoresinol
Pinoresinol diglucoside
Podophyllotoxin
Podophyllotoxone
(-)-Seco-isolariciresinol
(+/-)-Secoisolariciresinol
Sesamin
Sesamolin
Syringaresinol
Syringarsinol diglucoside
Syringin
Tracheloside

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LIMONOIDS (Citrus bitter principles)
Anthothecol
Deacetylnomilin
Deoxylimonin
Gedunin
Limonin
Limonin diosphenol
Nomilin
Obacunone
Rutaevin

SOYBEAN ISOFLAVONES
Daidzein (7,4′-Dihydroxyisoflavone)
Genistein (5,7,4′-Trihydroxyisoflavone)
Glycitein (7,4′-Dihydroxy-6-methoxyisoflavone)
Daidzin (Daidzein-7-O-glucoside)
Genistin (Genistein-7-O-glucoside)
Glycitin (Glycitein-7-O-glucoside)
6”-O-Acetyldaidzin
6”-O-Acetylgenistin
6”-O-Acetylglycitin
6′-O- Malonyldaidzin
6”-O-Malonylgenistin
6”-O-Malonylglycitin

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METABOLITES OF THE SOY ISOFLAVONES
Daidzein Metabolites
Dehydroequol (7,4′-Dihydroxyisoflav-3-ene)
Desmethylangolensin (O-Desmethylangolensin)
Dihydrodaidzein
6,3′-Dihydroxydaidzein
8,3′-Dihydroxydaidzein
rac-Equol
(-)-S-Equol (optically active)
6-Hydroxydaidzein
8-Hydroxydaidzein
3′-Hydroxydaidzein
Tetrahydrodaidzein (cis/trans-7,4′-Dihydroxyisoflavan-4-ol)
2,4,4′-Trihydroxydesoxybenzoin

Genistein Metabolites
p-Ethylphenol
Dihydrogenistein
6-Hydroxydesmethylangolensin
6-Hydroxygenistein
8-Hydroxygenistein
3′-Hydroxygenistein (orobol)
2,4,6,4′-Tetrahydroxydesoxybenzoin

Glycitein Metabolites
Demethylglycitein (Desmethylglycitein)

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Alkaloids
Allocryptopine
Californidine
Castanospermine
Coptisine
(+)-Corypalmine
Couropitine A
Cyclanoline
Cytisine
Flindersine
Galanthamine
epi-Galanthamine
Glucoerysodine (ca 90-92%)
Isocorydine
Isothebaine
Kokusaginine
Maculine
Magnoflorine
Menisperine
Milettonine
Protopine
Rhoeadine
Severine palmitate
Sinapine sulphate
Skimmianine
Solamargine
Solasodine
Solasonine
Trigonelline

Solanum Glyco-Alkaloids
Demissidine,
Solamargine
Solanine
Solasodine
Solasonine
Tomatidine

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Glucosinolates

Glucosinolates (mustard-oil glucosides) are water-soluble phytochemicals containing a central carbon atom which is tri-linked, a) to a glucose unit via a sulphur atom, b) to a sulphate group, and c) to a side chain of varying structure. It is the chemical nature of this side chain which determines the properties of each glucosinolate. Most glucosinolates are found in species belonging to the family Cruciferae which includes Brussels sprouts, cabbage, cauliflower, cress, horseradish, mustard, radish and many more besides. Although glucosinolates themselves are relatively inert, when plant tissues are crushed or prepared for cooking, release of the enzyme myrosinase removes the glucose unit to give an isothiocyanate (mustard oil) with an unpleasant sharp or bitter taste. Intestinal microflora can also convert glucosinolates to isothiocyanates. Although plant breeding has resulted in some food varieties which are low in glucosinolates and therefore more palatable, the loss of these compounds is not entirely desirable as some glucosinolates (e.g. sinigrin) are reported to have tumour-inhibiting activity as well as possibly destroying pre-cancerous cells in the colon. In addition, whilst egg-laying by some butterfly species such as the cabbage white can actually be stimulated by glucosinolates in their host plant, the presence of these compounds (and especially their bitter hydrolysis products) in the Cruciferae may act as a general deterrent to unadapted feeding insects and mammals. Sinalbin (glucosinalbin) from seeds of white mustard and sinigrin (from black mustard) are probably the best known examples of glucosinolates.

