A new arbutin derivative from the leaves of Vaccinium dunalianum wight

A new arbutin derivative, namely dunalianosides J (1), along with six known compounds, arbutin (2), robustaside A (3), 6′-O-caffeoylarbutin (4), dunalianoside D (5), kaempferol 3-O-β-D-glucopyranoside (6) and kaempferol 3-O-β-D-sambubioside (7) were isolated from the leaves of Vaccinium dunalianum Wight (Ericaceae). The structure of 1 was elucidated by extensive 1D and 2D NMR, HR-MS and CD spectroscopic analyses. In which, kaempferol 3-O-β-D-sambubioside (7) was isolated from the genus Vaccinium for the first time.     

Terretonin D1, a new meroterpenoid from marine-derived Aspergillus terreus ML-44

A new meroterpenoid, named terretonin D1 (1), and three known ones, terretonin (2), terretonin A (3), and terretonin D (4), were isolated from marine-derived fungus Aspergillus terreus ML-44. The structure of 1 was elucidated by extensive spectroscopic methods, including 1D and 2D NMR, HR-ESI-MS, and the absolute configuration was determined by X-ray crystallographic analysis. The anti-inflammation activity of 1–4 was preliminarily tested, and all of them weakly inhibited the nitric oxide (NO) production of RAW264.7 macrophages stimulated by lipopolysaccharide (LPS), with inhibitory rates of 22–34% at 50?μg/mL.     

A new lactam alkaloid from Portulaca oleracea L. and its cytotoxity

A new lactam alkaloid named oleraciamide D (1), indentified as (5R)-4-(3-methoxy-4-hydroxyphenyl)-5-(4-hydroxyphenyl)-5,6-dihydropyridin-2(1H)-one, together with five known compounds, indole-3-aldehyde (2), portulacatone (3), N-trans-feruloyloctopamine (4), N-trans-feruloyl-3′-O-methyldopamine (5) and N-trans-feruloyltyramine (6) were isolated from Potulaca oleracea L. Among them, indole-3-aldehyde (2) was isolated from the medicine for the first time. The structure of the new alkaloid was elucidated via UHPLC-ESI-Q-TOF/MS, 1D NMR and 2D NMR. The five known compounds were established by comparing the ¹H-NMR and ¹³C NMR with the reported literature. Oleraciamide D (1) showed cytotoxicity against SH-SY5Y cells when concentration at 50 uM by CCK-8 method.     

A new sesquiterpene from the barks of Manglietia hookeri

A new sesquiterpene manghookerins A (1) was isolated from the barks of Manglietia hookeri (Magnoliaceae) together with five known eudesmane-type sesquiterpenes. The structure of manghookerins A (1) was elucidated by physical and spectroscopic data analysis, including 1D and 2D NMR, HR-ESI-MS and X-ray diffraction. The structures of known sesquiterpenes were established by comparing their spectroscopic data with those in literatures.     

C-glucosyl flavones from the seeds of <Emphasis Type="Italic">Ziziphus jujuba</Emphasis> var. <Emphasis Type="Italic">spinosa</Emphasis>

A new C-glucosyl flavone, 6‴-vanilloylspinosin (1), was isolated from the seeds of Ziziphus jujuba var. spinosa, together with three known C-glucosyl flavones, spinosin (2), 6‴-feruloylspinosin (3), and isospinosin (4). The structure of 1 was elucidated by spectral methods (1D NMR, ESI-MS, HR-MS, 2D NMR).     

Auroglaucin-related neuroprotective compounds from Vietnamese marine sediment-derived fungus Aspergillus niveoglaucus

Abstract

Two new auroglaucin-derived compounds, niveoglaucins A (1) and B (2), together with four known related compounds were isolated from extract of the marine sediment-derived strain of Aspergillus niveoglaucus. The structures of these compounds were determined by 1D and 2D NMR spectroscopy and high resolution MS. The plausible biosynthetic pathway was proposed for new compounds 1 and 2. The neuroprotective activity in 6-OHDA-induced Parkinson’s disease cell model was shown for niveoglaucin A (1).     

A new chromene from the fruiting bodies of Chroogomphus rutilus

A new chromene, acetic acid 2R-(4,8-dimethylnona-3,7-dienyl)-8-hydroxy-2-methyl-2H-chromen-6-yl ester (1), was isolated from the fruiting bodies of Chroogomphus rutilus, together with six known compounds (2–7). The structures of these compounds were identified based on 1D and 2D NMR, including ¹H–¹H COSY, HMQC and HMBC spectroscopic methods. Of these seven compounds, 2 and 3 showed cytotoxicity against HSC-T6, SK-Hep1 and A549 cell lines.     

