Page last updated: 2024-12-08

dihydroguaiaretic acid

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Description

dihydroguaiaretic acid: lignan extracted form Larrea divaricata; inhibitory to beef heart mitochondrial succinoxidase & NADH-oxidase; RN given refers to cpd without isomeric designation [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID161924
CHEMBL ID1976696
SCHEMBL ID9087980
MeSH IDM0065355

Synonyms (25)

Synonym
4,4'-(2,3-dimethylbutane-1,4-diyl)bis(2-methoxyphenol)
nsc705084
4-butanediyldihydroguaiaretic acid
phenol,4'-(2,3-dimethyl-1,4-butanediyl)bis[2-methoxy-
NCI60_037533
dihydroguaiaretic acid
NCGC00180436-01
ACON1_001505
nsc-705084
BRD-A19129781-001-01-6
36469-60-0
FT-0696052
SCHEMBL9087980
4-[4-(4-hydroxy-3-methoxyphenyl)-2,3-dimethylbutyl]-2-methoxyphenol
ccris 7923
2,3-dimethyl-1-(3'-methoxy-4'-hydroxyphenyl)-4-(3''-methoxy-4''hydroxyphenyl)butane
4-[4-(4-hydroxy-3-methoxy-phenyl)-2,3-dimethyl-butyl]-2-methoxy-phenol
HMS3342F18
CHEMBL1976696
ADFOLUXMYYCTRR-UHFFFAOYSA-N
bdbm50030892
( inverted exclamation marka)-dihydroguaiaretic acid
AKOS032948494
DTXSID30957790
phenol, 4,4'-(2,3-dimethyl-1,4-butanediyl)bis[2-methoxy-

Research Excerpts

Overview

Nordihydroguaiaretic acid (NDGA) is a natural polyphenol with a broad spectrum of pharmacological properties. It is a major component of Myristica fragrans and Machilus thunbergii that is traditionally used as a spice and for medicinal purposes.

ExcerptReferenceRelevance
"Nordihydroguaiaretic acid (NDGA) is a natural polyphenol with a broad spectrum of pharmacological properties. "( Ring substitution influences oxidative cyclisation and reactive metabolite formation of nordihydroguaiaretic acid analogues.
Allen, KJ; Asiamah, I; Hodgson, HL; Krol, ES; Maloney, K, 2015
)
1.26
"meso-Dihydroguaiaretic acid (MDGA) is a major component of Myristica fragrans and Machilus thunbergii that is traditionally used as a spice and for medicinal purposes. "( Metabolic characterization of meso-dihydroguaiaretic acid in liver microsomes and in mice.
Jeon, JS; Kim, SK; Kim, YM; Lee, BH; Lee, JY; Oh, SJ; Ryu, CS, 2015
)
1.21
"meso-Dihydroguaiaretic acid (MDGA), which is a dibenzylbutane lignin isolated from the ethyl acetate fraction of Saururus chinensis, has various biological activities, including anti-oxidative, anti-inflammatory, anti-bacterial, and neuroprotective effects. "( meso-Dihydroguaiaretic acid attenuates airway inflammation and mucus hypersecretion in an ovalbumin-induced murine model of asthma.
Cho, ES; Kim, TI; Kwon, HJ; Seo, CS; Son, HY; Son, JK; Song, JW; Won, YS, 2016
)
1.46
"Meso-dihydroguaiaretic acid (MDGA) is a medicinal herbal product isolated from the aerial parts of Saururus chinensis that inhibits the cyclooxygenase-2 (COX-2)-dependent phase of prostaglandin D(2) (PGD(2)) generation in bone marrow-derived mast cells (BMMC) (IC(50) 9.8 microM). "( Meso-dihydroguaiaretic acid isolated from Saururus chinensis inhibits cyclooxygenase-2 and 5-lipoxygenase in mouse bone marrow-derived mast cells.
Chang, HW; Haa, K; Hong, TG; Hwang, NK; Kim, DH; Kim, JC; Kim, JH; Moon, TC; Seo, CS; Son, JK, 2008
)
1.37
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (3)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Proto-oncogene c-FosHomo sapiens (human)IC50 (µMol)0.21000.00790.10890.2100AID1178344
Transcription factor AP-1Homo sapiens (human)IC50 (µMol)0.21000.00790.39202.0300AID1178344
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
TransthyretinHomo sapiens (human)EC50 (µMol)6.30005.60007.54298.6000AID1169291
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (55)

