Page last updated: 2024-09-28

umbelliprenin

Description

umbelliprenin: RN given refers to cpd with unspecified isomeric designation [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID1781413
CHEMBL ID156127
CHEBI ID172086
SCHEMBL ID18265478
MeSH IDM0044841

Synonyms (29)

Synonym
CHEBI:172086
532-16-1
7-[(2e,6e)-3,7,11-trimethyldodeca-2,6,10-trienoxy]chromen-2-one
umbelliprenin
bdbm50143435
7-((2e,6e)-3,7,11-trimethyl-dodeca-2,6,10-trienyloxy)-chromen-2-one
MLS002472936
smr001397045
CHEMBL156127 ,
NCGC00247456-01
30413-87-7
coumarin, 7-((3,7,22-trimethyl-2,6,10-dodecatrienyl)oxy)-
HMS2205K17
(e,e)-7-((3,7,11-trimethyl-2,6,10-dodecatrienyl)oxy)-2h-1-benzopyran-2-one
angelin
msd8n8a1lq ,
23838-17-7
unii-msd8n8a1lq
7-farnesyloxycoumarin
2h-1-benzopyran-2-one, 7-(((2e,6e)-3,7,11-trimethyl-2,6,10-dodecatrien-1-yl)oxy)-
umbelliprenine
SCHEMBL18265478
7-(((2e,6e)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl)oxy)-2h-chromen-2-one
Q27284214
XU163805
DTXSID901317603
7-[[(2e,6e)-3,7,11-trimethyl-2,6,10-dodecatrienyl]oxy]-2h-1-benzopyran-2-one
AKOS040763680
2h-1-benzopyran-2-one, 7-[(3,7,11-trimethyl-2,6,10-dodecatrien-1-yl)oxy]-

Research Excerpts

Overview

ExcerptReference
"Umbelliprenin is a secondary plant metabolite that displays promising chemopreventive, anti-inflammatory, and antigenotoxic properties. "( Bize, C; de Medina, P; Epifano, F; Fiorito, S; Genovese, S; Rives, A; Taddeo, VA, 2017)
"Umbelliprenin is a sesquiterpene coumarin isolated from Artemisia absinthium L. "( Huang, X; Liu, Y; Wang, H; Wang, Y; Xia, G; Xu, T, 2023)
"Umbelliprenin (UMB) is a prenylated coumarin that acts as an in vitro antioxidant and inhibits lipoxygenase managing the inflammation pathways, while in vivo it exerts anti-inflammatory activities."( Bagheri, G; Hashemzaei, M; Jahantigh, H; Mohammadzehi Kenar, S; Rezaee, R; Setoodeh Nezhad, S; Shahraki, J; Tsarouhas, K, 2020)
"Umbelliprenin is a member of the 7-prenyloxycoumarins with potential therapeutic properties such as cytotoxic effects on various cancer cells. "( Ghaderi, A; Hosseinzadeh, M; Khaghanzadeh, N; Mojtahedi, Z; Ramezani, M; Samiei, A, 2014)
"Umbelliprenin is a prenylated compound, which belongs to the class of sesquiterpene coumarins. "( Iranshahi, M; Konoshima, T; Sahebkar, A; Takasaki, M; Tokuda, H, 2009)

Effects

ExcerptReference
"Umbelliprenin (UMB) has shown various pharmacological properties in vitro. "( Amani, D; Bazi, A; Jamshidi, H; Khalilnezhad, A; Muhammadnejad, A; Rashidi, M; Ziai, SA, 2018)

Drug Classes (1)

