(−)-thermarol, a new ent-pimarane-class diterpene diol from Jungermannia thermarum (liverwort)

Matsuo, Akihiko; Uto, S.; Nakayama, Mitsuru; Hayashi, Shûichi; Yamasaki, Kazuo; Kasai, Ryoji; Tanaka, Osamu

doi:10.1016/0040-4039(76)90017-4

Cited by 50 publications

(43 citation statements)

References 8 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Isolation and purification steps were carried out by 'flash' chromatography (hexaneEtOAc mixtures), PTLC (Si gel, hexane-EtOAc or hexane-CHCl 3 ) and recrystallization from MeOH. The structure of the diterpene was established by comparison of its 1 H and 13 C NMR spectral data with those reported in the literature [6,7].…”

Section: Plant Materialsmentioning

confidence: 99%

Evidence for the Mechanisms Underlying the Effects of Pimaradienoic Acid Isolated from the Roots of <i>Viguiera arenaria </i>on Rat Aorta

et al. 2003

View full text Add to dashboard Cite

The present study examines the effects of the diterpene ent-pimara-8(14),15-dien-19-oic acid (PA) on rat thoracic aorta. PA (10^–5, 3 × 10^–5 and 10^–4 mol/l) caused concentration-dependent inhibition of phenylephrine (Phe)-induced contraction in either endothelium-intact or endothelium-denuded aortic rings. PA attenuated the contraction induced by CaCl₂ in Ca²⁺-free solution containing Phe (10^–7 mol/l) or KCl (30 mmol/l). This diterpene did not interfere with Ca²⁺ release from intracellular stores mediated by either Phe (10^–6 mol/l) or caffeine (30 mmol/l). PA (10^–6 to 3 × 10^–4 mol/l) concentration dependently relaxed Phe-pre-contracted rings with intact (92.64 ± 7.60%) or denuded endothelium (98.82 ± 1.56%). Pre-incubation of denuded aortic rings with N^G-nitro-L-arginine methyl ester (10^–4 mol/l), 1H-[1,2,4]oxadiazolo[4,3-a]quinoxalin-1-one (10^–6 mol/l) or indomethacin (10^–5 mol/l) reduced PA-induced relaxation (percentage of relaxation: 77.50 ± 3.95, 78.56 ± 2.81, 77.11 ± 6.22, respectively). However, the relaxant responses induced by PA on Phe-pre-contracted rings were unaffected by tetraethylammonium (1 and 5 mmol/l). PA also relaxed KCl-pre-contracted rings with intact (97.44 ± 3.66%) or denuded endothelium (95.95 ± 3.72%). Collectively, these results support the notion that the effects elicited by PA on vascular smooth muscle are endothelium-independent and involve extracellular Ca²⁺ influx blocked. In addition, PA effects are partly dependent on the release of nitric oxide from the vascular smooth muscle through an activation of guanylyl cyclase-dependent mechanism and are related to the release of metabolites derived from the arachidonic acid pathway. Finally, our results demonstrated that the PA relaxant action is not related with the opening of potassium (K⁺) channels.

show abstract

Section: Plant Materialsmentioning

confidence: 99%

Evidence for the Mechanisms Underlying the Effects of Pimaradienoic Acid Isolated from the Roots of <i>Viguiera arenaria </i>on Rat Aorta

et al. 2003

View full text Add to dashboard Cite

show abstract

“…20) Very similar pathways could be drawn for Mastigophora diclados. Although a-formylherbertenol has been found in Herbertus, 4) its acid derivative (14) has been isolated only in the genus Mastigophora. However, (Ϫ)-1,2-dihydroxyherberten-12-al (18) and methyl 1,2-dihydroxyherberten-12-oate (19) were both isolated from Herbertus aduncus but not Mastigophora diclados.…”