Processvia Protein(s)Taxonomy
conditioned taste aversionProto-oncogene c-FosHomo sapiens (human)
regulation of transcription by RNA polymerase IIProto-oncogene c-FosHomo sapiens (human)
transcription by RNA polymerase IIProto-oncogene c-FosHomo sapiens (human)
inflammatory responseProto-oncogene c-FosHomo sapiens (human)
transforming growth factor beta receptor signaling pathwayProto-oncogene c-FosHomo sapiens (human)
nervous system developmentProto-oncogene c-FosHomo sapiens (human)
female pregnancyProto-oncogene c-FosHomo sapiens (human)
response to xenobiotic stimulusProto-oncogene c-FosHomo sapiens (human)
response to light stimulusProto-oncogene c-FosHomo sapiens (human)
response to gravityProto-oncogene c-FosHomo sapiens (human)
response to toxic substanceProto-oncogene c-FosHomo sapiens (human)
response to activityProto-oncogene c-FosHomo sapiens (human)
skeletal muscle cell proliferationProto-oncogene c-FosHomo sapiens (human)
osteoclast differentiationProto-oncogene c-FosHomo sapiens (human)
response to lipopolysaccharideProto-oncogene c-FosHomo sapiens (human)
response to progesteroneProto-oncogene c-FosHomo sapiens (human)
response to insulinProto-oncogene c-FosHomo sapiens (human)
cellular response to zinc ion starvationProto-oncogene c-FosHomo sapiens (human)
cellular response to reactive oxygen speciesProto-oncogene c-FosHomo sapiens (human)
response to immobilization stressProto-oncogene c-FosHomo sapiens (human)
skeletal muscle cell differentiationProto-oncogene c-FosHomo sapiens (human)
response to muscle stretchProto-oncogene c-FosHomo sapiens (human)
response to ethanolProto-oncogene c-FosHomo sapiens (human)
positive regulation of osteoclast differentiationProto-oncogene c-FosHomo sapiens (human)
positive regulation of DNA-templated transcriptionProto-oncogene c-FosHomo sapiens (human)
positive regulation of transcription by RNA polymerase IIProto-oncogene c-FosHomo sapiens (human)
response to corticosteroneProto-oncogene c-FosHomo sapiens (human)
myoblast proliferationProto-oncogene c-FosHomo sapiens (human)
response to cAMPProto-oncogene c-FosHomo sapiens (human)
SMAD protein signal transductionProto-oncogene c-FosHomo sapiens (human)
cellular response to cadmium ionProto-oncogene c-FosHomo sapiens (human)
cellular response to calcium ionProto-oncogene c-FosHomo sapiens (human)
cellular response to tumor necrosis factorProto-oncogene c-FosHomo sapiens (human)
cellular response to epidermal growth factor stimulusProto-oncogene c-FosHomo sapiens (human)
cellular response to parathyroid hormone stimulusProto-oncogene c-FosHomo sapiens (human)
cellular response to hypoxiaProto-oncogene c-FosHomo sapiens (human)
integrated stress response signalingProto-oncogene c-FosHomo sapiens (human)
positive regulation of miRNA transcriptionProto-oncogene c-FosHomo sapiens (human)
mononuclear cell differentiationProto-oncogene c-FosHomo sapiens (human)
cellular response to phorbol 13-acetate 12-myristateProto-oncogene c-FosHomo sapiens (human)
cellular response to prolactinProto-oncogene c-FosHomo sapiens (human)
signal transductionTransthyretinHomo sapiens (human)
purine nucleobase metabolic processTransthyretinHomo sapiens (human)
negative regulation of transcription by RNA polymerase IITranscription factor AP-1Homo sapiens (human)
regulation of transcription by RNA polymerase IITranscription factor AP-1Homo sapiens (human)
transforming growth factor beta receptor signaling pathwayTranscription factor AP-1Homo sapiens (human)
release from viral latencyTranscription factor AP-1Homo sapiens (human)
cellular response to reactive oxygen speciesTranscription factor AP-1Homo sapiens (human)
response to endoplasmic reticulum stressTranscription factor AP-1Homo sapiens (human)
positive regulation of apoptotic processTranscription factor AP-1Homo sapiens (human)
negative regulation of DNA bindingTranscription factor AP-1Homo sapiens (human)
negative regulation by host of viral transcriptionTranscription factor AP-1Homo sapiens (human)
positive regulation by host of viral transcriptionTranscription factor AP-1Homo sapiens (human)
negative regulation of DNA-templated transcriptionTranscription factor AP-1Homo sapiens (human)
positive regulation of DNA-templated transcriptionTranscription factor AP-1Homo sapiens (human)
positive regulation of transcription by RNA polymerase IITranscription factor AP-1Homo sapiens (human)
SMAD protein signal transductionTranscription factor AP-1Homo sapiens (human)
cellular response to cadmium ionTranscription factor AP-1Homo sapiens (human)
integrated stress response signalingTranscription factor AP-1Homo sapiens (human)
positive regulation of miRNA transcriptionTranscription factor AP-1Homo sapiens (human)
positive regulation of vascular associated smooth muscle cell proliferationTranscription factor AP-1Homo sapiens (human)
positive regulation of DNA-templated transcription initiationTranscription factor AP-1Homo sapiens (human)
regulation of cell population proliferationTranscription factor AP-1Homo sapiens (human)
regulation of cell cycleTranscription factor AP-1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (25)

