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
:
Isoflavanes
Isoflavandiols
Isoflavenes
Isoflavones
Pterocarpans
Misc.
Pterocarpans
Isoflavonoid biosynthesis
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 )
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
Metabotropic
GABAB Tooltip γ-Aminobutyric acid B receptor
Positive modulators: ADX-71441
BHF-177
BHFF
BSPP
CGP-7930
CGP-13501
GS-39783
rac-BHFF
KK-92A
Negative modulators: Compound 14
See also
Receptor/signaling modulators
GABAA receptor positive modulators
GABA metabolism/transport modulators