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 diarylheptanoid and a new diarylheptanoid glycoside isolated from the roots of Juglans mandshurica and their anti-inflammatory activities

A new diarylheptanoid, (2S,3S,5S)-2,3,5-trihydroxy-1,7-bis(4-hydroxy- 3-methoxyphenyl)heptane (1), and a new diarylheptanoid glycoside, (2S,3S,5S)-2,3-dihydroxy-5-O-β-d-xylopyranosyl-7-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)heptane (2), together with three known compounds, rhoiptelol C (3), rhoiptelol B (4) and 3′,4″-epoxy-2-O-β-d-glucopyanosyl-1-(4-hydroxyphenyl)- 7-(3-methoxyphenyl)heptan-3-one (5) were isolated from the roots of Juglans mandshurica (Juglandaceae). The structures of compounds 1 and 2 were identified based on HR-ESI-MS, 1D and 2D NMR spectroscopic methods. Compounds 1–5 were assayed for their inhibitory effects on the production of NO, TNF-α and IL-6 in LPS-stimulated RAW264.7 cells.     

New 3D and 2D supramolecular heteroleptic palladium(II) dithiocarbamates as potent anticancer agents

Three new heteroleptic palladium(II) dithiocarbamates with better in vitro anticancer activity than cisplatin were synthesized and characterized by different analytical techniques, elemental analysis, FTIR, NMR, and single crystal X-ray diffraction analysis. The Pd center is chelated by dithiocarbamate ligand {4-benzylpiperazine-1-carbodithioate (1) and (3) or (4-(2-methoxyphenyl)piperazine-1-carbodithioate (2)}, triorganophosphine {tris-(4-flourophenyl)-phosphine (1) and (2) or tris-(4-chlorophenyl)phosphine (3)}, and a chloro-group, resulting in a square planar geometry. The packing diagram reveals a 3D network (1 and 2) and a 2D network (3) composed of various 1D chains in which the molecules are linked via hydrogen bonds (1–3) and halide?π (1, 3) interactions. The anticancer activities of complexes against HeLa cell line varies in the sequence 2 (23.438 μM) > 1 (38.293 μM) > 3 (47.554 μM) > cisplatin (78.075 μM). The cytotoxicity of these complexes is due to their strong induction of oxidative stress and DNA-damage ability leading to apoptosis.     

Two new benzolactones from the leaves of Nicotiana tabacum and their anti-tobacco mosaic virus activities

Two new benzolactones, 5-methyl-6-prenyl-isobenzofuran-1(3H)-one (1), 5-hydroxymethyl-6-prenyl-isobenzofuran-1(3H)-one (2), together with four known phenolic compounds (3–6), were isolated from the leaves of Nicotiana tabacum. Their structures were elucidated by spectroscopic methods, including extensive 1D and 2D NMR techniques. Compounds 1–6 were evaluated for their anti-tobacco mosaic virus (anti-TMV) activities. The results showed that compounds 1–6 exhibited high anti-TMV activities with inhibition rates in the range of 16.9–26.2%, respectively.     

Two new flavonol glycosides from Dimocarpus longan leaves

From the extracts of Dimocarpus longan Lour leaves, 2 unusual flavonol glycosides, quercetin 3-O-(3″-O-2?-methyl-2?-hydroxylethyl)-β-d-xyloside (1) and quercetin 3-O-(3″-O-2?-methyl-2?-hydroxylethyl)-α-l-rhamnopyranoside (2), as well as 10 known compounds including 2 flavonol glycosides, afzelin (3) and kaempferol-3-O-α-l-rhamnopyranoside (4), 2 flavans, ( ? )-epicatechin (5) and proanthocyanidin A-2 (6), 3 triterpenoids, friedelin (7), epifriedelanol (8) and β-amyrin (9), a peptide, N-benzoylphenylalanyl-N-benzoylphenylalaninate (10), and 2 sterols, β-sitosterol (11) and daucosterol (12) were isolated and identified by using combination of mass spectrometry and various 1D and 2D NMR techniques. This is the first report of flavonoid glycosides possessing a 2-methyl-2-hydroxylethoxyl group in sugar moiety from D. longan.     

Two new diarylheptanoids isolated from the roots of Juglans mandshurica

Two new diarylheptanoids, ( ? )-threo-3′,4″-epoxy-1-(4-hydroxyphenyl)-7-(3-methoxyphenyl)heptan-2,3-diol (1) and (1α,3β,5α,6α)-1,5-epoxy-3,6-dihydroxy-1,7-bis(3-methoxy-4-hydroxy-phenyl)-heptane (2), along with one known diarylheptanoid, rhoiptelol B (3), were isolated from the roots of Juglans mandshurica. The structures of compounds 1 and 2 were identified based on HR-ESI-MS, 1D and 2D NMR including ¹H–¹H COSY, HMQC, HMBC and NOESY spectroscopic methods.     