ClassDescription
terpene lactone
[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 (16)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, TYROSYL-DNA PHOSPHODIESTERASEHomo sapiens (human)Potency44.66840.004023.8416100.0000AID485290
Chain A, JmjC domain-containing histone demethylation protein 3AHomo sapiens (human)Potency56.23410.631035.7641100.0000AID504339
acid sphingomyelinaseHomo sapiens (human)Potency31.622814.125424.061339.8107AID504937
thioredoxin reductaseRattus norvegicus (Norway rat)Potency63.09570.100020.879379.4328AID588456
TDP1 proteinHomo sapiens (human)Potency23.72460.000811.382244.6684AID686978; AID686979
PINK1Homo sapiens (human)Potency50.11872.818418.895944.6684AID624263
ParkinHomo sapiens (human)Potency50.11870.819914.830644.6684AID624263
chromobox protein homolog 1Homo sapiens (human)Potency50.11870.006026.168889.1251AID540317
importin subunit beta-1 isoform 1Homo sapiens (human)Potency112.20205.804836.130665.1308AID540263
flap endonuclease 1Homo sapiens (human)Potency79.43280.133725.412989.1251AID588795
snurportin-1Homo sapiens (human)Potency112.20205.804836.130665.1308AID540263
DNA polymerase iota isoform a (long)Homo sapiens (human)Potency79.43280.050127.073689.1251AID588590
gemininHomo sapiens (human)Potency0.46110.004611.374133.4983AID624297
[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)
Polyunsaturated fatty acid lipoxygenase ALOX15Homo sapiens (human)IC50 (µMol)16.70000.04002.099810.0000AID683124
Squalene--hopene cyclaseAlicyclobacillus acidocaldarius subsp. acidocaldarius DSM 446IC50 (µMol)70.00000.06003.53007.0000AID204671
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Melatonin receptor type 1AHomo sapiens (human)KiH0.00160.00160.00160.0016AID1347657
Melatonin receptor type 1AHomo sapiens (human)KiL0.00330.00330.00330.0033AID1347657
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (30)

Processvia Protein(s)Taxonomy
ossificationPolyunsaturated fatty acid lipoxygenase ALOX15Homo sapiens (human)
negative regulation of adaptive immune responsePolyunsaturated fatty acid lipoxygenase ALOX15Homo sapiens (human)
lipid metabolic processPolyunsaturated fatty acid lipoxygenase ALOX15Homo sapiens (human)
phosphatidylethanolamine biosynthetic processPolyunsaturated fatty acid lipoxygenase ALOX15Homo sapiens (human)
inflammatory responsePolyunsaturated fatty acid lipoxygenase ALOX15Homo sapiens (human)
positive regulation of cell-substrate adhesionPolyunsaturated fatty acid lipoxygenase ALOX15Homo sapiens (human)
arachidonic acid metabolic processPolyunsaturated fatty acid lipoxygenase ALOX15Homo sapiens (human)
lipoxygenase pathwayPolyunsaturated fatty acid lipoxygenase ALOX15Homo sapiens (human)
fatty acid oxidationPolyunsaturated fatty acid lipoxygenase ALOX15Homo sapiens (human)
bone mineralizationPolyunsaturated fatty acid lipoxygenase ALOX15Homo sapiens (human)
positive regulation of actin filament polymerizationPolyunsaturated fatty acid lipoxygenase ALOX15Homo sapiens (human)
response to endoplasmic reticulum stressPolyunsaturated fatty acid lipoxygenase ALOX15Homo sapiens (human)
regulation of peroxisome proliferator activated receptor signaling pathwayPolyunsaturated fatty acid lipoxygenase ALOX15Homo sapiens (human)
cellular response to interleukin-13Polyunsaturated fatty acid lipoxygenase ALOX15Homo sapiens (human)
wound healingPolyunsaturated fatty acid lipoxygenase ALOX15Homo sapiens (human)
long-chain fatty acid biosynthetic processPolyunsaturated fatty acid lipoxygenase ALOX15Homo sapiens (human)
apoptotic cell clearancePolyunsaturated fatty acid lipoxygenase ALOX15Homo sapiens (human)
linoleic acid metabolic processPolyunsaturated fatty acid lipoxygenase ALOX15Homo sapiens (human)
regulation of inflammatory responsePolyunsaturated fatty acid lipoxygenase ALOX15Homo sapiens (human)
hepoxilin biosynthetic processPolyunsaturated fatty acid lipoxygenase ALOX15Homo sapiens (human)
positive regulation of ERK1 and ERK2 cascadePolyunsaturated fatty acid lipoxygenase ALOX15Homo sapiens (human)
cellular response to calcium ionPolyunsaturated fatty acid lipoxygenase ALOX15Homo sapiens (human)
regulation of engulfment of apoptotic cellPolyunsaturated fatty acid lipoxygenase ALOX15Homo sapiens (human)
lipoxin A4 biosynthetic processPolyunsaturated fatty acid lipoxygenase ALOX15Homo sapiens (human)
lipid oxidationPolyunsaturated fatty acid lipoxygenase ALOX15Homo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messengerMelatonin receptor type 1AHomo sapiens (human)
adenylate cyclase-inhibiting G protein-coupled receptor signaling pathwayMelatonin receptor type 1AHomo sapiens (human)
mating behaviorMelatonin receptor type 1AHomo sapiens (human)
circadian rhythmMelatonin receptor type 1AHomo sapiens (human)
G protein-coupled receptor signaling pathwayMelatonin receptor type 1AHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (10)

