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01-01-2013 | Note

Vasorelaxant effect of FR900359 from Ardisia crenata on rat aortic artery

Authors: Kazumasa Zaima, Jun Deguchi, Yosuke Matsuno, Toshio Kaneda, Yusuke Hirasawa, Hiroshi Morita

Published in: Journal of Natural Medicines | Issue 1/2013

Abstract

A cyclic depsipeptide, FR900359, isolated from Ardisia crenata was evaluated for vasorelaxant effects on rat aortic arteries. FR900359 caused concentration-dependent relaxation (1 nM–10 μM) in phenylephrine-precontracted endothelium-intact aortic rings, which was inhibited by addition of l-NMMA, a NOS inhibitor. In endothelium-denuded rings, the relaxant effect of low concentrations of FR900359 was diminished, but remained at high concentrations. In endothelium-denuded rings, FR900359 at 0.1 μM significantly attenuated high-K⁺-induced contractions and completely inhibited Ca²⁺-induced contractions. These results suggest that the vasorelaxant effect of FR900359 is mediated through the increased release of NO from endothelial cells at low concentrations, and can be attributed to inhibitory effects on voltage-dependent Ca²⁺ channel- and receptor-operated Ca²⁺ channel-dependent Ca²⁺ influx at high concentrations.

Muller JM, Davis MJ, Kuo L, Chilian WM (1999) Changes in coronary endothelial cell Ca²⁺ concentration during shear stress- and agonist-induced vasodilation. Am J Physiol 276:H1706–H1714PubMed

Muller B, Kleschyov AV, Gyorgy K, Stoclet JC (2000) Inducible NO synthase activity in blood vessels and heart: new insight into cell origin and consequences. Physiol Res 49:19–26PubMed

Karasaki H, Ozaki K, Hori M, Mitsui-Saito M, Amono K, Harada K, Miyamoto S, Nakazawa H, Won KJ, Sato K (1997) Calcium movements, distribution, and functions in smooth muscle. Pharmacol Rev 49:157–230

Fujioka M, Koda S, Morimoto Y, Biemann K (1988) Structure of FR900359, a cyclic depsipeptide from Ardisia crenata sims. J Org Chem 53:2820–2825CrossRef

Maotian W, Xiongtai G, Xiuwen H, Shanhai H (1992) A new triterpenoid saponin from Ardisia crenata. Planta Med 58:205–207PubMedCrossRef

Jia Z, Koike K, Ohmoto T, Ni M (1994) Triterpenoid saponins from Ardisia crenata. Phytochemistry 37:1389–1396PubMedCrossRef

Miyamae A, Fujioka M, Koda S, Morimoto Y (1989) Structural studies of FR900359, a novel cyclic depsipeptide from Ardisia crenata Sims (Myrsinaceae). J Chem Soc Perkin Trans I 5:873–878CrossRef

Morita H, Iizuka T, Choo CY, Chan KL, Itokawa H, Takeya K (2005) Dichotomins J and K, vasodilator cyclic peptides from Stellaria dichotoma. J Nat Prod 68:1686–1688PubMedCrossRef

Morita H, Iizuka T, Choo CY, Chan KL, Takeya K, Kobayashi J (2006) Vasorelaxant activity of cyclic peptide, cyclosquamosin B, from Annona squamosa. Bioorg Med Chem Lett 16:4609–4611PubMedCrossRef

10.

Morita H, Eda M, Iizuka T, Hirasawa Y, Sekiguchi M, Yun YS, Itokawa H, Takeya K (2006) Structure of a new cyclic nonapeptide, segetalin F, and vasorelaxant activity of segetalins from Vaccaria segetalis. Bioorg Med Chem Lett 16:4458–4461PubMedCrossRef

11.

Morita H, Enomoto M, Hirasawa Y, Iizuka T, Ogawa K, Kawahara N, Goda Y, Matsumoto T, Takeya K (2007) Cyclonatsudamine A, a new vasodilator cyclic peptide from Citrus natsudaidai. Bioorg Med Chem Lett 17:5410–5413PubMedCrossRef

12.

Morita H, Tomizawa Y, Deguchi J, Ishikawa T, Arai H, Zaima K, Hosoya T, Hirasawa Y, Matsumoto T, Kamata K, Ekasari W, Widyawaruyanti A, Wahyuni TS, Zaini NC, Honda T (2009) Synthesis and structure-activity relationships of cassiarin A as potential antimalarials with vasorelaxant activity. Bioorg Med Chem 17:8234–8240PubMedCrossRef

13.

