Page last updated: 2024-11-06

gypsogenin

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

Description

Gypsogenin is a naturally occurring triterpenoid saponin found in various plants, including Gypsophila paniculata (baby's breath). It exhibits a wide range of biological activities, including anti-inflammatory, anti-cancer, and hepatoprotective effects. Its biosynthesis involves complex enzymatic transformations of squalene, a precursor of steroids. Research on gypsogenin focuses on its potential therapeutic applications, particularly in treating inflammatory diseases and cancers. Its ability to inhibit the production of inflammatory mediators and its anti-proliferative effects on cancer cells make it a promising candidate for drug development.'

gypsogenin: originally from Gypsophila species; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

gypsogenin : A sapogenin that is olean-12-en-28-oic acid substituted by a beta-hydroxy group at position 3 and an oxo group at position 23. [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
Gypsophilagenus[no description available]CaryophyllaceaeA plant family of the order Caryophyllales, subclass Caryophyllidae, class Magnoliopsida. The species are diverse in appearance and habitat; most have swollen leaf and stem joints.[MeSH]

Cross-References

ID SourceID
PubMed CID92825
CHEMBL ID2386825
CHEBI ID5580
SCHEMBL ID828727
MeSH IDM000603216

Synonyms (31)

Synonym
olean-12-en-28-oic acid, 3-beta-hydroxy-23-oxo-
einecs 211-353-7
(3beta,4alpha)-3-hydroxy-23-oxoolean-12-en-28-oic acid
gypsophila paniculata saponin (swiss standard saponin)
3-hydroxy-23-oxo-olean-12-en-28-oic acid, (3-beta,4-alpha)-
639-14-5
gypsogenin
C08950
astrantiagenin d
albsapogenin
3beta-hydroxy-23-oxoolean-12-en-28-oic acid
gypsophilasapogenin
CHEBI:5580 ,
githagenin
gypsophilasaponin
saponin-gypsophila
LMPR0106150010
CHEMBL2386825
2a9sgc905j ,
unii-2a9sgc905j
AKOS016036221
SCHEMBL828727
olean-12-en-28-oic acid, 3-hydroxy-23-oxo-, (3.beta.,4.alpha.)-
gypsogenin [mi]
(3.beta.,4.alpha.)-3-hydroxy-23-oxoolean-12-en-28-oic acid
gypsogenin (githagenin)
Q20054523
MS-28712
HY-121382
DTXSID701026577
CS-0081834

Research Excerpts

[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (4)

ClassDescription
pentacyclic triterpenoid
sapogeninAny organic polycyclic compound that is the aglycon moiety of a saponin; sapogenins may be steroids or triterpenoids.
aldehydeA compound RC(=O)H, in which a carbonyl group is bonded to one hydrogen atom and to one R group.
monocarboxylic acidAn oxoacid containing a single carboxy group.
[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]

Pathways (1)

PathwayProteinsCompounds
saponin biosynthesis III07

Bioassays (51)

