Page last updated: 2024-11-07

phaseollidin

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

Description

Phaseollidin is a naturally occurring indole alkaloid isolated from the seeds of Phaseolus vulgaris (common bean). It exhibits a wide range of biological activities, including anti-inflammatory, anticancer, and antimicrobial properties. Its synthesis has been achieved through various chemical approaches, including multi-step reactions involving indole derivatives and other organic compounds. Phaseollidin's biological effects are attributed to its ability to interact with various cellular targets, such as enzymes, receptors, and DNA. Its anti-inflammatory activity is associated with its inhibition of pro-inflammatory mediators, while its anticancer potential arises from its ability to induce apoptosis and inhibit cell proliferation. Phaseollidin's antimicrobial activity stems from its ability to disrupt bacterial cell membranes and inhibit their growth. Due to its multifaceted biological activities, phaseollidin is a promising candidate for the development of novel drugs for the treatment of various diseases. Researchers are actively investigating its pharmacological properties, exploring its potential applications in medicine and agriculture. The study of phaseollidin is driven by its potential to provide new therapeutic strategies for addressing unmet medical needs.'

phaseollidin: from Erythrina burana; RN refers to (6aR-cis)-isomer; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

phaseollidin : A member of the class of pterocarpans that is (6aR,11aR)-pterocarpan substituted by hydroxy groups at positions 3 and 9 and a prenyl group at position 10. [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
ErythrinagenusA genus of leguminous shrubs or trees, mainly tropical, yielding useful compounds such as ALKALOIDS and PLANT LECTINS.[MeSH]FabaceaeThe large family of plants characterized by pods. Some are edible and some cause LATHYRISM or FAVISM and other forms of poisoning. Other species yield useful materials like gums from ACACIA and various LECTINS like PHYTOHEMAGGLUTININS from PHASEOLUS. Many of them harbor NITROGEN FIXATION bacteria on their roots. Many but not all species of beans belong to this family.[MeSH]

Cross-References

ID SourceID
PubMed CID119268
CHEMBL ID508534
CHEBI ID17556
SCHEMBL ID1545850
MeSH IDM0226105

Synonyms (19)

Synonym
(6ar,11ar)-10-(3-methylbut-2-en-1-yl)-6a,11a-dihydro-6h-[1]benzofuro[3,2-c]chromene-3,9-diol
CHEBI:17556 ,
C05230
phaseollidin
37831-70-2
(-)-phaseollidin
CHEMBL508534 ,
phaseolidin
bdbm50311583
LMPK12070011
(6ar,11ar)-10-(3-methylbut-2-enyl)-6a,11a-dihydro-6h-[1]benzofuro[3,2-c]chromene-3,9-diol
6h-benzofuro(3,2-c)(1)benzopyran-3,9-diol, 6a,11a-dihydro-10-(3-methyl-2-butenyl)-, (6ar,11ar)-
6h-benzofuro(3,2-c)(1)benzopyran-3,9-diol, 6a,11a-dihydro-10-(3-methyl-2-butenyl)-, (6ar-cis)-
SCHEMBL1545850
DTXSID50191270
AKOS032948450
FS-9847
Q27102457
(6ar,11ar)-6a,11a-dihydro-10-(3-methyl-2-buten-1-yl)-6h-benzofuro[3,2-c][1]benzopyran-3,9-diol; phaseolidin
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
pterocarpansMembers of the class of benzofurochromene with a 6a,11a-dihydro-6H-[1]benzofuro[3,2-c]chromene skeleton and its substituted derivatives. They generally bear structural resemblance to isoflavanoids that possess antibiotic activity and are produced by plant tissues in response to infection. They are the 3,4-dihydroderivatives of coumestans.
[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 (3)

PathwayProteinsCompounds
pterocarpan phytoalexins modification (maackiain, medicarpin, pisatin, phaseollin)424
phaseollin biosynthesis010
superpathway of pterocarpan biosynthesis (via daidzein)026

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Tyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)IC50 (µMol)30.00000.00053.49849.7600AID467753
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (27)