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Flavonoids

The flavonoids are the most widespread and hence most commonly encountered group of natural products in the Plant Kingdom. Numerous types of flavonoid are known to exist including flavones and flavonols (3-hydroxyflavones), flavanones (2,3-dihydroflavones) and 3-hydroxyflavanones (flavanonols), flavans (catechins), chalcones and dihydrochalcones, aurones, and anthocyanidins and anthocyanins. The latter are responsible for many of the red, blue and purple colours often found in flowers and fruits (but not beetroot or tomato). Aurones and chalcones are intensely yellow or orange. Dihydrochalcones are white powders. When in powder form other flavonoids vary in colour from white or cream to pale yellow. Along with carotenoids (an entirely different class of natural product), the yellow flavonoids also contribute to the colours of flowers and fruits. Flavones and – but less often – other flavonoids, can exist either as aglycones (no sugar residue) or as glycosides in which one or more sugar molecules (glucose, galactose, rhamnose, xylose, arabinose etc.) is attached to one of the hydroxyl groups (most frequently at carbon 3, 7 or 4′, more rarely elsewhere). These compounds are referred to as flavonoid-O-glycosides. When glucuronic acid, rather than a sugar is attached, the compound is called a flavonoid-O-glucuronide. Some plants, and other organisms such as liverworts and mosses, also produce flavonoids in which a sugar unit is attached via a carbon bond directly to the molecule rather than through an O-linkage. These compounds, which are comparatively rare, are called flavonoid-C-glycosides. Occasionally two identical (or dissimilar) flavonoid molecules may be linked, giving a flavonoid subclass known as the biflavonoids. Amentoflavone, for example, is a biflavonoid in which two apigenin (5,7,4′-trihydroxyflavone) units are linked together. Compounds of this type have been found in Citrus species and in the flora of Australia and New Zealand. Although once considered to be nothing more than by-products of plant metabolism, it has been realised in recent years that flavonoids have numerous biological properties, perhaps the most frequently cited being their potential as anti-oxidants. Unlike compounds from some other groups of natural products (e.g. alkaloids), the flavonoids are harmless and, as part of a normal diet, are ingested in quantity by both humans and animals. The ring numbering and nomenclature system for flavonoids possessing a central heterocyclic (oxygen-containing) C-ring is identical to that used for isoflavones (ring A is numbered clockwise, 5, 6, 7, 8 starting at the bottom; ring B is numbered anticlockwise 2′, 3′, 4′, 5′ ,6′ starting from the point of attachment to the C-ring). In chalcones/dihydrochalcones, which have no C-ring, the numbering system is different. Here the A-ring is numbered anticlockwise 2′, 3′, 4′, 5′, 6′ (C-6′ and C-4′ being respectively equivalent to C-5 and C-7 of flavones) whilst the B-ring is numbered anticlockwise 2,3,4,5,6 starting at the point of attachment to the rest of the molecule.

