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
Daidzein
Equol
Flavonoid
Genistein
Glycitein
Homoisoflavonoids, related molecules with a 16-carbon skeleton
Isoflavone
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.
Xenoestrogens
Phytoestrogens
Flavanones
Hesperetin
Liquiritigenin
Naringenin
Pinocembrin
Flavones
Acacetin
7,8-Dihydroxyflavone
Mirificin
Prenylflavonoids
8-Prenylnaringenin
6-Prenylnaringenin
8-Geranylnaringenin
6,8-Diprenylnaringenin
Icaritin
Isoflavones
Biochanin A
Daidzein
Daidzin
Formononetin
Genistein
Genistin
Glycitein
Ononin
Prunetin
Puerarin
Tectorigenin
Isoflavanes
Equol (S -Equol)
Glabridin
Dihydrochalcones Isoflavenes Glabrene
Coumestans
Coumestan
Coumestrol
Desmethylwedelolactone
Wedelolactone
Lignans Flavonolignans Flavonols Others
Deoxymiroestrol
Miroestrol
Resveratrol
α-Isosparteine
Mycoestrogens
Zearalanone
Zearalenone
α-Zearalanol (zeranol)
α-Zearalenol
β-Zearalanol
β-Zearalenol
Synthetic
Alkylphenols
Atrazine
BHA
Bisphenol A
Bisphenol F
Bisphenol S
DDE
DDT
Dieldrin
Dioxins
Endosulfan
Enzacamene
Erythrosine
Heptachlor
Lindane
Methoxychlor
Nonylphenol
Parabens
PBBs
PCBs
Pentachlorophenol
PHBA
Phthalates
Propyl gallate
Perfluorinated compound
Metalloestrogens
Aluminium
Antimony
Arsenite
Barium
Cadmium
Chromium
Cobalt
Copper
Lead
Mercury
Nickel
Selenite
Tin
Vanadate
Flavonoids
Anthoxanthins
Flavones Flavonols
Quercetin, Kaempferol, et.c.
Isoflavones
Daidzein, Genistein, Orobol et.c.
Neoflavonoids
Flavans
Flavan Flavan-3-ols (flavanols)
Catechin, Gallocatechol, et.c.
Flavan-4-ols (flavanols)
Apiforol, Luteoforol, et.c.
Flavan-3,4-diols
Leucocyanidin, Leucodelphinidin, et.c.
Flavanones
Hesperidin
Naringenin
Eriodictyol
Flavanonols
Taxifolin
Aromadendrin, et.c.
Anthocyanidins
3-deoxyanthocyanidins 3-hydroxyanthocyanidin
Apigeninidin, Guibourtinidin, et.c.
Aurones Chalcones
Chalcones
Butein, Isoliquiritigenin, et.c.
Dihydrochalcone
Miscellaneous
Types of isoflavonoids
:
Isoflavanes
Isoflavandiols
Isoflavenes
Isoflavones
Pterocarpans
Misc.
Ionotropic
GABAA Tooltip γ-Aminobutyric acid A receptor
Agonists: (+)-Catechin
Bamaluzole
Barbiturates (e.g., phenobarbital)
Beta-Alanine
BL-1020
DAVA
Dihydromuscimol
GABA
Gabamide
GABOB
Gaboxadol (THIP)
Homotaurine (tramiprosate, 3-APS)
Ibotenic acid
iso-THAZ
iso-THIP
Isoguvacine
Isomuscimol
Isonipecotic acid
Kojic amine
L-838,417
Lignans (e.g., honokiol)
Methylglyoxal
Monastrol
Muscimol
Nefiracetam
Neuroactive steroids (e.g., allopregnanolone )
Org 20599
PF-6372865
Phenibut
Picamilon
4-PIOL
P4S
Progabide
Propofol
Quisqualamine
SL-75102
Taurine
TACA
TAMP
Terpenoids (e.g., borneol)
Thiomuscimol
Tolgabide
ZAPA
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)
Antagonists: Bicuculline
Coriamyrtin
Dihydrosecurinine
Famiraprinium
Gabazine (SR-95531)
Hydrastine
Hyenachin (mellitoxin)
PHP-501
Pitrazepin
Securinine
Sinomenine
SR-42641
Thiocolchicoside
Tutin
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
Agonists: BL-1020
CACA
CAMP
Homohypotaurine
GABA
GABOB
Ibotenic acid
Isoguvacine
Muscimol
N 4 -Chloroacetylcytosine arabinoside
Picamilon
Progabide
TACA
TAMP
Thiomuscimol
Tolgabide
Antagonists: (S)-2-MeGABA
(S)-4-ACPBPA
(S)-4-ACPCA
2-MeTACA
3-APMPA
4-ACPAM
4-GBA
cis -3-ACPBPA
CGP-36742 (SGS-742)
DAVA
Gabazine (SR-95531)
Gaboxadol (THIP)
I4AA
Isonipecotic acid
Loreclezole
P4MPA
P4S
SKF-97541
SR-95318
SR-95813
TPMPA
trans -3-ACPBPA
ZAPA
Negative modulators: 5α-Dihydroprogesterone
Bilobalide
Loreclezole
Picrotoxin (picrotin, picrotoxinin)
Pregnanolone
ROD-188
THDOC
Zinc
Metabotropic
GABAB Tooltip γ-Aminobutyric acid B receptor
Agonists: 1,4-Butanediol
3-APPA
4-Fluorophenibut
Aceburic acid
Arbaclofen
Arbaclofen placarbil
Baclofen
BL-1020
GABA
Gabamide
GABOB
GBL
GHB
GHBAL
GHV
GVL
Isovaline
Lesogaberan
Phenibut
Picamilon
Progabide
Sodium oxybate
SKF-97,541
SL 75102
Tolgabide
Tolibut
Positive modulators: ADX-71441
BHF-177
BHFF
BSPP
CGP-7930
CGP-13501
GS-39783
rac-BHFF
KK-92A
Antagonists: 2-Hydroxysaclofen
CGP-35348
CGP-36742
CGP-46381
CGP-52432
CGP-54626
CGP-55845
CGP-64213
DAVA
Homotaurine (tramiprosate, 3-APS)
Phaclofen
Saclofen
SCH-50911
Negative modulators: Compound 14
See also
Receptor/signaling modulators
GABAA receptor positive modulators
GABA metabolism/transport modulators