New fatty acid,aromatic ester and monoterpenic benzyl glucoside from the fruits of Withania coagulans Dunal

The fruits of Withania coagulans Dunal (family: Solanaceae) are sweet, sedative, emetic, alterative and diuretic; used to treat asthma, biliousness, strangury, wounds, dyspepsia, flatulent colic, liver complaints and intestinal infections in the indigenous system of medicine. Phytochemical investigation of the methanolic extract of W. coagulans fruits led to the isolation of a new fatty acid, an aromatic ester and a monoterpenic benzyl glucoside characterised as n-octatriacont-17-enoic acid (3), geranilan-10-olyl dihydrocinnamoate (4) and geranilan-8-oic acid-10-olyl salicyloxy-2-O-β-d-glucofuranosyl-(6″→1?)-O-β-d-glucofuranosyl-6?-n-octadec-9?′,11?′-dienoate (5) along with two known fatty acids, n-dotriacont-21-enoic acid (1) and n-tetratriacontanoic acid (2). The structures of isolated phytoconstituents were established on the basis of 1D and 2D NMR, FT-IR, UV, and MS data and chemical means.     

A new 2-alkylhydroquinone glucoside from Phagnalon saxatile (L.) Cass

A new 2-alkylhydroquinone glucoside, 1-O-β-d-glucopyranosyl-1,4-dihydroxy-2-((E) 2-oxo-3-butenyl)benzene (1), in addition to nine known compounds were isolated from the aerial parts of Phagnalon saxatile (L.) Cass. (Asteraceae). Their structures were identified based on spectroscopic methods including 1D and 2D NMR, mass spectrometry (HR-ESI-MS), UV spectral analyses and by comparison with literature data. The cytotoxic activity of three isolated compounds (1–3) was evaluated against fibrosarcoma (HT1080), human lung cancer (A549) and breast cancer (MCF7) cell lines.     

Anti-bacterial effect of four extracts from leaves of Dracontomelon dao on Escherichia coli growth using microcalorimetry coupled with principal component analysis

The anti-Escherichia coli activities of four extracts in leaves of Dracontomelon dao, a traditional folk herb in China were investigated and compared by microcalorimetry. The four extracts are PE fraction, CHCl₃ fraction, EtOAc fraction, and n-BuOH fraction. The heat flow power–time (HFP–time) curves of E. coli growth in the presence of the four extracts were measured using an ampoule method. Then the nine thermal kinetic parameters were obtained from the curves. From the result of principal component analysis, it can be seen that parameters k ₁, k ₂, P ₁, and Q _p2 might be the main parameters in evaluating the anti-E. coli effects. In the presence of CHCl₃ fraction, EtOAc fraction, and n-BuOH fraction, k ₂, Q _p2 of E. coli decreased with increasing concentrations of the extracts. The EtOAc fraction was observed to have the strongest anti-bacterial activity with half-inhibitory concentration IC50 of 98.5 μg mL^?1. So, it can be concluded that EtOAc fraction can be further developed as anti-bacterial bioactive fraction of leaves of Dracontomelon dao.     

A new monoterpene glucoside and complete assignments of dihydroflavonols of Pulicaria jaubertii: potential cytotoxic and blood pressure lowering activity

One new monoterpene glucoside and five dihydroflavonols were isolated for the first time from the aerial parts of Pulicaria jaubertii and identified as p-menthane-2-O-β-D-glucopyranoside [1], dihydroquercetin (taxifolin) [2], 7,3′-di-O-methyltaxifolin [3], 3′-O-methyltaxifolin [4], 7-O-methyltaxifolin (padmatin) [5] and 7-O-methyl-dihydrokampferol (7-O-methylaromadenderin) [6]. The structures of these compounds were unambiguously assigned on the basis of NMR spectroscopic data (¹H, ¹³C, DEPT, HSQC, HMBC) and MS analysis. 2D-NMR methods required revision of assignments of H-6 and H-8 for dihydroflavonol compounds. Possible cytotoxic activity as well as blood pressure (BP) lowering activity were tested. The alcoholic extract showed cytotoxic activity against prostate carcinoma (PC-3), breast carcinoma (MCF-7) and hepatocellular carcinoma (HepG-2) human cell lines with IC₅₀ 19.1, 20.0 and 24.1 μg, respectively. The higher dose levels of the alcoholic extract significantly reduced normal BP of rats in a dose-dependent manner.     

3-芳烷氨基-6-氯哒嗪的合成及其除草活性

通过3,6-二氯哒嗪与(未)取代芳烷基胺在DMF/NaH或正丁醇体系缩合, 合成了13个3-芳甲(乙)氨基-6-氯哒嗪类化合物, 其中11个为新化合物, 它们的结构均经¹H NMR, IR和元素分析确证. 初步的生物活性测试结果表明, 所合成的化合物对阔叶杂草有一定的抑制作用, 如化合物4f在施药量为10 µg•mL^－1时对油菜的抑制率是76.42%. 讨论了其结构与除草活性的关系.     