Flavone and Flavonol (3-Hydroxyflavone) Aglycones

Acacetin (Apigenin-4′-methyl ether; 5,7-Dihydroxy-4′-methoxyflavone)
Alnustin (5-Hydroxy-3,6,7-trimethoxyflavone)
Apigenin (5,7,4′-Trihydroxyflavone)
Ayanin (Quercetin-3,7,4′-trimethyl ether; 5,3′-Dihydroxy-3,7,4′ trimethoxyflavone)
Azaleatin (Quercetin-5-methyl ether; 3,7,3′,4′-Tetrahydroxy-5 methoxyflavone)
Baicalein (5,6,7-Trihydroxyflavone)
Caryatin (Quercetin-3,5-dimethyl ether; 7,3′,4′-Trihydroxy-3,5 dimethoxyflavone)
Casticin (Quercetagetin-3,6,7,4′-tetramethyl ether; 5,3′-Dihydroxy-3,6,7,4′ tetramethoxyflavone)
Cirsimaritin (Scutellarein-6,7-dimethyl ether; 5,4′-Dihydroxy-6,7-dimethoxyflavone)
Chrysoeriol (Luteolin-3′-methyl ether; 5,7,4′-Trihydroxy-3′-methoxyflavone)
Cochliophilin A
Datiscetin (3,5,7,2′-Tetrahydroxyflavone)
Diosmetin (Luteolin-4′-methyl ether; 5,7,3′-Trihydroxy-4′-methoxyflavone)
5-Deoxykaempferol (Resokaempferol; 3,7,4′-Trihydroxyflavone)
3,7-Dihydroxy-3′,4′,5′-trimethoxyflavone (Robinetin-3′,4′,5′-trimethyl ether)
5,7-Dihydroxy-3′,4′,5′-Trimethoxyflavone (Tricetin-3′,4′,5′-trimethylether)
6,7-Dihydroxyflavone
7,8-Dihydroxyflavone
7,4′-Dihydroxyflavone (5-Deoxyapigenin)
3′,4′-Dihydroxyflavone
Dillenetin (Quercetin-3′,4′-Dimethyl ether)
5,7-Dihydroxyflavone
5,3′-Dihydroxyflavone
7,4′-Dihydroxyflavone
5,7-Dimethoxyflavone (Chrysin-5,7-dimethyl ether; Chrysin dimethyl ether)
7,8-Dimethoxyflavone
3′,4′-Dimethoxyflavone
Eucalyptin (5-Hydroxy-7,4′-dimethoxy-6,8-dimethylflavone)
Eupatorin (6-Hydroxyluteolin-6,7′,4′-trimethyl ether; 5,3′-Dihydroxy-6,7,4′-trimethoxyflavone)
Fisetin 3,7,3′,4′-Tetrahydroxyflavone)
Galangin (3,5,7-Trihydroxyflavone)
Gardenin B (5-Hydroxy-6,7,8,4′-tetrahydroxyflavone)
Genkwanin (Apigenin-7-methyl ether; 5,4′-Dihydroxy-7-methoxyflavone)
Gossypetin (3,5,7,8,3′,4′-Hexahydroxyflavone)
3,5,6,7,8,3′,4′-Heptamethoxyflavone
Herbacetin (3,5,7,8,4′-Pentahydroxyflavone)
Hispidulin (Scutellarein-6-methyl ether; 5,7,4′-Trihydroxy-6-methoxyflavone)
3-Hydroxy-5,6,2′-trimethoxyflavone
5-Hydroxy-7,4′-dimethoxyflavone (Apigenin-7,4′-dimethyl ether; Acacetin-7-methyl ether)
3′-Hydroxy-5,6,7,4′-tetramethoxyflavone (eupatorin-5-methyl ether)
5-Hydroxy-3,6,2′-trimethoxyflavone
5-Hydroxy-7,8,2′-trimethoxyflavone
5-Hydroxy-3,7,3′,4′-tetramethoxyflavone (Quercetin-3,7,3′,4′-tetramethyl ether)
6-Hydroxy-5,7,4′-trimethoxyflavone (Scutellarein-5,7,4′-trimethyl ether)
7-Hydroxyflavone (ca 80 – 85% and greater)
3′-Hydroxy-3,5,7,8,4′-pentamethoxyflavone (Gossypetin-3,5,7,8,4′-penta methyl ether)
Isoetin (5,7,2′,4′,5′-Pentahydroxyflavone)
Isosakuranetin
