Records of Natural Products Articles

The aerial parts of Cephalariaanatolica yielded two previously undescribed hederagenin-type triterpene glycosides, namely cephosides B (1) and C (2), in addition to eleven known natural compounds. The new compounds were identified as 3-O-β- D -glucopyranosyl-(1 ® 3)- b - D -glucopyranosyl-(1 ® 3)-α- L -rhamnopyranosyl-(1 ® 2)-α- L -arabinopyranosyl hederagenin 28-O-β- D -galactopyranosyl-(1 ® 6)-β- D -glucopyranosyl ester (1) and 3-O-α- L -rhamnopyranosyl-(1 ® 4)- b - D -glucopyranosyl-( 1 ® 3)-α- L -rhamnopyranosyl-(1 ® 2)-α- L -arabinopyranosyl hederagenin 28-O-β- D -galactopyranosyl-(1 ® 6)-β- D -glucopyranosyl ester (2) by 1D and 2D NMR spectroscopic data, HRESIMS analysis and chemical evidence. The two new triterpenoid saponins and the n-butanol extract were evaluated for their hemolytic activity in human erythrocyte cells and immunomodulatory properties in activated whole blood cells by PMA plus ionomycin. While only n-butanol extract increased IL-1β concentration strongly with a value of 760.52 pg/mL, cephoside C and n-butanol extract augmented a slight IFN-γ secretion with values of 4874.11 and 4750.20 pg/mL, respectively. None of the compounds changed IL-2 levels significantly and showed hemolytic activity.

Three populations of Mastigophora diclados were collected from Mount Kinabalu, Mount Alab, and Mount Trus Madi. Each population yielded a total of four, four, and five secondary metabolites, respectively. A new compound, dicladoic acid (1) and the enantiomer of the known chlorantene G (8), along with six known compounds (2-7) were isolated from the MeOH extract of Bornean liverwort Mastigophora diclados. The structures of the novel metabolites were established by analyses of the spectroscopic data, including 1D NMR, 2D NMR, HRESIMS and IR. Isolated compounds shed some light into the chemosystematics of secondary metabolites in M. diclados. Herbertane-type sesquiterpenes were identified as the major metabolites in all three populations in Sabah and could be regarded as a suitable chemotaxonomical marker.

Human neutrophil elastase (HNE) has been linked to immune system functions, including inflammation, as well as the development of skin wrinkles, suggesting that HNE inhibitors have many practical applications. In this study, the methanol extract of Epimedium koreanum Nakai contained potent HNE inhibitory flavonoids (1–4) with IC 50 values of 6.06–125.80 μM. Prenyl groups within these flavonoids were critical for the inhibitory effects. For example, epimedokoreanin B (1) (IC 50 = 6.06 μM) showed 6-fold higher efficacy than that of its parent luteolin (IC 50 = 36.01 μM). A similar trend was observed for compound 2 (IC 50 = 6.28 μM) and its parent, apigenin (IC 50 = 37.94 μM). Lineweaver–Burk plots showed that the compounds exhibit mixed-type inhibition. In a detailed kinetic study, compound 1 was assigned to mixed type I and exhibited the greatest binding to the free enzyme (K I = 11.7 μM, K IS = 40.9 μM).

The essential oils of the five Scrophularia species; Scrophularia chrysantha Jaub. et Spach, Scrophularia kotschyana Benth., Scrophularia olympica Boiss., Scrophularia cinerascens Boiss. and Scrophularia zuvandica Grossh. were obtained by hydrodistillation (HD) with a range of 0.10% to 0.16% yield and analysed by GC-FID/MS. In the meantime, the volatile organic compounds (VOCs) of S. chrysantha, S. kotschyana, S. olympica,S. cinerascens and S. zuvandica were also identified with the technique of SPME GC-FID/MS and the phytochemical results were evaluated. The experimental results of this study showed that the major compounds of essential oils which were taken by the hydrodistillation were carvacrol (52.4%), 2-pentadecanone (26.7%), 2-pentadecanone (12.2%), (Z)-2-nonenal (11.2%) and carvacrol (69.1%) respectively. Isovaleraldehyde (37.1%, 27.9%), eucalyptol (13.8%), 2-ethyl furan (14.8%) and 3(Z)-hexenol (91.3%) were respectively found as the main constituents of the five Scrophularia species with SPME method. Also antimicrobial activities of the essential oils of the five Scrophularia species were screened by using agar well diffusion method. It was identified that S. olympica, S.chrysantha, and S. kotschyana, have anti-tuberculosis activity, whereas, the essential oils gained from S. zuvandica and S. cinerascens have anti-fungal activity.

In vitro antiviral effect of a crude methanol extract and six fractions isolated from Rhoeo discolor against pandemic influenza A (H1N1) evaluated herein. The phytochemical analysis to identify the main classes of secondary metabolites was performed by thin layer chromatography (TLC). The cytotoxic effect and cell viability was determined in MDCK cells, and the antiviral activity was evaluated by qRT-PCR to detect influenza virus nucleoprotein (NP) gene. Finally a metabolomic analysis was performed using UPLC-MS. The phytochemical analysis revealed the presence of coumarins, tannins, saponins and flavonoids in the methanol extracts. Cytotoxicity related to 50% cell viability indicated concentrations of <1μg/mL for the six fractions tested and >1μg/mL for the crude extracts. Fraction MF1 inhibited synthesis of viral NP at co-treatment level at a concentration of 0.02 + 0.07 g/mL with a selectivity index (SI) of 32. The metabolomic analysis identified the presence of five flavonoids kaempferol, quercetin, isoquercetin luteolin-5-glucoside and rutin. Antiviral activity of flavonoids from R. discolor against the influenza AH1N1 virus are reported for the first time.

