Page last updated: 2024-12-07

galgravin

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth

Description

galgravin: an anti-PAF constituent from the stems of Piper futokadsura, the Chinese drug haifengteng; structures of the isomers galgravin, galbelgin (10569-12-7) and veraguensin (19950-55-1) given in first source; RN given refers to galgravin, the (2alpha,3beta,4beta,5alpha)-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

galgravin : A member of the class of aryltetrahydrofurans carrying two 3,4-dimethoxyphenyl substituents at positions 2 and 5 as well as two methyl groups at positions 3 and 4. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

FloraRankFlora DefinitionFamilyFamily Definition
PipergenusA plant genus of the family PIPERACEAE that includes species used for spicy and stimulating qualities.[MeSH]PiperaceaeA family of flowering plants in the order Piperales best known for the black pepper widely used in SPICES, and for KAVA and Betel used for neuroactive properties.[MeSH]

Cross-References

ID SourceID
PubMed CID101749
CHEMBL ID418309
CHEBI ID132648
SCHEMBL ID4808653
MeSH IDM0223512

Synonyms (17)

Synonym
NCGC00160185-01
(2r,3r,4s,5s)-2,5-bis(3,4-dimethoxyphenyl)-3,4-dimethyloxolane
CHEBI:132648
528-63-2
galgravin
(2r,3r,4s,5s)-2,5-bis(3,4-dimethoxyphenyl)-3,4-dimethyl-tetrahydrofuran
CHEMBL418309 ,
bdbm50021519
furan, 2,4-bis(3,4-dimethoxyphenyl)tetrahydro-3,4-dimethyl-, (2alpha,3beta,4beta,5alpha)-
SCHEMBL4808653
rel-(2r,3r,4s,5s)-2,5-bis(3,4-dimethoxyphenyl)-3,4-dimethyltetrahydrofuran
HY-N5007
CS-0032064
(2s,3s,4r,5r)-2,5-bis(3,4-dimethoxyphenyl)-3,4-dimethyloxolane
DTXSID901318613
(invertedexclamationmarka)-galgravin
AKOS040760118
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (4)

RoleDescription
bone density conservation agentAn agent that inhibits bone resorption and/or favor bone mineralization and bone regeneration. Used to heal bone fractures and to treat bone diseases such as osteopenia and osteoporosis.
neuroprotective agentAny compound that can be used for the treatment of neurodegenerative disorders.
platelet aggregation inhibitorA drug or agent which antagonizes or impairs any mechanism leading to blood platelet aggregation, whether during the phases of activation and shape change or following the dense-granule release reaction and stimulation of the prostaglandin-thromboxane system.
plant metaboliteAny eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (4)

ClassDescription
aryltetrahydrofuran
dimethoxybenzeneAny methoxybenzene that consists of a benzene skeleton substituted with two methoxy groups and its derivatives.
ring assemblyTwo or more cyclic systems (single rings or fused systems) which are directly joined to each other by double or single bonds are named ring assemblies when the number of such direct ring junctions is one less than the number of cyclic systems involved.
lignanAny phenylpropanoid derived from phenylalanine via dimerization of substituted cinnamic alcohols, known as monolignols, to a dibenzylbutane skeleton. Note that while individual members of the class have names ending ...lignane, ...lignene, ...lignadiene, etc., the class names lignan, neolignan, etc., do not end with an "e".
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (2)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, CruzipainTrypanosoma cruziPotency39.81070.002014.677939.8107AID1476
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Platelet-activating factor receptorCavia porcellus (domestic guinea pig)IC50 (µMol)4.50000.00430.75777.8000AID154451
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (14)