Isosinensetin (Hypolaetin-5,7,8,3′,4′-pentamethyl ether; 5,7,8,3′,4′ Pentamethoxyflavone)
Izalpinin (Galangin-7-methyl ether; 3,5-Dihydroxy-7-methoxyflavone)
Kaempferol (3,5,7,4′-Tetrahydroxyflavone)
Kumatakenin (Kaempferol-3,7-Dimethyl ether; 5,4′-Dihydroxy-3,7 dimethoxyflavone)
Luteolin (5,7,3′,4′-Tetrahydroxyflavone)
Melanoxetin (3,7,8,3′,4′-Pentahydroxyflavone)
6-Methoxykaempferol (6-Hydroxykaempferol-6-methyl ether; 3,5,3′,4′ Tetrahydroxy-6-methoxyflavone)
Morin (3,5,7,2′,4′-Pentahydroxyflavone)
Mosloflavone (5-Hydroxy-6,7-dimethoxyflavone)
Myricetin (3,5,7,3′,4′,5′-Hexahydroxyflavone)
Nevadensin (5,7-Dihydroxy-6,8,4′-trimethoxyflavone)
Negletein (Baicalein-7-methyl ether; 5,6-Dihydroxy-7-methoxyflavone)
Nobiletin (5,6,7,8,3′,4′-Hexamethoxyflavone)
Ombuin (Quercetin-7,4′-dimethyl ether; 3,5,3′-Trihydroxy-7,4′ dimethoxyflavone)
Patuletin (Quercetagetin-6-methyl ether; 3,5,7,3′,4′-Pentahydroxy-6 methoxyflavone)
Penduletin (6-Hydroxykaempferol-3,6,7-trimethyl ether; 5,4′-Dihydroxy 3,6,7-trimethoxyflavone
5,7,3′,4′,5′-Pentamethoxyflavone
Quercetin (3,5,7,3′,4′-Pentahydroxyflavone)
Quercetagetin (3,5,6,7,3′,4′-Pentahydroxyflavone)
Rhamnazin (Quercetin-7,3′-dimethyl ether; 3,5,4′-Trihydroxy-7,3′ dimethoxyflavone)
Robinetin (3,7,3′,4′,5′-Pentahydroxyflavone)
Salvigenin (Scutellarein-6,7,4′-trimethyl ether; 5-Hydroxy-6,7,4′ trimethoxyflavone)
Scutellarein (5,6,7,4′-Tetrahydroxyflavone)
Sideritiflavone (5,3′,4′-Trihydroxy-6,7,8,-trimethoxyflavone)
Sorbifolin (Scutellarein-7-methyl ether; 5,6,4′-Trihydroxy-7 methoxyflavone)
Tamarixetin (Quercetin-4′-methyl ether; 3,5,7,3′-Tetrahydroxy-4′ methoxyflavone)
Tangeretin (5,6,7,8,4′-Pentahydroxyflavone)
Tectochrysin (Chrysin-7-methyl ether; 5-Hydroxy-7-methoxyflavone)
3,5,6,2′-Tetrahydroxyflavone
5,6,7,2′-Tetrahydroxyflavone
5,7,3′,4′-Tetrahydroxy-3-methoxyflavone (Quercetin-3-methyl ether)
5,6,7,4′-Tetramethoxyflavone (Scutellarein-5,6,7,4′-tetramethyl ether)
5,6,7,2′-Tetramethoxyflavone
5,7,8,2′-Tetramethoxyflavone
5,7,8,4′-Tetramethoxyflavone (Isoscutellarein-5,7,8,4′-tetramethyl ether)
Thevetiaflavone (Apigenin-5-methyl ether; 7,4′-Dihydroxy-5-methoxyflavone)
Tricetin (5,7,3′,4′,5′-Pentahydroxyflavone)
Tricin (Tricetin-3′,5′-dimethyl ether; 5,7,4′-Trihydroxy-3′,5′-dimethyl ether)
5,7,3′-Trihydroxyflavone
5,3′,4′-Trihydroxy-3,7-dimethoxyflavone (Quercetin-3,7-dimethyl ether)
5,6,7-Trimethoxyflavone (Baicalein-5,6,7-trimethyl ether)
5,6,2′-Trimethoxyflavone
5,7,4′-Trimethoxyflavone (Apigenin-5,7,4′-trimethyl ether)
Xanthomicrol (5,4′-Dihydroxy-6,7,8-trimethoxyflavone)
Zapotin (5,6,2′,6′-Tetramethoxyflavone)

