General Information of the Drug (ID: ferrodrug0118)
Name
Caryophyllene
Synonyms
Isocaryophyllene; Caryophyllene; 118-65-0; (-)-ISOCARYOPHYLLENE; Cis-caryophyllene; gamma-caryophyllene; NRY8I0KNIR; UNII-NRY8I0KNIR; 87-44-5; Isocaryophyllene (80per cent); (1R,4Z,9S)-4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-4-ene; EINECS 204-267-6; CHEBI:5993; beta-Caryophyllen; DTXSID10881246; CARYOPHYLLENE ISOCARYOPHYLLENE; Bicyclo(7.2.0)undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R,4Z,9S)-; g-Caryophyllene; E-Caryophyllene; EINECS 201-746-1; .gamma.-Caryophyllene; (1R-(1R*,4Z,9S*))-4,11,11-Trimethyl-8-methylenebicyclo(7.2.0)undec-4-ene; (-)-E-Caryophyllene; AI3-36121; .beta.-cis-Caryophyllene; Caryophyllene (VAN); UNII-BHW853AU9H; CCRIS 8094; 2-Methylene-6,10,10-trimethylbicyclo(7.2.0)undec-5-ene; beta-Caryophyllene (natural); -Caryophyllene; ss-Caryophyllene; Bicyclo(7.2.0)undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R,4E,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*))-; 4,11,11-Trimethyl-8-methylenebicyclo[7.2.0]undec-4-ene #; CHEMBL448700; (1R,9S,E)-4,11,11-trimethyl-8-methylenebicyclo[7.2.0]undec-4-ene; DTXCID401474828; (-)-Caryophyllene sum of enantiomers; LMPR0103120002; BS-48823; CARYOPHYLLENE ISOCARYOPHYLLENE [MI]; CARYOPHYLLENE, ALPHA + BETA MIXT.; C09691; E75762; Q27106968; (-)-(E)-Caryophyllene;()--caryophyllene;()-trans-Caryophyllene

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Structure
Formula
C15H24
IUPAC Name
(1R,4Z,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-FLFDDASRSA-N
PubChem CID
5281522
Full List of Ferroptosis Target Related to This Drug
Nuclear factor erythroid 2-related factor 2 (NFE2L2)
In total 1 item(s) under this Target
Experiment 1 Reporting the Ferroptosis-centered Drug Act on This Target [1]
Target for Ferroptosis Marker/Suppressor
Responsed Disease Cerebral ischemia ICD-11: 8B10
Pathway Response Fatty acid metabolism hsa01212
Cell Process Cell ferroptosis
In Vitro Model rPAs (Rat primary astrocytes)
In Vivo Model
Rats were anesthetized withisoflurane(2-3% oxygen) and placed in asupine position. And theright common carotid artery (CCA),external carotid artery (ECA), andinternal carotid artery (ICA) were exposed in sequence and separated carefully. Then we ligated the CCA and the ECA in turn, and at the same time, we clamped the internal carotid artery with an arterial clamp. Finally, we inserted a silicone nylon monofilament from the CCA into themiddle cerebral arteryand temporarily fixed it. After 1.5 h ofischemia, the monofilament was taken out and the blood vessels were ligated at theincision. The neck wound was sutured with surgical sutures. Subsequent experiments were performed after 12 h ofreperfusion. In thesham operationrats, except for the absence of the monofilament, the sham operation rats underwent the same surgical procedures as the MCAO/R model rats.

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Response regulation Our results indicated the critical role of ferroptosis in cerebral ischemia reperfusion injury. For the first time, we showed that the significant neuroprotective effects of b-Caryophyllene (BCP) in attenuating ischemic stroke injury are correlated with ferroptosis regulation, and its mechanism is associated with activation of the NRF2/HO-1 axis.
Heme oxygenase 1 (HMOX1)
In total 1 item(s) under this Target
Experiment 1 Reporting the Ferroptosis-centered Drug Act on This Target [1]
Target for Ferroptosis Suppressor
Responsed Disease Cerebral ischemia ICD-11: 8B10
Pathway Response Fatty acid metabolism hsa01212
Cell Process Cell ferroptosis
In Vitro Model rPAs (Rat primary astrocytes)
In Vivo Model
Rats were anesthetized withisoflurane(2-3% oxygen) and placed in asupine position. And theright common carotid artery (CCA),external carotid artery (ECA), andinternal carotid artery (ICA) were exposed in sequence and separated carefully. Then we ligated the CCA and the ECA in turn, and at the same time, we clamped the internal carotid artery with an arterial clamp. Finally, we inserted a silicone nylon monofilament from the CCA into themiddle cerebral arteryand temporarily fixed it. After 1.5 h ofischemia, the monofilament was taken out and the blood vessels were ligated at theincision. The neck wound was sutured with surgical sutures. Subsequent experiments were performed after 12 h ofreperfusion. In thesham operationrats, except for the absence of the monofilament, the sham operation rats underwent the same surgical procedures as the MCAO/R model rats.

    Click to Show/Hide
Response regulation Our results indicated the critical role of ferroptosis in cerebral ischemia reperfusion injury. For the first time, we showed that the significant neuroprotective effects of b-Caryophyllene (BCP) in attenuating ischemic stroke injury are correlated with ferroptosis regulation, and its mechanism is associated with activation of the NRF2/HO-1 axis.
References
Ref 1 -Caryophyllene suppresses ferroptosis induced by cerebral ischemia reperfusion via activation of the NRF2/HO-1 signaling pathway in MCAO/R rats. Phytomedicine. 2022 Jul 20;102:154112. doi: 10.1016/j.phymed.2022.154112. Epub 2022 Apr 22.