Cytotoxicity of new secondary metabolites,fatty acids and tocols composition of seeds of Ducrosia anethifolia (DC.) Boiss

Two new monoterpene Ducrosin A (1) and sesquiterpene Ducrosin B (2) were isolated along with three known compounds, stigmasterol (3) and two furanocoumarins (4 and 5), from the dichloromethane extract of the seeds of Ducrosia anethifolia (DC.) Boiss. Their structures were determined using extensive 1D and 2D NMR, (ES)-HRMS and IR spectroscopic analyses and by comparison with literature data. Gas chromatography analysis of the fatty acids (FAs) of D. anethifolia seed oils (DAOs) showed high percentages of elaidic acid (C18:1 Δ9t) 65% and oleic acid (C18:1 Δ9c) 15%. The total tocopherol (tocols) content in DAOs was found to be 164 mg/100 g. The cytotoxic effect of the isolates was also evaluated using the MTT assay against the HCT-116 and SKOV-3 cell lines. The results showed that compound 2 was the most cytotoxic agent followed by compounds 1 and 4, which has an epoxide moiety that most likely contributes to its activity.     

Synthetic α,β(1→4)-Glucan Oligosaccharides as Models for Heparan Sulfate

Abstract

α,β-(1→4)-Glucans were devised as models for heparan sulfate with the simplifying assumptions that carboxyl-reduction and sulfation of heparan sulfate does not decrease the SMC antiproliferative activity and that N-sulfates in glucosamines can be replaced by O-sulfates. The target oligo-saccharides were synthesized using maltosyl building blocks. Glycosylation of methyl 2,3,6,2′,3′,6′-hexa-O-benzyl-β-maltoside (1) with hepta-O-acetyl-α-maltosyl bromide (2) furnished tetrasaccharide 3 which was deprotected to α-D-Glc-(1→4)-β-D-Glc-(1→4)-α-D-Glc-(1→4)-β-D-Glc-(1→OCH₃) (5) or, alternatively, converted to the tetrasaccharide glycosyl acceptor (8) with one free hydroxyl function (4?′-OH). Further glycosylation with glucosyl or maltosyl bromide followed by deblocking gave the pentasaccharide [β-D-Glc-(1→4)-α-D-Glc-(1→4)]₂-β-D-Glc-(1→OCH₃) (11) and hexasaccharide [α-D-Glc-(1→4)-β-D-Glc-(1→4)₂-α-D-Glc-(1→4)-β-D-Glc-(1→OCH₃) (14). The protected tetrasaccharide 3 and hexasaccharide 12 were fully characterized by ¹H and ¹³C NMR spectroscopy. Assignments were possible using 1D TOCSY, T-ROESY, ¹H,¹H 2D COSY supplemented by ¹H-detected one-bond and multiple-bond ¹H,¹³C 2D COSY experiments.     

A new furanosteroid from Talaromyces sp. lgt-4, a fungal endophyte isolated from Tripterygium wilfordii

Wortmannolol (1), a new furanosteroid, along with five known compounds, wortmannolone (2), ergosterol (3), p-hydroxyphenyl ethanol (4), trans-6-dodecene (5), (2Z, 4E) -5-(8-hydroxy-1,5-dimethyl-3-oxo-6-oxabicyclo [3.2.1] octan-8-yl) -3-methylpenta-2,4-dienoic acid (6) were isolated from a fungal endophyte Talaromyces sp. lgt-4. Their structures were elucidated by IR, MS, 1D and 2D NMR spectra. Compound 1 show weak monoamine oxidase inhibitory activity.     

New cyclic tetrapeptide from the coral-derived endophytic bacteria Brevibacterium sp. L-4 collected from the South China Sea

One new cyclic tetrapeptide cyclic-(Tyr-Ala-Leu-Ser) (1) along with four natural compounds firstly obtained 3H-imidazole-4-carboxylic acid (2), 2-methyl-3H-imidazole-4-carboxylic acid (3), 3-ethylidene-6-isopropyl-piperazine-2,5-dione (4), and 3-isobutylidene-6-methyl piperazine-2,5-dione (5) have been isolated from the coral derived endophytic bacteria Brevibacterium sp. L-4 collected from the South China Sea. Their structures were elucidated through spectroscopic techniques including NMR (1D and 2D), MS, and EA, and their relative configurations were also assigned by NMR analysis.     

MDN-0171, a new medermycin analogue from Streptomyces albolongus CA-186053

A new medermycin derivative, MDN-0171 (1), and two known structurally related compounds, medermycin (2) and antibiotic G15-F (3) were isolated from the acetone extract of culture broths of the marine-derived Streptomyces albolongus strain CA-186053. Their structures were determined using a combination of spectroscopic techniques, including 1D and 2D NMR and electrospray-time of flight mass spectrometry (ESI-TOF MS). Compounds 2 and 3 accounted for the antimicrobial activity (against methicillin-resistant Staphylococcus aureus and Escherichia coli) previously detected in the crude extract of this actinomycete.     

Identification of sesquiterpene coumarins of oleo-gum resin of Ferula assa-foetida L. from the Yasuj region

Chemical investigation of the oleo-gum resin of Ferula assa-foetida L. from Yasuj region led to the identification of five sesquiterpene coumarins namely, conferone (1), badrakemin (2), feslol (3), isosamarcandin (4) and samarcandin (5). The compounds were characterised by detailed 1D (¹H and ¹³C) and 2D NMR (HMBC, HSQC and NOESY) experiments. Among these compounds, conferone (1) and isosamarcandin (4) are being newly reported in F. assa-foetida L.     

