Structural and spectral assignment of three forskolin‐like diterpenoids isolated from <i>Plectranthus ornatus</i>

Rijo, Patrícia; Simões, M. Fátima; Rodrı́guez, Benjamı́n

doi:10.1002/mrc.1600

Cited by 18 publications

(25 citation statements)

References 17 publications

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“…(18). The compounds were obtained by a phytochemical study that was previously performed in the described plant, using bioguided studies (18)(19)(20)(21). The structural elucidation of the bioactive metabolites was based on physicochemical data (melting point, specific rotation), spectroscopic data (UV, IR, 1D-and 2D-1 H and 13 C NMR), mass spectra, elemental analysis, and comparison with bibliographic data.…”

Section: Compound Isolationmentioning

confidence: 99%

“…(18). Os compostos foram obtidos por um estudo fitoquímico que foi previamente realizado nesta planta, utilizando estudos bioguiados (18)(19)(20)(21). A elucidação estrutural dos metabolitos bioativos baseou-se em dados físicoquímicos (ponto de fusão, rotação específica), principalmente espectroscópicos UV, IR, 1D e espectros 2D-1 H e 13 C-RMN, espectros de massa, análise elementar e comparação com dados bibliográficos.…”

Section: Isolamento De Compostosunclassified

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Anti-mycobacterial activity of labdane and halimane diterpenes obtained from Plectranthus ornatus Codd

Andrade

Romagnoli

Almeida

et al. 2018

BBR

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Natural products are a unique source of lead compounds for medicinal chemistry. Several diterpenes isolated from Plectranthus spp. have been reported to have interesting tuberculostatic activity and P. ornatus Codd. has been used in some regions of Brazil as an anti-infective. Previously, diterpenes with halimane and labdane skeletons were isolated in large quantities from P. ornatus Codd. We assessed the anti-mycobacterial activity of these compounds, performing a preliminar assay with the non-virulent strain Mycobacterium smegmatis. The cytotoxicity of the diterpenes with halimane and labdane skeletons was tested with the lactate dehydrogenase assay, where no considerable cytotoxic effects were found up to 25 µg.mL-1. Subsequently, the microdilution method was used to determine the minimum inhibitory concentration (MIC) against M. smegmatis. The MIC that inhibited the growth of the non-virulent mycobacteria by ≥99% was 100 µg.mL-1 for the diterpene with halimane skeleton, whereas for the diterpene with a labdane skeleton was >100 µg.mL-1. To the best of our knowledge, this is the first report on diterpenes with halimane and labdane skeletons isolated from P. ornatus in macrophages cytotoxicity, and in a preliminar assay for anti-mycobacterial activity. Further studies are suggested on M. tuberculosis, particularly for the diterpenes with halimane skeleton.

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Section: Compound Isolationmentioning

confidence: 99%

Section: Isolamento De Compostosunclassified

Anti-mycobacterial activity of labdane and halimane diterpenes obtained from Plectranthus ornatus Codd

Andrade

Romagnoli

Almeida

et al. 2018

BBR

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“…Many Plectranthus species (Lamiaceae family) are plants of ornamental, economical and medicinal interest. Several species are used in tropical Africa and Polynesia as vermicides, antiseptics and purgatives, for the treatment of ear infections, toothache and stomach ache, as a remedy for vomiting, nausea and against a vast array of other [2] diseases . Some Africa native Plectranthus species were introduced in the New World, following the th Portuguese Discoveries (16 century), and P. ornatus (Fig.…”

Section: Introductionmentioning

confidence: 99%

“…Previous studies on the secondary metabolites of Plectranthus ornatus Codd. reported the isolation of [2,[5][6][7] labdane, clerodane and halimane diterpenoids , but the pharmacological properties of such compounds still remain unknown.…”

Section: Introductionmentioning

confidence: 99%

Evaluation of diterpenoids from P. ornatus as potential COX-1 inhibitors

Rijo

Fernandes

Simões

et al. 2012

BBR

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Natural products are a rich source of drug candidates for clinical use. The Plectranthus ornatus Codd. belongs to a genus associated to the isolation of diterpenoids which are responsible for various biological activities. The three diterpenoids under study were isolated in the past from P. ornatus and are now being evaluated as potential COX-1 inhibitors. Obtained results suggest that rhinocerotinoic acid (2), but not halimane (3) and plectrornatin C (1), has a mild COX-1 inhibitory activity. Current studies are being carried out to understand if these compounds have effect as COX-2 inhibitors. This will contribute to establish their possible interest as anti-inflammatory agents.

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“…: Coleus comosus Hochst. Ex Gürke) reported the isolation of labdane and clerodane derivatives [2,3]. A labdane diterpenoid structure belonging to the normal-labdane series according to NMR analyses was previously isolated from P. ornatus [2].…”

Section: Introductionmentioning

confidence: 99%

A New Configurational Analysis of 1,6,7-triacetoxy-8,13-epoxy-14-labden-11-one Isolated from Plectranthus ornatus Based on NMR and Theoretical Calculations

Oliveira¹,

Pacheco²,

Pacheco³

et al. 2009

TONPJ

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This work describes the configurational and conformational analyses of 1,6,7-triacetoxy-8,13-epoxy-14-labden-11-one, a labdane diterpenoid isolated from Plectranthus ornatus. Its relative stereochemistry was previously proposed by comparison with 1 H and 13 C NMR data of forskolin (2); however, the configurations of C-8 and C-13 have not been confirmed. Correlations between 13 C NMR experimental data and HF/6-31G* calculated values of carbon chemical shifts were performed for configurational and conformational analyses. This procedure was formerly applied to the configurational analysis of 2. Among the seven different forskolin-type structures investigated, the 13 C NMR data of 2 correlated best with those with the same stereochemistry of 2 described in the literature. Thus, the same procedure was considered valid for configurational analysis of the labdane diterpenoid isolated from P. ornatus. The relative stereochemistry of this compound based on theoretical calculations was similar to the structure previously proposed, but the best results were obtained considering configurational inversion at C-13.

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Structural and spectral assignment of three forskolin‐like diterpenoids isolated from Plectranthus ornatus

Cited by 18 publications

References 17 publications

Anti-mycobacterial activity of labdane and halimane diterpenes obtained from Plectranthus ornatus Codd

Anti-mycobacterial activity of labdane and halimane diterpenes obtained from Plectranthus ornatus Codd

Evaluation of diterpenoids from P. ornatus as potential COX-1 inhibitors

A New Configurational Analysis of 1,6,7-triacetoxy-8,13-epoxy-14-labden-11-one Isolated from Plectranthus ornatus Based on NMR and Theoretical Calculations

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