anemonin profile

Anemonin is a toxic, lactone derivative produced by several species of buttercup (Ranunculus) and anemone plants. It is synthesized through the dimerization of protoanemonin, a highly reactive molecule formed from the breakdown of the precursor compound, ranunculin. Anemonin has demonstrated various pharmacological effects, including anti-inflammatory, antimicrobial, and cytotoxic activities. It exhibits these effects by inhibiting enzymes involved in cell signaling pathways and disrupting cellular processes. The potent cytotoxic nature of anemonin has led to its exploration as a potential anticancer agent, however, its toxicity to healthy cells presents a significant challenge. Research on anemonin focuses on understanding its biosynthetic pathway, elucidating its mechanisms of action, and potentially developing safer and more targeted therapeutic applications.'

anemonin: a furanone dimer found in RANUNCULACEAE; do not confuse with anemonine which is 5-(carboxymethyl)-1,1-dimethylimidazolium hydroxide inner salt; ranunculine is hydrolyzed to protoanemonin which dimerizes to anemonin; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

ID Source	ID
PubMed CID	10496
CHEMBL ID	1972777
SCHEMBL ID	165744
MeSH ID	M0091247

Synonym
NCI60_042100
1,7-dioxadispiro[4.0.4.2]dodeca-3,9-diene-2,8-dione
90921-11-2
4,7-dioxadispiro[4.0.4^{6}.2^{5}]dodeca-1,9-diene-3,8-dione
anemonin
NSC94101 ,
nsc-94101
AKOS006278221
1,7-dioxadispiro(4.0.4.2)dodeca-3,9-diene-2,8-dione
nsc 94101
SCHEMBL165744
CHEMBL1972777
Q-100925
JLUQTCXCAFSSLD-UHFFFAOYSA-N
FT-0699191
CS-0018238
(rac)-anemonin
Q416699
1,-7--dioxadispiro[4.0.4.2-]-dodeca--3,-9--diene--2,-8--dione
DTXSID80871710
1,7-dioxadispiro[4.0.4~6~.2~5~]dodeca-3,9-diene-2,8-dione
AMY19500
anemonine; pulsatilla camphor; trans-anemonin
4,7-dioxadispiro[4.0.46.25]dodeca-1,9-diene-3,8-dione
A860664
1,7-dioxadispiro[4.0.4?.2?]dodeca-3,9-diene-2,8-dione
HY-N0278A

Excerpt	Reference	Relevance
"Anemonin (ANE) is a small natural molecule extracted from various kinds of Chinese traditional herbs and has been shown to inhibiting inflammation response."	( Anemonin attenuates osteoarthritis progression through inhibiting the activation of IL-1β/NF-κB pathway. Chen, H; Chen, L; Du, X; Huang, J; Luo, F; Tan, Q; Wang, J; Wang, Q; Wang, Z; Xie, Y; Xu, W; Zhou, S, 2017)	2.62