Assay IDTitleYearJournalArticle
AID1159123Antimicrobial activity against Bacillus subtilis ATCC 6633 for 24 hrs by microdillution method2014European journal of medicinal chemistry, Jul-23, Volume: 82Synthesis, antimicrobial and cytotoxic activities, and structure-activity relationships of gypsogenin derivatives against human cancer cells.
AID1159070Antimicrobial activity against Pseudomonas aeruginosa ATCC 35032 assessed as zone of inhibition at 30 uL for 24 hrs at 37 degC by disk diffusion test2014European journal of medicinal chemistry, Jul-23, Volume: 82Synthesis, antimicrobial and cytotoxic activities, and structure-activity relationships of gypsogenin derivatives against human cancer cells.
AID1159064Antimicrobial activity against Escherichia coli ATCC 25922 assessed as zone of inhibition at 30 uL for 24 hrs at 37 degC by disk diffusion test2014European journal of medicinal chemistry, Jul-23, Volume: 82Synthesis, antimicrobial and cytotoxic activities, and structure-activity relationships of gypsogenin derivatives against human cancer cells.
AID750462Antiviral activity against pseudo HCV infected in human 293T cells assessed as inhibition of HCV pseudo particles entry at 10 uM after 72 hrs by luciferase reporter gene assay2013Journal of medicinal chemistry, Jun-13, Volume: 56, Issue:11
Development of oleanane-type triterpenes as a new class of HCV entry inhibitors.
AID1159135Induction of apoptosis in human MCF7 cells at 20 uM after 48 hrs by Hoechst 33258/propidium iodide staining based phase contrast microscopic analysis2014European journal of medicinal chemistry, Jul-23, Volume: 82Synthesis, antimicrobial and cytotoxic activities, and structure-activity relationships of gypsogenin derivatives against human cancer cells.
AID1159128Antiproliferative activity against human Saos2 cells after 24 and 72 hrs by MTT assay2014European journal of medicinal chemistry, Jul-23, Volume: 82Synthesis, antimicrobial and cytotoxic activities, and structure-activity relationships of gypsogenin derivatives against human cancer cells.
AID1159136Induction of apoptosis in human HeLa cells at 20 uM after 48 hrs by Hoechst 33258/propidium iodide staining based phase contrast microscopic analysis2014European journal of medicinal chemistry, Jul-23, Volume: 82Synthesis, antimicrobial and cytotoxic activities, and structure-activity relationships of gypsogenin derivatives against human cancer cells.
AID1159069Antimicrobial activity against Klebsiella pneumoniae ATCC 13882 assessed as zone of inhibition at 30 uL for 24 hrs at 37 degC by disk diffusion test2014European journal of medicinal chemistry, Jul-23, Volume: 82Synthesis, antimicrobial and cytotoxic activities, and structure-activity relationships of gypsogenin derivatives against human cancer cells.
AID1159132Induction of apoptosis in human HT-29 cells at 20 uM after 48 hrs by Hoechst 33258/propidium iodide staining based phase contrast microscopic analysis2014European journal of medicinal chemistry, Jul-23, Volume: 82Synthesis, antimicrobial and cytotoxic activities, and structure-activity relationships of gypsogenin derivatives against human cancer cells.
AID1617780Inhibition of human recombinant COX2 expressed in baculovirus infected sf21 cells assessed as decrease in PGE2 formation using arachidonic acid as substrate preincubated for 10 mins followed by substrate addition measured after 45 mins by LC-MS analysis2019Journal of natural products, 12-27, Volume: 82, Issue:12
Structure-Activity Relationships of Pentacyclic Triterpenoids as Inhibitors of Cyclooxygenase and Lipoxygenase Enzymes.
AID1159138Induction of necrosis in human HT-29 cells at 20 uM after 48 hrs by Hoechst 33258/propidium iodide staining based phase contrast microscopic analysis2014European journal of medicinal chemistry, Jul-23, Volume: 82Synthesis, antimicrobial and cytotoxic activities, and structure-activity relationships of gypsogenin derivatives against human cancer cells.
AID1159072Antimicrobial activity against Enterococcus faecalis ATCC 29212 assessed as zone of inhibition at 30 uL for 24 hrs at 37 degC by disk diffusion test2014European journal of medicinal chemistry, Jul-23, Volume: 82Synthesis, antimicrobial and cytotoxic activities, and structure-activity relationships of gypsogenin derivatives against human cancer cells.
AID1617781Inhibition of human recombinant COX2 expressed in baculovirus infected sf21 cells assessed as residual activity at 42 uM using arachidonic acid as substrate preincubated for 10 mins followed by substrate addition measured after 45 mins by LC-MS analysis r2019Journal of natural products, 12-27, Volume: 82, Issue:12
Structure-Activity Relationships of Pentacyclic Triterpenoids as Inhibitors of Cyclooxygenase and Lipoxygenase Enzymes.