Hirasawa Y, Hara M, Nugroho AE, Sugai M, Zaima K, Kawahara N, Goda Y, Awang K, Hadi AHA, Litaudon M, Morita H (2010) Bisnicalaterines B and C, atropisomeric bisindole alkaloids from Hunteria zeylanica, showing vasorelaxant activity. J Org Chem 75:4218–4223PubMedCrossRef

14.

Matsumoto T, Kobayashi T, Ishida K, Hirasawa Y, Morita H, Honda T, Kamata K (2010) Vasodilator effect of Cassiarin A, a novel antiplasmodial alkaloid from Cassia siamea, in rat isolated mesenteric artery. Bio Pharm Bull 33:844–848CrossRef

15.

Morita H, Zaima K, Koga I, Saito A, Tamamoto H, Okazaki H, Kaneda T, Hashimoto T, Asakawa Y (2011) Vasorelaxant effects of macrocyclic bis(bibenzyls) from liverworts. Bioorg Med Chem 19:4051–4056PubMedCrossRef

16.

Lemos VS, Freitas MR, Muller B, Lino YD, Queiroga CE, Cortes SF (1999) Dioclein, a new nitric oxide- and endothelium-dependent vasodilator flavonoid. Eur J Pharmacol 386:41–46PubMedCrossRef

17.

Trigueiro F, Cortes SF, Almeida RN, Lemos VS (2000) Endothelium-independent vasorelaxant effect of dioclein, a new flavonoid isolated from Dioclea grandiflora, in the rat aorta. J Pharm Pharmacol 52:1431–1434PubMedCrossRef

18.

Jimenez R, Zarzuelo A, Galisteo M, Duarte J (2002) Involvement of protein kinase C and Na⁺/K⁺-ATPase in the contractile response induced by myricetin in rat isolated aorta. Planta Med 68:133–137PubMedCrossRef

19.

Rezende BA, Cortes SF, Lemos VS (2004) Mechanisms involved in the vasodilator effect of the flavanol floranol in rat small mesenteric arteries. Planta Med 70:465–467PubMedCrossRef

20.

Zhu XM, Fang LH, Li YJ, Du GH (2007) Endothelium-dependent and -independent relaxation induced by pinocembrin in rat aortic rings. Vascul Pharmacol 46:160–165PubMedCrossRef

21.

Saponara S, Testai L, Iozzi D, Martinotti E, Martelli A, Chriconi S, Sgaragli G, Fusi F, Calderone V (2006) (+/−)-Naringenin as large conductance Ca²⁺-activated K⁺ (BK_Ca) channel opener in vascular smooth muscle cells. Br J Pharmacol 149:1013–1021PubMedCrossRef

22.

Hernandez-Abreu O, Castillo-Espana P, Leon-Rivera I, Ibarra-Barajas M, Villalobos-Molina R, Gonzalez-Christen J, Vergara-Galicia J, Estrada-Soto S (2009) Antihypertensive and vasorelaxant effects of tilianin isolated from Agastache mexicana are mediated by NO/cGMP pathway and potassium channel opening. Biochem Pharmacol 78:54–61PubMedCrossRef

23.

Lin YL, Dai ZK, Lin RJ, Chu KS, Chen IJ, Wu JR, Wu BN (2010) Baicalin, a flavonoid from Scutellaria baicalensis Georgi, activates large-conductance Ca²⁺-activated K⁺ channels via cyclic nucleotide-dependent protein kinases in mesenteric artery. Phytomedicine 17:760–770PubMedCrossRef

24.

Rodriguez-Rodriguez R, Herrera MD, Perona JS, Ruiz-Gutierrez V (2004) Potential vasorelaxant effects of oleanolic acid and erythrodiol, two triterpenoids contained in ‘orujo’ olive oil, on rat aorta. Br J Nutr 92:635–642PubMedCrossRef

25.

Aguirre-Crespo F, Vergara-Galicia J, Villalobos-Molina R, Javier Lopez-Guerrero J, Navarrete-Vazquez G, Estrada-Soto S (2006) Ursolic acid mediates the vasorelaxant activity of Lepechinia caulescens via NO release in isolated rat thoracic aorta. Life Sci 79:1062–1068PubMedCrossRef

26.