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	6 (26.09)	18.7374
1990's	0 (0.00)	18.2507
2000's	8 (34.78)	29.6817
2010's	7 (30.43)	24.3611
2020's	2 (8.70)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	0 (0.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	23 (100.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
protocatechuic acid protocatechuic acid: RN given refers to parent cpd; structure. 3,4-dihydroxybenzoic acid : A dihydroxybenzoic acid in which the hydroxy groups are located at positions 3 and 4.	2.04	1	catechols; dihydroxybenzoic acid	antineoplastic agent; EC 1.1.1.25 (shikimate dehydrogenase) inhibitor; EC 1.14.11.2 (procollagen-proline dioxygenase) inhibitor; human xenobiotic metabolite; plant metabolite
1-butanol 1-Butanol: A four carbon linear hydrocarbon that has a hydroxy group at position 1.. butan-1-ol : A primary alcohol that is butane in which a hydrogen of one of the methyl groups is substituted by a hydroxy group. It it produced in small amounts in humans by the gut microbes.	2.04	1	alkyl alcohol; primary alcohol; short-chain primary fatty alcohol	human metabolite; mouse metabolite; protic solvent
palmitic acid Palmitic Acid: A common saturated fatty acid found in fats and waxes including olive oil, palm oil, and body lipids.. hexadecanoic acid : A straight-chain, sixteen-carbon, saturated long-chain fatty acid.	2.03	1	long-chain fatty acid; straight-chain saturated fatty acid	algal metabolite; Daphnia magna metabolite; EC 1.1.1.189 (prostaglandin-E2 9-reductase) inhibitor; plant metabolite
berberine [no description available]	2.05	1	alkaloid antibiotic; berberine alkaloid; botanical anti-fungal agent; organic heteropentacyclic compound	antilipemic drug; antineoplastic agent; antioxidant; EC 1.1.1.141 [15-hydroxyprostaglandin dehydrogenase (NAD(+))] inhibitor; EC 1.1.1.21 (aldehyde reductase) inhibitor; EC 1.13.11.52 (indoleamine 2,3-dioxygenase) inhibitor; EC 1.21.3.3 (reticuline oxidase) inhibitor; EC 2.1.1.116 [3'-hydroxy-N-methyl-(S)-coclaurine 4'-O-methyltransferase] inhibitor; EC 2.1.1.122 [(S)-tetrahydroprotoberberine N-methyltransferase] inhibitor; EC 2.7.11.10 (IkappaB kinase) inhibitor; EC 3.1.1.4 (phospholipase A2) inhibitor; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor; EC 3.4.14.5 (dipeptidyl-peptidase IV) inhibitor; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; geroprotector; hypoglycemic agent; metabolite; potassium channel blocker
scoparone scoparone: structure. scoparone : A member of the class of coumarins that is esculetin in which the two hydroxy groups at positions 6 and 7 are replaced by methoxy groups. It is a major constituent of the Chinese herbal medicine Yin Chen Hao, and exhibits a variety of pharmacological activities such as anti-inflammatory, anti-allergic, and anti-tumor activities.	2.04	1	aromatic ether; coumarins	anti-allergic agent; anti-inflammatory agent; antihypertensive agent; antilipemic drug; immunosuppressive agent; plant metabolite
2-naphthol 2-naphthol: RN given refers to parent cpd. 2-naphthol : A naphthol carrying a hydroxy group at position 2.. naphthols : Any hydroxynaphthalene derivative that has a single hydroxy substituent.	2.03	1	naphthol	antinematodal drug; genotoxin; human urinary metabolite; human xenobiotic metabolite; mouse metabolite; radical scavenger
ethyl acetate ethyl acetate : The acetate ester formed between acetic acid and ethanol.	2.04	1	acetate ester; ethyl ester; volatile organic compound	EC 3.4.19.3 (pyroglutamyl-peptidase I) inhibitor; metabolite; polar aprotic solvent; Saccharomyces cerevisiae metabolite
flavone flavone: RN given refers to unlabeled cpd; structure given in first source. flavone : The simplest member of the class of flavones that consists of 4H-chromen-4-one bearing a phenyl substituent at position 2.	2.04	1	flavones	metabolite; nematicide
malondialdehyde Malondialdehyde: The dialdehyde of malonic acid.. malonaldehyde : A dialdehyde that is propane substituted by two oxo groups at the terminal carbon atoms respectively. A biomarker of oxidative damage to lipids caused by smoking, it exists in vivo mainly in the enol form.	2.53	2	dialdehyde	biomarker
palmatine burasaine: structure in first source	2.05	1	berberine alkaloid; organic heterotetracyclic compound	plant metabolite
phenyl acetate phenyl acetate: The ester formed between phenol and acetic acid. Don't confuse with phenylacetic acid derivatives listed under PHENYLACETATES.. phenyl acetate : An acetate ester obtained by the formal condensation of phenol with acetic acid.	2.04	1	benzenes; phenyl acetates
laurocapram laurocapram: enhances percutaneous absorption of different chemicals; structure given in first source	2.03	1
protoanemonin protoanemonin: a furanone found in RANUNCULACEAE plants; structure given in first source; has antifungal & antibiotic properties; ranunculine is hydrolyzed to protoanemonin which dimerizes to anemonin	2.87	4	butenolide
jatrorrhizine jatrorrhizine: isolated from bark of Enantia chlorantha (Annonaceae); structure given in first source	2.05	1	alkaloid
friedelin 3-friedelanone: from the stem bark of Irvingia gabonensis; structure in first source. friedelin : A pentacyclic triterpenoid that is perhydropicene which is substituted by an oxo group at position 3 and by methyl groups at the 4, 4a, 6b, 8a, 11, 11, 12b, and 14a-positions (the 4R,4aS,6aS,6bR,8aR,12aR,12bS,14aS,14bS-enantiomer). It is the major triterpenoid constituent of cork.	2.03	1	cyclic terpene ketone; pentacyclic triterpenoid	anti-inflammatory drug; antipyretic; non-narcotic analgesic; plant metabolite