Flavone-O-Glycosides

Aequinetin (Chrysin-7-glucoside)
Afzelin (Kaempferol-3-rhamnoside)
Avicularin (Quercetin-3-arabinofuranoside)
Baicalein-7-glucoside
Cosmosiin (Apigenin-7-glucoside)
Datiscin (Datiscetin-3-rutinoside)
Diosmin (Diosmetin-7-rutinoside)
Fortunellin (Acacetin-7-neohesperidoside)
Galuteolin (Luteolin-5-glucoside)
Genkwanin-4′-glucoside
Gossypetin-7-glucoside
Guaijaverin (Quercetin-3-arabinopyranoside)
Herbacetin-8-glucoside
Herbacetin-8-glucoside-3-sophoroside
8-Hydroxyluteolin-7-sambubioside
Isorhamnetin-5-O-methyl ether-3-glucoside
Isorhoifolin (Apigenin-7-rutinoside)
Juglanin (Kaempferol-3-arabinofuranoside)
Kaempferol-3-glucoside
Kaempferol-3-glucoside(6”-O-acetate)-7-glucoside
Kaempferol-3-glucoside-7-rhamnoside
Kaempferol-3-glucoside(6”-O-acetate)-7-rhamnoside
Kaempferol-3-rhamnoglucoside-7-glucoside
Kaempferol-3-rutinoside
Kaempferol-3-rutinoside-7-glucoside
Kaempferol-3-rutinoside-7-rhamnoside
Kaempferol-3-sophoroside-7-glucoside
Kaempferol-3,7-diglucoside
Kaempferol-3,4′-diglucoside
Kaempferol-3,7-dirhamnoside
Laricitrin-3,5′-diglucoside
Laricitrin-3,7,5′-triglucoside
Luteolin-7-glucoside
Myricetin-3-galactoside
Myricetin-3-rhamnoside
Patulitrin (Patuletin-7-glucoside)
Plantaginin Scutellarein-7-glucoside)
Protogenkwanin-4′-glucoside
Quercetagetin-7-glucoside
Quercetin-3-galactoside
Quercetin-3-glucoside
Quercetin-3-sophoroside
Quercetin-3,4′-diglucoside
Quercetin-7,4′-diglucoside
Quercetin-3-rhamnoside-7-glucoside
Quercetin-7,3′,4′-trimethyl ether-3-rhamnoside
Quercimeritrin (Quercetin-7-glucoside)
Quercitrin (Quercetin-3-rhamnoside)
Reynoutrin (Quercetin-3-xyloside)
Rhamnetin-3-rhamnoside
Rhamnetin-3-rutinoside
Rhoifolin (Apigenin-7-neohesperidoside
Scutellarein-7-rutinoside
Spireoside (Quercetin-4′-glucoside)
Tamarixetin-7-rutinoside
Tilianin (Acacetin-7glucoside)
Tricetin-7-glucoside

Flavone-O-Glucuronides

Apigenin-7-glucuronide
Apigenin-7-diglucuronide
Baicalein-6-glucuronide
Baicalein-7-glucuronide
Chrysoeriol-7-diglucoside
Kaempferol-3-glucuronide
Luteolin-5-glucuronide
Luteolin-7-glucuronide
Gossypetin-8-glucuronide
Quercetin-3-glucuronide
Takakkin-8-glucuronide
Scutellarin (Scutellarein-7-glucuronide)

Flavone-C-Glycosides

Carlinoside
Isoaffinetin
Isoschaftoside
Kaempferol-6-C-glucoside
Lucenin-2
Neoschaftoside
2”-O-Rhamnosylvitexin
Schaftoside
Swertisin
Tricetin-6,8-di-C-glucoside
Vitexin

Biflavones

Agathisflavone-7,7”-dimethyl ether
Amentoflavone (3′,8”-biapigenin)
Amentoflavone-7”,4”’-dimethyl ether
Amentoflavone-7,7”,4′,4”’- tetramethyl ether
Bilobetin (amentoflavone-4′-methyl ether)
3′,8”-Biluteolin
5′,8”-Biluteolin
Campylosaurone (aureusidin linked to eriodictyol)
Cryptomerin A (hinokiflavone-4”’-methyl ether)
Cryptomerin B (hinokiflavone-7”,4”’-dimethyl ether)
Cupressuflavone (8,8”-biapigenin)
Cupressuflavone-7,7”-dimethyl ether
2,3-Dihydroamentoflavone
2,3-Dihydroamentoflavone-7”,4”’-dimethyl ether
2,3-Dihydro-5′,8”-biluteolin
2,3-Dihydrohinokiflavone
5′,3”’-Dihydroxyrobustaflavone
Ginkgetin (amentoflavone-7,4′-dimethyl ether)
Hinokiflavone (4′,6”-biapigenin)
Hinokiflavone pentamethyl ether
Hinokiflavone-7,7”,4”’-trimethyl ether
Isocryptomerin (hinokiflavone-7”-methyl ether)
Isoginketin (amentoflavone-4′,4”’-dimethyl ether)
Podocarpusflavone A (amentoflavone-4”’-methyl ether)
Sciadopitysin (amentoflavone 7,4′,4”’-trimethyl ether)

