Ferroptosis-centered Drug Response Information

General Information of the Drug (ID: ferrodrug0070)
Name
Caryophyllene
Synonyms
BETA-CARYOPHYLLENE; Caryophyllene; trans-Caryophyllene; (-)-trans-Caryophyllene; 87-44-5; (-)-beta-caryophyllene; L-Caryophyllene; (-)-(E)-Caryophyllene; (E)-Caryophyllene; .beta.-Caryophyllene; b-caryophyllene; FEMA No. 2252; (E)-beta-caryophyllene; trans-beta-caryophyllene; CHEBI:10357; Beta-Caryophylene; trans-.beta.-Caryophyllene; (-)-Caryophyllene; .beta.-Caryophyllen; DTXSID8024739; (E)-beta-caryophylene; NSC 11906; NSC-11906; .beta.-(E)-Caryophyllene; BHW853AU9H; Cannabinoid; E-Caryophyllene; DTXCID304739; beta-Caryophyllen; (-)-E-Caryophyllene; 8-Methylene-4,11,11-(trimethyl)bicyclo(7.2.0)undec-4-ene; UNII-BHW853AU9H; (1R,4E,9S)-4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-4-ene; Bicyclo(7.2.0)undec-4-ene, 8-methylene-4,11,11-trimethyl-, (E)-(1R,9S)-(-)-; g-Caryophyllene; CCRIS 8094; EINECS 201-746-1; (1R,4E,9S)-4,11,11-trimethyl-8-methylenebicyclo[7.2.0]undec-4-ene; trans-(1R,9S)-4,11,11-trimethyl-8-methylenebicyclo[7.2.0]undec-4-ene; (1R,4E,9S)-4,11,11-TRIMETHYL-8-METHYLENEBICYCLO(7.2.0)UNDEC-4-ENE; E-.beta.-caryophyllene; AI3-36121; .beta.-Caryophyllene, (-); CHEBI:63191; 2-Methylene-6,10,10-trimethylbicyclo(7.2.0)undec-5-ene; cariofileno; Tincturoid; Copaiba; 8-Methylene-4,11,11-(trimethyl)bicyclo[7.2.0]undec-4-ene; clove terpenes; NSC11906; Caryophyllene B; Caryophyllene hg; beta-cariofillene; cb2 receptor; (1R,4E,9S)-4,11,11-trimethyl-8-methylene-bicyclo[7.2.0]undec-4-ene; (1R,4E,9S)-4,11,11-trimethyl-8-methylidenebicyclo(7.2.0)undec-4-ene; trans-(1R,9S)-4,11,11-trimethyl-8-methylenebicyclo(7.2.0)undec-4-ene; beta-caryophillene; BICYCLO(7.2.0)UNDEC-4-ENE, 4,11,11-TRIMETHYL-8-METHYLENE-, (E)-(1R,9S)-(-)-; Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, (E)-(1R,9S)-(-)-; Bicyclo[7.2.0]undec-4-ene, 8-methylene-4,11,11-trimethyl-, (E)-(1R,9S)-(-)-; 4,11,11-Trimethyl-8-methylenebicyclo(7.2.0)undec-4-ene, (1R-(1R*,4E,9S))-; Bicyclo(7.2.0)undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R-(1R*,4E,9S*))-; Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, [1R-(1R*,4E,9S*)]-; trans caryophyllene; caryophyllene 917; E-beta-caryophyllene; MFCD00075925; Caryophyllene, (E); 02 - Terpenes; (?)-b-caryophyllene; 1-CARYOPHYLLENE; beta-(e)-caryophyllene; beta-trans-caryophyllene; clove terpene derivative; (?)-trans-Caryophyllene; caryophyllene beta natural; CARYOPHYLLENE [MI]; .beta.-trans-Caryophyllene; (-)-I(2)-caryophyllene; 12 - Analysis of terpenes; Bicyclo(7.2.0)undec-4-ene, 4,11,11-trimethyl-8-methylene-; CHEMBL445740; BETA-CARYOPHYLLENE [FCC]; BETA-CARYOPHYLLENE [INCI]; Bicyclo(7.2.0)undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R,4E,9S)-; HY-N1415; .BETA.-CARYOPHYLLENE [FHFI]; Tox21_301497; (1S,9R)-6,10,10-trimethyl-2-methylenebicyclo[7.2.0]undec-5-ene; 11CAR7501; BDBM50529607; s6058; AKOS024283988; LMPR0103120001; beta-Caryophyllene, >=80%, FCC, FG; CAS-87-44-5; NCGC00142620-01; NCGC00255159-01; (-)-trans-Caryophyllene, analytical standard; CS-0016839; C09629; beta-Caryophyllene 2000 microg/mL in Acetonitrile; P198906; Q421614; W-109317; (-)-trans-Caryophyllene, >=98.5% (sum of enantiomers, GC); 8-Methylene-4,11,11-(trimethyl)bicyclo(7.2.0)undec-4-ene, (1R,4E,9S)-; BICYCLO(7.2.0)UNDEC-4-ENE, 4,11,11-TRIMETHYL-8-METHYLENE-, (1R-(1R*,4E,9S*)-; Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, [1R- (1R*,4E,9S*)]-