carboxypolymethylene carbomer: high molecular polyanionic substance	2.13	1
isolariciresinol isolariciresinol: RN given refers to ((1-S-(1alpha,2beta,3alpha))-isomer); structure given in first source. (+)-isolariciresinol : A lignan that is 5,6,7,8-tetrahydronaphthalen-2-ol substituted by hydroxymethyl groups at positions 6 and 7, a methoxy group at position 3 and a 4-hydroxy-3-methoxyphenyl group at position 8. It has been isolated from the roots of Rubia yunnanensis.	2.03	1	guaiacols; lignan; polyphenol; primary alcohol	plant metabolite
lignin Lignin: The most abundant natural aromatic organic polymer found in all vascular plants. Lignin together with cellulose and hemicellulose are the major cell wall components of the fibers of all wood and grass species. Lignin is composed of coniferyl, p-coumaryl, and sinapyl alcohols in varying ratios in different plant species. (From Merck Index, 11th ed). lignin : A polyphenylpropanoid derived from three monolignol monomers: trans-p-coumaryl alcohol, coniferol and trans-sinapyl alcohol. There is extensive cross-linking and no defined primary structure.	2.03	1
ranunculin ranunculin: toxic constituent of Ceratocephalus and Ranunculus	1.92	1	glycoside
gamma-sitosterol clionasterol : A member of the class of phytosterols that is poriferast-5-ene carrying a beta-hydroxy substituent at position 3.	2.03	1	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; phytosterols	marine metabolite; plant metabolite
penicillic acid Penicillic Acid: A mycotoxin with antibiotic and carcinogenic activity produced by various strains of PENICILLIUM and ASPERGILLUS. It has been found in tobacco, sausages, and corn.	6.92	1
cytellin cytellin: a phytosterol preparation of mainly B-sitosterol, that was marketed by Eli Lilly to lower cholesterol 1957 to 1982	2.03	1
luteolin [no description available]	2.04	1	3'-hydroxyflavonoid; tetrahydroxyflavone	angiogenesis inhibitor; anti-inflammatory agent; antineoplastic agent; apoptosis inducer; c-Jun N-terminal kinase inhibitor; EC 2.3.1.85 (fatty acid synthase) inhibitor; immunomodulator; nephroprotective agent; plant metabolite; radical scavenger; vascular endothelial growth factor receptor antagonist
scopoletin [no description available]	2.04	1	hydroxycoumarin	plant growth regulator; plant metabolite
esculetin esculetin: used in filters for absorption of ultraviolet light; structure. esculetin : A hydroxycoumarin that is umbelliferone in which the hydrogen at position 6 is substituted by a hydroxy group. It is used in filters for absorption of ultraviolet light.	2.05	1	hydroxycoumarin	antioxidant; plant metabolite; ultraviolet filter
esculin [no description available]	2.05	1	beta-D-glucoside; hydroxycoumarin	antioxidant; metabolite
tricin tricin: from Spartina cynosuroides and other plants; structure	2.04	1	3'-methoxyflavones; dimethoxyflavone; trihydroxyflavone	EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; metabolite
thromboxane b2 Thromboxane B2: A stable, physiologically active compound formed in vivo from the prostaglandin endoperoxides. It is important in the platelet-release reaction (release of ADP and serotonin).. thromboxane B2 : A member of the class of thromboxanes B that is (5Z,13E)-thromboxa-5,13-dien-1-oic acid substituted by hydroxy groups at positions 9, 11 and 15.	2.05	1	thromboxanes B	human metabolite; mouse metabolite
endothelin-1 Endothelin-1: A 21-amino acid peptide produced in a variety of tissues including endothelial and vascular smooth-muscle cells, neurons and astrocytes in the central nervous system, and endometrial cells. It acts as a modulator of vasomotor tone, cell proliferation, and hormone production. (N Eng J Med 1995;333(6):356-63)	2.03	1
interleukin-8 Interleukin-8: A member of the CXC chemokine family that plays a role in the regulation of the acute inflammatory response. It is secreted by variety of cell types and induces CHEMOTAXIS of NEUTROPHILS and other inflammatory cells.	2.05	1
warfarin Warfarin: An anticoagulant that acts by inhibiting the synthesis of vitamin K-dependent coagulation factors. Warfarin is indicated for the prophylaxis and/or treatment of venous thrombosis and its extension, pulmonary embolism, and atrial fibrillation with embolization. It is also used as an adjunct in the prophylaxis of systemic embolism after myocardial infarction. Warfarin is also used as a rodenticide.. warfarin : A racemate comprising equal amounts of (R)- and (S)-warfarin. Extensively used as both an anticoagulant drug and as a pesticide against rats and mice.. 4-hydroxy-3-(3-oxo-1-phenylbutyl)-1-benzopyran-2-one : A member of the class of coumarins that is 4-hydroxycoumarin which is substituted at position 3 by a 1-phenyl-3-oxo-1-butyl group.	2.04	1	benzenes; hydroxycoumarin; methyl ketone
epidermal growth factor Epidermal Growth Factor: A 6-kDa polypeptide growth factor initially discovered in mouse submaxillary glands. Human epidermal growth factor was originally isolated from urine based on its ability to inhibit gastric secretion and called urogastrone. Epidermal growth factor exerts a wide variety of biological effects including the promotion of proliferation and differentiation of mesenchymal and EPITHELIAL CELLS. It is synthesized as a transmembrane protein which can be cleaved to release a soluble active form.	2.13	1