Assay IDTitleYearJournalArticle
AID1364692Neuroprotective activity against Abeta (25 to 35)-induced cytotoxicity in human SH-SY5Y cells at 0.08 uM pre-incubated for 2 hrs before Abeta (25 to 35) addition for 14 hrs by MTT assay (Rvb = 60.2 to 73.5%)2017Journal of natural products, 04-28, Volume: 80, Issue:4
Neuroprotective Lignans from the Fruits of Schisandra bicolor var. tuberculata.
AID1364687Neuroprotective activity against H2O2-induced cytotoxicity in human SH-SY5Y cells at 0.0032 to 2 uM pre-incubated for 2 hrs before H2O2 addition for 14 hrs by MTT assay relative to untreated control2017Journal of natural products, 04-28, Volume: 80, Issue:4
Neuroprotective Lignans from the Fruits of Schisandra bicolor var. tuberculata.
AID1364688Neuroprotective activity against Abeta (25 to 35)-induced cytotoxicity in human SH-SY5Y cells at 0.0032 to 2 uM pre-incubated for 2 hrs before Abeta (25 to 35) addition for 14 hrs by MTT assay relative to untreated control2017Journal of natural products, 04-28, Volume: 80, Issue:4
Neuroprotective Lignans from the Fruits of Schisandra bicolor var. tuberculata.
AID1364691Neuroprotective activity against Abeta (25 to 35)-induced cytotoxicity in human SH-SY5Y cells at 0.0032 uM pre-incubated for 2 hrs before Abeta (25 to 35) addition for 14 hrs by MTT assay (Rvb = 60.2 to 73.5%)2017Journal of natural products, 04-28, Volume: 80, Issue:4
Neuroprotective Lignans from the Fruits of Schisandra bicolor var. tuberculata.
AID1364693Neuroprotective activity against Abeta (25 to 35)-induced cytotoxicity in human SH-SY5Y cells at 2 uM pre-incubated for 2 hrs before Abeta (25 to 35) addition for 14 hrs by MTT assay (Rvb = 60.2 to 73.5%)2017Journal of natural products, 04-28, Volume: 80, Issue:4
Neuroprotective Lignans from the Fruits of Schisandra bicolor var. tuberculata.
AID399192Trypanocidal activity against Trypanosoma cruzi Y trypomastigotes infected in mouse macrophage at 8 uM2004Journal of natural products, Jan, Volume: 67, Issue:1
Tetrahydrofuran lignans from Nectandra megapotamica with trypanocidal activity.
AID399191Trypanocidal activity against Trypanosoma cruzi Y trypomastigotes infected in mouse macrophage at 2 uM2004Journal of natural products, Jan, Volume: 67, Issue:1
Tetrahydrofuran lignans from Nectandra megapotamica with trypanocidal activity.
AID429826Selectivity index, ratio of CC50 for human C8166 cells to EC50 for HIV1 3B2009Journal of natural products, Jun, Volume: 72, Issue:6
Lignans with anti-HIV activity from Schisandra propinqua var. sinensis.
AID399193Antitrypanosomal activity against Trypanosoma cruzi Y trypomastigotes infected in mouse macrophage2004Journal of natural products, Jan, Volume: 67, Issue:1
Tetrahydrofuran lignans from Nectandra megapotamica with trypanocidal activity.
AID429825Antiviral activity against HIV1 3B in human C8166 cells assessed as inhibition of virus-induced cytopathogenicity2009Journal of natural products, Jun, Volume: 72, Issue:6
Lignans with anti-HIV activity from Schisandra propinqua var. sinensis.
AID399190Trypanocidal activity against Trypanosoma cruzi Y trypomastigotes infected in mouse macrophage at 32 uM2004Journal of natural products, Jan, Volume: 67, Issue:1
Tetrahydrofuran lignans from Nectandra megapotamica with trypanocidal activity.
AID154451Inhibition of PAF receptor binding to rabbit platelet plasma membranes1986Journal of medicinal chemistry, Oct, Volume: 29, Issue:10
Conformation and activity of tetrahydrofuran lignans and analogues as specific platelet activating factor antagonists.
AID429824Cytotoxicity against human C8166 cells by MTT assay2009Journal of natural products, Jun, Volume: 72, Issue:6
Lignans with anti-HIV activity from Schisandra propinqua var. sinensis.
AID1508630Primary qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay2021Cell reports, 04-27, Volume: 35, Issue:4
A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (14)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (7.14)18.7374
1990's2 (14.29)18.2507
2000's5 (35.71)29.6817
2010's5 (35.71)24.3611
2020's1 (7.14)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other14 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]