Compounds > rugulactone
Page last updated: 2024-11-13

rugulactone

Description

rugulactone: inhibitor of the NF-kappaB activation pathway from Cryptocarya rugulosa; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

FloraRankFlora DefinitionFamilyFamily Definition
CryptocaryagenusA plant genus of the family LAURACEAE. Members contain cryptofolione, caryachine, grandisin and other compounds. Some PEUMUS species have been reclassified as CRYPTOCARYA.[MeSH]LauraceaeA family of mainly aromatic evergreen plants in the order Laurales. The laurel family includes 2,200 species in 45 genera and from these are derived medicinal extracts, essential oils, camphor and other products.[MeSH]

Cross-References

ID SourceID
PubMed CID52948504
CHEMBL ID1253688
MeSH IDM0545450

Synonyms (5)

Synonym
CHEMBL1253688
r-rugulactone
rugulactone
(6r)-6-[(2e)-4-oxo-6-phenyl-2-hexen-1-yl]-5,6-dihydro-2h-pyran-2-one
(r)-rugulactone

Research Excerpts

Overview

Rugulactone is a dihydro-α-pyrone isolated from the plant Cryptocarya rugulosa.

ExcerptReferenceRelevance
"Rugulactone is a natural product isolated from the plant "( An Efficient Chemoenzymatic Approach towards the Synthesis of Rugulactone.
Giannopoulos, V; Smonou, I; Tyrikos-Ergas, T, 2018)		2.16
"Rugulactone is a dihydro-α-pyrone isolated from the plant Cryptocarya rugulosa in 2009. "( Rugulactone and its analogues exert antibacterial effects through multiple mechanisms including inhibition of thiamine biosynthesis.
Kirsch, SF; Menz, H; Nodwell, MB; Sieber, SA, 2012)		3.26
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (37)

