Page last updated: 2024-11-13

arzanol

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

Description

arzanol: a prenylated alpha-pyrone-phloroglucinol etherodimer from Helichrysum italicum subsp.microphyllum; has antioxidant and cytotoxic activity; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

FloraRankFlora DefinitionFamilyFamily Definition
HelichrysumgenusA plant genus of the family ASTERACEAE. Members contain CHALCONE, helichrysetin, arenarin, and flamin.[MeSH]AsteraceaeA large plant family of the order Asterales, subclass Asteridae, class Magnoliopsida. The family is also known as Compositae. Flower petals are joined near the base and stamens alternate with the corolla lobes. The common name of daisy refers to several genera of this family including Aster; CHRYSANTHEMUM; RUDBECKIA; TANACETUM.[MeSH]
Helichrysum italicumspecies[no description available]AsteraceaeA large plant family of the order Asterales, subclass Asteridae, class Magnoliopsida. The family is also known as Compositae. Flower petals are joined near the base and stamens alternate with the corolla lobes. The common name of daisy refers to several genera of this family including Aster; CHRYSANTHEMUM; RUDBECKIA; TANACETUM.[MeSH]

Cross-References

ID SourceID
PubMed CID54682566
CHEMBL ID225421
MeSH IDM0507509

Synonyms (8)

Synonym
arzanol
2h-pyran-2-one, 3-[[3-acetyl-2,4,6-trihydroxy-5-(3-methyl-2-butenyl)phenyl]methyl]-6-ethyl-4-hydroxy-5-methyl-
3-[[3-acetyl-2,4,6-trihydroxy-5-(3-methylbut-2-enyl)phenyl]methyl]-6-ethyl-4-hydroxy-5-methyl-pyran-2-one
CHEMBL225421
32274-52-5
arzanol, from helichrysum italicum, >=98%
bdbm50109833
3-[4-acetyl-2,3,6-trihydroxy-5-(3-methyl-2-butenyl)benzyl]-6-ethyl-4-hydroxy-5-methyl-2h-pyran-2-one

Research Excerpts

Overview

Arzanol is a novel phloroglucinol α -pyrone, isolated from a Mediterranean plant Helichrysum italicum.

ExcerptReferenceRelevance
"Arzanol is a novel phloroglucinol α -pyrone, isolated from a Mediterranean plant Helichrysum italicum (Roth) Don ssp. "( Arzanol, a potent mPGES-1 inhibitor: novel anti-inflammatory agent.
Bulani, VD; Juvekar, AR; Kothavade, PS; Nagmoti, DM, 2013
)
3.28

Effects

ExcerptReferenceRelevance
"Arzanol has been reported to possess a variety of pharmacological activities."( Arzanol, a potent mPGES-1 inhibitor: novel anti-inflammatory agent.
Bulani, VD; Juvekar, AR; Kothavade, PS; Nagmoti, DM, 2013
)
2.55
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Prostaglandin E synthaseHomo sapiens (human)IC50 (µMol)0.40000.00102.030810.0000AID1239703; AID1357408
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (10)

Processvia Protein(s)Taxonomy
prostaglandin biosynthetic processProstaglandin E synthaseHomo sapiens (human)
prostaglandin metabolic processProstaglandin E synthaseHomo sapiens (human)
signal transductionProstaglandin E synthaseHomo sapiens (human)
cell population proliferationProstaglandin E synthaseHomo sapiens (human)
negative regulation of cell population proliferationProstaglandin E synthaseHomo sapiens (human)
sensory perception of painProstaglandin E synthaseHomo sapiens (human)
regulation of fever generationProstaglandin E synthaseHomo sapiens (human)
positive regulation of prostaglandin secretionProstaglandin E synthaseHomo sapiens (human)
regulation of inflammatory responseProstaglandin E synthaseHomo sapiens (human)
cellular oxidant detoxificationProstaglandin E synthaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (6)

Processvia Protein(s)Taxonomy
glutathione transferase activityProstaglandin E synthaseHomo sapiens (human)
glutathione peroxidase activityProstaglandin E synthaseHomo sapiens (human)
prostaglandin-D synthase activityProstaglandin E synthaseHomo sapiens (human)
protein bindingProstaglandin E synthaseHomo sapiens (human)
glutathione bindingProstaglandin E synthaseHomo sapiens (human)
prostaglandin-E synthase activityProstaglandin E synthaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (4)

Processvia Protein(s)Taxonomy
nuclear envelope lumenProstaglandin E synthaseHomo sapiens (human)
endoplasmic reticulum membraneProstaglandin E synthaseHomo sapiens (human)
membraneProstaglandin E synthaseHomo sapiens (human)
perinuclear region of cytoplasmProstaglandin E synthaseHomo sapiens (human)
membraneProstaglandin E synthaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (18)

