Page last updated: 2024-12-07

perezone

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

Description

Perezone is a naturally occurring sesquiterpene lactone found in the leaves and stems of the plant _Perezia multiflora_. It has attracted considerable attention for its diverse pharmacological activities, including anti-inflammatory, antimicrobial, and anticancer properties. Perezone is known to inhibit the production of pro-inflammatory cytokines, such as TNF-alpha and IL-6. It also exhibits potent antimicrobial activity against a range of bacteria and fungi. Its anticancer properties have been investigated in various studies, demonstrating potential activity against leukemia, breast cancer, and colon cancer cells. Perezone's mode of action is believed to involve modulation of various cellular pathways, including the NF-κB signaling pathway and the apoptotic cascade. Its unique structure and biological activity make it a promising lead compound for the development of new therapeutic agents.'

perezone: isolated from roots of Pereziae adnata; structure given in Merck Index [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID Source	ID
PubMed CID	92964
CHEMBL ID	2071234
SCHEMBL ID	3609795
MeSH ID	M0152155

Synonyms (18)

Synonym
perezone
3600-95-1
SCHEMBL3609795
l7yl69207z ,
unii-l7yl69207z
2,5-cyclohexadiene-1,4-dione, 2-(1,5-dimethyl-4-hexenyl)-3-hydroxy-5-methyl-, (r)-
CHEMBL2071234
p-benzoquinone, 2-(1,5-dimethyl-4-hexenyl)-3-hydroxy-5-methyl-
2,5-cyclohexadiene-1,4-dione, 2-(1,5-dimethyl-4-hexenyl)-3-hydroxy-5-methyl-, (-)-
JZXORCGMYQZBBQ-SNVBAGLBSA-N
2-(1,5-dimethyl-4-hexenyl)-3-hydroxy-5-methylbenzo-1,4-quinone #
2,5-cyclohexadiene-1,4-dione, 2-((1r)-1,5-dimethyl-4-hexen-1-yl)-3-hydroxy-5-methyl-
2-(1,5-dimethyl-4-hexenyl)-3-hydroxy-5-methyl-p-benzoquinone, pipitzahoic acid
2-((1r)-1,5-dimethyl-4-hexen-1-yl)-3-hydroxy-5-methyl-2,5-cyclohexadiene-1,4-dione
perezone [mi]
2,5-cyclohexadiene-1,4-dione,2-[(1r)-1,5-dimethyl-4-hexen-1-yl]-3-hydroxy-5-methyl-
Q27282818
DTXSID50877865

Research Excerpts

Overview

Perezone is an electron-donor and electron-acceptor compound. It behaves similarly to naphtoquinone.

Excerpt	Reference	Relevance
"Perezone is an electron-donor and electron-acceptor compound that behaves similarly to naphtoquinone."	( The action of the sesquiterpenic benzoquinone, perezone, on electron transport in biological membranes. Carabez, A; Sandoval, F, 1988)	1.25

Actions

Excerpt	Reference	Relevance
"Perezone promotes Ca2+ efflux by inducing collapse of the membrane potential and oxidation of pyridine nucleotides."	( Ca2+ releasing effect of perezone on adrenal cortex mitochondria. Cárabez, A; Chávez, E; Cuéllar, A, 1987)	1.3

Dosage Studied

Excerpt	Relevance	Reference
" The effect of perezone on mitochondrial Ca2+ release follows a dose-response relationship and is dependent of the reduction of the drug."	( Ca2+ releasing effect of perezone on adrenal cortex mitochondria. Cárabez, A; Chávez, E; Cuéllar, A, 1987)	0.93

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

Bioassays (10)