Processvia Protein(s)Taxonomy
transcription cis-regulatory region bindingProto-oncogene c-FosHomo sapiens (human)
RNA polymerase II cis-regulatory region sequence-specific DNA bindingProto-oncogene c-FosHomo sapiens (human)
RNA polymerase II core promoter sequence-specific DNA bindingProto-oncogene c-FosHomo sapiens (human)
DNA-binding transcription factor activity, RNA polymerase II-specificProto-oncogene c-FosHomo sapiens (human)
transcription coregulator bindingProto-oncogene c-FosHomo sapiens (human)
DNA-binding transcription activator activity, RNA polymerase II-specificProto-oncogene c-FosHomo sapiens (human)
chromatin bindingProto-oncogene c-FosHomo sapiens (human)
DNA-binding transcription factor activityProto-oncogene c-FosHomo sapiens (human)
protein bindingProto-oncogene c-FosHomo sapiens (human)
identical protein bindingProto-oncogene c-FosHomo sapiens (human)
RNA polymerase II-specific DNA-binding transcription factor bindingProto-oncogene c-FosHomo sapiens (human)
R-SMAD bindingProto-oncogene c-FosHomo sapiens (human)
sequence-specific double-stranded DNA bindingProto-oncogene c-FosHomo sapiens (human)
hormone activityTransthyretinHomo sapiens (human)
protein bindingTransthyretinHomo sapiens (human)
identical protein bindingTransthyretinHomo sapiens (human)
thyroid hormone bindingTransthyretinHomo sapiens (human)
transcription cis-regulatory region bindingTranscription factor AP-1Homo sapiens (human)
RNA polymerase II cis-regulatory region sequence-specific DNA bindingTranscription factor AP-1Homo sapiens (human)
DNA-binding transcription factor activity, RNA polymerase II-specificTranscription factor AP-1Homo sapiens (human)
DNA-binding transcription repressor activity, RNA polymerase II-specificTranscription factor AP-1Homo sapiens (human)
DNA-binding transcription activator activity, RNA polymerase II-specificTranscription factor AP-1Homo sapiens (human)
DNA bindingTranscription factor AP-1Homo sapiens (human)
DNA-binding transcription factor activityTranscription factor AP-1Homo sapiens (human)
RNA bindingTranscription factor AP-1Homo sapiens (human)
GTPase activator activityTranscription factor AP-1Homo sapiens (human)
protein bindingTranscription factor AP-1Homo sapiens (human)
enzyme bindingTranscription factor AP-1Homo sapiens (human)
ubiquitin protein ligase bindingTranscription factor AP-1Homo sapiens (human)
cAMP response element bindingTranscription factor AP-1Homo sapiens (human)
identical protein bindingTranscription factor AP-1Homo sapiens (human)
ubiquitin-like protein ligase bindingTranscription factor AP-1Homo sapiens (human)
RNA polymerase II-specific DNA-binding transcription factor bindingTranscription factor AP-1Homo sapiens (human)
R-SMAD bindingTranscription factor AP-1Homo sapiens (human)
general transcription initiation factor bindingTranscription factor AP-1Homo sapiens (human)
sequence-specific double-stranded DNA bindingTranscription factor AP-1Homo sapiens (human)
transcription factor bindingTranscription factor AP-1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (15)