Assay IDTitleYearJournalArticle
AID515292Antibacterial activity against Staphylococcus aureus MTCC 96 by broth dilution method2010European journal of medicinal chemistry, Oct, Volume: 45, Issue:10
Stereoselective synthesis and biological evaluation of (R)-rugulactone, (6R)-((4R)-hydroxy-6-phenyl-hex-2-enyl)-5,6-dihydro-pyran-2-one and its 4S epimer.
AID600599Inhibition of IKK-beta in human OCI-LY10 cells assessed as decrease in renilla values at 2.5 to 10 ug/ml after 10 hrs by IkB-photinus/Renilla assay2009Journal of natural products, Mar-27, Volume: 72, Issue:3
Inhibitors of the NF-kappaB activation pathway from Cryptocarya rugulosa.
AID600602Inhibition of IKK-beta in human OCI-LY19 cells assessed as decrease in renilla values at 10 ug/ml after 10 hrs by IkB-photinus/Renilla assay2009Journal of natural products, Mar-27, Volume: 72, Issue:3
Inhibitors of the NF-kappaB activation pathway from Cryptocarya rugulosa.
AID515298Antifungal activity against Aspergillus niger MTCC 1344 at 30 ug/ml after 24 to 96 hrs by agar cup diffusion method2010European journal of medicinal chemistry, Oct, Volume: 45, Issue:10
Stereoselective synthesis and biological evaluation of (R)-rugulactone, (6R)-((4R)-hydroxy-6-phenyl-hex-2-enyl)-5,6-dihydro-pyran-2-one and its 4S epimer.
AID1075967Cytotoxicity against estrogen receptor-negative human MDA-MB-231 cells assessed as cell viability after 72 hrs by MTT assay2014Bioorganic & medicinal chemistry letters, Mar-01, Volume: 24, Issue:5
Rugulactone derivatives act as inhibitors of NF-κB activation and modulates the transcription of NF-κB dependent genes in MDA-MB-231cells.
AID1075946Reduction in HDAC-8 nuclear expression in estrogen receptor-negative human MDA-MB-231 cells at 2 uM after 24 hrs by Western blotting analysis2014Bioorganic & medicinal chemistry letters, Mar-01, Volume: 24, Issue:5
Rugulactone derivatives act as inhibitors of NF-κB activation and modulates the transcription of NF-κB dependent genes in MDA-MB-231cells.
AID1075960Cell cycle arrest in estrogen receptor-negative human MDA-MB-231 cells assessed as decrease in Cyclin E expression at 2 uM after 24 hrs by Western blotting analysis2014Bioorganic & medicinal chemistry letters, Mar-01, Volume: 24, Issue:5
Rugulactone derivatives act as inhibitors of NF-κB activation and modulates the transcription of NF-κB dependent genes in MDA-MB-231cells.
AID515297Antifungal activity against Rhizopus oryzae MTCC 262 at 30 ug/ml after 24 to 96 hrs by agar cup diffusion method2010European journal of medicinal chemistry, Oct, Volume: 45, Issue:10
Stereoselective synthesis and biological evaluation of (R)-rugulactone, (6R)-((4R)-hydroxy-6-phenyl-hex-2-enyl)-5,6-dihydro-pyran-2-one and its 4S epimer.
AID1075962Cell cycle arrest in estrogen receptor-negative human MDA-MB-231 cells assessed as accumulation at S phase at 2 uM after 24 hrs by Propidium iodide staining-based flow cytometric analysis (Rvb = 19 +/- 1%)2014Bioorganic & medicinal chemistry letters, Mar-01, Volume: 24, Issue:5
Rugulactone derivatives act as inhibitors of NF-κB activation and modulates the transcription of NF-κB dependent genes in MDA-MB-231cells.
AID600597Induction of IkappaB in human OCI-LY3 cells assessed as fold increase in luciferase reporter gene2009Journal of natural products, Mar-27, Volume: 72, Issue:3
Inhibitors of the NF-kappaB activation pathway from Cryptocarya rugulosa.
AID1075959Cell cycle arrest in estrogen receptor-negative human MDA-MB-231 cells assessed as decrease in CDK2 expression at 2 uM after 24 hrs by Western blotting analysis2014Bioorganic & medicinal chemistry letters, Mar-01, Volume: 24, Issue:5
Rugulactone derivatives act as inhibitors of NF-κB activation and modulates the transcription of NF-κB dependent genes in MDA-MB-231cells.
AID515300Antifungal activity against Saccharomyces cerevisiae MTCC 171 at 30 ug/ml after 24 to 96 hrs by agar cup diffusion method2010European journal of medicinal chemistry, Oct, Volume: 45, Issue:10