Processvia Protein(s)Taxonomy
arachidonate 12(S)-lipoxygenase activityPolyunsaturated fatty acid lipoxygenase ALOX15Homo sapiens (human)
iron ion bindingPolyunsaturated fatty acid lipoxygenase ALOX15Homo sapiens (human)
protein bindingPolyunsaturated fatty acid lipoxygenase ALOX15Homo sapiens (human)
phosphatidylinositol-4,5-bisphosphate bindingPolyunsaturated fatty acid lipoxygenase ALOX15Homo sapiens (human)
linoleate 13S-lipoxygenase activityPolyunsaturated fatty acid lipoxygenase ALOX15Homo sapiens (human)
arachidonate 15-lipoxygenase activityPolyunsaturated fatty acid lipoxygenase ALOX15Homo sapiens (human)
protein bindingMelatonin receptor type 1AHomo sapiens (human)
melatonin receptor activityMelatonin receptor type 1AHomo sapiens (human)
hormone bindingMelatonin receptor type 1AHomo sapiens (human)
organic cyclic compound bindingMelatonin receptor type 1AHomo sapiens (human)
G protein-coupled receptor activityMelatonin receptor type 1AHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (6)

Processvia Protein(s)Taxonomy
lipid dropletPolyunsaturated fatty acid lipoxygenase ALOX15Homo sapiens (human)
cytosolPolyunsaturated fatty acid lipoxygenase ALOX15Homo sapiens (human)
plasma membranePolyunsaturated fatty acid lipoxygenase ALOX15Homo sapiens (human)
cytoplasmic side of plasma membranePolyunsaturated fatty acid lipoxygenase ALOX15Homo sapiens (human)
membranePolyunsaturated fatty acid lipoxygenase ALOX15Homo sapiens (human)
plasma membranePolyunsaturated fatty acid lipoxygenase ALOX15Homo sapiens (human)
cytosolPolyunsaturated fatty acid lipoxygenase ALOX15Homo sapiens (human)
plasma membraneMelatonin receptor type 1AHomo sapiens (human)
receptor complexMelatonin receptor type 1AHomo sapiens (human)
plasma membraneMelatonin receptor type 1AHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (95)

