A new neolignan glucoside from hairy roots of Cichorium intybus

A new neolignan glucoside was isolated from hairy roots of Cichorium intybus. Its structure was determined as (7S, 8R)-3′-demethyl-dehydrodiconiferyl alcohol-3′-O-β-glucopyranoside based on a combination of 1D and 2D NMR techniques and CD data. In addition, further water soluble constituents, including four known phenolic compounds and one known sesquiterpene lactone glucoside, were isolated from the same source.     

Furostanol saponins from Yucca gloriosa L. rhizomes

Two new and one known furostanol saponins were isolated from the rhizomes of Yucca gloriosa. The structures of the isolated compounds were established by detailed spectroscopic analysis (1D-, 2D NMR, ESI-MS, HR-MALDI-MS). The glycosidic profile of Y. gloriosa in comparison to that of Yucca schidigera, the well known commercial source of saponins, is briefly discussed. The similarity between the two species regarding the high steroidal content suggests that it might be possible to use Y. gloriosa for the same applications as Y. schidigera.     

Oxytrofalcatins A–F,N-benzoylindole analogues from the roots of Oxytropis falcata (Leguminosae)

Indole alkaloids, oxytrofalcatins A–F (1–6), together with five other known alkaloids (7–11), were isolated from the roots of Oxytropis falcata. Their structures were elucidated by comprehensive spectroscopic analyses, including using 1D and 2D NMR spectroscopy and mass spectrometry. This is the first report of N-benzoylindoles from a natural source. Compounds 1–6 lacked significant cytotoxicity against SGC-7901 and HL-60 tumor cell lines.     

Trinorguaian and germacradiene type sesquiterpenes along with flavonoids from the herbs of Pimpinella cappadocica Boiss. & Bal.

A trinorguaian-type sesquiterpenoid named kanalpin and two acylated flavonol glycosides named erzurumin and ilicanin have been isolated from Pimpinella cappadocica Boiss. & Bal., together with three known sesquiterpenoids and six known flavonoid glycosides. The structures of these compounds were determined by extensive spectroscopic (UV, IR, EI–MS, APCI–MS, HR-ESI-MS, 1D and 2D NMR) analyses. Antioxidant capacity of isolated secondary metabolites containing extracts of P. cappadocica was evaluated.     

Glucosidic iridoids from Molopanthera paniculata Turcz. (Rubiaceae,Posoquerieae)

One new veratroyl derivative, together with the known iridoids barlerin and shanzhiside methyl ester were isolated from Molopanthera paniculata. The structures of compounds were established by 1D and 2D NMR and HRMS analyses.     

Development and characterization of microsatellite markers in sawih tree (Duabanga moluccana Blume) using ISSR-suppression PCR techniques

Duabanga moluccana (or locally known as sawih) is an indigenous fast growing tropical tree species that confers various advantages for the timber industry and for planted forests development. In this paper, we isolated and characterized 8 polymorphic microsatellite markers from the D. moluccana genome using ISSR-suppression PCR techniques. The number of alleles and PIC values ranged from 3 to 8 alleles per locus and from 0.488 to 0.792, respectively. Three microsatellite loci were deviated from Hardy-Weinberg equilibrium (P < 0.05). The transferability rate ranged from 24 to 100 % among the three indigenous tree species tested. This indicates that the newly developed microsatellite markers would be useful tools for population genetic studies on D. moluccana and other indigenous tree species.     

Viridin-like steroids from Hymenoscyphus pseudoalbidus

Three furanosteroids were isolated from the ash dieback causing fungus Hymenoscyphus pseudoalbidus along with the known compounds viridiol and demethoxyviridiol. The compounds were characterized by 1D and 2D NMR spectroscopy, LC–HRMS and polarimetry.     

Two new butanolides from the roots of Litsea acuminata

Two new butanolides, licunolides A (1) and B (2), were isolated from the roots of Litsea acuminata, together with three known compounds: isolancifolide (3), longifolin (4), and sesquirose furan (5). The structures of compounds 1 and 2 were determined by spectroscopic studies (IR, MS, 1D and 2D NMR) and chemical evidence. This is the first report of 4-hydroxy-5-methylbutanolides with a C₁₀-side chain from a natural source. Longifolin (4) and sesquirose furan (5) showed a significant cytotoxicity against HeLa cell lines in vitro.     