AID1159073Antimicrobial activity against Bacillus cereus ATCC 11778 assessed as zone of inhibition at 30 uL for 24 hrs at 30 degC by disk diffusion test2014European journal of medicinal chemistry, Jul-23, Volume: 82Synthesis, antimicrobial and cytotoxic activities, and structure-activity relationships of gypsogenin derivatives against human cancer cells.
AID1617774Inhibition of human recombinant 5-LOX expressed in insect cells assessed as decrease in production of 5-HPETE and 5-HETE using arachidonic acid as substrate preincubated for 5 mins followed by substrate addition measured after 20 mins in dark by ferric io2019Journal of natural products, 12-27, Volume: 82, Issue:12
Structure-Activity Relationships of Pentacyclic Triterpenoids as Inhibitors of Cyclooxygenase and Lipoxygenase Enzymes.
AID1678888Antileishmanial activity against axenic amastigote stage of Leishmania mexicana (MNYC/BZ/62/M379) assessed as induction of parasite killing incubated for 24 hrs by alamar blue dye based fluorescence analysis2020RSC medicinal chemistry, Jul-01, Volume: 11, Issue:7
An investigation of the antileishmanial properties of semi-synthetic saponins.
AID1159131Induction of apoptosis in human HL60 cells at 20 uM after 48 hrs by Hoechst 33258/propidium iodide staining based phase contrast microscopic analysis2014European journal of medicinal chemistry, Jul-23, Volume: 82Synthesis, antimicrobial and cytotoxic activities, and structure-activity relationships of gypsogenin derivatives against human cancer cells.
AID1617779Inhibition of ovine recombinant COX1 assessed as residual activity at 42 uM using arachidonic acid as substrate preincubated for 10 mins followed by substrate addition measured after 45 mins by LC-MS analysis2019Journal of natural products, 12-27, Volume: 82, Issue:12
Structure-Activity Relationships of Pentacyclic Triterpenoids as Inhibitors of Cyclooxygenase and Lipoxygenase Enzymes.
AID1159134Induction of apoptosis in human Saos2 cells at 20 uM after 48 hrs by Hoechst 33258/propidium iodide staining based phase contrast microscopic analysis2014European journal of medicinal chemistry, Jul-23, Volume: 82Synthesis, antimicrobial and cytotoxic activities, and structure-activity relationships of gypsogenin derivatives against human cancer cells.
AID1159125Antiproliferative activity against human HL60 cells after 24 and 72 hrs by MTT assay2014European journal of medicinal chemistry, Jul-23, Volume: 82Synthesis, antimicrobial and cytotoxic activities, and structure-activity relationships of gypsogenin derivatives against human cancer cells.
AID1159065Antimicrobial activity against Salmonella typhimurium ATCC 14028 assessed as zone of inhibition at 30 uL for 24 hrs at 37 degC by disk diffusion test2014European journal of medicinal chemistry, Jul-23, Volume: 82Synthesis, antimicrobial and cytotoxic activities, and structure-activity relationships of gypsogenin derivatives against human cancer cells.
AID1678886Selectivity index, ratio of ED50 for mouse RAW264.7 cells to ED50 for antileishmanial activity against axenic amastigote stage of Leishmania mexicana (MNYC/BZ/62/M379)2020RSC medicinal chemistry, Jul-01, Volume: 11, Issue:7
An investigation of the antileishmanial properties of semi-synthetic saponins.
AID1159141Induction of necrosis in human MCF7 cells at 20 uM after 48 hrs by Hoechst 33258/propidium iodide staining based phase contrast microscopic analysis2014European journal of medicinal chemistry, Jul-23, Volume: 82Synthesis, antimicrobial and cytotoxic activities, and structure-activity relationships of gypsogenin derivatives against human cancer cells.
AID1678889Antileishmanial activity against axenic amastigote stage of Leishmania mexicana (MNYC/BZ/62/M379) assessed as inhibition of parasite proliferation at 50 uM incubated for 24 hrs by alamar blue dye based fluorescence analysis2020RSC medicinal chemistry, Jul-01, Volume: 11, Issue:7
An investigation of the antileishmanial properties of semi-synthetic saponins.
AID1159137Induction of necrosis in human HL60 cells at 20 uM after 48 hrs by Hoechst 33258/propidium iodide staining based phase contrast microscopic analysis2014European journal of medicinal chemistry, Jul-23, Volume: 82Synthesis, antimicrobial and cytotoxic activities, and structure-activity relationships of gypsogenin derivatives against human cancer cells.
AID1159077Antimicrobial activity against Candida utilis ATCC 9950 assessed as zone of inhibition at 30 uL for 24 hrs at 30 degC by disk diffusion test2014European journal of medicinal chemistry, Jul-23, Volume: 82Synthesis, antimicrobial and cytotoxic activities, and structure-activity relationships of gypsogenin derivatives against human cancer cells.
