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Planta Med 2020; 86(09): 631-642
DOI: 10.1055/a-1154-8832
Biological and Pharmacological Activity
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Vasorelaxing Activity of Stilbenoid and Phenanthrene Derivatives from Brasiliorchis porphyrostele: Involvement of Smooth Muscle CaV1.2 Channels

Watcharee Waratchareeyakul
1   Natural Products Research Group, Department of Chemistry, University of Surrey, Guildford, United Kingdom
2   Department of Chemistry, Rambhai Barni Rajabhat University, Chanthaburi, Thailand
,
Fabio Fusi
3   Dipartimento di Biotecnologie, Chimica e Farmacia, Università degli Studi di Siena, Siena, Italy
,
Miriam Durante
4   Dipartimento di Scienze della Vita, Università degli Studi di Siena, Siena, Italy
,
Amer Ahmed
4   Dipartimento di Scienze della Vita, Università degli Studi di Siena, Siena, Italy
,
Walter Knirsch
5   Institute of Plant Sciences, Karl-Franzens-University, Graz, Austria
,
Eduard Mas-Claret
1   Natural Products Research Group, Department of Chemistry, University of Surrey, Guildford, United Kingdom
,
Dulcie A. Mulholland
1   Natural Products Research Group, Department of Chemistry, University of Surrey, Guildford, United Kingdom
6   School of Chemistry and Physics, University of KwaZulu-Natal, Durban, South Africa
› Author AffiliationsSupported by: National Science and Technology Development Agency, Thailand
Supported by: National Research Council of Thailand
Further Information

Publication History

received 18 January 2020
revised 29 March 2020

accepted 04 April 2020

Publication Date:
29 April 2020 (online)

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Abstract

Five compounds, 3,4′-dihydroxy-3′,5,5′-trimethoxydihydrostilbene, 1; 3,4′-ihydroxy-3′,5′-dimethoxydihydrostilbene, 2; 3,4′-dihydroxy-5,5′-dimethoxydihydrostilbene, 3; 9,10-dihydro-2,7-dihydroxy-4,6-dimethoxyphenanthrene, 4; and the previously unreported 1,2,6,7-tetrahydroxy-4-methoxyphenanthrene, 5 were isolated from the South American orchid, Brasiliorchis porphyrostele. An in-depth analysis of their vascular effects was performed on in vitro rat aorta rings and tail main artery myocytes. Compounds 1 – 4 were shown to possess vasorelaxant activity on rings pre-contracted by the α 1 receptor agonist phenylephrine, the CaV1.2 stimulator (S)-(−)-Bay K 8644, or depolarized with high K+ concentrations. However, compound 5 was active solely on rings stimulated by 25 mM but not 60 mM K+. The spasmolytic activity of compounds 1 and 4 was significantly affected by the presence of an intact endothelium. The KATP channel blocker glibenclamide and the KV channel blocker 4-aminopyridine significantly antagonized the vasorelaxant activity of compounds 4 and 1, respectively. In patch-clamp experiments, compounds 1 – 4 inhibited Ba2+ current through CaV1.2 channels in a concentration-dependent manner, whereas neither compound 4 nor compound 1 affected K+ currents through KATP and KV channels, respectively. The present in vitro, comprehensive study demonstrates that Brasiliorchis porphyrostele may represent a source of vasoactive agents potentially useful for the development of novel antihypertensive agents that has now to be validated in vivo in animal models of hypertension.

Key words

Brasiliorchis porphyrostele - phenanthrenes - stilbenoids - vasorelaxing - vascular CaV1.2 channel - vascular endothelium - Orchidaceae

Supporting Information

    Plant material, isolation procedure, NMR data for compounds 1 – 5, NMR and UV spectra for compound 5, and the effect of 2 mM TEA, 3 mM 4-aminopyridine, and 5 µM glibenclamide on K 25-induced contraction (endothelium denuded rat aorta rings) are available as Supporting Information.

  • Supporting Information
 

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