Assay ID	Title	Year	Journal	Article
AID678020	Cytotoxicity against human K562 cells after 48 hrs by SRB assay	2012	Bioorganic & medicinal chemistry, Sep-01, Volume: 20, Issue:17	Synthesis, cytotoxic and antioxidant evaluations of amino derivatives from perezone.
AID678025	Antioxidant activity in Wistar rat brain homogenates assessed as inhibition of lipid peroxidation at 17.78 uM by spectrophotometry based TBARS assay relative to untreated control	2012	Bioorganic & medicinal chemistry, Sep-01, Volume: 20, Issue:17	Synthesis, cytotoxic and antioxidant evaluations of amino derivatives from perezone.
AID678023	Antioxidant activity in Wistar rat brain homogenates assessed as inhibition of lipid peroxidation at 10 uM by spectrophotometry based TBARS assay relative to untreated control	2012	Bioorganic & medicinal chemistry, Sep-01, Volume: 20, Issue:17	Synthesis, cytotoxic and antioxidant evaluations of amino derivatives from perezone.
AID678024	Antioxidant activity in Wistar rat brain homogenates assessed as inhibition of lipid peroxidation by spectrophotometry based TBARS assay	2012	Bioorganic & medicinal chemistry, Sep-01, Volume: 20, Issue:17	Synthesis, cytotoxic and antioxidant evaluations of amino derivatives from perezone.
AID676962	Antioxidant activity in Wistar rat brain homogenates assessed as inhibition of lipid peroxidation at 100 uM by spectrophotometry based TBARS assay relative to untreated control	2012	Bioorganic & medicinal chemistry, Sep-01, Volume: 20, Issue:17	Synthesis, cytotoxic and antioxidant evaluations of amino derivatives from perezone.
AID678019	Cytotoxicity against human PC3 cells after 48 hrs by SRB assay	2012	Bioorganic & medicinal chemistry, Sep-01, Volume: 20, Issue:17	Synthesis, cytotoxic and antioxidant evaluations of amino derivatives from perezone.
AID678021	Cytotoxicity against human HCT15 cells after 48 hrs by SRB assay	2012	Bioorganic & medicinal chemistry, Sep-01, Volume: 20, Issue:17	Synthesis, cytotoxic and antioxidant evaluations of amino derivatives from perezone.
AID678022	Cytotoxicity against human SKLU1 cells after 48 hrs by SRB assay	2012	Bioorganic & medicinal chemistry, Sep-01, Volume: 20, Issue:17	Synthesis, cytotoxic and antioxidant evaluations of amino derivatives from perezone.
AID678027	Antioxidant activity in Wistar rat brain homogenates assessed as inhibition of lipid peroxidation at 56.23 uM by spectrophotometry based TBARS assay relative to untreated control	2012	Bioorganic & medicinal chemistry, Sep-01, Volume: 20, Issue:17	Synthesis, cytotoxic and antioxidant evaluations of amino derivatives from perezone.
AID678026	Antioxidant activity in Wistar rat brain homogenates assessed as inhibition of lipid peroxidation at 31.62 uM by spectrophotometry based TBARS assay relative to untreated control	2012	Bioorganic & medicinal chemistry, Sep-01, Volume: 20, Issue:17	Synthesis, cytotoxic and antioxidant evaluations of amino derivatives from perezone.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (20)

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	3 (15.00)	18.7374
1990's	3 (15.00)	18.2507
2000's	4 (20.00)	29.6817
2010's	7 (35.00)	24.3611
2020's	3 (15.00)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 25.13

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.

Metric	This Compound (vs All)
Research Demand Index	25.13 (24.57)
Research Supply Index	3.04 (2.92)
Research Growth Index	4.84 (4.65)
Search Engine Demand Index	26.67 (26.88)
Search Engine Supply Index	2.00 (0.95)

This Compound (25.13)

All Compounds (24.57)

