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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)
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)
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*
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)
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)
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
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)
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
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