5E- and 5Z-farnesylacetones from Sargassum siliquastrum as novel selective L-type calcium channel blockers

Vascul Pharmacol. 2013 Apr;58(4):299-306. doi: 10.1016/j.vph.2013.02.001. Epub 2013 Feb 13.

Abstract

A specific blocker of L-type Ca(2+) channels may be useful in decreasing arterial tone by reducing the open-state probability of L-type Ca(2+) channels. The aim of the present study was to evaluate the farnesylacetones, which are major active constituents of Sargassum siliquastrum, regarding their vasodilatation efficacies, selectivities toward L-type Ca(2+) channels, and in vivo antihypertensive activities. The application of 5E-(farnesylacetone 311) or 5Z-farnesylacetone (farnesylacetone 312) induced concentration-dependent vasodilatation effects on the basilar artery that was pre-contracted with depolarization and showed an ignorable potential role of endothelial-derived nitric oxide. We also tested farnesylacetone 311 or 312 to determine their pharmacological profiles for the blockade of native L-type Ca(2+) channels in basilar arterial smooth muscle cells (BASMCs) and ventricular myocytes (VMCs), cloned L- (α1C/β2a/α2δ), N- (α1B/β1b/α2δ), and T-type Ca(2+) channels (α1G, α1H, and α1I). Farnesylacetone 311 or 312 showed greater selectivity toward the L-type Ca(2+) channels among the tested voltage-gated Ca(2+) channels. The ranked order of the potency for farnesylacetone 311 was cloned α1C≒L-type (BASMC)≒L-type (VMCs)>α1B>α1H>α1I>α1G and that for farnesylacetone 312 was cloned α1C≒L-type (BASMCs)≒L-type (VMCs)>α1H>α1G>α1B>α1I. The oral administration of the farnesylacetone 311 (80mg/kg) conferred potent, long-lasting antihypertensive activity in spontaneous hypertensive rats, but it did not alter the heart rate.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Administration, Oral
  • Animals
  • Antihypertensive Agents / chemistry
  • Antihypertensive Agents / isolation & purification
  • Antihypertensive Agents / pharmacology
  • Basilar Artery / drug effects
  • Basilar Artery / metabolism
  • Blood Circulation Time
  • Calcium Channel Blockers / chemistry
  • Calcium Channel Blockers / isolation & purification
  • Calcium Channel Blockers / pharmacology*
  • Calcium Channels, L-Type / drug effects*
  • Calcium Channels, L-Type / metabolism
  • Dose-Response Relationship, Drug
  • HEK293 Cells
  • Heart Rate / drug effects
  • Humans
  • Hypertension / drug therapy
  • Male
  • Myocytes, Smooth Muscle / drug effects
  • Myocytes, Smooth Muscle / metabolism
  • Nitric Oxide / metabolism
  • Rabbits
  • Rats
  • Rats, Inbred SHR
  • Rats, Sprague-Dawley
  • Sargassum / chemistry*
  • Terpenes / chemistry
  • Terpenes / isolation & purification
  • Terpenes / pharmacology*
  • Vasodilation / drug effects

Substances

  • Antihypertensive Agents
  • Calcium Channel Blockers
  • Calcium Channels, L-Type
  • Terpenes
  • Nitric Oxide
  • farnesylacetone