Study Types

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	1 (5.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	19 (95.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
histamine [no description available]	1.98	1	aralkylamino compound; imidazoles	human metabolite; mouse metabolite; neurotransmitter
kojic acid [no description available]	3.18	1	4-pyranones; enol; primary alcohol	Aspergillus metabolite; EC 1.10.3.1 (catechol oxidase) inhibitor; EC 1.10.3.2 (laccase) inhibitor; EC 1.13.11.24 (quercetin 2,3-dioxygenase) inhibitor; EC 1.14.18.1 (tyrosinase) inhibitor; EC 1.4.3.3 (D-amino-acid oxidase) inhibitor; NF-kappaB inhibitor; skin lightening agent
adenosine diphosphate Adenosine Diphosphate: Adenosine 5'-(trihydrogen diphosphate). An adenine nucleotide containing two phosphate groups esterified to the sugar moiety at the 5'-position.	2	1	adenosine 5'-phosphate; purine ribonucleoside 5'-diphosphate	fundamental metabolite; human metabolite
cyclopropane cyclopropane : A cycloalkane composed of three carbon atoms to form a ring.	3.18	1	cycloalkane; cyclopropanes	inhalation anaesthetic
d-alpha tocopherol Vitamin E: A generic descriptor for all TOCOPHEROLS and TOCOTRIENOLS that exhibit ALPHA-TOCOPHEROL activity. By virtue of the phenolic hydrogen on the 2H-1-benzopyran-6-ol nucleus, these compounds exhibit varying degree of antioxidant activity, depending on the site and number of methyl groups and the type of ISOPRENOIDS.. tocopherol : A collective name for a group of closely related lipids that contain a chroman-6-ol nucleus substituted at position 2 by a methyl group and by a saturated hydrocarbon chain consisting of three isoprenoid units. They are designated as alpha-, beta-, gamma-, and delta-tocopherol depending on the number and position of additional methyl substituents on the aromatic ring. Tocopherols occur in vegetable oils and vegetable oil products, almost exclusively with R,R,R configuration. Tocotrienols differ from tocopherols only in having three double bonds in the hydrocarbon chain.. vitamin E : Any member of a group of fat-soluble chromanols that exhibit biological activity against vitamin E deficiency. The vitamers in this class consists of a chroman-6-ol core which is substituted at position 2 by a methyl group and (also at position 2) either a saturated or a triply-unsaturated hydrocarbon chain consisting of three isoprenoid units. The major function of vitamin E is to act as a natural antioxidant by scavenging free radicals and molecular oxygen.. (R,R,R)-alpha-tocopherol : An alpha-tocopherol that has R,R,R configuration. The naturally occurring stereoisomer of alpha-tocopherol, it is found particularly in sunflower and olive oils.	2.07	1	alpha-tocopherol	algal metabolite; antiatherogenic agent; anticoagulant; antioxidant; antiviral agent; EC 2.7.11.13 (protein kinase C) inhibitor; immunomodulator; micronutrient; nutraceutical; plant metabolite
rhodium Rhodium: A hard and rare metal of the platinum group, atomic number 45, atomic weight 102.905, symbol Rh.. rhodium atom : A cobalt group element atom of atomic number 45.	3.18	1	cobalt group element atom
ruthenium Ruthenium: A hard, brittle, grayish-white rare earth metal with an atomic symbol Ru, atomic number 44, and atomic weight 101.07. It is used as a catalyst and hardener for PLATINUM and PALLADIUM.	3.18	1	iron group element atom; platinum group metal atom
alkenes [no description available]	3.18	1
sesquiterpenes [no description available]	5.43	19
nadp [no description available]	1.97	1
valinomycin Valinomycin: A cyclododecadepsipeptide ionophore antibiotic produced by Streptomyces fulvissimus and related to the enniatins. It is composed of 3 moles each of L-valine, D-alpha-hydroxyisovaleric acid, D-valine, and L-lactic acid linked alternately to form a 36-membered ring. (From Merck Index, 11th ed) Valinomycin is a potassium selective ionophore and is commonly used as a tool in biochemical studies.. valinomycin : A twelve-membered cyclodepsipeptide composed of three repeating D-alpha-hydroxyisovaleryl-D-valyl-L-lactoyl-L-valyl units joined in sequence. An antibiotic found in several Streptomyces strains.	1.97	1	cyclodepsipeptide; macrocycle	antimicrobial agent; antiviral agent; bacterial metabolite; potassium ionophore
quercetin [no description available]	2.07	1	7-hydroxyflavonol; pentahydroxyflavone	antibacterial agent; antineoplastic agent; antioxidant; Aurora kinase inhibitor; chelator; EC 1.10.99.2 [ribosyldihydronicotinamide dehydrogenase (quinone)] inhibitor; geroprotector; phytoestrogen; plant metabolite; protein kinase inhibitor; radical scavenger
barium Barium: An element of the alkaline earth group of metals. It has an atomic symbol Ba, atomic number 56, and atomic weight 138. All of its acid-soluble salts are poisonous.	1.98	1	alkaline earth metal atom; elemental barium
allylsilane allylsilane: structure in first source	3.18	1
nad NAD(1-) : An anionic form of nicotinamide adenine dinucleotide arising from deprotonation of the two OH groups of the diphosphate moiety.	1.97	1	organophosphate oxoanion	cofactor; human metabolite; hydrogen acceptor; Saccharomyces cerevisiae metabolite

