Effects of naturally occurring prenylated flavonoids on enzymes metabolizing arachidonic acid: cyclooxygenases and lipoxygenases - PubMed (original) (raw)
Effects of naturally occurring prenylated flavonoids on enzymes metabolizing arachidonic acid: cyclooxygenases and lipoxygenases
Y S Chi et al. Biochem Pharmacol. 2001.
Abstract
Prenylated flavonoids are chemical entities having an isoprenyl, a geranyl, a 1,1-dimethylallyl, and/or a lavandulyl moiety as part of their flavonoid backbone structure. In this study, the effects of 19 naturally occurring prenylated flavonoids, isolated from medicinal plants, on cyclooxygenase (COX)-1 and COX-2 and on 5-lipoxygenase (5-LOX) and 12-LOX were investigated using [14C]arachidonic acid as a substrate. The homogenates of bovine platelets and polymorphonuclear leukocytes were used as COX-1, 12-LOX, and 5-LOX enzyme sources; the homogenate of aspirin-pretreated lipopolysaccharide-induced RAW 264.7 cells was used for the COX-2 enzyme source. Among the 19 prenylated flavonoids, morusin, kuwanon C, sanggenon B, sanggenon D and kazinol B inhibited COX-2 activity (ic(50) = 73-100 microM), but the potencies were far less than that of NS-398 (ic(50) = 2.9 microM). In contrast, many prenylated flavonoids, such as kuraridin, kuwanon C and sophoraisoflavanone A, inhibited COX-1 activity. Of the COX-1 inhibiting prenylated flavonoids, kuraridin, kurarinone, and sophoraflavanone G, all having a C-8 lavandulyl moiety, showed potent activity (ic(50) = 0.1 to 1 microM) comparable to that of indomethacin (ic(50) = 0.7 microM). Most of the prenylated flavonoids tested inhibited 5-LOX activity with ic(50) values ranging from 0.09 to 100 microM. Of these, only kuwanon C, papyriflavonol A and sophoraflavanone G showed inhibitory activity against 12-LOX at low concentration ranges (ic(50) = 19-69 microM) comparable to that of NDGA (ic(50) = 2.6 microM). Our results suggest that the position and the nature of the prenyl substitution greatly influence in vitro biological activities of these molecules.
Similar articles
- Effects of sophoraflavanone G, a prenylated flavonoid from Sophora flavescens, on cyclooxygenase-2 and in vivo inflammatory response.
Kim DW, Chi YS, Son KH, Chang HW, Kim JS, Kang SS, Kim HP. Kim DW, et al. Arch Pharm Res. 2002 Jun;25(3):329-35. doi: 10.1007/BF02976635. Arch Pharm Res. 2002. PMID: 12135106 - Prenylated flavonoids as tyrosinase inhibitors.
Lee NK, Son KH, Chang HW, Kang SS, Park H, Heo MY, Kim HP. Lee NK, et al. Arch Pharm Res. 2004 Nov;27(11):1132-5. doi: 10.1007/BF02975118. Arch Pharm Res. 2004. PMID: 15595416 - Biologically active prenylated flavonoids from the genus Sophora and their structure-activity relationship-A review.
Boozari M, Soltani S, Iranshahi M. Boozari M, et al. Phytother Res. 2019 Mar;33(3):546-560. doi: 10.1002/ptr.6265. Epub 2019 Jan 16. Phytother Res. 2019. PMID: 30652369 Review. - A systematic review on biological activities of prenylated flavonoids.
Chen X, Mukwaya E, Wong MS, Zhang Y. Chen X, et al. Pharm Biol. 2014 May;52(5):655-60. doi: 10.3109/13880209.2013.853809. Epub 2013 Nov 21. Pharm Biol. 2014. PMID: 24256182 Review.
Cited by
- Mulberry Component Kuwanon C Exerts Potent Therapeutic Efficacy In Vitro against COVID-19 by Blocking the SARS-CoV-2 Spike S1 RBD:ACE2 Receptor Interaction.
Kim YS, Kwon EB, Kim B, Chung HS, Choi G, Kim YH, Choi JG. Kim YS, et al. Int J Mol Sci. 2022 Oct 19;23(20):12516. doi: 10.3390/ijms232012516. Int J Mol Sci. 2022. PMID: 36293371 Free PMC article. - Therapeutic Potential of Leaves from Fridericia chica (Bonpl.) L. G. Lohmann: Botanical Aspects, Phytochemical and Biological, Anti-Inflammatory, Antioxidant and Healing Action.
Batalha ADSJ, Souza DCM, Ubiera RD, Chaves FCM, Monteiro WM, da Silva FMA, Koolen HHF, Boechat AL, Sartim MA. Batalha ADSJ, et al. Biomolecules. 2022 Aug 31;12(9):1208. doi: 10.3390/biom12091208. Biomolecules. 2022. PMID: 36139047 Free PMC article. Review. - Prenylated Flavonoids in Topical Infections and Wound Healing.
Sychrová A, Škovranová G, Čulenová M, Bittner Fialová S. Sychrová A, et al. Molecules. 2022 Jul 13;27(14):4491. doi: 10.3390/molecules27144491. Molecules. 2022. PMID: 35889363 Free PMC article. Review. - The Long Search for Pharmacologically Useful Anti-Inflammatory Flavonoids and Their Action Mechanisms: Past, Present, and Future.
Kim HP. Kim HP. Biomol Ther (Seoul). 2022 Mar 1;30(2):117-125. doi: 10.4062/biomolther.2022.004. Biomol Ther (Seoul). 2022. PMID: 35131949 Free PMC article. Review. - Five-Decade Update on Chemopreventive and Other Pharmacological Potential of Kurarinone: a Natural Flavanone.
Kumar S, Prajapati KS, Shuaib M, Kushwaha PP, Tuli HS, Singh AK. Kumar S, et al. Front Pharmacol. 2021 Sep 27;12:737137. doi: 10.3389/fphar.2021.737137. eCollection 2021. Front Pharmacol. 2021. PMID: 34646138 Free PMC article. Review.
Publication types
MeSH terms
Substances
LinkOut - more resources
Full Text Sources
Other Literature Sources
Research Materials
Miscellaneous