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Cannabidiol-2',6'-dimethyl ether as an effective protector of 15-lipoxygenase-mediated low-density lipoprotein oxidation in vitro.
Biol Pharm Bull. 2011; 34(8):1252-6.BP

Abstract

15-Lipoxygenase (15-LOX) is one of the key enzymes responsible for the formation of oxidized low-density lipoprotein (ox-LDL), a major causal factor for atherosclerosis. Both enzymatic (15-LOX) and non-enzymatic (Cu(2+)) mechanisms have been proposed for the production of ox-LDL. We have recently reported that cannabidiol-2',6'-dimethyl ether (CBDD) is a selective and potent inhibitor of 15-LOX-catalyzed linoleic acid oxygenation (Takeda et al., Drug Metab. Dispos., 37, 1733-1737 (2009)). In the LDL, linoleic acid is present as cholesteryl linoleate, the major fatty acid esterified to cholesterol, and is susceptible to oxidative modification by 15-LOX or Cu(2+). In this investigation, we examined the efficacy of CBDD on i) 15-LOX-catalyzed oxygenation of cholesteryl linoleate, and ii) ox-LDL formation catalyzed by 15-LOX versus Cu(2+)-mediated non-enzymatic generation of this important mediator. The results obtained demonstrate that CBDD is a potent and selective inhibitor of ox-LDL formation generated by the 15-LOX pathway. These studies establish CBDD as both an important experimental tool for characterizing 15-LOX-mediated ox-LDL formation, and as a potentially useful therapeutic agent for treatment of atherosclerosis.

Authors+Show Affiliations

Department of Molecular Biology, Daiichi University of Pharmacy, Fukuoka 815–8511, Japan.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

21804214

Citation

Takeda, Shuso, et al. "Cannabidiol-2',6'-dimethyl Ether as an Effective Protector of 15-lipoxygenase-mediated Low-density Lipoprotein Oxidation in Vitro." Biological & Pharmaceutical Bulletin, vol. 34, no. 8, 2011, pp. 1252-6.
Takeda S, Hirayama A, Urata S, et al. Cannabidiol-2',6'-dimethyl ether as an effective protector of 15-lipoxygenase-mediated low-density lipoprotein oxidation in vitro. Biol Pharm Bull. 2011;34(8):1252-6.
Takeda, S., Hirayama, A., Urata, S., Mano, N., Fukagawa, K., Imamura, M., Irii, A., Kitajima, S., Masuyama, T., Nomiyama, M., Tatei, S., Tomita, S., Kudo, T., Noguchi, M., Yamaguchi, Y., Okamoto, Y., Amamoto, T., Fukunishi, Y., Watanabe, K., ... Aramaki, H. (2011). Cannabidiol-2',6'-dimethyl ether as an effective protector of 15-lipoxygenase-mediated low-density lipoprotein oxidation in vitro. Biological & Pharmaceutical Bulletin, 34(8), 1252-6.
Takeda S, et al. Cannabidiol-2',6'-dimethyl Ether as an Effective Protector of 15-lipoxygenase-mediated Low-density Lipoprotein Oxidation in Vitro. Biol Pharm Bull. 2011;34(8):1252-6. PubMed PMID: 21804214.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Cannabidiol-2',6'-dimethyl ether as an effective protector of 15-lipoxygenase-mediated low-density lipoprotein oxidation in vitro. AU - Takeda,Shuso, AU - Hirayama,Akari, AU - Urata,Shino, AU - Mano,Nobutaka, AU - Fukagawa,Keiko, AU - Imamura,Midori, AU - Irii,Ayumi, AU - Kitajima,Satomi, AU - Masuyama,Tomoko, AU - Nomiyama,Mai, AU - Tatei,Sachiko, AU - Tomita,Saari, AU - Kudo,Taichi, AU - Noguchi,Momoko, AU - Yamaguchi,Yasuhiro, AU - Okamoto,Yoshiko, AU - Amamoto,Toshiaki, AU - Fukunishi,Yoshifumi, AU - Watanabe,Kazuhito, AU - Omiecinski,Curtis John, AU - Aramaki,Hironori, PY - 2011/8/2/entrez PY - 2011/8/2/pubmed PY - 2012/3/1/medline SP - 1252 EP - 6 JF - Biological & pharmaceutical bulletin JO - Biol Pharm Bull VL - 34 IS - 8 N2 - 15-Lipoxygenase (15-LOX) is one of the key enzymes responsible for the formation of oxidized low-density lipoprotein (ox-LDL), a major causal factor for atherosclerosis. Both enzymatic (15-LOX) and non-enzymatic (Cu(2+)) mechanisms have been proposed for the production of ox-LDL. We have recently reported that cannabidiol-2',6'-dimethyl ether (CBDD) is a selective and potent inhibitor of 15-LOX-catalyzed linoleic acid oxygenation (Takeda et al., Drug Metab. Dispos., 37, 1733-1737 (2009)). In the LDL, linoleic acid is present as cholesteryl linoleate, the major fatty acid esterified to cholesterol, and is susceptible to oxidative modification by 15-LOX or Cu(2+). In this investigation, we examined the efficacy of CBDD on i) 15-LOX-catalyzed oxygenation of cholesteryl linoleate, and ii) ox-LDL formation catalyzed by 15-LOX versus Cu(2+)-mediated non-enzymatic generation of this important mediator. The results obtained demonstrate that CBDD is a potent and selective inhibitor of ox-LDL formation generated by the 15-LOX pathway. These studies establish CBDD as both an important experimental tool for characterizing 15-LOX-mediated ox-LDL formation, and as a potentially useful therapeutic agent for treatment of atherosclerosis. SN - 1347-5215 UR - https://www.unboundmedicine.com/medline/citation/21804214/Cannabidiol_2'6'_dimethyl_ether_as_an_effective_protector_of_15_lipoxygenase_mediated_low_density_lipoprotein_oxidation_in_vitro_ L2 - http://joi.jlc.jst.go.jp/JST.JSTAGE/bpb/34.1252?from=PubMed DB - PRIME DP - Unbound Medicine ER -