Aurones

Aureusidin (4,6,3′,4′-tetrahydroxyaurone)
Dihydrosulphuretin (6,3′,4′-trihydroxydihydroaurone)
Hispidol (6,4′-dihydroxyaurone)
Maritimein (maritimetin-6-glucoside)
Maritimetin (6,7,3′,4′-tetrahydroxyaurone)
Rengasin (aureusidin-4-methyl ether; 6,3′,4′-trihydroxy-4-methoxyaurone)
Rengasin-3′-glucoside
Rengasin-4′-glucoside
Sulphuretin (6,3′,4′-trihydroxyaurone)
4,3′,4′-Trihydroxy-6-methoxyaurone (aureusidin-6-methyl ether)

Biflavanones (linked 3,8”)

4”’-O-Demethylkolaflavanone (naringenin linked to taxifolin)
2”,3”-Dihydrofukugetin (2”,3”-dihydromorelloflavanone; naringenin linked to eriodictyol)
Garciniflavanone (manniflavanone; eriodictyol linked to taxifolin)

Flavanones

Abyssinone IV (7,4′-dihydroxy-3′,5′-diprenylflavanone)
Ampelopsin (dihydromyricetin)
Aromadendrin (dihydrokaempferol; 3,7,4′-trihydroxyflavanone)
Aromadendrin-7-methyl ether (3,4′-dihydroxy-7-methoxyflavanone)
Aromadendrin-3-rhamnoside
Astilbin (taxifolin-3-rhamnoside)
Bavachinin (7-methoxy-4′-hydroxy-6-prenylflavanone)
Butin (7,3′,4′-trihydroxyflavanone)
Didymin (isosakuranetin-7-rutinoside; neoponcirin)
Dihydrogenkwanin (5,4′-dihydroxy-7-methoxyflavanone)
Dihydrokaempferol (3,7,4′-trihydroxyflavanone)
Dihydrokaempferol-3-glucoside
Dihydrolonchocarpin
Dihydromyricetin (3,5,7,3′,4′-pentahydroxyflavanone; dihydrocannabiscetin)
Dihydromyricetin-3′-glucoside(ampelopsin-3′-glucoside)
Dihydroquercetin (3,5,7,4′-Tetrahydroxyflavanone)
Dihydrorobinetin (3,7,3′,4′,5′-pentahydroxyflavanone)
Dihydrorobinetin-3′,4′,5′-trimethyl ether (3,7-dihydroxy-3′,4′,5′-trimethoxyflavanone)
Dihydrowogonin (5,7-dihydroxy-8-methoxyflavanone)
3,7-Dihydroxy-5,8-dimethoxyflavanone
3′,4′-Dihydroxyflavanone
5,7-Dimethoxyflavanone (pinocembrin dimethyl ether)
5,7-Di-O-methyl-8-prenylflavanone
3′,5′-Diprenyl-dihydroacacetin (5,7-dihydroxy-4′-methoxy-3′,5′-diprenylflavanone)
Eriodictyol (5,7,3′,4′-tetrahydroxyflavanone)
Eriodictylol-7-glucoside (pyracanthoside)
Eriodictyol-7-neohesperidoside
Eriodictylo-7-rutinoside
Erythrisenegalone
Flavanomarein (7,8,3′,4′-tetrahydroxy-7-glucoside)
Fustin (3,7,3′,4′-tetrahydroxyflavanone)
Hesperetin (5,7,3′-trihydroxy-4′-methoxyflavanone; eriodictyol-4′-methyl ether)
Hesperetin-7-neohesperidoside
Hesperidin (hesperetin-7-rutinoside)
Homoeriodictyol (5,7,4′-trihydroxy-3′-methoxyflavanone ; eriodictyol-3′-methyl ether)
6-Hydroxyflavanone
7-Hydroxyflavanone
2′-Hydroxyflavanone
4′-Hydroxyflavanone
3-Hydroxy-6-methoxyflavanone
3-Hydroxy-7-methoxyflavanone
Isolonchocarpin
Isosakuranetin (5,7-dihydroxy-4′-methoxyflavanone; naringenin-4′-methyl ether)
Isoxanthohumol (hop flavanone)
5-Hydroxy-7-methoxy-8-prenylflavanone
Liquiritigenin (7,4′-dihydroxyflavanone)
Liquiritigenin-7-methyl ether (7-methoxy-4′-hydroxyflavanone)
5-Methoxyflavanone
6-Methoxyflavanone
4′-Methoxyflavanone
Naringenin (5,7,4′-trihydroxyflavanone)
Naringin (naringenin-7-neohesperidoside)
Naringenin trimethyl ether
Narirutin (naringenin-7-rutinoside; isonaringin)
Neoeriocitrin (eriodictyol-7-neohesperidoside)
Neohesperidin (hesperetin-7-neohesperidoside)
Pinobanksin
Pinocembrin (5,7-dihydroxyflavanone)
Pinocembrin dimethyl ether
Pinocembrin-3-acetate
Pinostrobin (5-hydroxy-7-methoxyflavanone; pinocembrin-7-methyl ether)
Poncirin (isosakuranetin-7-neohesperidoside)
Pratol (7-hydroxy-4′-methoxyflavanone; liquiritigenin-4′-methyl ether)
3′-Prenylliquiritigenin (7,4′-dihydroxy-3′-prenylflavanone)
7-O-Prenyloxyflavanone
8-Prenylpinocembrin
Prunin (naringenin-7-glucoside)
Sakuranetin 5,4′-dihydroxy-7-methoxyflavanone; naringenin-7-methyl ether)
Sigmoidin A (5,7,3′,4′-tetrahydroxy-2′,5′-diprenylflavanone)
Sigmoidin B (5,7,3′,4′-tetrahydroxy-5′-prenylflavanone)
Sigmoidin C
Steppogenin
Taxifolin (3,5,7,3′,4′-pentahydroxyflavanone)
5,7,8,4′-Tetramethoxyflavanone (carthamidin tetramethyl ether)