Fruiting bodies of the Chilean mushroom Dermocybe nahuelbutenis Garrido & E. Horak (syn.: Cortinariusnahuelbutensis (Garrido & E. Horak) E. Valenz. & G. Moreno) were chemically investigated for the first time and afforded the new dimeric anthraqinone 7,7 ' -emodinphyscion (1) beside the know anthraquinones dermolutein (2), endocrocin (3), skyrin (4) and the dimeric pre-anthraquinone derivative flavomannin C (5 ) . The chemotaxonomic significance of the pigments is discussed.

The phytochemical investigation of Ochrosia eliptica leaves resulted in isolation and identification of eight compounds; lupeol, lupeol acetate, uvaol, ursolic acid, β-sitosterol glucoside, rutin, 8-methoxy and 9-methoxy ellipticine . The ethanolic extract and fractions were studied for their cytotoxic, antioxidant and anti-inflammatory activities. The cytotoxic activity was performed on human mammary adenocarcinoma (MCF7), its multidrug-resistant ‎ counterpart (VCREMS), estrogen receptor negative human metastatic breast ‎ adenocarcinoma cells (MDA-MB-231) and the non-cancerous, immortalized by ‎ telomerase, human breast epithelial cell line (hTERT-HME1). Additionally, the inhibitory potential on Cdc25s proteins was determined. The results showed that the dichloromethane (DCM) fraction and the major alkaloid; 9-methoxyellipticine exhibited high inhibitory activity against all tested cell lines particularly MCF7 and VCREMS cell lines, whereas t he DCM fraction showed a significant inhibitory action on Cdc25 A isoform. In contrast, the n-butanol fraction and 9-methoxyellipticine displayed the highest antioxidant potential. The DCM fraction showed significant anti-inflammatory activity compared to indomethacin. This work comprises the first comprehensive work to be conducted on O. elliptica leaves showing its potential in multiple biological activities .

Lignans are a large group of chemical compounds found in plants. They also have effects on enzymes, protein synthesis, proliferation, angiogenesis, growth factor and cell differentiation. In this study, α-(-)-conidendrin, enterodiole, enterolactone, nordihydroguaiaretic acid, secoisolariciresinol, and secoisolariciresinol diglucoside were used. Also, the inhibition effects of these lignans against the carbonic anhydrase CA I and II isoenzymes (CA I, and II) and acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) enzymes were investigated. The Ki values of the lignans were found in range of 1.7-3.30 nM for CA I, in range of 1.11-2.68 nM for CA II, in range of 0.72-1.62 nM for AChE, and in range of 0.08-0.20 nM for AChE, respectively.

The purpose of this work is to reveal the fatty acid composition of phospholipids, neutral and total lipid content of edible land snails Helix lucorum, Eobania vermiculata and non-edible land slug Limax flavus(Gastropoda: Pulmonata). The analyses revealed that the snails and slug are rich in C16:0, C18:0, C18:1ω9 and C18:2ω6 acids. Phospholipid fractions contained very high amounts of C20:4ω6 (15.37% in H. lucorum, 12.37% in E. vermiculata and 8.59% in L. flavus) which is the most importantprecursor of eicosanoids. The level of ΣPUFA, in edible snails, was found to be higher than ΣSFA and ΣMUFA. However, in the slug, ΣMUFA level was higher than ΣSFA and ΣPUFA levels in neutral and total lipid contents. Ʃω6 / Ʃω3 (Omega 6 / Omega 3) ratio was defined to be very high in the phospholipid of H. lucorum, E. vermiculata and L. flavus; 6.07, 8.29 and 5.39, respectively. Furthermore, the study showed that all three species are valuable sources of omega 6 and essential fatty acids; C18:2ω6 and C18:3ω6

Nicotiana plumbaginifolia Viv. is an annual herb of the family Solanaceae, which grows abundantly in the weedy lands of Bangladesh . This plant possesses analgesic, antibacterial, anti-anxiety and hepatoprotective properties, and produces various phenolic compounds including flavonoids. The present study afforded determination of total phenolic and flavonoid contents, and for the first time, the isolation and characterization of highly oxygenated flavonoids, e.g., 3,3' ,5,6,7,8-hexamethoxy- 4',5'-methylenedioxyflavone (1), 3,3' ,4' ,5',5,6,7,8-octamethoxyflavone (2, exoticin), 6,7,4',5'-dimethylenedioxy-3,5,3'-trimethoxyflavone (3) and ( 3,3' ,4',5,5',8-hexamethoxy-6,7-methylenedioxyflavone (4) from the leaves of N. plumbaginifolia . All these flavonoids are rather rare natural products, and only found in a few genera, e.g.,Polygonum and Murraya. The structures of the isolated flavonoids were elucidated by comprehensive spectroscopic analyses, e.g., UV, 1H, 13C NMR, DEPT, HSQC, HMBC and MS.