Zeylleucapenoids A–D, Highly Oxygenated Diterpenoids with Anti-Inflammatory Activity from Leucas zeylanica (L.) R. Br.
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Four previously undescribed highly oxygenated diterpenoids (1-4), zeylleucapenoids A-D, characterized by halimane and labdane skeletons, were isolated from the aerial parts of Leucas zeylanica. Their structures were elucidated primarily via NMR experiments. The absolute configuration of 1 was established using theoretical ECD calculations and X-ray crystallographic analysis, whereas those for 2-4 were assigned using theoretical ORD calculations. Zeylleucapenoids A-D were tested for anti-inflammatory activity against nitric oxide (NO) production in RAW264.7 macrophages, of which only 4 showed significant efficacy with an IC50 value of 38.45 μM. Further, active compound 4 was also evaluated for the inhibition of the release of pro-inflammatory cytokines TNF-α and IL-6 and was found to have a dose-dependent inhibitory effect, while it showed nontoxic activity for zebrafish embryos. A subsequent Western blotting experiment revealed that 4 inhibited the expression of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2). Furthermore, molecular docking analysis indicated that the possible mechanism of action for 4 may be bind to targets via hydrogen and hydrophobic bond interactions.Keywords:
Labdane
Proinflammatory cytokine
Docking (animal)
IC50
Anti-inflammatory
Six undescribed stilbene derivatives Reflexanbene DH (1-4, 6) and Reflexanbene J (5), as well as one known stilbene 3,5-dimethoxystilbene (7), were isolated from the dried roots of Lindera reflexa Hemsl. Their structures and absolute configurations were elucidated using spectroscopy and electronic circular dichroism (ECD) analysis. In cytotoxic assays, moderately inhibitory activities of Reflexanbene F (3) against MGC80-3 and A549 cell lines were observed, with IC50 values of 15.42 and 5.09 μM, respectively. The IC50 value of Reflexanbene E (2) on A549 cell lines was 19.78 μM. The isolated compounds were also tested for their inhibitory effect against LPS-induced NO and IL-6 production in RAW 264.7 cells. In particular, Reflexanbene J (5) and Reflexanbene H (6) showed significant inhibition of NO production in LPS-stimulated macrophage RAW 264.7 cells at the concentration of 20 μM. Furthermore, the expression of IL-6 protein in the LPS-induced RAW 264.7 cells can also be significantly inhibited by different concentrations (5, 10 and 20 μM, p < 0.05 or p < 0.01) of compounds 1-7.
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Accumulation of furanic labdane diterpenes has been investigated in different parts of field-grown plants of MARRUBIUM VULGARE (Lamiaceae) and LEONURUS CARDIACA (Lamiaceae). Furanic labdane diterpenes were produced and accumulated only in the aerial parts. Greatest amounts were measured in leaves and flowers. Up to 4 mg furanic labdane diterpenes per g fresh weight were found. Accumulation of furanic labdane diterpenes in plantlets seemingly depends on a developmental programme. No furanic labdane diterpenes were detected in plantlets during the first four to five weeks following germination. At this time the leaves became more differentiated and the number of trichomes on leaves was obviously increasing. Young leaves and buds contained most furanic labdane diterpenes. It was proven that at least a part of the non-volatile furanic labdane diterpenes is stored in peltate glandular trichomes. NMR signals of marrubiin were investigated with correlated spectra. Some (1)H- and (13)C-NMR assignments reported in literature were revised.
Labdane
Trichome
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Labdane
Andrographis Paniculata
Andrographolide
Acanthaceae
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Labdane
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The ethanol extract of roots of Solidago canadensis yielded eight labdane-type diterpenes. Five of those were new natural compounds (9,13,15,16-bisepoxy-labdane-7-ene-6,15-dione (3a), 13-epi-9,13,15,16-bisepoxy-labdane-7-ene-6,15-dione (3b), 15,16-epoxy-labdane-7,13-diene-6,16-dione (5), 15-ethoxy-9,13,15,16-bisepoxy-labdane-7-ene-6-one (6a) and 13-epi-15-ethoxy-9,13,15,16-bisepoxy-labdane-7-ene-6-one (6b). The known labdane diterpenes deoxysolidagenone (1), solidagenone (2) and 15,16-epoxy-labdane-7,13-diene-6,15-dione (4) were also isolated. Chemical structures were determined using 1D and 2D NMR techniques and MS analysis.
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Seven new and two known ent-labdane diterpenoids have been isolated from a single plant specimen of Dodonaea viscosa ssp. spatulata, found in Tasmania, Australia. Prior to this study, only seven different labdane diterpenoids had been isolated from D. viscosa. The structures of the natural products were assigned via 1D and 2D NMR spectroscopy and other standard spectroscopic methods. The absolute configuration of three ent-labdane diterpenoids was determined by single-crystal X-ray crystallography of synthetic derivatives. Significantly, the results of this study suggest that the absolute configuration of some known labdane diterpenoids may have been misassigned.
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Absolute Configuration
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Ten new labdane diterpenoids, lagopsins A–H (1–3, 5, 7–10) and 15-epi-lagopsins C and D (4, 6), together with five known labdane diterpenoids (11–15), were isolated from the whole plants of Lagopsis supina. The absolute configuration of lagopsin A (1) was determined by single-crystal X-ray crystallographic analysis. Compounds 7, 9, 13, and 15 exhibited moderate inhibition of nitric oxide production stimulated by lipopolysaccharide in BV-2 microglial cells with IC50 values in the range 14.9–34.9 μM.
Labdane
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