A new diketopiperazine derivative from a deep sea-derived Streptomyces sp. SCSIO 04496

A new diketopiperazine (DKP) derivative, (6R,3Z)-3-benzylidene-6-isobutyl-1-methyl piperazine-2,5-dione (1), as well as five known DKPs 2–6 was isolated from a deep sea-derived Streptomyces sp. SCSIO 04496. The structure of 1 was elucidated using a combination of 1D and 2D NMR, HR-ESI-MS and chiral-phase HPLC techniques. Compounds 1–6 did not show cytotoxic activity at a concentration of 100 μM in bioactivity assay.     

Ascomycotin A,a new citromycetin analogue produced by Ascomycota sp. Ind19F07 isolated from deep sea sediment

A new citromycetin analogue, ascomycotin A (1), together with eight known compounds, wortmannilactone E (2), orcinol (3), orsellinic acid (4), isosclerone (5), (3R,4S)-( ? )-4-hydroxymellein (6), diorcinol (7), chaetocyclinone B (8) and 2,5-dimethoxy-3,6-di(p-methoxypheny1)-1,4-benzoquinone (9), was isolated from the fungal strain Ascomycota sp. Ind19F07, which was isolated from the deep sea sediment of the Indian Ocean. The structures of the compounds were established by spectroscopic data including 1D and 2D NMR and HR-ESI-MS. Compounds (1–9) were evaluated for antibacterial activity.     

Paenibacillin A,a new 2(1H)-pyrazinone ring-containing natural product from the endophytic bacterium Paenibacillus sp. Xy-2

A new 2(1H)-pyrazinone ring-containing natural product, paenibacillin A (1), together with five known diketopiperazine derivatives 2–6 and two known isoflavones 7–8, was isolated from the culture of an endophytic bacterium Paenibacillus sp. Xy-2. The structure of compound 1 was elucidated by extensive spectral methods, including UV, IR, HR-ESI-MS, 1D and 2D NMR and ECD experiments. Compound 1 exhibited moderate cytotoxicity against HL-60 cell line with IC₅₀ value of 50.48 μM.     

4-dehydroxyepisarcovagine A,a new steroidal alkaloid from Sarcococca pruniformis Lindl.

A new steroidal alkaloid, 4-dehydroxyepisarcovagine A (1), along with seven known alkaloids, sarcovagine D (2), sarcovagenine C (3), epoxysarcovagenine D (4), Pachysamine L (5), Pachysamine E (6), sarcovagine A (7) and sarcovagine B (8), was isolated from the roots and stems of Sarcococca pruniformis Lindl. The structure of compound 1 was elucidated by means of spectroscopic analysis.     

New naphthopyrones from marine-derived fungus Aspergillus niger 2HL-M-8 and their in vitro antiproliferative activity

A new cytotoxic dimeric naphthopyrone, aurasperone H (1), together with eight related known polyketides (2–9) was isolated from a marine-derived fungus Aspergillus niger 2HL-M-8. The structure of new compound 1 was elucidated on the basis of its spectroscopic data (1D, 2D NMR and CD). Compound 1 exhibited moderate inhibitory activity against the human lung adenocarcinoma A549 and the human leukaemia HL-60 cell lines. Compound 5 displayed significant in vitro antiproliferative activity against HL-60 cell line with an IC₅₀ value of 0.8 μM.     

Trichosordarin A,a norditerpene glycoside from the marine-derived fungus Trichoderma harzianum R5

Abstract

A new sordarin derivative, trichosordarin A (1), with a unique norditerpene aglycone was isolated from the culture of a marine-sediment-derived fungal strain, Trichoderma harzianum R5. Its structure and relative configuration were unequivocally identified by a combination of 1D/2D NMR, IR, and mass spectrometric methods. Compound 1 was assayed to be toxic to the marine zooplankton Artemia salina.     

Isolation and identification of a new neo-clerodane diterpenoid from Teucrium chamaedrys L.

Teucrium chamaedrys L. is an aromatic and medicinal plant used as traditional medicine. Aerial parts of the plant material were dried and extracted with hexane–dichloromethane (extract 1), ethyl acetate–dichloromethane (extract 2) and methanol–dichloromethane (extract 3) in a ratio of 1:1 at rt successively. The solvents were evaporated to give crude extracts. Extract 1 was suspended in water at 60°C then partitioned successively with hexane and ethyl acetate to give hexane and ethyl acetate portions. After the column chromatography (silica gel) of ethyl acetate extract, one new and four known compounds were isolated. The new compound was named as 1(12S,18R)-15,16-epoxy-2β,6β-dihydroxy-neo-cleroda-13(16),14-dien-20,l2-olide-l8,l9-hemiacetal (teuchamaedryn D) (4). The known compounds were teucrin A (1), dihydroteugin (2), teucroxide (3), syspirensin A (5). The chromatographic methods were also applied for extract 3 to isolate verbascoside (6) and teucrioside (7). The structure of isolated compounds was elucidated by spectroscopic methods including LC-TOF/MS, 1D NMR and 2D NMR.     

