Antispasmodic and Antimicrobial Diterpenic Acids from Viguiera hypargyrea Roots

Abstract

Two spasmolytic diterpene acids, ent-beyer-15-en-19-oic acid and ent-kaur-16-en-19-oic acid, have been isolated from the roots of Viguiera hypargyrea by bioassay-guided fractionation. Beyerenoic acid was also active against Staphylococcus aureus, Enterococcus feacalis and Candida albicans.

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

“…More recently, it was demonstrated that the inhibitory effect displayed by ent-beyer-15-en-19-oic acid, on electrically induced contractions of guinea-pig ileum, is more pronounced than that found for kaurenoic acid (Zamilpa et al, 2002). The structure of this compound is slightly different from that of kaurenoic acid because of some differences in ring D, such as the relative stereochemistry, the presence of a double bond between C-15 and C-16, a methyl group attached to C-13 and the lack of the exocyclic methylene group at C-16.…”

Pharmacological comparison of the vasorelaxant action displayed by kaurenoic acid and pimaradienoic acid

“…Furthermore, after incubation for 15 min, the inhibitory effect displayed by PA at both concentrations was much greater than that found for KA. Such findings indicate that structural differences between these compounds potentiate and accelerate the inhibitory activity displayed by PA. Zamilpa et al (2000) demonstrated that the inhibitory effect displayed by ent-beyer-15-en-19-oic acid on electrically induced contractions of guinea-pig ileum was more pronounced than that found for KA. The structure of this compound is slightly different from that of KA because of some differences in ring D. The other three rings (A, B and C) of both structures are identical.…”

“…It has been demonstrated that the inhibitory effect displayed by the kaurane ent-beyer-15-en-19-oic acid on electrically induced contractions of guinea-pig ileum was more pronounced than that found for KA (Zamilpa et al 2000). The structure of this compound is slightly different from that of KA because of some differences in ring D, such as the relative stereochemistry, the presence of a double bond between C-15 and C-16, a methyl group attached to C-13 and the lack of the exocyclic methylene group at C-16.…”

“…Diterpenes from the kaurane and pimarane classes are reported to exert antispasmodic and relaxant actions on smooth muscle Campos-Bedolla et al 1997;Ohashi et al 2000;Ambrosio et al 2002;Zamilpa et al 2000). We have previously demonstrated that the kaurane-type diterpene ent-kaur-16-en-19-oic acid (kaurenoic acid; KA) attenuated KCl and phenylephrine-induced contraction of rat carotid artery (Da Costa et al 2000;Tirapelli et al 2002).…”

Synthesis, Characterization and Biological Evaluation of a Glycine-Rich Peptide - Cherimolacyclopeptide E

“…During past decades, plants have well proved their potential to produce a wide spectrum of natural products with interesting bioactivities [1][2][3][4][5][6] . Among these, cyclic peptides and related congeners with unique structures and wide pharmacological profile [7][8][9][10] have received special attention which may prove better candidates to overcome the problem of wide spread increase of resistance towards conventional drugs.…”