Section: Resultsmentioning

confidence: 99%

“…Long-range correlations were observed in H-3/C-2, C-3, C-4 and C-12, H-5/C-1, C-4, C-6 and C-12, while the partial structure -CH 2 -CH 2 -CH 2 -of the five member ring could be drawn from the 1 H-1 H COSY spectrum. Therefore, mastigophoric acid methyl ester (14) was determined to be 1-hydroxyherbertene 12-oic acid methyl ester as shown in Chart 1. Although compound 14 has been obtained from one step in the synthesis of (Ϫ) a-formylherbertenol, 17) this is the first report on the isolation of compound 14 from a natural source.…”

Section: Resultsmentioning

confidence: 99%

“…The remaining extract was chromatographed on silica gel to afford eighteen fractions. Each fraction was purified with size exclusion chromatography by Sephadex LH-20, silica gel and preparative HPLC or TLC to yield a-and b-herbertenols (2, 3), 12,13) herbertene 1,2-diol (4), sandaracopimaric acid and ent-pimara-8 (14), 15-dien-19-oic acid, 14,15) mastigophorene C and D (9, 10), 2,3) riccardin C (15), 16) a-formylherbertenol (16), 12) stigmasterol, mastigophoric acid methyl ester (14) and a mixture of two cycloartenyl esters (17). The known compounds were identified by comparison of their spectral data with those of authentic samples and those reported in the literature.…”

Section: Resultsmentioning

confidence: 99%

“…Fraction 1 was applied to a Sephadex LH-20 column to afford 2 (25 mg). Size exclusion chromatography of fraction 2 yielded 3 (5.8 mg), ent-pimara-8 (14), 15-dien-19-oic acid (11.2 mg) and sandaracopimaric acid (38 mg). Compound 4 (580 mg) was obtained from fraction 3 using a Sephadex LH-20 column and preparative HPLC (70% aqueous CH 3 CN).…”

Section: Methodsmentioning

confidence: 99%

See 2 more Smart Citations

Chemical Constituents of Malagasy Liverworts, Part II: Mastigophoric Acid Methyl Ester of Biogenetic Interest from Mastigophora diclados (Lepicoleaceae Subf. Mastigophoroideae)

Harinantenaina

Asakawa

2004

CHEMICAL & PHARMACEUTICAL BULLETIN

View full text Add to dashboard Cite

Fungal Transformation and Schistosomicidal Effects of Pimaradienoic Acid

Porto

Filho

Magalhães

et al. 2012

Chemistry & Biodiversity

View full text Add to dashboard Cite

The schistosomicidal effects of pimaradienoic acid (PA) and two derivatives, obtained by fungal transformation in the presence of Aspergillus ochraceus, were investigated. PA was the only compound with antischistosomal activity among the three diterpenes studied, with the ability to significantly reduce the viability of the parasites at concentrations ranging from 25 to 100 μM. PA also promoted morphological alterations of the tegument of Schistosoma mansoni, separated all the worm couples, and affected the production and development of eggs. Moreover, this compound was devoid of toxicity toward human fibroblasts. In a preliminary in vivo experiment, PA at a dose of 100 mg/kg significantly diminished the number of parasites in infected Balb/c mice. Taken together, these results show that PA may be potentially employed in the discovery of novel schistosomicidal agents, and that diterpenes are an important class of natural compounds for the investigation of agents capable of fighting the parasite responsible for human schistosomiasis.

show abstract

(−)-thermarol, a new ent-pimarane-class diterpene diol from Jungermannia thermarum (liverwort)

Cited by 50 publications

References 8 publications

Evidence for the Mechanisms Underlying the Effects of Pimaradienoic Acid Isolated from the Roots of <i>Viguiera arenaria </i>on Rat Aorta

Evidence for the Mechanisms Underlying the Effects of Pimaradienoic Acid Isolated from the Roots of <i>Viguiera arenaria </i>on Rat Aorta

Chemical Constituents of Malagasy Liverworts, Part II: Mastigophoric Acid Methyl Ester of Biogenetic Interest from Mastigophora diclados (Lepicoleaceae Subf. Mastigophoroideae)

Fungal Transformation and Schistosomicidal Effects of Pimaradienoic Acid

Contact Info

Product

Resources

About