Condition	Relationship Strength	Studies
Benign Neoplasms, Brain [description not available]	2.41	1
Astrocytoma, Grade IV [description not available]	2.41	1
Brain Neoplasms Neoplasms of the intracranial components of the central nervous system, including the cerebral hemispheres, basal ganglia, hypothalamus, thalamus, brain stem, and cerebellum. Brain neoplasms are subdivided into primary (originating from brain tissue) and secondary (i.e., metastatic) forms. Primary neoplasms are subdivided into benign and malignant forms. In general, brain tumors may also be classified by age of onset, histologic type, or presenting location in the brain.	2.41	1
Glioblastoma A malignant form of astrocytoma histologically characterized by pleomorphism of cells, nuclear atypia, microhemorrhage, and necrosis. They may arise in any region of the central nervous system, with a predilection for the cerebral hemispheres, basal ganglia, and commissural pathways. Clinical presentation most frequently occurs in the fifth or sixth decade of life with focal neurologic signs or seizures.	7.41	1
Benign Neoplasms [description not available]	2.15	1
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.	2.15	1
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	2.02	1
Ache [description not available]	2.02	1
Pain An unpleasant sensation induced by noxious stimuli which are detected by NERVE ENDINGS of NOCICEPTIVE NEURONS.	2.02	1
Muscle Contraction A process leading to shortening and/or development of tension in muscle tissue. Muscle contraction occurs by a sliding filament mechanism whereby actin filaments slide inward among the myosin filaments.	2.39	2
Arrhythmia [description not available]	7	1
Injury, Myocardial Reperfusion [description not available]	2	1
Heart Disease, Ischemic [description not available]	2	1
Arrhythmias, Cardiac Any disturbances of the normal rhythmic beating of the heart or MYOCARDIAL CONTRACTION. Cardiac arrhythmias can be classified by the abnormalities in HEART RATE, disorders of electrical impulse generation, or impulse conduction.	2	1
Myocardial Ischemia A disorder of cardiac function caused by insufficient blood flow to the muscle tissue of the heart. The decreased blood flow may be due to narrowing of the coronary arteries (CORONARY ARTERY DISEASE), to obstruction by a thrombus (CORONARY THROMBOSIS), or less commonly, to diffuse narrowing of arterioles and other small vessels within the heart. Severe interruption of the blood supply to the myocardial tissue may result in necrosis of cardiac muscle (MYOCARDIAL INFARCTION).	2	1
Muscle Relaxation That phase of a muscle twitch during which a muscle returns to a resting position.	1.98	1
Allergy, Drug [description not available]	1.97	1
Drug Hypersensitivity Immunologically mediated adverse reactions to medicinal substances used legally or illegally.	1.97	1

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