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Status
Phase 2
Drug Type
Small molecular drug
Structure
Formula
C15H24
IUPAC Name
(1R,4E,9S)-4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-4-ene
Canonical SMILES
CC1=CCCC(=C)C2CC(C2CC1)(C)C
InChI
InChI=1S/C15H24/c1-11-6-5-7-12(2)13-10-15(3,4)14(13)9-8-11/h6,13-14H,2,5,7-10H2,1,3-4H3/b11-6+/t13-,14-/m1/s1
InChIKey
NPNUFJAVOOONJE-GFUGXAQUSA-N
PubChem CID
5281515
TTD Drug ID
D53QMP
Full List of Ferroptosis Target Related to This Drug
Unspecific Target
In total 1 item(s) under this Target
Experiment 1 Reporting the Ferroptosis-centered Drug Act on This Target [1]
Responsed Disease Ulcerative colitis ICD-11: DD71
 Disease Info 
Responsed Regulator Cannabinoid receptor 2 (CNR2) Suppressor
 Regulator Info 
Pathway Response Glutathione metabolism hsa00480
Ferroptosis hsa04216
Cell Process Cell ferroptosis
In Vitro Model RAW 264.7 cells Leukemia Mus musculus CVCL_0493
In Vivo Model
After 10 days of acclimation, the mice were randomly assigned to five groups (n = 6 each): control, model (3% DSS), BCP (50 mg/kg body weight), AM630 (10 mg/kg body weight) and AM630 + BCP. All mice (except those in the control group) were provided with a solution of filtered water containing 3% (w/v) DSS ad libitum during the experiment period. The mice in the control group received only normal drinking water. For the treatment groups, BCP was dissolved in corn oil at doses of 50 mg/kg and administered orally once a day. The mice in the AM630 group were injected intraperitoneally with AM630 (10 mg/kg). The mice in the AM630 + BCP group received an intraperitoneal injection of AM630 (10 mg/kg) given 30 min before the BCP (50 mg/kg). During the study, symptomatic parameters including body weight, stool character and bleeding were recorded daily. The disease activity index (DAI) was calculated according to our previous study. After 8 days of treatment, all mice were anesthetized with pentobarbital sodium. The blood and colon samples were collected for subsequent analysis. The collected blood was left to coagulate for 20 min at room temperature and centrifuged for 15 min at 3000 g to obtain the serum.

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Response regulation B-Caryophyllene (BCP) activated the type 2 cannabinoid receptor (CB2R) to inhibit macrophage ferroptosis and its induced inflammatory response both in vivo and in vitro. These results revealed that macrophage ferroptosis is a potential therapeutic target for ulcerative colitis and identified a novel mechanism of BCP in ameliorating experimental colitis.
References
Ref 1 -Caryophyllene Acts as a Ferroptosis Inhibitor to Ameliorate Experimental Colitis. Int J Mol Sci. 2022 Dec 16;23(24):16055. doi: 10.3390/ijms232416055.