Labdane diterpenes from Marrubium thessalum

Argyropoulou, Catherine; Karioti, Anastasia; Skaltsa, Helen

doi:10.1016/j.phytochem.2009.03.011

Cited by 26 publications

(34 citation statements)

References 40 publications

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“…The identity of isolated marrubiin was confirmed by FTIR, 1 H, and 13 C NMR [20]. Analysis of proton spectra (Fig.…”

Section: Marrubiin Contentmentioning

confidence: 84%

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How Salt Stress Represses the Biosynthesis of Marrubiin and Disturbs the Antioxidant Activity of Marrubium Vulgare L

Rezgui¹,

Majdoub²,

Ben-Kaab³

et al. 2017

Pol. J. Environ. Stud.

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“…The identity of isolated marrubiin was confirmed by FTIR, 1 H, and 13 C NMR [20]. Analysis of proton spectra (Fig.…”

Section: Marrubiin Contentmentioning

confidence: 84%

“…The identity of marrubiin was confirmed by FTIR and 1H and 13C NMR. Spectroscopic data was identical to the literature [20]. Quantification was carried out based on a calibration curve performed with known amounts of marrubiin by H1NMR as described by [21].…”

Section: Isolation and Quantification Of Marrubiinmentioning

confidence: 99%

How Salt Stress Represses the Biosynthesis of Marrubiin and Disturbs the Antioxidant Activity of Marrubium Vulgare L

Rezgui¹,

Majdoub²,

Ben-Kaab³

et al. 2017

Pol. J. Environ. Stud.

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“…The presence of a MeO group in the structure was easily recognized in the 1 H-NMR spectrum, and this MeO group was at C(15), based on the correlations in the HMBC spectrum (MeO/C(15)). All the above data could be accommodated by a structure that was analogous to (13R)-9a,13 : 15,16-diepoxy-15b-methoxy-3-oxolabdan-19,6b-olide, previously isolated from M. thessalum [4]. Due to its high similarity with the present diterpenes, we name this previously isolated compound thessaline C. The differences between thessaline C and compound 3 were mainly associated with the outer ring thus suggesting that they are epimers, more probably at C(13) or C(15).…”

mentioning

confidence: 77%

“…Complete 13 C-NMR assignments are also reported for (13R)-9a,13 : 15,16-diepoxy-15b-methoxy-3-oxolabdan-19,6b-olide, named here thessaline C, previously isolated from M. thessalum [4].…”

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confidence: 84%

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Minor Labdane Diterpenes from Marrubium thessalum

Argyropoulou

Karioti

Skaltsa

2011

Chemistry & Biodiversity

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Five new labdane diterpenes, thessalines A, B, and D, 14β-hydroxythessaline A, and 14β-hydroxythessaline B (1-5, resp.) were isolated from the aerial parts of Marrubium thessalum, along with the known labdane diterpene deacetylvitexilactone (6) and the methoxylated flavones 4',7-dimethylapigenin and salvigenin. (3S,5R)-Loliolide was also found in the same source. Their structures were established by 1D- and 2D-NMR (COSY, HSQC, HMBC, NOESY, and ROESY) and MS analyses. The plant produces a great variety of labdane-type diterpenes, with variations in functionalities, particularly in the side chain. Their structures could be of chemotaxonomic significance for the genus Marrubium.

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Polar Constituents of Marrubium thessalum Boiss. & Heldr. (Lamiaceae) and their Cytotoxic/Cytostatic Activity

Argyropoulou

Samara

Tsitsilonis

et al. 2012

Phytotherapy Research

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The methanol extract of the aerial parts of Marrubium thessalum Boiss. & Heldr. (Lamiaceae) afforded 30 phenolic metabolites, belonging to the classes of phenylethanoid glycosides, flavonoids and simple phenolic compounds. The crude methanol extract as well as the secondary metabolites were screened for their cytotoxic/cytostatic effects against four human cancer cell lines, specifically HeLa, MCF-7, FM3 and HCT-116 and demonstrated considerable cell growth-inhibitory activity. The differential cytotoxicity of the compounds implied possible structure-activity relationships. Selected compounds were evaluated for their toxicity against human peripheral blood mononuclear cells, where some of them showed marginal toxic effects. The results suggest that M. thessalum produces secondary metabolites that demonstrate selective anticancer activity concomitantly with reduced toxicity on lymphocytes. The structure of such compounds can eventually lead to the development of novel pharmaceutical agents.

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Labdane diterpenes from Marrubium thessalum

Cited by 26 publications

References 40 publications

How Salt Stress Represses the Biosynthesis of Marrubiin and Disturbs the Antioxidant Activity of Marrubium Vulgare L

How Salt Stress Represses the Biosynthesis of Marrubiin and Disturbs the Antioxidant Activity of Marrubium Vulgare L

Minor Labdane Diterpenes from Marrubium thessalum

Polar Constituents of Marrubium thessalum Boiss. & Heldr. (Lamiaceae) and their Cytotoxic/Cytostatic Activity

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