Saponins from the roots of Chenopodium bonus-henricus L.

Two new glycosides of phytolaccagenin and 2β-hydroxyoleanoic acid, namely bonushenricoside A (3) and bonushenricoside B (5) together with four known saponins, respectively compounds 3-O-L-α-arabinopyranosyl-bayogenin-28-O-β-glucopyranosyl ester (1), 3-O-β-glucuronopyranosyl-2β-hydroxygypsogenin-28-O-β-glucopyranosyl ester (2), 3-O-β-glucuronopyranosyl-bayogenin-28-O-β-glucopyranosyl ester (4) and 3-O-β-glucuronopyranosyl-medicagenic acid-28-β-xylopyranosyl(1→4)-α-rhamnopyranosyl(1→2)-α-arabinopyranosyl ester (6) were isolated from the roots of Chenopodium bonus-henricus L. The structures of the compounds were determined by means of spectroscopic methods (1D and 2D NMR, IR and HRMS). The MeOH extract and compounds were tested for cytotoxic activity on five leukemic cell lines (HL-60, SKW-3, Jurkat E6-1, BV-173 and K-562). In addition, the ability of metanolic extract and saponins to modulate the interleukin-2 production in PHA/PMA stimulated Jurkat E6-1 cells was investigated as well.     

Two new compounds,Talaromycin A and B,isolated from an endophytic fungus,Talaromyces aurantiacus

Abstract

Two new compounds Talaromycin A (1) and Talaromycin B (2) were isolated from a liquid culture of Talaromyces aurantiacus. The structures of 1 and 2 were elucidated by IR, MS, 1D and 2D NMR spectra and comparison of the experimental and calculated electronic circular dichroism spectra. Additional known compounds (3–6) were also isolated. These compounds were tested for monoamine oxidase, acetylcholinesterase and PI3K inhibitory activity, but showed only weak activity.     

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.     

New anti-bacterial halogenated tricyclic sesquiterpenes from Bornean Laurencia majuscula (Harvey) Lucas

Three new halogenated tricyclic sesquiterpenes, omphalaurediol (1), rhodolaurenones B (2) and C (3) were isolated together with nine known haloganated sesquiterpenes such as rhodolaurenone A (4), rhodolaureol (5), isorhodolaureol (6), (?)-laurencenone D (7), elatol (8), (+)-deschloroelatol (9), cartilagineol (10), (+)-laurencenone B (11) and 2-chloro-3-hydroxy-α-chamigren-9-one (12) from a population of Bornean red algae Laurencia majuscula. The structures of three new metabolites were determined based on their spectroscopic data (IR, 1D and 2D NMR, and MS). These compounds showed antibacterial activity against three human pathogenic bacteria (Escherichia coli, Salmonella typhi and Vibrio cholera).     

Oligoamide,a new lactam from the leaves of Angylocalyx oligophyllus

A new lactam, oligoamide (1), along with three known compounds (2–4), stigmasterol-3-O-β-D-glucopyranoside (2), formononetin (3) and (-)-pinitol (4) were isolated from the CH₂Cl₂/CH₃OH (1:1) extract of the leaves of Angylocalyx oligophyllus by chromatographic separation. Their structures were elucidated on the basis of spectroscopic analysis (UV, IR, MS, 1D, and 2D NMR). Compound 1 was found to have weak antioxidant and urease inhibitory potential.     

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.     

Hydroxylation of a vitamin D A-ring fragment

Summary When the benzoate of (S)-(Z)-2-(5-(tert-butyldimethylsiloxy)-2-methylencyclohexyliden)-ethanol (5) is treated with 2.5 equivalents of Hg(OOCCF₃)₂ in dryTHF, a smooth and selective allylic hydroxylation occurs. The C-1 functionalized vitamin D A-ring synthon6 is isolated in 65 to 70% yield in a single step.

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Hydroxylierung eines Vitamin D A-Ring-Fragments (Kurze Mitt.)

Zusammenfassung Umsetzung des Benzoats von (S)-(Z)-2-(5-(tert-Butyldimethylsiloxy)-2-methylencyclohexyliden)-ethanol (5) mit 2.5 Äquivalenten Hg(OOCCF₃)₂ in trockenemTHF führt zu einer selektiven allylischen Hydroxylierung. Damit ist das an C-1 funktionalisierte Vitamin D A-Ring-Fragment6 in einem einzigen Schritt in einer Ausbeute von 65 bis 70% zugänglich.

     

A new sesquiterpenoid from Saussurea lappa roots

A new sesquiterpenoid, 10α-methoxyartemisinic acid (1) was isolated from Saussurea lappa roots along with two known compounds, costunolide (2) and dehydrocostus lactone (3) by high-speed countercurrent chromatography with purities of 85, 95 and 98%, respectively. Their structures were determined on the basis of spectral data including 1D and 2D NMR and HREIMS.