Dihydrochalcones

Asebotin (2′,4-dihydroxy-4′-methoxydihydrochalcone-6′-glucoside; asebogenin-6′-glucoside)
Dihydroisosakuranetin (2′,6′,4-trihydroxy-4′-methoxydihydrochalcone)
2′,4′-Dihydroxy-4-methoxydihydrochalcone
2′,6′-Dihydroxy-4′,4-dimethoxydihydrochalcone
Dihydrosakuranetin (2′,4′,6′-trihydroxy-4-methoxydihydrochalcone)
4′,4-Dimethoxydihydrochalcone
3-Hydroxyphloretin-4′-glucoside
4′-Hydroxydihydrochalcone
4′-Hydroxy-4-methoxydihydrochalcone
Isosakuranetin dihydrochalcone (2′,6′,4-trihydroxy-4′-methoxydihydrochalcone)
4′-Methoxy-4-hydroxydihydrochalcone
Neohesperidin dihydrochalcone
2′,3′,4′,3,4-Pentahydroxydihydrochalcone
2′,4′,6′,3,4-PentahydroxydihydrochalconePhloracetophenone
Phloracetophenone-4′-neohesperidoside
Phloretin
Phloretin-4′-glucoside
Phloridzin dihydrate
Pinocembrin dihydrochalcone (2′,4′,6′-trihydroxydihydrochalcone)
2′,4′,6′,4-Tetrahydroxy-3-methoxydihydrochalcone
2′,4′,4-Trihydroxydihydrochalcone-4-glucoside
2′,4′,6′-Trihydroxy-3,4-dimethoxydihydrochalcone
2′,4′,6′-Trihydroxy-4-methoxydihydrochalcone
2′,4′,6′-Trihydroxy-3,4-methylenedioxydihydrochalcone

Homoisoflavanones

The homoisoflavanones belong to a relatively small class of natural products, the first members of which (eucomin and eucomol) were isolated in 1967 from the bulbs of Eucomis bicolor (Liliaceae), an African lily. Since then, homoisoflavanones have been obtained from Scilla spp and several other Liliaceae, as well as the legume Lespedeza. Despite their name, biosynthetic studies have shown that homoisoflavanones, are not really isoflavanone derivatives although structurally there is a passing resemblance between the two. For this reason, and as long ago as 1975, it has been suggested that it would be better to use the systematic name 3-benzylchroman-4-one, although the rather misleading term “homoisoflavanone” is still commonly found in research papers. The numbering system of the aromatic A- and B-rings of homoisoflavanones, and of the non-aromatic C-ring, follows that used for isoflavones/isoflavanones. The extra carbon atom between C-3 (C-ring) and C-1′ (B-ring) is designated C-9.