Condition	Relationship Strength	Studies
Degenerative Disc Disease [description not available]	2.6	1
Innate Inflammatory Response [description not available]	2.6	1
Inflammation A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.	7.6	1
Intervertebral Disc Degeneration Degenerative changes in the INTERVERTEBRAL DISC due to aging or structural damage, especially to the vertebral end-plates.	2.6	1
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	2.54	2
Arthritis, Degenerative [description not available]	2.15	1
Osteoarthritis A progressive, degenerative joint disease, the most common form of arthritis, especially in older persons. The disease is thought to result not from the aging process but from biochemical changes and biomechanical stresses affecting articular cartilage. In the foreign literature it is often called osteoarthrosis deformans.	7.15	1
Alloxan Diabetes [description not available]	2.21	1
Diabetic Glomerulosclerosis [description not available]	2.21	1
Diabetic Nephropathies KIDNEY injuries associated with diabetes mellitus and affecting KIDNEY GLOMERULUS; ARTERIOLES; KIDNEY TUBULES; and the interstitium. Clinical signs include persistent PROTEINURIA, from microalbuminuria progressing to ALBUMINURIA of greater than 300 mg/24 h, leading to reduced GLOMERULAR FILTRATION RATE and END-STAGE RENAL DISEASE.	2.21	1
Cerebral Infarction, Middle Cerebral Artery [description not available]	2.1	1
Infarction, Middle Cerebral Artery NECROSIS occurring in the MIDDLE CEREBRAL ARTERY distribution system which brings blood to the entire lateral aspects of each CEREBRAL HEMISPHERE. Clinical signs include impaired cognition; APHASIA; AGRAPHIA; weak and numbness in the face and arms, contralaterally or bilaterally depending on the infarction.	2.1	1
Rheumatoid Arthritis [description not available]	2.13	1
Anasarca [description not available]	2.13	1
Arthritis, Rheumatoid A chronic systemic disease, primarily of the joints, marked by inflammatory changes in the synovial membranes and articular structures, widespread fibrinoid degeneration of the collagen fibers in mesenchymal tissues, and by atrophy and rarefaction of bony structures. Etiology is unknown, but autoimmune mechanisms have been implicated.	2.13	1
Edema Abnormal fluid accumulation in TISSUES or body cavities. Most cases of edema are present under the SKIN in SUBCUTANEOUS TISSUE.	2.13	1
Gastritis Inflammation of the GASTRIC MUCOSA, a lesion observed in a number of unrelated disorders.	2.13	1
Sensitivity and Specificity Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)	2.04	1
Rheumatism [description not available]	1.95	1
Rheumatic Diseases Disorders of connective tissue, especially the joints and related structures, characterized by inflammation, degeneration, or metabolic derangement.	1.95	1

anemonin

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Synonyms (27)

Research Excerpts

Overview

Research

Studies (23)

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Research Demand Index: 45.82

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