3-phenylchromen-4-one 3-phenylchroman (isoflavan) backbone of the isoflavanes Isoflavonoids are a class of flavonoid phenolic compounds, many of which are biologically active. Isoflavonoids and their derivatives are sometimes referred to as phytoestrogens , as many isoflavonoid compounds have biological effects via the estrogen receptor .
Medically, isoflavonoids and related compounds have been used in many dietary supplements but the medical and scientific community is generally skeptical of their use. Recently, some natural isoflavonoids have been identified as toxins, including biliatresone which may cause biliary atresia when infants are exposed to the plant product.[ 1]
The isoflavonoid group is broad, and includes many structurally similar groups, including:
Isoflavonoids are derived from the flavonoid biosynthesis pathway via liquiritigenin or naringenin .[ 3]
Chemical makeup While flavonoids (in the narrow sense) have the 2-phenylchromen-4-one backbone, isoflavonoids have the 3-phenylchromen-4-one backbone with no hydroxyl group substitution at position 2 (case of the isoflavones) or the 3-phenylchroman (isoflavan) backbone (case of isoflavanes, such as equol ).
See also
References ^ Lorent, Kristin; Gong, Weilong; Koo, Kyung A.; Waisbourd-Zinman, Orith; Karjoo, Sara; Zhao, Xiao; Sealy, Ian; Kettleborough, Ross N.; Stemple, Derek L. (2015-05-06). "Identification of a plant isoflavonoid that causes biliary atresia" . Science Translational Medicine . 7 (286): 286ra67. doi :10.1126/scitranslmed.aaa1652 . ISSN 1946-6234 . PMC 4784984 . PMID 25947162 . ^ superpathway of pterocarpan biosynthesis (via formononetin) on metacyc.org ^ "Isoflavonoid biosynthesis" . BioSystems . U.S. National Library of Medicine. Archived from the original on August 5, 2012.
Types of isoflavonoids
: Misc.
Ionotropic
GABAA Tooltip γ-Aminobutyric acid A receptor Positive modulators (abridged; see here for a full list): α-EMTBL Alcohols (e.g., drinking alcohol , 2M2B ) Anabolic steroids Avermectins (e.g., ivermectin ) Barbiturates (e.g., phenobarbital ) Benzodiazepines (e.g., diazepam ) Bromide compounds (e.g., potassium bromide ) Carbamates (e.g., meprobamate ) Carbamazepine Chloralose Chlormezanone Clomethiazole Dihydroergolines (e.g., ergoloid (dihydroergotoxine) ) Etazepine Etifoxine Fenamates (e.g., mefenamic acid ) Flavonoids (e.g., apigenin , hispidulin ) Fluoxetine Flupirtine Imidazoles (e.g., etomidate ) Kava constituents (e.g., kavain ) Lanthanum Loreclezole Monastrol Neuroactive steroids (e.g., allopregnanolone , cholesterol , THDOC ) Niacin Niacinamide Nonbenzodiazepines (e.g., β-carbolines (e.g., abecarnil ), cyclopyrrolones (e.g., zopiclone ), imidazopyridines (e.g., zolpidem ), pyrazolopyrimidines (e.g., zaleplon )) Norfluoxetine Petrichloral Phenols (e.g., propofol ) Phenytoin Piperidinediones (e.g., glutethimide ) Propanidid Pyrazolopyridines (e.g., etazolate ) Quinazolinones (e.g., methaqualone ) Retigabine (ezogabine) ROD-188 Skullcap constituents (e.g., baicalin ) Stiripentol Sulfonylalkanes (e.g., sulfonmethane (sulfonal) ) Topiramate Valerian constituents (e.g., valerenic acid ) Volatiles /gases (e.g., chloral hydrate , chloroform , diethyl ether , paraldehyde , sevoflurane ) Negative modulators: 1,3M1B 3M2B 11-Ketoprogesterone 17-Phenylandrostenol α3IA α5IA (LS-193,268) β-CCB β-CCE β-CCM β-CCP β-EMGBL Anabolic steroids Amiloride Anisatin β-Lactams (e.g., penicillins , cephalosporins , carbapenems ) Basmisanil Bemegride Bicyclic phosphates (TBPS , TBPO , IPTBO ) BIDN Bilobalide Bupropion CHEB Chlorophenylsilatrane Cicutoxin Cloflubicyne Cyclothiazide DHEA DHEA-S Dieldrin (+)-DMBB DMCM DMPC EBOB Etbicyphat FG-7142 (ZK-31906) Fiproles (e.g., fipronil ) Flavonoids (e.g., amentoflavone , oroxylin A ) Flumazenil Fluoroquinolones (e.g., ciprofloxacin ) Flurothyl Furosemide Golexanolone Iomazenil (123 I) IPTBO Isopregnanolone (sepranolone) L-655,708 Laudanosine Lindane MaxiPost Morphine Morphine-3-glucuronide MRK-016 Naloxone Naltrexone Nicardipine Nonsteroidal antiandrogens (e.g., apalutamide , bicalutamide , enzalutamide , flutamide , nilutamide ) Oenanthotoxin Pentylenetetrazol (pentetrazol) Phenylsilatrane Picrotoxin (i.e., picrotin , picrotoxinin and dihydropicrotoxinin ) Pregnenolone sulfate Propybicyphat PWZ-029 Radequinil Ro 15-4513 Ro 19-4603 RO4882224 RO4938581 Sarmazenil SCS Suritozole TB-21007 TBOB TBPS TCS-1105 Terbequinil TETS Thujone U-93631 Zinc ZK-93426 GABAA -ρ Tooltip γ-Aminobutyric acid A-rho receptor
Metabotropic
GABAB Tooltip γ-Aminobutyric acid B receptor Negative modulators: Compound 14
See also Receptor/signaling modulators GABAA receptor positive modulators GABA metabolism/transport modulators