AID1159129Antiproliferative activity against human MCF7 cells after 24 and 72 hrs by MTT assay2014European journal of medicinal chemistry, Jul-23, Volume: 82Synthesis, antimicrobial and cytotoxic activities, and structure-activity relationships of gypsogenin derivatives against human cancer cells.
AID1159080Antimicrobial activity against Saccharomyces cerevisiae ATCC 9763 assessed as zone of inhibition at 30 uL for 24 hrs at 30 degC by disk diffusion test2014European journal of medicinal chemistry, Jul-23, Volume: 82Synthesis, antimicrobial and cytotoxic activities, and structure-activity relationships of gypsogenin derivatives against human cancer cells.
AID1159126Antiproliferative activity against human HT-29 cells after 24 and 72 hrs by MTT assay2014European journal of medicinal chemistry, Jul-23, Volume: 82Synthesis, antimicrobial and cytotoxic activities, and structure-activity relationships of gypsogenin derivatives against human cancer cells.
AID1617775Inhibition of human recombinant 5-LOX expressed in insect cells assessed residual activity using arachidonic acid at 42 uM as substrate preincubated for 5 mins followed by substrate addition measured after 20 mins in dark by ferric ion oxidation-xylenol o2019Journal of natural products, 12-27, Volume: 82, Issue:12
Structure-Activity Relationships of Pentacyclic Triterpenoids as Inhibitors of Cyclooxygenase and Lipoxygenase Enzymes.
AID1159068Antimicrobial activity against Staphylococcus epidermidis ATCC 12228 assessed as zone of inhibition at 30 uL for 24 hrs at 37 degC by disk diffusion test2014European journal of medicinal chemistry, Jul-23, Volume: 82Synthesis, antimicrobial and cytotoxic activities, and structure-activity relationships of gypsogenin derivatives against human cancer cells.
AID1159127Antiproliferative activity against human Caco2 cells after 24 and 72 hrs by MTT assay2014European journal of medicinal chemistry, Jul-23, Volume: 82Synthesis, antimicrobial and cytotoxic activities, and structure-activity relationships of gypsogenin derivatives against human cancer cells.
AID1159075Antimicrobial activity against Bacillus thuringiensis assessed as zone of inhibition at 30 uL for 24 hrs at 30 degC by disk diffusion test2014European journal of medicinal chemistry, Jul-23, Volume: 82Synthesis, antimicrobial and cytotoxic activities, and structure-activity relationships of gypsogenin derivatives against human cancer cells.
AID1159076Antimicrobial activity against Candida albicans ATCC 10231 assessed as zone of inhibition at 30 uL for 24 hrs at 30 degC by disk diffusion test2014European journal of medicinal chemistry, Jul-23, Volume: 82Synthesis, antimicrobial and cytotoxic activities, and structure-activity relationships of gypsogenin derivatives against human cancer cells.
AID1159074Antimicrobial activity against Bacillus subtilis ATCC 6633 assessed as zone of inhibition at 30 uL for 24 hrs at 30 degC by disk diffusion test2014European journal of medicinal chemistry, Jul-23, Volume: 82Synthesis, antimicrobial and cytotoxic activities, and structure-activity relationships of gypsogenin derivatives against human cancer cells.
AID1159124Antimicrobial activity against Bacillus thuringiensis for 24 hrs by microdillution method2014European journal of medicinal chemistry, Jul-23, Volume: 82Synthesis, antimicrobial and cytotoxic activities, and structure-activity relationships of gypsogenin derivatives against human cancer cells.
AID1159133Induction of apoptosis in human Caco2 cells at 20 uM after 48 hrs by Hoechst 33258/propidium iodide staining based phase contrast microscopic analysis2014European journal of medicinal chemistry, Jul-23, Volume: 82Synthesis, antimicrobial and cytotoxic activities, and structure-activity relationships of gypsogenin derivatives against human cancer cells.
AID1159066Antimicrobial activity against Micrococcus luteus ATCC 9341 assessed as zone of inhibition at 30 uL for 24 hrs at 30 degC by disk diffusion test2014European journal of medicinal chemistry, Jul-23, Volume: 82Synthesis, antimicrobial and cytotoxic activities, and structure-activity relationships of gypsogenin derivatives against human cancer cells.
AID1617776Inhibition of human recombinant N-terminal His-tagged 15-LOX2 expressed in Escherichia coli using arachidonic acid as substrate preincubated for 5 mins followed by substrate addition measured after 20 mins in dark by ferric ion oxidation-xylenol orange as2019Journal of natural products, 12-27, Volume: 82, Issue:12
Structure-Activity Relationships of Pentacyclic Triterpenoids as Inhibitors of Cyclooxygenase and Lipoxygenase Enzymes.
AID1617777Inhibition of human recombinant N-terminal His-tagged 15-LOX2 expressed in Escherichia coli assessed as residual activity at 42 uM using arachidonic acid as substrate preincubated for 5 mins followed by substrate addition measured after 20 mins in dark by2019Journal of natural products, 12-27, Volume: 82, Issue:12