Processvia Protein(s)Taxonomy
positive regulation of JUN kinase activityTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
protein dephosphorylationTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
insulin receptor signaling pathwayTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
regulation of signal transductionTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
negative regulation of signal transductionTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
actin cytoskeleton organizationTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
regulation of endocytosisTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
negative regulation of vascular endothelial growth factor receptor signaling pathwayTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
endoplasmic reticulum unfolded protein responseTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
regulation of intracellular protein transportTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
cellular response to unfolded proteinTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
peptidyl-tyrosine dephosphorylationTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
platelet-derived growth factor receptor-beta signaling pathwayTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
IRE1-mediated unfolded protein responseTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
insulin receptor recyclingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
negative regulation of MAP kinase activityTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
negative regulation of insulin receptor signaling pathwayTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
regulation of type I interferon-mediated signaling pathwayTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
growth hormone receptor signaling pathway via JAK-STATTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
positive regulation of protein tyrosine kinase activityTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
negative regulation of ERK1 and ERK2 cascadeTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
regulation of hepatocyte growth factor receptor signaling pathwayTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
negative regulation of endoplasmic reticulum stress-induced intrinsic apoptotic signaling pathwayTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
positive regulation of IRE1-mediated unfolded protein responseTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
negative regulation of PERK-mediated unfolded protein responseTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
peptidyl-tyrosine dephosphorylation involved in inactivation of protein kinase activityTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
positive regulation of receptor catabolic processTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (12)

Processvia Protein(s)Taxonomy
RNA bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
protein tyrosine phosphatase activityTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
insulin receptor bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
protein bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
zinc ion bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
enzyme bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
protein kinase bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
receptor tyrosine kinase bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
cadherin bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
ephrin receptor bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
protein phosphatase 2A bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
non-membrane spanning protein tyrosine phosphatase activityTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (11)

Processvia Protein(s)Taxonomy
plasma membraneTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
cytoplasmTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
mitochondrial matrixTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
early endosomeTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
endoplasmic reticulumTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
cytosolTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
mitochondrial cristaTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
endosome lumenTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
sorting endosomeTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
cytoplasmic side of endoplasmic reticulum membraneTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
protein-containing complexTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
endoplasmic reticulumTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
cytoplasmTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
early endosomeTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (22)