Stereoselective synthesis and biological evaluation of (R)-rugulactone, (6R)-((4R)-hydroxy-6-phenyl-hex-2-enyl)-5,6-dihydro-pyran-2-one and its 4S epimer.
AID1075948Reduction in HDAC-3 nuclear expression in estrogen receptor-negative human MDA-MB-231 cells at 2 uM after 24 hrs by Western blotting analysis2014Bioorganic & medicinal chemistry letters, Mar-01, Volume: 24, Issue:5
Rugulactone derivatives act as inhibitors of NF-κB activation and modulates the transcription of NF-κB dependent genes in MDA-MB-231cells.
AID1075947Inhibition of NFkappaB activity in estrogen receptor-negative human MDA-MB-231 cells assessed as retention of NFKappaB/Rel A in cytoplasm at 2 uM after 24 hrs by DAPI/PI staining-based confocal microscopy2014Bioorganic & medicinal chemistry letters, Mar-01, Volume: 24, Issue:5
Rugulactone derivatives act as inhibitors of NF-κB activation and modulates the transcription of NF-κB dependent genes in MDA-MB-231cells.
AID515303Antifungal activity against Candida albicans MTCC 227 at 100 ug/ml after 24 to 96 hrs by agar cup diffusion method2010European journal of medicinal chemistry, Oct, Volume: 45, Issue:10
Stereoselective synthesis and biological evaluation of (R)-rugulactone, (6R)-((4R)-hydroxy-6-phenyl-hex-2-enyl)-5,6-dihydro-pyran-2-one and its 4S epimer.
AID1075964Inhibition of NFkappaB activity in estrogen receptor-positive human MCF7 cells at 2 uM after 24 hrs by SEAP reporter assay2014Bioorganic & medicinal chemistry letters, Mar-01, Volume: 24, Issue:5
Rugulactone derivatives act as inhibitors of NF-κB activation and modulates the transcription of NF-κB dependent genes in MDA-MB-231cells.
AID1075955Effect on p21 gene expression in estrogen receptor-negative human MDA-MB-231 cells at 2 uM after 24 hrs by luciferase reporter gene assay2014Bioorganic & medicinal chemistry letters, Mar-01, Volume: 24, Issue:5
Rugulactone derivatives act as inhibitors of NF-κB activation and modulates the transcription of NF-κB dependent genes in MDA-MB-231cells.
AID515296Antibacterial activity against Klebsiella pneumoniae MTCC 39 by broth dilution method2010European journal of medicinal chemistry, Oct, Volume: 45, Issue:10
Stereoselective synthesis and biological evaluation of (R)-rugulactone, (6R)-((4R)-hydroxy-6-phenyl-hex-2-enyl)-5,6-dihydro-pyran-2-one and its 4S epimer.
AID600601Inhibition of IKK-beta in human OCI-LY19 cells assessed as decrease in renilla values at 10 ug/ml after 2.5 to 10 hrs by IkB-photinus/Renilla assay2009Journal of natural products, Mar-27, Volume: 72, Issue:3
Inhibitors of the NF-kappaB activation pathway from Cryptocarya rugulosa.
AID600598Induction of IkappaB in human OCI-LY3 cells assessed as fold increase in luciferase reporter gene after 10 hrs2009Journal of natural products, Mar-27, Volume: 72, Issue:3
Inhibitors of the NF-kappaB activation pathway from Cryptocarya rugulosa.
AID1075965Inhibition of NFkappaB activity in estrogen receptor-negative human MDA-MB-231 cells at 2 uM after 24 hrs by SEAP reporter assay2014Bioorganic & medicinal chemistry letters, Mar-01, Volume: 24, Issue:5
Rugulactone derivatives act as inhibitors of NF-κB activation and modulates the transcription of NF-κB dependent genes in MDA-MB-231cells.
AID515302Antifungal activity against Aspergillus niger MTCC 1344 at 100 ug/ml after 24 to 96 hrs by agar cup diffusion method2010European journal of medicinal chemistry, Oct, Volume: 45, Issue:10
Stereoselective synthesis and biological evaluation of (R)-rugulactone, (6R)-((4R)-hydroxy-6-phenyl-hex-2-enyl)-5,6-dihydro-pyran-2-one and its 4S epimer.
AID515301Antifungal activity against Rhizopus oryzae MTCC 262 at 100 ug/ml after 24 to 96 hrs by agar cup diffusion method2010European journal of medicinal chemistry, Oct, Volume: 45, Issue:10
Stereoselective synthesis and biological evaluation of (R)-rugulactone, (6R)-((4R)-hydroxy-6-phenyl-hex-2-enyl)-5,6-dihydro-pyran-2-one and its 4S epimer.