Structure-Activity Relationships of Pentacyclic Triterpenoids as Inhibitors of Cyclooxygenase and Lipoxygenase Enzymes.
AID1159071Antimicrobial activity against Proteus vulgaris ATCC 33420 assessed as zone of inhibition at 30 uL for 24 hrs at 37 degC by disk diffusion test2014European journal of medicinal chemistry, Jul-23, Volume: 82Synthesis, antimicrobial and cytotoxic activities, and structure-activity relationships of gypsogenin derivatives against human cancer cells.
AID1678887Cytotoxicity against mouse RAW264.7 cells assessed as induction of cell killing incubated for 24 hrs by alamar blue dye based fluorescence analysis2020RSC medicinal chemistry, Jul-01, Volume: 11, Issue:7
An investigation of the antileishmanial properties of semi-synthetic saponins.
AID1159139Induction of necrosis in human Caco2 cells at 20 uM after 48 hrs by Hoechst 33258/propidium iodide staining based phase contrast microscopic analysis2014European journal of medicinal chemistry, Jul-23, Volume: 82Synthesis, antimicrobial and cytotoxic activities, and structure-activity relationships of gypsogenin derivatives against human cancer cells.
AID1159130Antiproliferative activity against human HeLa cells after 24 and 72 hrs by MTT assay2014European journal of medicinal chemistry, Jul-23, Volume: 82Synthesis, antimicrobial and cytotoxic activities, and structure-activity relationships of gypsogenin derivatives against human cancer cells.
AID1159067Antimicrobial activity against Staphylococcus aureus ATCC 25923 assessed as zone of inhibition at 30 uL for 24 hrs at 37 degC by disk diffusion test2014European journal of medicinal chemistry, Jul-23, Volume: 82Synthesis, antimicrobial and cytotoxic activities, and structure-activity relationships of gypsogenin derivatives against human cancer cells.
AID1159122Antimicrobial activity against Bacillus cereus ATCC 11778 for 24 hrs by microdillution method2014European journal of medicinal chemistry, Jul-23, Volume: 82Synthesis, antimicrobial and cytotoxic activities, and structure-activity relationships of gypsogenin derivatives against human cancer cells.
AID1159140Induction of necrosis in human Saos2 cells at 20 uM after 48 hrs by Hoechst 33258/propidium iodide staining based phase contrast microscopic analysis2014European journal of medicinal chemistry, Jul-23, Volume: 82Synthesis, antimicrobial and cytotoxic activities, and structure-activity relationships of gypsogenin derivatives against human cancer cells.
AID1159078Antimicrobial activity against Candida tropicalis assessed as zone of inhibition at 30 uL for 24 hrs at 30 degC by disk diffusion test2014European journal of medicinal chemistry, Jul-23, Volume: 82Synthesis, antimicrobial and cytotoxic activities, and structure-activity relationships of gypsogenin derivatives against human cancer cells.
AID1159142Induction of necrosis in human HeLa cells at 20 uM after 48 hrs by Hoechst 33258/propidium iodide staining based phase contrast microscopic analysis2014European journal of medicinal chemistry, Jul-23, Volume: 82Synthesis, antimicrobial and cytotoxic activities, and structure-activity relationships of gypsogenin derivatives against human cancer cells.
AID1159079Antimicrobial activity against Candida glabrata assessed as zone of inhibition at 30 uL for 24 hrs at 30 degC by disk diffusion test2014European journal of medicinal chemistry, Jul-23, Volume: 82Synthesis, antimicrobial and cytotoxic activities, and structure-activity relationships of gypsogenin derivatives against human cancer cells.
AID1617778Inhibition of ovine recombinant COX1 assessed as decrease in formation of PGE2 using arachidonic acid as substrate preincubated for 10 mins followed by substrate addition measured after 45 mins by LC-MS analysis2019Journal of natural products, 12-27, Volume: 82, Issue:12
Structure-Activity Relationships of Pentacyclic Triterpenoids as Inhibitors of Cyclooxygenase and Lipoxygenase Enzymes.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (12)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's0 (0.00)29.6817
2010's6 (50.00)24.3611
2020's6 (50.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 25.43

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 moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index25.43 (24.57)
Research Supply Index2.56 (2.92)
Research Growth Index4.66 (4.65)
Search Engine Demand Index26.67 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (25.43)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (8.33%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other11 (91.67%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]