Alkaloids of Litsaea laeta and L. salicifolia

The structure for laetine (2-hydroxy-1-methyl 10,11-methylenedioxy noraporphine), a new alkaloid from the bark of Litsaea laeta has been established. N,O-Dimethylharnovine and glaucine were also isolated from the same source. C-2 hydroxy aporphines are characteristic of L. laeta. Two known alkaloids, dicentrinone and nordicentrine, have also been isolated from the leaves of L. salicifolia.     

Two new saponins from Paronychia capitata

Two new oleanane-type triterpene glycosides, 3˗O˗β˗D˗glucopyranosyl˗28˗O˗[β˗D˗glucopyranosyl˗(1→2)˗β˗D˗xylopyranosyl˗(1→6)˗β˗D˗glucopyranosyl]medicagenic acid (1) and 3˗O˗β˗D˗glucopyranosyl˗28˗O˗[β˗D˗glucopyranosyl˗(1→6)˗β˗D˗glucopyranosyl˗(1→2)˗ β˗D˗xylopyranosyl]oleanolic acid (2), named capitatosides A and B respectively, were isolated from the butanol extract of Paronychia capitata (L.) Lam., along with seven known compounds. The structures of the isolated compounds were established by spectroscopic methods, mainly HRMS, 1D and 2D NMR (¹H, ¹³C, COSY, HSQC, HMBC and NOESY) techniques, whereas those of the known compounds were identified by spectral comparison with reported literature data.     

Teuchamaedrin C,a neo-clerodane diterpenoid from Teucrium chamaedrys

A new neo-clerodane diterpenoid, teuchamaedrin C, has been isolated from the aerial parts of Teucrium chamaedrys. Its structure, (12S,18S)-15,16-epoxy-neo-clerodane-13(16)14-dien-19,20-olide-18,6β-hemiacetal, was established by spectroscopic and chemical means. In addition, the previously known diterpenoids 6α-hydroxyteuscordin and dihydroteugin were isolated from the same source.     

New styrylpyrones from the fungal endophyte Penicillium glabrum isolated from Punica granatum

The endophytic fungus Penicillium glabrum was isolated from pomegranate fruits (Punica granatum) collected in Uzbekistan. Extracts of the fungus grown on rice yielded two new styrylpyrones, namely 3-methyldesmethoxyyangonin (1) and 3-methylbisnoryangonin (2), together with four known metabolites. The structures of the isolated compounds were elucidated on the basis of comprehensive spectral analysis (1D and 2D NMR and MS).     

Triterpenoid saponins from Impatiens siculifer

Triterpenoid saponins, impatienosides A-G, together with 12 known saponins, were isolated from the whole plants of Impatiens siculifer. Their structures were established on the basis of extensive 1D and 2D NMR and MS analyses coupled with chemical degradation. Cytotoxic activities of the isolated saponins were evaluated against three human cancer cell lines: human myeloid leukemia HL-60 cells, human stomach KATO-III adenocarcinoma, and human lung A549 adenocarcinoma.     

Alkamides and a neolignan from Echinacea purpurea roots and the interaction of alkamides with G-protein-coupled cannabinoid receptors

Multiple chromatographic separations of the CHCl₃-soluble extract of the roots of Echinacea purpurea led to the isolation of 19 compounds. Four natural products, three alkamides and nitidanin diisovalerianate, were identified, and five further compounds were detected for the first time in this species. Additionally, 10 known E. purpurea metabolites were isolated. The structures were determined by mass spectrometry and advanced 1D and 2D NMR techniques. The bioactivity of the isolated compounds was studied in [³⁵S]GTPγS-binding experiments performed on rat brain membrane preparations. Both partial and inverse agonist compounds for cannabinoid (CB1) receptors were identified among the metabolites, characterized by weak to moderate interactions with the G-protein signaling mechanisms. The G-protein-modulating activities of the Echinacea compounds are rather far from the full agonist effects seen with the CB1 receptor agonist reference compound arachidonyl-2′-chloroethylamide (ACEA). However, upon coadministration with ACEA, a number of them proved capable of inhibiting the stimulation of the pure agonist, thereby demonstrating cannabinoid receptor antagonist properties.     