AID600600Inhibition of IKK-beta in human OCI-LY3 cells assessed as decrease in renilla values at 2.5 to 5 ug/ml after 10 hrs by IkB-photinus/Renilla assay2009Journal of natural products, Mar-27, Volume: 72, Issue:3
Inhibitors of the NF-kappaB activation pathway from Cryptocarya rugulosa.
AID1075963Cell cycle arrest in estrogen receptor-negative human MDA-MB-231 cells assessed as accumulation at G1 phase at 2 uM after 24 hrs by Propidium iodide staining-based flow cytometric analysis (Rvb = 54.66 +/- 2.51%)2014Bioorganic & medicinal chemistry letters, Mar-01, Volume: 24, Issue:5
Rugulactone derivatives act as inhibitors of NF-κB activation and modulates the transcription of NF-κB dependent genes in MDA-MB-231cells.
AID515304Antifungal activity against Saccharomyces cerevisiae MTCC 171 at 100 ug/ml after 24 to 96 hrs by agar cup diffusion method2010European journal of medicinal chemistry, Oct, Volume: 45, Issue:10
Stereoselective synthesis and biological evaluation of (R)-rugulactone, (6R)-((4R)-hydroxy-6-phenyl-hex-2-enyl)-5,6-dihydro-pyran-2-one and its 4S epimer.
AID1075966Cytotoxicity against estrogen receptor-positive human MCF7 cells assessed as cell viability after 72 hrs by MTT assay2014Bioorganic & medicinal chemistry letters, Mar-01, Volume: 24, Issue:5
Rugulactone derivatives act as inhibitors of NF-κB activation and modulates the transcription of NF-κB dependent genes in MDA-MB-231cells.
AID1075958Induction of apoptosis in estrogen receptor-negative human MDA-MB-231 cells assessed as increase in PARP cleavage at 2 uM after 24 hrs by Western blotting analysis2014Bioorganic & medicinal chemistry letters, Mar-01, Volume: 24, Issue:5
Rugulactone derivatives act as inhibitors of NF-κB activation and modulates the transcription of NF-κB dependent genes in MDA-MB-231cells.
AID1075961Cell cycle arrest in estrogen receptor-negative human MDA-MB-231 cells assessed as accumulation at G2/M phase at 2 uM after 24 hrs by Propidium iodide staining-based flow cytometric analysis (Rvb = 26.33 +/- 3.05%)2014Bioorganic & medicinal chemistry letters, Mar-01, Volume: 24, Issue:5
Rugulactone derivatives act as inhibitors of NF-κB activation and modulates the transcription of NF-κB dependent genes in MDA-MB-231cells.
AID1075956Induction of apoptosis in estrogen receptor-negative human MDA-MB-231 cells assessed as reduced procaspase-3 level at 2 uM after 24 hrs by Western blotting analysis2014Bioorganic & medicinal chemistry letters, Mar-01, Volume: 24, Issue:5
Rugulactone derivatives act as inhibitors of NF-κB activation and modulates the transcription of NF-κB dependent genes in MDA-MB-231cells.
AID515293Antibacterial activity against Staphylococcus epidermidis MTCC 437 by broth dilution method2010European journal of medicinal chemistry, Oct, Volume: 45, Issue:10
Stereoselective synthesis and biological evaluation of (R)-rugulactone, (6R)-((4R)-hydroxy-6-phenyl-hex-2-enyl)-5,6-dihydro-pyran-2-one and its 4S epimer.
AID600595Induction of IkappaB in human OCI-LY3 cells assessed as fold increase in luciferase reporter gene at 11 uM2009Journal of natural products, Mar-27, Volume: 72, Issue:3
Inhibitors of the NF-kappaB activation pathway from Cryptocarya rugulosa.
AID515294Antibacterial activity against Escherichia coli MTCC 443 by broth dilution method2010European journal of medicinal chemistry, Oct, Volume: 45, Issue:10
Stereoselective synthesis and biological evaluation of (R)-rugulactone, (6R)-((4R)-hydroxy-6-phenyl-hex-2-enyl)-5,6-dihydro-pyran-2-one and its 4S epimer.
AID515299Antifungal activity against Candida albicans MTCC 227 at 30 ug/ml after 24 to 96 hrs by agar cup diffusion method2010European journal of medicinal chemistry, Oct, Volume: 45, Issue:10
Stereoselective synthesis and biological evaluation of (R)-rugulactone, (6R)-((4R)-hydroxy-6-phenyl-hex-2-enyl)-5,6-dihydro-pyran-2-one and its 4S epimer.