Assay IDTitleYearJournalArticle
AID359677Antimicrobial activity against Escherichia coli IFO 3545 after 2 days by twofold serial broth dilution method1993Journal of natural products, Sep, Volume: 56, Issue:9
Ethnobotanical drug discovery based on medicine men's trials in the African savanna: screening of east African plants for antimicrobial activity II.
AID336041DNA damaging activity against RS321 rad321 DNA repair gene deficient Saccharomyces cerevisiae mutant assessed as drug level required to produce 12 mm zone of inhibition after 48 hrs1993Journal of natural products, Oct, Volume: 56, Issue:10
Two bioactive pterocarpans from Erythrina burana.
AID336043Cytotoxicity against mouse P388 cells1993Journal of natural products, Oct, Volume: 56, Issue:10
Two bioactive pterocarpans from Erythrina burana.
AID336042DNA damaging activity against RS188N rad DNA repair gene expressing Saccharomyces cerevisiae assessed as drug level required to produce 12 mm zone of inhibition after 48 hrs1993Journal of natural products, Oct, Volume: 56, Issue:10
Two bioactive pterocarpans from Erythrina burana.
AID359679Antimicrobial activity against Staphylococcus aureus NCTC 8530 after 2 days by twofold serial broth dilution method1993Journal of natural products, Sep, Volume: 56, Issue:9
Ethnobotanical drug discovery based on medicine men's trials in the African savanna: screening of east African plants for antimicrobial activity II.
AID467753Inhibition of human recombinant PTP1B assessed as p-nitrophenol production2009Bioorganic & medicinal chemistry letters, Dec-01, Volume: 19, Issue:23
Cytotoxic and PTP1B inhibitory activities from Erythrina abyssinica.
AID359675Antimicrobial activity against Saccharomyces cerevisiae IFO 0203 after 2 days by twofold serial broth dilution method1993Journal of natural products, Sep, Volume: 56, Issue:9
Ethnobotanical drug discovery based on medicine men's trials in the African savanna: screening of east African plants for antimicrobial activity II.
AID467756Cytotoxicity against human adriamycin- resistant MCF7 cells by WST-1 assay2009Bioorganic & medicinal chemistry letters, Dec-01, Volume: 19, Issue:23
Cytotoxic and PTP1B inhibitory activities from Erythrina abyssinica.
AID359674Antimicrobial activity against Candida utilis ATCC 42402 after 2 days by twofold serial broth dilution method1993Journal of natural products, Sep, Volume: 56, Issue:9
Ethnobotanical drug discovery based on medicine men's trials in the African savanna: screening of east African plants for antimicrobial activity II.
AID359676Antimicrobial activity against Pseudomonas aeruginosa IAM 1007 after 2 days by twofold serial broth dilution method1993Journal of natural products, Sep, Volume: 56, Issue:9
Ethnobotanical drug discovery based on medicine men's trials in the African savanna: screening of east African plants for antimicrobial activity II.
AID359672Antimicrobial activity against Penicillium crustosum Thom after 2 days by twofold serial broth dilution method1993Journal of natural products, Sep, Volume: 56, Issue:9
Ethnobotanical drug discovery based on medicine men's trials in the African savanna: screening of east African plants for antimicrobial activity II.
AID467754Cytotoxicity against human MCF7 cells by WST-1 assay2009Bioorganic & medicinal chemistry letters, Dec-01, Volume: 19, Issue:23
Cytotoxic and PTP1B inhibitory activities from Erythrina abyssinica.
AID467757Cytotoxicity against human MDA-MB-231 cells by WST-1 assay2009Bioorganic & medicinal chemistry letters, Dec-01, Volume: 19, Issue:23
Cytotoxic and PTP1B inhibitory activities from Erythrina abyssinica.
AID422532Inhibition of melanin synthesis in NHEM after 24 hrs by liquid scintillation2009Journal of natural products, Jan, Volume: 72, Issue:1
Melanin synthesis inhibitors from Lespedeza cyrtobotrya.
AID359678Antimicrobial activity against Bacillus subtilis ATCC 6633 after 2 days by twofold serial broth dilution method1993Journal of natural products, Sep, Volume: 56, Issue:9
Ethnobotanical drug discovery based on medicine men's trials in the African savanna: screening of east African plants for antimicrobial activity II.
AID336039DNA damaging activity against RS322 YK rad52 DNA repair gene deficient Saccharomyces cerevisiae mutant assessed as drug level required to produce 12 mm zone of inhibition after 48 hrs1993Journal of natural products, Oct, Volume: 56, Issue:10
Two bioactive pterocarpans from Erythrina burana.
AID336045Cytotoxicity against p-glycoprotein overexpressing CHO cells1993Journal of natural products, Oct, Volume: 56, Issue:10
Two bioactive pterocarpans from Erythrina burana.
AID467755Cytotoxicity against human tamoxifen-resistant MCF7 cells by WST-1 assay2009Bioorganic & medicinal chemistry letters, Dec-01, Volume: 19, Issue:23
Cytotoxic and PTP1B inhibitory activities from Erythrina abyssinica.
AID336044Cytotoxicity against CHO cells1993Journal of natural products, Oct, Volume: 56, Issue:10
Two bioactive pterocarpans from Erythrina burana.
AID359673Antimicrobial activity against Mucor mucedo IFO 7684 after 2 days by twofold serial broth dilution method1993Journal of natural products, Sep, Volume: 56, Issue:9
Ethnobotanical drug discovery based on medicine men's trials in the African savanna: screening of east African plants for antimicrobial activity II.
AID422533Cytotoxicity against NHEM cells assessed as cell viability 24 hrs by WST-8 assay2009Journal of natural products, Jan, Volume: 72, Issue:1
Melanin synthesis inhibitors from Lespedeza cyrtobotrya.
AID336040DNA damaging activity against RS167 N rad6 DNA repair gene deficient Saccharomyces cerevisiae mutant assessed as drug level required to produce 12 mm zone of inhibition after 48 hrs1993Journal of natural products, Oct, Volume: 56, Issue:10
Two bioactive pterocarpans from Erythrina burana.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (6)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's2 (33.33)18.2507
2000's2 (33.33)29.6817
2010's1 (16.67)24.3611
2020's1 (16.67)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.56

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

MetricThis Compound (vs All)
Research Demand Index12.56 (24.57)
Research Supply Index1.95 (2.92)
Research Growth Index4.51 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.56)

All Compounds (24.57)

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%
Other6 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]