Filamentous fungi from the Atlantic marine sponge Dragmacidon reticulatum

Dragmacidon reticulatum is a marine sponge of wide occurrence in the Eastern and Western Atlantic. Little is known about D. reticulatum fungal diversity. Filamentous fungi recovered from D. reticulatum were assessed in the present study using a polyphasic taxonomic approach, including classical morphology, molecular biology and MALDI-TOF ICMS. Ninety-eight fungal strains were isolated from two D. reticulatum samples by using six different culture media, which were identified up to the genus level. Sixty-four distinct fungal ribotypes were obtained, distributed among twenty-four different genera belonging to the Ascomycota and Zygomycota. Representatives of Penicillium and Trichoderma were the most diverse and abundant fungi isolated. Amongst Penicillium spp. three isolates belonged to the same ribotype can be considered as a putative new species. Data derived from the present study highlight the importance of using a polyphasic approach to get an accurate identification in order to structure a reliable culture collection.     

Indole alkaloids from Hunteria zeylanica

Fourteen indole alkaloids were isolated and identified from the leaves and bark of Hunteria zeylanica: isocorymine, vobasine, (+)-eburnamenine, eburnamine, isoeburnamine, O-ethyleburnamine, O-methyleburnamine, O-methylisoeburnamine, pleiocarpamine, dihydrocorynantheol, yohimbol, epiyohimbol, tuboxenine and hydroxy-17-decarbomethoxy-16-dihydroepiajmalicine. O-Ethyleburnamine, O-methylisoeburnamine, epiyobimbol and hydroxy-17-decarbomethoxy-16-dihydroepiajmalicine, although known products, were isolated for the first time from a natural source.     

Acrocalysterols A and B,two new steroids from endophytic fungus Acrocalymma sp

Two new steroids, named acrocalysterols A (1) and B (2), together with five known compounds were isolated and characterized from an endophytic fungus Acrocalymma sp., isolated from the tender stems of Sinomenium acutum. The structures of the isolated metabolites were identified based on UV, IR NMR (1D and 2D), HR-ESI-TOF-MS, single-crystal X-ray diffraction experiment using Cu Kα radiation and CD spectra associated with TD-DFT calculation. The bioassay showed that compound 2 displayed potent cytotoxicity against three cancer cell lines HeLa, HCC-1806, and RKO with IC₅₀ values ranging from 18.37 to 19.64 μM.     

New diplosporin and agistatine derivatives produced by the fungal endophyte Xylaria sp. isolated from Vitis labrusca

A Xylaria sp. was isolated as an endophyte from a surface-sterilized Concord grape leaf (Vitis labrusca). Dereplication and LC–MS analysis of the filtrate extracts identified two new structures, compound 1, 13-O-methyl-(5R) diplosporin, and 2 a new agistatine. Additionally, five known compounds 3–7 including an agistatine, coriloxin, (5R)-diplosporin, and two mellein derivatives were also isolated. This is the first report of these structurally-related metabolites isolated from the same fungus, suggesting they share a related biosynthesis. Metabolites were isolated using liquid chromatography-solid phase extraction (LC-SPE) and semi-preparative HPLC. Structures were elucidated on the basis of 1D and 2D NMR analysis, HRMS measurements and X-ray structural analysis for compound 1.     

Prenylated flavanones and flavanonols as chemical markers in Glycosmis species (Rutaceae)

Fifteen prenylated or geranylated flavanones and flavanonols were isolated from the leaf extracts of different Glycosmis species collected in Thailand and Malaysia. All structures were elucidated by spectroscopic methods, especially 1D and 2D NMR. Six compounds were described for the first time and two were only known so far as synthetic products. The chemotaxonomic significance of flavanoid accumulation within the genus Glycosmis is highlighted.     

Cytotoxic cycloartane triterpene and rare isomeric bisclerodane diterpenes from the leaves of Polyalthia longifolia var. pendula

A 24-methylenecycloartane-3β, 16β, 23β-triol, Longitriol (1), rare bisclerodane imides, Longimide A (2) and previously known Longimide B (3) were isolated from ethanolic extract of the leaves of Polyalthia longifolia var. pendula. This is the first example of isolation of any cycloartane triterpene from this plant source. Structures were determined by extensive (1D and 2D NMR) spectroscopic data analysis combined with ESI MS/MS fragmentation and X-ray analysis. Furthermore, Compounds 1 and 2 were evaluated for their cytotoxic effects against four human cancer cell lines and found to be most active against cervical carcinoma cell lines with IC₅₀ value of 10.03 and 4.12 μg/mL, respectively.