Processvia Protein(s)Taxonomy
nucleusProto-oncogene c-FosHomo sapiens (human)
nucleoplasmProto-oncogene c-FosHomo sapiens (human)
endoplasmic reticulumProto-oncogene c-FosHomo sapiens (human)
cytosolProto-oncogene c-FosHomo sapiens (human)
transcription factor AP-1 complexProto-oncogene c-FosHomo sapiens (human)
RNA polymerase II transcription regulator complexProto-oncogene c-FosHomo sapiens (human)
chromatinProto-oncogene c-FosHomo sapiens (human)
protein-DNA complexProto-oncogene c-FosHomo sapiens (human)
nucleusProto-oncogene c-FosHomo sapiens (human)
extracellular regionTransthyretinHomo sapiens (human)
extracellular spaceTransthyretinHomo sapiens (human)
azurophil granule lumenTransthyretinHomo sapiens (human)
extracellular exosomeTransthyretinHomo sapiens (human)
extracellular spaceTransthyretinHomo sapiens (human)
nuclear chromosomeTranscription factor AP-1Homo sapiens (human)
nucleusTranscription factor AP-1Homo sapiens (human)
nucleoplasmTranscription factor AP-1Homo sapiens (human)
transcription factor AP-1 complexTranscription factor AP-1Homo sapiens (human)
RNA polymerase II transcription regulator complexTranscription factor AP-1Homo sapiens (human)
chromatinTranscription factor AP-1Homo sapiens (human)
euchromatinTranscription factor AP-1Homo sapiens (human)
transcription regulator complexTranscription factor AP-1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (9)

Assay IDTitleYearJournalArticle
AID1169299Competitive binding to TTR V30M mutant (unknown origin) expressed in Escherichia coli at 1 to 80 uM by fluorescence assay2014Journal of medicinal chemistry, Nov-13, Volume: 57, Issue:21
Inhibitory activities of propolis and its promising component, caffeic acid phenethyl ester, against amyloidogenesis of human transthyretin.
AID1253353Drug degradation in 0.5M phosphate citric acid buffer at 0.5 mM at pH 7.4 at 37 degC by HPLC-UV analysis2015Bioorganic & medicinal chemistry, Nov-01, Volume: 23, Issue:21
Ring substitution influences oxidative cyclisation and reactive metabolite formation of nordihydroguaiaretic acid analogues.
AID1169291Inhibition of TTR V30M mutant (unknown origin) expressed in Escherichia coli assessed as inhibition of amyloid fibril formation by fluorescence assay2014Journal of medicinal chemistry, Nov-13, Volume: 57, Issue:21
Inhibitory activities of propolis and its promising component, caffeic acid phenethyl ester, against amyloidogenesis of human transthyretin.
AID1253354Half life of the compound in 0.5M phosphate citric acid buffer at 0.5 mM at pH 7.4 at 37 degC by HPLC-UV analysis2015Bioorganic & medicinal chemistry, Nov-01, Volume: 23, Issue:21
Ring substitution influences oxidative cyclisation and reactive metabolite formation of nordihydroguaiaretic acid analogues.
AID1110759Nematocidal activity against Caenorhabditis elegans assessed as mortality2002Annual review of phytopathology, , Volume: 40Phytochemical based strategies for nematode control.
AID1253356Stability of compound in 0.5M phosphate citric acid buffer assessed as autoxidative conversion at 0.1 mM at pH 7.4 at 37 degC for 90 mins by HPLC-UV analysis2015Bioorganic & medicinal chemistry, Nov-01, Volume: 23, Issue:21
Ring substitution influences oxidative cyclisation and reactive metabolite formation of nordihydroguaiaretic acid analogues.
AID1178344Inhibition of Fos-Jun dimer formation (unknown origin)2014Journal of medicinal chemistry, Aug-28, Volume: 57, Issue:16
Small molecule inhibitors targeting activator protein 1 (AP-1).
AID1169300Displacement of ANS from TTR V30M mutant (unknown origin) expressed in Escherichia coli at 1 to 50 uM after 5 mins by fluorescence assay2014Journal of medicinal chemistry, Nov-13, Volume: 57, Issue:21
Inhibitory activities of propolis and its promising component, caffeic acid phenethyl ester, against amyloidogenesis of human transthyretin.
AID1169294Inhibition of TTR V30M mutant (unknown origin) expressed in Escherichia coli assessed as inhibition of amyloid fibril formation at 20 uM by fluorescence assay2014Journal of medicinal chemistry, Nov-13, Volume: 57, Issue:21
Inhibitory activities of propolis and its promising component, caffeic acid phenethyl ester, against amyloidogenesis of human transthyretin.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (49)

TimeframeStudies, This Drug (%)All Drugs %
pre-19902 (4.08)18.7374
1990's7 (14.29)18.2507
2000's16 (32.65)29.6817
2010's23 (46.94)24.3611
2020's1 (2.04)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 43.46

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index43.46 (24.57)
Research Supply Index3.93 (2.92)
Research Growth Index5.09 (4.65)
Search Engine Demand Index61.68 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (43.46)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (2.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other49 (98.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]