Assay IDTitleYearJournalArticle
AID283726Inhibition of IL1-beta production in LPS-stimulated human primary monocytes by ELISA2007Journal of natural products, Apr, Volume: 70, Issue:4
Arzanol, an anti-inflammatory and anti-HIV-1 phloroglucinol alpha-Pyrone from Helichrysum italicum ssp. microphyllum.
AID283728Inhibition of IL6 production in LPS-stimulated human primary monocytes by ELISA2007Journal of natural products, Apr, Volume: 70, Issue:4
Arzanol, an anti-inflammatory and anti-HIV-1 phloroglucinol alpha-Pyrone from Helichrysum italicum ssp. microphyllum.
AID736331Antibacterial activity against Staphylococcus aureus 1199B overexpressing NorA pump after 18 hrs by MTT assay2013Journal of natural products, Mar-22, Volume: 76, Issue:3
Antimicrobial phenolics and unusual glycerides from Helichrysum italicum subsp. microphyllum.
AID736326Antibacterial activity against epidemic methicillin-resistant Staphylococcus aureus EMRSA-16 after 18 hrs by MTT assay2013Journal of natural products, Mar-22, Volume: 76, Issue:3
Antimicrobial phenolics and unusual glycerides from Helichrysum italicum subsp. microphyllum.
AID1357408Inhibition of mPGES1 in human A549 cell microsomal membrane using pGH2 as substrate pretreated for 15 mins followed by substrate addition and measured after 1 min by RP-HPLC method2018European journal of medicinal chemistry, Jun-10, Volume: 153Plant-derived mPGES-1 inhibitors or suppressors: A new emerging trend in the search for small molecules to combat inflammation.
AID283731Inhibition of TNFalpha activated NF-kappaB dependent transactivation of HIV-1 LTR Luc in 5.1 cells2007Journal of natural products, Apr, Volume: 70, Issue:4
Arzanol, an anti-inflammatory and anti-HIV-1 phloroglucinol alpha-Pyrone from Helichrysum italicum ssp. microphyllum.
AID283729Inhibition of IL8 production in LPS-stimulated human primary monocytes by ELISA2007Journal of natural products, Apr, Volume: 70, Issue:4
Arzanol, an anti-inflammatory and anti-HIV-1 phloroglucinol alpha-Pyrone from Helichrysum italicum ssp. microphyllum.
AID736329Antibacterial activity against Staphylococcus aureus ATCC 25923 after 18 hrs by MTT assay2013Journal of natural products, Mar-22, Volume: 76, Issue:3
Antimicrobial phenolics and unusual glycerides from Helichrysum italicum subsp. microphyllum.
AID283725Inhibition of VSV-pseudotyped HIV1 replication in Jurkat T cells2007Journal of natural products, Apr, Volume: 70, Issue:4
Arzanol, an anti-inflammatory and anti-HIV-1 phloroglucinol alpha-Pyrone from Helichrysum italicum ssp. microphyllum.
AID736330Antibacterial activity against Staphylococcus aureus XU212 overexpressing TetK tetracycline efflux pump after 18 hrs by MTT assay2013Journal of natural products, Mar-22, Volume: 76, Issue:3
Antimicrobial phenolics and unusual glycerides from Helichrysum italicum subsp. microphyllum.
AID1357409Antiinflammatory activity against carrageenan-induced pleurisy in rat assessed as reduction in exudate formation at 3.6 mg/kg, ip relative to control2018European journal of medicinal chemistry, Jun-10, Volume: 153Plant-derived mPGES-1 inhibitors or suppressors: A new emerging trend in the search for small molecules to combat inflammation.
AID283727Inhibition of TNFalpha production in LPS-stimulated human primary monocytes by ELISA2007Journal of natural products, Apr, Volume: 70, Issue:4
Arzanol, an anti-inflammatory and anti-HIV-1 phloroglucinol alpha-Pyrone from Helichrysum italicum ssp. microphyllum.
AID283730Inhibition of PGE2 production in LPS-stimulated human primary monocytes by ELISA2007Journal of natural products, Apr, Volume: 70, Issue:4
Arzanol, an anti-inflammatory and anti-HIV-1 phloroglucinol alpha-Pyrone from Helichrysum italicum ssp. microphyllum.
AID736328Antibacterial activity against Staphylococcus aureus RN4220 overexpressing MsrA macrolide efflux protein after 18 hrs by MTT assay2013Journal of natural products, Mar-22, Volume: 76, Issue:3
Antimicrobial phenolics and unusual glycerides from Helichrysum italicum subsp. microphyllum.
AID1357410Antiinflammatory activity against carrageenan-induced pleurisy in rat assessed as reduction in cell infiltration at 3.6 mg/kg, ip relative to control2018European journal of medicinal chemistry, Jun-10, Volume: 153Plant-derived mPGES-1 inhibitors or suppressors: A new emerging trend in the search for small molecules to combat inflammation.
AID1357411Antiinflammatory activity against carrageenan-induced pleurisy in rat assessed as reduction in PGE2 level at 3.6 mg/kg, ip relative to control2018European journal of medicinal chemistry, Jun-10, Volume: 153Plant-derived mPGES-1 inhibitors or suppressors: A new emerging trend in the search for small molecules to combat inflammation.
AID736327Antibacterial activity against epidemic methicillin-resistant Staphylococcus aureus EMRSA-15 after 18 hrs by MTT assay2013Journal of natural products, Mar-22, Volume: 76, Issue:3
Antimicrobial phenolics and unusual glycerides from Helichrysum italicum subsp. microphyllum.
AID1239703Inhibition of mPGES-1 in IL-1beta-stimulated human A549 cell microsomal membranes assessed as reduction in PGE2 formation incubated for 15 mins using PGH2 substrate by RP-HPLC method2015Bioorganic & medicinal chemistry, Aug-01, Volume: 23, Issue:15
Discovery of novel, non-acidic mPGES-1 inhibitors by virtual screening with a multistep protocol.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (13)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's2 (15.38)29.6817
2010's10 (76.92)24.3611
2020's1 (7.69)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 30.26

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 Index30.26 (24.57)
Research Supply Index2.64 (2.92)
Research Growth Index5.23 (4.65)
Search Engine Demand Index27.81 (26.88)
Search Engine Supply Index1.75 (0.95)

This Compound (30.26)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (15.38%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other11 (84.62%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]