Assay IDTitleYearJournalArticle
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID504812Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID1347083qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: Viability assay - alamar blue signal for LASV Primary Screen2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347082qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: LASV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347086qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lymphocytic Choriomeningitis Arenaviruses (LCMV): LCMV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID504810Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID1359349Decrease in TRP1 mRNA expression in mouse Melan-a cells at 40 uM after 24 hrs by SYBR green dye based qRT-PCR analysis relative to control2018European journal of medicinal chemistry, May-25, Volume: 152Natural oxyprenylated coumarins are modulators of melanogenesis.
AID1501422Photochemical stability of the compound assessed as compound degradation under sunlight using solid samples measured up to 96 hrs by HPLC analysis2017Journal of natural products, 09-22, Volume: 80, Issue:9
Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species.
AID1501419Stability of the compound assessed as compound degradation in 0.1 M NaOH solution at 60 degC in EtOH solution after 96 hrs by HPLC analysis2017Journal of natural products, 09-22, Volume: 80, Issue:9
Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species.
AID1501439Photostability of the compound assessed as parent compound remaining under sunlight exposed for 3 days in EtOH solution measured by TLC method2017Journal of natural products, 09-22, Volume: 80, Issue:9
Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species.
AID1501437Photostability of the compound assessed as parent compound remaining under sunlight exposed for 6 days in EtOH solution measured in presence of UV-B filter octinoxate by TLC method2017Journal of natural products, 09-22, Volume: 80, Issue:9
Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species.
AID1501428Drug metabolism assessed as P2 metabolite formation under sunlight in EtOH solution after 4 days by TLC analysis2017Journal of natural products, 09-22, Volume: 80, Issue:9
Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species.
AID1347667Inhibition of cell migration in mouse mammary carcinoma cell at 100 uM after 24 hrs by inverted fluorescence microscopy based scratch assay relative to control2017Journal of natural products, 12-22, Volume: 80, Issue:12
Oxyprenylated Phenylpropanoids Bind to MT1 Melatonin Receptors and Inhibit Breast Cancer Cell Proliferation and Migration.
AID1501433Photostability of the compound assessed as parent compound remaining under sunlight exposed for 3 days in EtOH solution measured in presence of UV-B filter octinoxate by TLC method2017Journal of natural products, 09-22, Volume: 80, Issue:9
Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species.
AID1163511Cytotoxicity against human PANC1 cells under nutrient-rich condition after 24 hrs by WST8 dye based assay2014Bioorganic & medicinal chemistry letters, Oct-01, Volume: 24, Issue:19
Synthesis and biological evaluation of isoprenylated coumarins as potential anti-pancreatic cancer agents.
AID1501434Photostability of the compound assessed as parent compound remaining under sunlight exposed for 3 days in EtOH solution measured in presence of antioxidant DL-alpha-tocopherol acetate by TLC method2017Journal of natural products, 09-22, Volume: 80, Issue:9
Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species.
AID1347662Antiproliferative activity against human MCF7 cells at 1 nM to 100 uM after 24 hrs by MTT assay relative to control2017Journal of natural products, 12-22, Volume: 80, Issue:12
Oxyprenylated Phenylpropanoids Bind to MT1 Melatonin Receptors and Inhibit Breast Cancer Cell Proliferation and Migration.
AID1347666Inhibition of cell migration in human MCF7 cells at 100 uM after 24 hrs by inverted fluorescence microscopy based scratch assay relative to control2017Journal of natural products, 12-22, Volume: 80, Issue:12
Oxyprenylated Phenylpropanoids Bind to MT1 Melatonin Receptors and Inhibit Breast Cancer Cell Proliferation and Migration.
AID1501423Photochemical stability of the compound assessed as compound degradation under 254 nm UV-light exposure using solid samples measured up to 96 hrs by HPLC analysis2017Journal of natural products, 09-22, Volume: 80, Issue:9
Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species.
AID1359353Effect on TRP2 expression in mouse Melan-a cells at 40 uM after 72 hrs by western blot analysis (Rvb = 1 No_unit)2018European journal of medicinal chemistry, May-25, Volume: 152Natural oxyprenylated coumarins are modulators of melanogenesis.