4′-Demethyleucomin
4′-O-Methyldihydropunctatin
4′-O-Methylpunctatin
Dihydropunctatin
Eucomin (5,7-dihydroxy-4′-methoxyhomoisoflavanone)
Eucomin dimethyl ether (5,7,4′-trimethoxyhomoisoflavanone)
Eucomnalin (5,7,4′-trihydroxy-6-methoxyhomoisoflavanone)
Eucomol (3,5,7-trihydroxy-4′-methoxyhomoisoflavanone)
Punctatin (5,7,4′-trihydroxy-8-methoxyhomoisoflavanone)

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Xanthones

The xanthones are a group of natural products of fairly limited distribution but common in the family Guttiferae, including mangosteen (Garcinia sp.), an Asian tree yielding an edible fruit. Gamboge, a yellowish pigment from the dried latex of Garcinia hanburyi contains gambogic acid and a variety of other xanthones with antitumour or antimicrobial properties. Xanthones such as gentisein, gentisin and isogentisin have been isolated from the roots of yellow gentian (Gentiana lutea; Gentianaceae) and other gentian species, whilst mangostin occurs in mango (Mangifera sp.) The name “xanthone” is derived from the greek “xanthos” meaning “yellow” as some, but by no means all, naturally occurring xanthones are orange or various shades of yellow. Some xanthones have been reported to have powerful antioxidant properties. In appearance, xanthone, the parent molecule, bears a passing resemblence to that of flavone having an identical arrangement of the A (aromatic) and C (pyrano, non-aromatic) rings. In xanthones, however, another aromatic ring is attached at the positions equivalent to C-2/C-3 of flavone giving a 3-ring planar (rigid) molecule (in flavones the molecule is non-planar because the aromatic B-ring, which is attached only at C-2, does not have a fixed orientation). In the literature, the xanthone system is often confusingly depicted with the carbonyl group of the non-aromatic ring pointing upwards. However, because the molecule is symmetrical, and in order to better show the relationship between xanthones and flavones, we advise that the xanthone system is drawn with the carbonyl group facing downwards as in flavones. The numbering system (which differs significantly from that of flavones) then runs clockwise around the aromatic rings starting with the carbon atom (C-1) immediately to the left of the carbonyl — thus, C-1, 2, 3 and 4 (on ring A), then 5, 6, 7 and 8 on ring B. The carbon of the carbonyl group is designated C-9. C-1 in xanthones is therefore equivalent to C-5 in flavones, and C-3 (xanthones) to C-7 (flavones).

Caloxanthone A
Cowanin
1,8-Dihydroxy-3-methylxanthone
1,8-Dihydroxy-6-methylxanthone
3,8-Dihydroxy-6-methylxanthone
3,6-Dihydroxyxanthone
3,8-Dihydroxyxanthone
6,8-Dihydroxyxanthone
3,6-Dimethoxyxanthone
3,8-Dimethoxyxanthone
1,3-Dimethoxy-5,8-dihydroxyxanthone
Gentisein (1,3,7-trihydroxyxanthone)
Gentisin (1,7-dihydroxy-3-methoxyxanthone)
1-Hydroxyxanthone
1-Hydroxy-3,7-dimethoxyxanthone (gentisein-3,7-dimethyl ether)
2-Hydroxy-5,6,7,8-tetramethoxyxanthone
8-Hydroxy-3,4,6-trimethoxyxanthone
1-Hydroxy-3,5,6-trimethoxyxanthone
Inoxanthone
Isogentisin (1,3-dihydroxy-7-methoxyxanthone)
Macluraxanthone
Mangiferin
Mangostin (alpha-mangostin
Manglexanthone
5-Methoxyxanthone
7-O-Methylgarcinone E
2,3,5,6,7,8-Pentamethoxyxanthone
Rheediaxanthone B
Swirchirin
Tovophyllin A
3,4,8-Trihydroxyxanthone
1,3,8-Trihydroxyxanthone
1,3,7-Trimethoxyxanthone

Xanthone Starter Pack: Gentisein, Gentisein-3,7-dimethyl ether, Gentisein trimethyl ether, Gentisin (gentisein-3-methyl ether), Isogentisin (gentisein-7-methyl ether). Analytical grade material. 1mg (or 2 mg) units according to need.

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