Estrada O, Gonzalez-Guzman JM, Salazar-Bookaman M, Fernandez AZ, Cardozo A, Alvarado-Castillo C (2011) Pomolic acid of Licania pittieri elicits endothelium-dependent relaxation in rat aortic rings. Phytomedicine 18:464–469PubMedCrossRef

27.

Les S, Orensanz LM, Mulvany MJ, Simonsen U (1999) Mechanisms involvement in the vasorelaxant effect of (−)-stepholidine in rat mesenteric small arteries. Eur J Pharmacol 365:193–204CrossRef

28.

Orallo F, Alzueta AF (2001) Preliminary study of the vasorelaxant effects of (+)-nantenine, an alkaloid isolated from Platycapnos spicata, in rat aorta. Planta Med 67:800–806PubMedCrossRef

29.

Yuzurihara M, Ikarashi Y, Goto K, Sakakibara I, Hayakawa T, Sasaki H (2002) Geissoschizine methyl ester, an indole alkaloid extracted from Uncaria Ramulus et Uncus, is a potent vasorelaxant of isolated rat aorta. Eur J Pharmacol 444:183–189PubMedCrossRef

30.

Berrougui H, Martin-Cordero C, Khalil A, Hmamouchi M, Ettaib A, Marhuenda E, Herrera MD (2006) Vasorelaxant effects of harmine and harmaline extracted from Peganum harmala L. seeds in isolated rat aorta. Pharmacol Res 54:150–157PubMedCrossRef

31.

Astulla A, Zaima K, Matsuno Y, Hirasawa Y, Ekasari W, Widyawaruyanti A, Zaini NC, Morita H (2008) Alkaloids from the seeds of Peganum harmala showing antiplasmodial and vasorelaxant activities. J Nat Med 62:470–472PubMedCrossRef

32.

Jia S, Hu C (2010) Pharmacological effects of rutaecarpine as a cardiovascular protective agent. Molecules 15:1873–1881PubMedCrossRef

33.

Medeiros MA, Pinho JF, De-Lira DP, Barbosa-Filho JM, Araujo DA, Cortes SF, Lemos VS, Cruz JS (2011) Curine, a bisbenzylisoquinoline alkaloid, blocks l-type Ca²⁺ channels and decreases intracellular Ca²⁺ transients in A7r5 cells. Eur J Pharmacol 669:100–107PubMedCrossRef

34.

Sulaiman SN, Mukhtar MR, Hadi AHA, Awang K, Hazni H, Zahari A, Litaudon M, Zaima K, Mortia H (2011) Lancifoliaine, a new bisbenzylisoquinoline from the bark of Litsea lancifolia. Molecules 16:3119–3127PubMedCrossRef

35.

Morita H, Iizuka T, Gonda A, Itokawa H, Takeya K (2006) Cycloleonuripeptides E and F, cyclic nonapeptides from Leonurus heterophyllus. J Nat Prod 69:839–841PubMedCrossRef

36.

Taniguchi M, Suzumura K, Nagai K, Kawasaki T, Saito T, Takasaki J, Suzuki K, Fujita S, Tsukamoto S (2003) Structure of YM-254890, a novel G_q/11 inhibitor from Chromobacterium sp. QS3666. Tetrahedron 59:4533–4538CrossRef

37.

Uemura T, Takamatsu H, Kawasaki T, Taniguchi M, Yamamoto E, Tomura Y, Uchida W, Miyata K (2006) Effect of YM-254890, a specific Gα_q/11 inhibitor, on experimental peripheral arterial disease in rats. Eur J Pharmacol 536:154–161PubMedCrossRef

Title: Vasorelaxant effect of FR900359 from Ardisia crenata on rat aortic artery
Authors: Kazumasa Zaima
Jun Deguchi
Yosuke Matsuno
Toshio Kaneda
Yusuke Hirasawa
Hiroshi Morita
Publication date: 01-01-2013
Publisher: Springer Japan
Published in: Journal of Natural Medicines / Issue 1/2013
Print ISSN: 1340-3443
Electronic ISSN: 1861-0293
DOI: https://doi.org/10.1007/s11418-012-0644-0

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Vasorelaxant effect of FR900359 from Ardisia crenata on rat aortic artery

Abstract

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Abstract

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