AID515295Antibacterial activity against Pseudomonas aeruginosa MTCC 741 by broth dilution method2010European journal of medicinal chemistry, Oct, Volume: 45, Issue:10
Stereoselective synthesis and biological evaluation of (R)-rugulactone, (6R)-((4R)-hydroxy-6-phenyl-hex-2-enyl)-5,6-dihydro-pyran-2-one and its 4S epimer.
AID1075957Induction of apoptosis in estrogen receptor-negative human MDA-MB-231 cells assessed as increase in Rb cleavage at 2 uM after 24 hrs by Western blotting analysis2014Bioorganic & medicinal chemistry letters, Mar-01, Volume: 24, Issue:5
Rugulactone derivatives act as inhibitors of NF-κB activation and modulates the transcription of NF-κB dependent genes in MDA-MB-231cells.
AID515291Antibacterial activity against Bacillus subtilis MTCC 441 by broth dilution method2010European journal of medicinal chemistry, Oct, Volume: 45, Issue:10
Stereoselective synthesis and biological evaluation of (R)-rugulactone, (6R)-((4R)-hydroxy-6-phenyl-hex-2-enyl)-5,6-dihydro-pyran-2-one and its 4S epimer.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (7)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's1 (14.29)29.6817
2010's5 (71.43)24.3611
2020's1 (14.29)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%
Other7 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
thiamine
thiamine(1+) : A primary alcohol that is 1,3-thiazol-3-ium substituted by (4-amino-2-methylpyrimidin-5-yl)methyl, methyl and 2-hydroxyethyl groups at positions 3, 4 and 5, respectively.		7.0710primary alcohol;
vitamin B1		Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
clotrimazole
[no description available]		2.0510conazole antifungal drug;
imidazole antifungal drug;
imidazoles;
monochlorobenzenes		antiinfective agent;
environmental contaminant;
xenobiotic
penicillin g
Penicillin G: A penicillin derivative commonly used in the form of its sodium or potassium salts in the treatment of a variety of infections. It is effective against most gram-positive bacteria and against gram-negative cocci. It has also been used as an experimental convulsant because of its actions on GAMMA-AMINOBUTYRIC ACID mediated synaptic transmission.. benzylpenicillin : A penicillin in which the substituent at position 6 of the penam ring is a phenylacetamido group.		2.0510penicillin allergen;
penicillin		antibacterial drug;
drug allergen;
epitope
streptomycin
[no description available]		2.0510antibiotic antifungal drug;
antibiotic fungicide;
streptomycins		antibacterial drug;
antifungal agrochemical;
antimicrobial agent;
antimicrobial drug;
bacterial metabolite;
protein synthesis inhibitor
nitrofurantoin
Nitrofurantoin: A urinary anti-infective agent effective against most gram-positive and gram-negative organisms. Although sulfonamides and antibiotics are usually the agents of choice for urinary tract infections, nitrofurantoin is widely used for prophylaxis and long-term suppression.. nitrofurantoin : An imidazolidine-2,4-dione that is hydantoin substituted at position 1 by a [(5-nitro-2-furyl)methylene]amino group. An antibiotic that damages bacterial DNA.		2.0510imidazolidine-2,4-dione;
nitrofuran antibiotic;
organonitrogen heterocyclic antibiotic;
organooxygen heterocyclic antibiotic		antibacterial drug;
antiinfective agent;
hepatotoxic agent
cryptocaryone
cryptocaryone: inhibitor of the NF-kappaB activation pathway from Cryptocarya rugulosa; structure in first source		2.0510benzofurans
ConditionIndicatedRelationship StrengthStudiesTrials
Bacterial Disease
[description not available]		02.0510
Fungal Diseases
[description not available]		02.0510
Bacterial Infections
Infections by bacteria, general or unspecified.		02.0510
Mycoses
Diseases caused by FUNGI.		02.0510
Benign Neoplasms
[description not available]		02.2510
Neoplasms
New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.		02.2510
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