Isolation Of Diterpenoids Research Articles

Anti-HIV diterpenoids from Daphne pseudomezereum.

The plants of the genus Daphne (Thymelaeaceae) are known to be sources of anti-HIV diterpenoids. Therefore, the present study focused on investigating the anti-HIV diterpenoids in Daphne pseudomezereum, for which the isolation of diterpenoids has not been previously reported. The results showed that three previously undescribed daphnane diterpenoids, onishibarins A-C (1-3), along with seven known compounds (4-10) were isolated from the fruits of Daphne pseudomezereum. Their structures were established by comprehensive analysis of physicochemical and spectroscopic data. Evaluation of the anti-HIV activity and cytotoxicity of the isolated compounds showed that compounds 1, 9, and 10 exhibited potent anti-HIV activity at EC50 = 1.26, 0.84, and 0.78 nM, respectively, with cytotoxicity at IC50 > 5 μM.

Targeted isolation of diterpenoids and sesquiterpenoids from Daphne gemmata E. Pritz. ex Diels using molecular networking together with network annotation propagation and MS2LDA

Investigation of the whole plant of Daphne gemmata E. Pritz. ex Diels (Thymelaeaceae) using molecular networking coupled to Network Annotation Propagation (NAP) and unsupervised substructure annotation (MS2LDA) led to the discovery of five tigliane diterpenoids, 14 guaiane sesquiterpenoids, one rhamnofolane diterpenoid and three carotene sesquiterpenoids. The structures of the eight undescribed compounds, daphnorbol A and daphnegemmatoids A-G, were characterized by detailed spectroscopic analyses, NMR and ECD calculations, application of Snatzke's method and single-crystal X-ray diffraction analysis. All isolated compounds were evaluated for their cytotoxic activities against HepG2, A549, and MCF-7 cells by MTT assay. Daphnorbol A exhibited significant cytotoxic activity against HepG2 and A549 cells with IC50 values of 4.06 μM and 6.35 μM, respectively. Prostratin showed potent cytotoxic activity against HepG2 and A549 cells with IC50 values of 6.06 μM and 5.45 μM, respectively. Further Hoechst 33,258 and AO-EB staining assays indicated that daphnorbol A and prostratin could induce apoptosis in HepG2 and A549 cells.

Preparative isolation of diterpenoids from Salvia bowleyana Dunn roots by high-speed countercurrent chromatography combined with high-performance liquid chromatography.

The root of Salvia bowleyana Dunn (Lamiaceae) is used as a traditional Chinese medicine that has multiple therapeutic effects. In this study, an efficient strategy was developed to separate diterpenoid compounds, which are the main active ingredients in Salvia bowleyana Dunn roots, from complex crude extracts by high-speed countercurrent chromatography combined with preparative high-performance liquid chromatography. A two-phase solvent system comprising n-hexane-ethyl acetate-methanol-water (7:3:7:3, v/v/v/v) was selected for high-speed countercurrent chromatographic separation. Three major diterpenoids, 6α-hydroxysugiol (7), sugiol (8), and 6, 12-dihydroxyabieta-5,8,11,13-tetraen-7-one (9) were obtained at purities of 98.9, 95.4, and 96.2%, respectively, and minor diterpenoids were enriched via one-step separation. The enriched minor diterpenoids were further purified by continuous preparative high-performance liquid chromatography to yield two new norabietanoids (1, 6) and four known compounds (2-5). The structures of these new compounds were determined using NMR spectroscopy, high-resolution electrospray ionization mass spectrometry, and electronic circular dichroism spectroscopy. The results suggest that high-speed countercurrent chromatography combined with preparative high-performance liquid chromatography efficiently isolates diterpenoids, including minor components, from complex natural products.

Isolation of diterpenoids from sugi wood-drying byproducts and their bioactivities

Diterpenoids are the main components of the byproducts discharged from sugi wood-drying process (BWP), making BWP a source of these useful compounds. Since there is no method for purifying these compounds from BWP, we sought to develop one. In this study, seven diterpenoids compounds were isolated: abietatriene (I), phyllocladenes (II-i and II-ii; a complex of isophyllocladene and phyllocladene), abietadiene (III), sandaracopimarinal (IV), 6,7-dehydroferruginol (V), ferruginol (VI), and sandaracopimarinol (VII) using medium-pressure liquid chromatography (MPLC) and high-performance liquid chromatography (HPLC). We tested the biological activities of these diterpenoids. Compounds V and VI showed antioxidant activity in the DPPH radical scavenging method, β-carotene bleaching method, and linoleic acid method. Furthermore, compounds V–VII showed antimicrobial activity against Propionibacterium acnes, and III, VI, and VII showed antifungal activity against Trichophyton mentagrophytes and Trichophyton rubrum. These results contribute to the accumulation of knowledge on diterpenoids and will help in developing new ways of utilizing BWP, a currently unused woody biomass.

LC-MS guided isolation of diterpenoids from Sapium insigne with α-glucosidase inhibitory activities

Ten new (1−10) and ten known (11−20) diterpenoids involving ent-atisane, ent-seco-atisane, ent-kaurane and ent-seco-kaurane types were isolated from Sapium insigne under the guidance of LCMS-IT-TOF analyses. Their structures were characterized by extensive spectroscopic analyses (HRESIMS, UV, IR, 1D and 2D NMR). A putative biosynthetic pathway was proposed for ent-seco-atisane diterpenoids. Their inhibitory activities on α-glucosidase in vitro were tested for the first time. Compound 4 showed moderate inhibitory effect on α-glucosidase with an IC50 value of 0.34 mM via a noncompetitive inhibition mechanism (Ki = 0.27 mM). The preliminary structure-activity relationships of the ent-atisane diterpenoids inhibiting α-glucosidase were discussed.

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

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.

Antioxidant diterpenoids from the roots of Salvia barrelieri

The phytochemical and biological studies carried out on Salvia species showed that their extracts and constituents have various biological activities. The aim of this study was the isolation of diterpenoids from the roots of Salvia barrelieri Ettling and the determination of the antioxidant activity. Chromatographic methods were used for fractionation and isolation, respectively. Structure elucidation was established by spectroscopic methods. Five antioxidant assays were performed. Three new abietane diterpenoids barreliol, royleanone 12-methyl ether and 7-epi-salviviridinol, and six known diterpenoids, with a known dammarane triterpenoid, pyxinol were isolated. The absolute stereochemistry of pyxinol was confirmed by X-ray analysis. Taxodione exhibited the highest antioxidant activity among the tested compounds.

Two New Abietane Diterpenes from Cordia latifolia

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Two new abietane diterpenes from Cordia latifolia

Two new abietane diterpenes cordioic acid and cordifolic acid were isolated from the methanolic extract of Cordia latifolia stem bark. The structures of these diterpenes were elucidated using spectroscopic techniques. To the best of our knowledge, this is the first instance of isolation of diterpenoids from this source. Furthermore, cordifolic acid is a rare 2,3- seco-abietane suggestive of its biogenesis from 3-keto-analogue.

Isolation of Diterpenoids of the Cladiellane Class from Gorgonians of the Genus Muricella

Six diterpenoids of the cladiellane class have been isolated from two morphologically distinct populations of gorgonians of the genus Muricella. The structures of two novel compounds have been determined by combined spectroscopic methods. These compounds exhibited significant brine shrimp lethality and cytotoxicity.