AID1501429Drug metabolism assessed as (6aR,6bS,12bS,12cR)-3,10-Bis-((2E,6E)-3,7,11-trimethyl-dodeca-2,6,10-trienyloxy)-6a,6b,12b,12c-tetrahydro-5,8-dioxa-dibenzo[a,i]biphenylene-6,7-dione formation under sunlight in EtOH solution after 6 days by 1H-NMR analysis2017Journal of natural products, 09-22, Volume: 80, Issue:9
Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species.
AID1359363Antimelanogenic activity in mouse Melan-a cells assessed as inhibition of UV irradiation-stimulated melanin synthesis at 40 uM measured after 72 hrs2018European journal of medicinal chemistry, May-25, Volume: 152Natural oxyprenylated coumarins are modulators of melanogenesis.
AID683122Inhibition of soybean 15-lipoxygenase by MBTH-DMAB method2012European journal of medicinal chemistry, Nov, Volume: 57Synthesis and SAR studies of mono O-prenylated coumarins as potent 15-lipoxygenase inhibitors.
AID1501413Thermal stability of the compound assessed as compound degradation at 80 degC in EtOH solution measured up to 96 hrs by HPLC analysis2017Journal of natural products, 09-22, Volume: 80, Issue:9
Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species.
AID607594Cytotoxicity against human OE21 cells after 72 hrs by MTT assay2011Bioorganic & medicinal chemistry letters, Jul-15, Volume: 21, Issue:14
Growth inhibitory activities of oxyprenylated and non-prenylated naturally occurring phenylpropanoids in cancer cell lines.
AID1359352Effect on tyrosinase expression in mouse Melan-a cells at 40 uM after 72 hrs by western blot analysis (Rvb = 1 No_unit)2018European journal of medicinal chemistry, May-25, Volume: 152Natural oxyprenylated coumarins are modulators of melanogenesis.
AID1501407Photochemical stability of the compound assessed as compound degradation under 254 nm UV-light exposure in EtOH solution measured after 24 hrs by HPLC analysis2017Journal of natural products, 09-22, Volume: 80, Issue:9
Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species.
AID607598Cytotoxicity against human LoVo cells after 72 hrs by MTT assay2011Bioorganic & medicinal chemistry letters, Jul-15, Volume: 21, Issue:14
Growth inhibitory activities of oxyprenylated and non-prenylated naturally occurring phenylpropanoids in cancer cell lines.
AID1359348Decrease in tyrosinase mRNA expression in mouse Melan-a cells at 40 uM after 24 hrs by SYBR green dye based qRT-PCR analysis relative to control2018European journal of medicinal chemistry, May-25, Volume: 152Natural oxyprenylated coumarins are modulators of melanogenesis.
AID1347668Inhibition of cell migration in human MDA-MB-231 cells at 100 uM after 24 hrs by inverted fluorescence microscopy based scratch assay relative to control2017Journal of natural products, 12-22, Volume: 80, Issue:12
Oxyprenylated Phenylpropanoids Bind to MT1 Melatonin Receptors and Inhibit Breast Cancer Cell Proliferation and Migration.
AID1501412Thermal stability of the compound at 40 degC in EtOH solution after 3 to 4 days by HPLC analysis2017Journal of natural products, 09-22, Volume: 80, Issue:9
Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species.
AID607600Induction of human U373 cell death assessed as morphological changes at MTT assay-related IC50 after 72 hrs by quantitative video microscopy2011Bioorganic & medicinal chemistry letters, Jul-15, Volume: 21, Issue:14
Growth inhibitory activities of oxyprenylated and non-prenylated naturally occurring phenylpropanoids in cancer cell lines.
AID1359355Effect on MITF expression in mouse Melan-a cells at 40 uM after 72 hrs by western blot analysis (Rvb = 1 No_unit)2018European journal of medicinal chemistry, May-25, Volume: 152Natural oxyprenylated coumarins are modulators of melanogenesis.
AID1272821Antileishmanial activity against stationary-phase promastigotes of Leishmania major MRHO/IR/75/ER assessed as parasite growth inhibition after 48 hrs by Neubar chamber method2016Bioorganic & medicinal chemistry letters, Feb-01, Volume: 26, Issue:3
Antileishmanial activity of novel indolyl-coumarin hybrids: Design, synthesis, biological evaluation, molecular docking study and in silico ADME prediction.
AID1359350Decrease in TRP2 mRNA expression in mouse Melan-a cells at 40 uM after 24 hrs by SYBR green dye based qRT-PCR analysis relative to control2018European journal of medicinal chemistry, May-25, Volume: 152Natural oxyprenylated coumarins are modulators of melanogenesis.
AID1347664Antiproliferative activity against human MDA-MB-231 cells at 1 nM to 100 uM after 24 hrs by MTT assay relative to control2017Journal of natural products, 12-22, Volume: 80, Issue:12
Oxyprenylated Phenylpropanoids Bind to MT1 Melatonin Receptors and Inhibit Breast Cancer Cell Proliferation and Migration.
AID1501415Stability of the compound assessed as compound degradation in 3% H2O2 solution at 40 degC in EtOH solution after 24 hrs by HPLC analysis2017Journal of natural products, 09-22, Volume: 80, Issue:9
Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species.
