Terpenoid constituents of Viguiera tucumanensis

Meragelman, Karina M.; Espinar, L. Ariza; Sosa, Virginia E.; Uriburu, María L.; Fuente, Juana R. de la

doi:10.1016/0031-9422(95)00584-6

Cited by 24 publications

(14 citation statements)

References 22 publications

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“…Despite the fact that kauranes have usually been found to be the major secondary metabolites in most Viguiera species, some studies demonstrated the presence of diterpenes with clerodane (Vaccarini et al, 1999;Meragelman et al, 1996), trachylobane (Da Costa et al, 1996a), labdane (Tamayo-Castillo et al, 1990), beyerane and other minor skeletons (Domingues et al, 1988). Ambrosio et al (2004a) described for the first time the occurrence of pimarane derivatives in a Brazilian Viguiera, i.e.…”

Section: Chemistry Of Brazilian Asteraceae: Isolation Of Bioactive Tementioning

confidence: 96%

Kaurane and pimarane-type diterpenes from the Viguiera species inhibit vascular smooth muscle contractility

et al. 2006

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Section: Chemistry Of Brazilian Asteraceae: Isolation Of Bioactive Tementioning

confidence: 96%

Kaurane and pimarane-type diterpenes from the Viguiera species inhibit vascular smooth muscle contractility

et al. 2006

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“…However, some studies have also demonstrated the presence of diterpenes with clerodane [55,56], trachylobane [57], labdane [58], beyerane and other minor skeletons [59]. In most species of this genus, kaurane-type diterpenes have usually been found to be the major secondary metabolites.…”

Section: Brazilian Viguiera As Source Of Kaurane and Pimarane-type DImentioning

confidence: 99%

Diterpenes: A Therapeutic Promise for Cardiovascular Diseases

Oliveira

Tirapelli

Ambrósio³

et al. 2008

PRC

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The research, development and use of natural products as therapeutic agents, especially those derived from plants, have been increasing in recent years. There has been great deal of focus on the naturally occurring antispasmodic phytochemicals as potential therapy for cardiovascular diseases. Naturally occurring diterpenes exert several biological activities such as anti-inflammatory action, antimicrobial and antispasmodic activities. Several diterpenes have been shown to have pronounced cardiovascular effects, for example, grayanotoxin I produces positive inotropic responses, forskolin is a well-known activator of adenylate cyclase, eleganolone and 14-deoxyandrographolide exhibit vasorelaxant properties and marrubenol inhibits smooth muscle contraction by blocking L-type calcium channels. In the last few years, we have investigated the biological activity of kaurane and pimarane-type diterpenes, which are the main secondary metabolites isolated from the roots of Viguiera robusta and V. arenaria, respectively. These diterpenoids exhibit vasorelaxant action and inhibit the vascular contractility mainly by blocking extracellular Ca 2+ influx. Moreover, kaurane and pimarane-type diterpenes decreased mean arterial blood pressure in normotensive rats. Diterpenes likely fulfil the definition of a pharmacological preconditioning class of compounds and give hope for the therapeutic use in cardiovascular diseases. This article will review patents, structure-activity relationship, pharmacology, antihypertensive efficiency, and the vascular mechanisms underlying the effects of diterpenes. Careful examination of the cardiovascular effects exhibited by kaurane and pimarane-type diterpenes will be provided.

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“…Besides one ketonic carbonyl and a C-C double bond, the degrees of unsaturation required two rings to meet the molecular formula. Close similarities of the chemical shifts and coupling constants of 1 with the known compound clerod-14-ene-3α,4β,13ξ-triol [17] revealed that 1 possessed a clerodane diterpenoid skeleton (l " Tables 1 and 2). The difference was the presence of a ketonic carbonyl (δ C 212.9, C-3) in 1 instead of one oxymethine at δ C 76.2 (C-3) in clerod-14-ene-3α,4β,13ξ-triol, which was further confirmed by the HMBC correlations of δ H 1.54 (H-1b), 2.98 (H-2a), 2.03 (H-2b), and 1.06 (H 3 -18) with δ C 212.9 (C-3) (l " Fig.…”

mentioning

confidence: 92%

“…Their structures were elucidated by extensive spectroscopic analysis. The six known diterpenoids were determined as rosestachone [16], roseostachenone [16], clerod-14-ene-3α,4β,13ξ-triol [17], clerod-14-ene-3α-acetyl-4β,13ξ-triol [17], (3α,4β,13E)-neoclerod-13-ene-3,4,15-triol [18], and 15-hydroxy-3-cleroden-2-one [19]. All the compounds were evaluated for their cytotoxic activities against human HL-60, SMMC-7721, A-549, MCF-7, and SW480 cell lines, using the MTT method [20].…”

mentioning

confidence: 99%