Two new eremophilenolides from the roots of Ligulariopsis shichuana and their anti-phytopathogenic fungal and antifeedant activities

Two new eremophilenolides, ligushicins A (1) and B (2), and two known compounds including β-sitosterol and ursolic acid were isolated from Ligulariopsis shichuana. The structures of new compounds were established on the basis of 1D and 2D NMR data and HRESIMS data interpretation. The absolute configuration of new compounds was assigned by ECD spectroscopy, and that of ligushicins A (1) was confirmed by X-ray diffraction analysis. The antifungal and antifeedant activities of new compounds were evaluated against four plant pathogenic fungi and third-instar larvae of Plutella xylostella, respectively. Ligushicins A (1) and B (2) exhibited potent antifungal activity against Botrytis cinerea and Fusarium oxysporum with minimum inhibitory concentration (MIC) values ranging from 50 to 100 mg/L, while they also exhibited weak antifeedant activities.     

Terpenoids from the barks of Magnolia maudiae (Dunn) Figlar

A new germacrenolide (1) and fourteen known terpenoids (2–15) were isolated from the barks of Magnolia maudiae (Dunn) Figlar (Magnoliaceae). The structure of (7αH,11βH)-2α,8α-dihydroxy-4α,5β-epoxy-germacr-1(10)-en-6α,12-olide (1) was elucidated by physical and spectroscopic data analysis, including 1D, 2D NMR and HR-ESI-MS. Lyratol F (9) was isolated from Magnolia for the first time. The structures of known compounds were established by comparing their spectroscopic data with those in literatures.     

Colletotrichine A,a new sesquiterpenoid from Colletotrichum gloeosporioides GT-7, a fungal endophyte of Uncaria rhynchophylla

One new compound, Colletotrichine A (1), was produced by the fungal Colletotrichum gloeosporioides GT-7. The structure was established by 1D and 2D NMR spectra. Monoamine oxidase (MAO) and acetylcholinesterase (AChE) inhibitory activity of 1 was also evaluated. Compound 1 showed AChE-inhibiting activity with IC₅₀ value of 28 μg/mL.     

A new di-C-prenylated coumarin from Sophora interrupta

A new di-C-prenylated coumarin, 7-methoxy-6,8-bis-(2,3-dihydroxy-3-methylbutyl)-coumarin (1), together with seven known compounds, isopimpinellin (2), an arylbenzofuran (3), three flavonoids (4–6), (+)-maackianin (7) and echinoisoflavanone (8), were isolated from the leaves of Sophora interrupta Bedd. The structure of the new compound 1 as well as known compounds was elucidated by extensive 1D and 2D NMR spectral studies.     

A new cyclopentanone derivative from <Emphasis Type="Italic">Euphorbia hirta</Emphasis>

A new cyclopentanone derivative, (1'R,5'R)-5-(5'-carboxymethyl-2'-oxocyclopentyl)-3Z-pentenyl acetate (1), was isolated from Euphorbia hirta. Its structure was elucidated on the basis of spectroscopic analysis including 1D and 2D NMR techniques. The EtOAc extract of Euphorbia hirta was evaluated against K562 and A549 cancer cell lines.     

Iridoid,phenylethanoid and flavonoid glycosides from Forsythia suspensa

Abstract

As part of our continuing efforts to explore bioactive compounds from natural resources, a new iridoid glycoside, adoxosidic acid-6′-oleuroperic ester (1), together with one known phenylethanoid glycoside (2) and two known flavonoid glycosides (3–4) were isolated from the fruit of Forsythia suspensa. The structure of the new compound (1) was elucidated through 1D and 2D NMR spectroscopic data and HR-ESIMS. Interestingly, compound 1 was a monoterpene ester of one iridoid glycoside. Compounds 2–4 were identified as calceolarioside A (2), kaempferol-3-O-rutinoside (3), kampferol-3-O-robinobioside (4) on the basis of NMR spectroscopic data analyses and comparison with the data reported in the literature. The antiviral activity aganisist influenza A (H5N1) virus of compound 1 was studied as well.