AID1501410Thermal stability of the compound assessed as compound degradation at 40 degC in EtOH solution after 48 hrs by HPLC analysis2017Journal of natural products, 09-22, Volume: 80, Issue:9
Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species.
AID1359343Inhibition of melanogenesis in mouse Melan-a cells assessed as effect on pigmentation at 40 uM after 72 hrs by photography2018European journal of medicinal chemistry, May-25, Volume: 152Natural oxyprenylated coumarins are modulators of melanogenesis.
AID1359354Effect on TRP1 expression in mouse Melan-a cells at 40 uM after 72 hrs by western blot analysis (Rvb = 1 No_unit)2018European journal of medicinal chemistry, May-25, Volume: 152Natural oxyprenylated coumarins are modulators of melanogenesis.
AID1501418Stability of the compound assessed as compound degradation in 0.1 M NaOH solution at room temperature in EtOH solution after 96 hrs by HPLC analysis2017Journal of natural products, 09-22, Volume: 80, Issue:9
Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species.
AID1359362Antimelanogenic activity in mouse Melan-a cells assessed as inhibition of alpha-MSH-stimulated melanin synthesis at 40 uM measured after 72 hrs2018European journal of medicinal chemistry, May-25, Volume: 152Natural oxyprenylated coumarins are modulators of melanogenesis.
AID1501438Photostability of the compound assessed as parent compound remaining under sunlight exposed for 6 days in EtOH solution measured in presence of antioxidant DL-alpha-tocopherol acetate by TLC method2017Journal of natural products, 09-22, Volume: 80, Issue:9
Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species.
AID607601Cytotoxicity against human U373 cells assessed as growth inhibition at MTT assay-related IC50 by quantitative video microscopy relative to control2011Bioorganic & medicinal chemistry letters, Jul-15, Volume: 21, Issue:14
Growth inhibitory activities of oxyprenylated and non-prenylated naturally occurring phenylpropanoids in cancer cell lines.
AID1501435Photostability of the compound assessed as parent compound remaining under sunlight exposed for 6 days in EtOH solution measured in presence of UV-A filter avobenzone by TLC method2017Journal of natural products, 09-22, Volume: 80, Issue:9
Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species.
AID1347657Displacement of 2-[125I]iodomelatonin from human MT1 receptor expressed in CHO cell lysates after 1 hr by gamma counting analysis2017Journal of natural products, 12-22, Volume: 80, Issue:12
Oxyprenylated Phenylpropanoids Bind to MT1 Melatonin Receptors and Inhibit Breast Cancer Cell Proliferation and Migration.
AID1501417Stability of the compound assessed as compound degradation in 3% H2O2 solution at 40 degC in EtOH solution after 96 hrs by HPLC analysis2017Journal of natural products, 09-22, Volume: 80, Issue:9
Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species.
AID1501440Photostability of the compound assessed as parent compound remaining under sunlight exposed for 6 days in EtOH solution measured by TLC method2017Journal of natural products, 09-22, Volume: 80, Issue:9
Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species.
AID1501406Photochemical stability of the compound assessed as compound degradation under sunlight in EtOH solution measured after 24 hrs by HPLC analysis2017Journal of natural products, 09-22, Volume: 80, Issue:9
Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species.
AID204671Inhibitory activity against squalene hopene cyclase from Alicyclobacillus acidocaldarius expressed in Escherichia coli2004Bioorganic & medicinal chemistry letters, Apr-19, Volume: 14, Issue:8
Farnesyloxycoumarins, a new class of squalene-hopene cyclase inhibitors.
AID683124Inhibition of recombinant human 15-lipoxygenase by MBTH-DMAB method2012European journal of medicinal chemistry, Nov, Volume: 57Synthesis and SAR studies of mono O-prenylated coumarins as potent 15-lipoxygenase inhibitors.
AID1359336Inhibition of melanogenesis in mouse Melan-a cells assessed as effect on whitening property measured after 48 hrs2018European journal of medicinal chemistry, May-25, Volume: 152Natural oxyprenylated coumarins are modulators of melanogenesis.
AID1501408Photochemical stability of the compound assessed as compound degradation under sunlight in EtOH solution measured after 4 days by HPLC analysis2017Journal of natural products, 09-22, Volume: 80, Issue:9
Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species.
AID1501427Drug metabolism assessed as (6aR,6bS,12bS,12cR)-3,10-Bis-((2E,6E)-3,7,11-trimethyl-dodeca-2,6,10-trienyloxy)-6a,6b,12b,12c-tetrahydro-5,8-dioxa-dibenzo[a,i]biphenylene-6,7-dione formation under sunlight in EtOH solution after 4 days by TLC analysis2017Journal of natural products, 09-22, Volume: 80, Issue:9
Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species.
AID1347661Antiproliferative activity against human BT549 cells after 24 hrs by MTT assay2017Journal of natural products, 12-22, Volume: 80, Issue:12
Oxyprenylated Phenylpropanoids Bind to MT1 Melatonin Receptors and Inhibit Breast Cancer Cell Proliferation and Migration.
AID1163510Cytotoxicity against human PANC1 cells under nutrient-deprived condition after 24 hrs by WST8 dye based assay2014Bioorganic & medicinal chemistry letters, Oct-01, Volume: 24, Issue:19
Synthesis and biological evaluation of isoprenylated coumarins as potential anti-pancreatic cancer agents.
AID1501409Thermal stability of the compound assessed as compound degradation at 37 degC in EtOH solution after 48 hrs by HPLC analysis2017Journal of natural products, 09-22, Volume: 80, Issue:9
Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species.
AID1347660Antiproliferative activity against human MDA-MB-231 cells after 24 hrs by MTT assay2017Journal of natural products, 12-22, Volume: 80, Issue:12
Oxyprenylated Phenylpropanoids Bind to MT1 Melatonin Receptors and Inhibit Breast Cancer Cell Proliferation and Migration.
AID1501426Stability of the compound assessed as compound degradation in 0.1 M HCl solution at 60 to 80 degC using solid sample up to 96 hrs by HPLC analysis2017Journal of natural products, 09-22, Volume: 80, Issue:9
Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species.
AID1501432Photostability of the compound assessed as parent compound remaining under sunlight exposed for 3 days in EtOH solution measured in presence of UV-A filter DHHB by TLC method2017Journal of natural products, 09-22, Volume: 80, Issue:9
Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species.
AID607602Chemical stability of the compound in MEM cell culture medium after 72 hrs at 37 degC2011Bioorganic & medicinal chemistry letters, Jul-15, Volume: 21, Issue:14
Growth inhibitory activities of oxyprenylated and non-prenylated naturally occurring phenylpropanoids in cancer cell lines.
AID1359356Effect on Rab27a expression in mouse Melan-a cells at 40 uM after 72 hrs by western blot analysis (Rvb = 1 No_unit)2018European journal of medicinal chemistry, May-25, Volume: 152Natural oxyprenylated coumarins are modulators of melanogenesis.
AID1501420Stability of the compound assessed as compound degradation in 0.1 M HCl solution at room temperature in EtOH solution after 96 hrs by HPLC analysis2017Journal of natural products, 09-22, Volume: 80, Issue:9
Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species.
AID607596Cytotoxicity against human PC3 cells after 72 hrs by MTT assay2011Bioorganic & medicinal chemistry letters, Jul-15, Volume: 21, Issue:14
Growth inhibitory activities of oxyprenylated and non-prenylated naturally occurring phenylpropanoids in cancer cell lines.
AID1359331Cytotoxicity against mouse Melan-a cells assessed as effect on cell viability at 40 uM after 24 to 72 hrs by trypan blue exclusion assay2018European journal of medicinal chemistry, May-25, Volume: 152Natural oxyprenylated coumarins are modulators of melanogenesis.
AID607595Cytotoxicity against human A549 cells after 72 hrs by MTT assay2011Bioorganic & medicinal chemistry letters, Jul-15, Volume: 21, Issue:14
Growth inhibitory activities of oxyprenylated and non-prenylated naturally occurring phenylpropanoids in cancer cell lines.
AID1347659Antiproliferative activity against mouse mammary carcinoma cell after 24 hrs by MTT assay2017Journal of natural products, 12-22, Volume: 80, Issue:12
Oxyprenylated Phenylpropanoids Bind to MT1 Melatonin Receptors and Inhibit Breast Cancer Cell Proliferation and Migration.
AID1501416Stability of the compound assessed as compound degradation in 3% H2O2 solution at room temperature in EtOH solution after 96 hrs by HPLC analysis2017Journal of natural products, 09-22, Volume: 80, Issue:9
Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species.
AID1359339Inhibition of melanogenesis in mouse Melan-a cells assessed as reduction in melanin content at 40 uM2018European journal of medicinal chemistry, May-25, Volume: 152Natural oxyprenylated coumarins are modulators of melanogenesis.
AID1347669Inhibition of cell migration in human BT549 cells at 100 uM after 24 hrs by inverted fluorescence microscopy based scratch assay relative to control2017Journal of natural products, 12-22, Volume: 80, Issue:12
Oxyprenylated Phenylpropanoids Bind to MT1 Melatonin Receptors and Inhibit Breast Cancer Cell Proliferation and Migration.
AID1501411Thermal stability of the compound at 37 degC in EtOH solution after 3 to 4 days by HPLC analysis2017Journal of natural products, 09-22, Volume: 80, Issue:9
Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species.
AID607597Cytotoxicity against human SK-MEL-28 cells after 72 hrs by MTT assay2011Bioorganic & medicinal chemistry letters, Jul-15, Volume: 21, Issue:14
Growth inhibitory activities of oxyprenylated and non-prenylated naturally occurring phenylpropanoids in cancer cell lines.
AID1359366Binding affinity to ERbeta in mouse Melan-a cells2018European journal of medicinal chemistry, May-25, Volume: 152Natural oxyprenylated coumarins are modulators of melanogenesis.
AID1501425Stability of the compound assessed as compound degradation in 0.1 M NaOH solution at 60 to 80 degC using solid sample up to 96 hrs by HPLC analysis2017Journal of natural products, 09-22, Volume: 80, Issue:9
Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species.
AID1347665Antiproliferative activity against human BT549 cells at 1 nM to 100 uM after 24 hrs by MTT assay relative to control2017Journal of natural products, 12-22, Volume: 80, Issue:12
Oxyprenylated Phenylpropanoids Bind to MT1 Melatonin Receptors and Inhibit Breast Cancer Cell Proliferation and Migration.
AID1347663Antiproliferative activity against mouse mammary carcinoma cell at 1 nM to 100 uM after 24 hrs by MTT assay relative to control2017Journal of natural products, 12-22, Volume: 80, Issue:12
Oxyprenylated Phenylpropanoids Bind to MT1 Melatonin Receptors and Inhibit Breast Cancer Cell Proliferation and Migration.
AID1359341Inhibition of melanogenesis in mouse Melan-a cells assessed as reduction in melanin content at 40 uM after 72 hrs relative to control2018European journal of medicinal chemistry, May-25, Volume: 152Natural oxyprenylated coumarins are modulators of melanogenesis.
AID140324Compound was tested for the inhibitory activity against mouse macrophage RAW 264.7 cells at the concentration of 50 uM; Inactive2000Bioorganic & medicinal chemistry letters, Jan-03, Volume: 10, Issue:1
1,1-Dimethylallylcoumarins potently suppress both lipopolysaccharide- and interferon-gamma-induced nitric oxide generation in mouse macrophage RAW 264.7 cells.
AID1501431Photostability of the compound assessed as parent compound remaining under sunlight exposed for 3 days in EtOH solution measured in presence of UV-A filter avobenzone by TLC method2017Journal of natural products, 09-22, Volume: 80, Issue:9
Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species.
AID1359351Decrease in MITF mRNA expression in mouse Melan-a cells at 40 uM after 24 hrs by SYBR green dye based qRT-PCR analysis relative to control2018European journal of medicinal chemistry, May-25, Volume: 152Natural oxyprenylated coumarins are modulators of melanogenesis.
AID607593Cytotoxicity against human U373 cells after 72 hrs by MTT assay2011Bioorganic & medicinal chemistry letters, Jul-15, Volume: 21, Issue:14
Growth inhibitory activities of oxyprenylated and non-prenylated naturally occurring phenylpropanoids in cancer cell lines.
AID1501421Stability of the compound assessed as compound degradation in 0.1 M HCl solution at 60 degC in EtOH solution after 24 hrs by HPLC analysis2017Journal of natural products, 09-22, Volume: 80, Issue:9
Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species.
AID1501414Stability of the compound assessed as compound degradation in 3% H2O2 solution at room temperature in EtOH solution after 24 hrs by HPLC analysis2017Journal of natural products, 09-22, Volume: 80, Issue:9
Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species.
AID1501436Photostability of the compound assessed as parent compound remaining under sunlight exposed for 6 days in EtOH solution measured in presence of UV-A filter DHHB by TLC method2017Journal of natural products, 09-22, Volume: 80, Issue:9
Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species.
AID1501424Thermal stability of the compound assessed as compound degradation at 37 to 80 degC using solid samples after 96 hrs by HPLC analysis2017Journal of natural products, 09-22, Volume: 80, Issue:9
Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (34)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (2.94)18.7374
1990's0 (0.00)18.2507
2000's7 (20.59)29.6817
2010's19 (55.88)24.3611
2020's7 (20.59)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%
Reviews1 (2.86%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other34 (97.14%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research Highlights

Safety/Toxicity (2)

ArticleYear
Comparing toxicity of galbanic acid, auraptene and umbelliprenin on adult T-cell leukaemia-lymphoma in normoxia and hypoxia.
Cellular and molecular biology (Noisy-le-Grand, France), Dec-31, Volume: 68, Issue: 12
2022
Evaluating cytotoxic effect of nanoliposomes encapsulated with umbelliprenin on 4T1 cell line.
In vitro cellular & developmental biology. Animal, Volume: 53, Issue: 1
2017
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Natural Sources (1)

ArticleYear
Comparing toxicity of galbanic acid, auraptene and umbelliprenin on adult T-cell leukaemia-lymphoma in normoxia and hypoxia.
Cellular and molecular biology (Noisy-le-Grand, France), Dec-31, Volume: 68, Issue: 12
2022
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]