New sesquiterpenoid glycoside from the rhizomes of Atractylodes lancea

Abstract

Six sesquiterpenoids and four lignans (1–10) were isolated from the n-BuOH extract of the rhizomes of Atractylodes lancea. Among them, the new sesquiterpenoid glycoside named (4?R, 5S, 7R)-hinesolone-11-O-β-?-glucopyranoside (1), along with three known compounds (2–4) were first obtained from this genus. All the isolates were elucidated by spectroscopic analyses and chemical methods, and the absolute configurations were assigned by electronic circular dichroism spectroscopy technique. In addition, the cytotoxic bioassay of compound 1 was evaluated and results showed it had no significant antitumor activity against human cancer cell lines MCF-7, HepG-2 and Hela.     

Three new spirostanol glycosides from Helleborus thibetanus

Abstract

An ongoing chemical investigation on n-BuOH extract of roots and rhizomes of Helleborus thibetanus afforded three new spirostanol glycosides (1–3). Their structures were elucidated by extensive analysis of 1?D, 2?D NMR spectra, together with IR and MS methods and acid hydrolysis. This is the first report of the isolation of spirostanol glycoside with xylose at C-24 of the aglycone in Helleborus.     

Insecticidal and α-glucosidase inhibitory activities of chemical constituents from Viburnum fordiae Hance

The ethanolic extract of the stems of Viburnum fordiae Hance showed insecticidal and α-glucosidase inhibitory activities and then was fractionated by bioactivity-guided fractionation to obtain a rare C₁₃-norisoprenoid (1), together with a new phenolic glycoside (2), and seven known compounds, alangionoside C (3), pisumionoside (4), koaburaside (5), 3,5-dimethoxy-benzyl alcohol 4-O-β-d-glucopyranoside (6), 3,4,5-trimethoxybenzyl-β-d-glucopyranoside (7), arbutin (8), and salidroside (9). The previously undescribed compounds were elucidated as (3R,9R)-3-hydroxy-7,8-didehydro-β-ionyl 9-O-α-d-arabinopyranosyl-(1→6)-β-d-glucopyranoside (1) and 2-(4-O-β-d-glucopyranosyl)syringylpropane-1,3-diol (2) by spectroscopic data (¹H and ¹³C NMR, HSQC, HMBC, ¹H-¹H COSY, HSQC-TOCSY, HRESIMS, IR and ORD) and chemical methods. Compound 1 showed potent insecticidal effect against Mythimna separata with LD₅₀ value of 140 μg g^?1. Compounds 2, 5, 6, 8 and 9 showed varying α-glucosidase inhibitory activity with IC₅₀ values ranging from 148.2 to 230.9 μM.     

Officinalioside,a new lignan glucoside from Borago officinalis L.

A new lignan glucoside, officinalioside (1), was isolated from n-BuOH fraction of the aerial parts of Borago officinalis L., together with four known compounds: actinidioionoside (2), roseoside (3), crotalionoside C (4) and kaempferol 3-O-β-D-galactopyranoside (5). The structure of the new compound was established by means of spectroscopic and chemical analyses. Compounds 1 and 2 showed a moderate DPPH radical scavenging activity (IC₅₀: 52.6 ± 1.70 and 41.3 ± 0.25 μM, respectively) comparable with that of the standard trolox (16.6 ± 2.2 μM) without any significant cytotoxicity towards human cell line A549 (IC₅₀ > 100 μM).     

Ailanthus altissima (Miller) Swingle fruit - new acyl β-sitosteryl glucoside and in vitro pharmacological evaluation

β-Sitosterol-3-O-(6?-O-13?-octadecenoyl)-β-D-glucoside (1), a new acyl β-sitosteryl glucoside, along with three known compounds β-sitosterol-3-O-β-D-glucoside (2), β-sitosterol (3) and methyl gallate (4) have been isolated from the ethyl acetate soluble fraction of methanolic extract of Ailanthus altissima fruits. Their structures were elucidated through spectroscopic data including 2D NMR, ESI-MS, methanolysis and oxidative cleavage of double bond. Antibacterial, antifungal, cytotoxic, phytotoxic and insecticidal activities were evaluated of compound 1, crude extract and its fractions so far for the first time. Pharmacological activities results showed that n-butanol fraction was good active against Pseudomonas aeruginosa and Salmonella typhi bacteria, and moderate active against Microsporum canis fungus. Crude extract, n-butanol and aqueous fractions showed good cytotoxicity. Moreover, compound 1, extract and all fractions showed notable phytotoxicity at higher concentrations, whereas all inactive against assayed insects.     

The isolation and structural elucidation of three new biflavonoid glycosides from Lomatogonium carinthiacum

Three biflavonoid glycosides, named carinoside B, C and D (1, 2 and 3, respectively), were isolated from the n-BuOH crude extract of the aerial part of Lomatogonium carinthiacum (Wulfen) Rchb (L. carinthiacum). The structures of 1, 2 and 3 were elucidated by spectroscopic methods, including UV, IR, HR-ESI-MS and extensive 1D and 2D NMR techniques.     

Chemical composition of Helietta parvifolia and its in vitro anticholinesterase activity

The chemical composition of the essential oil and the n-hexane (Hex), Ethyl Acetate (EtOAc) and butanol (BuOH) extracts from the leaves of Helietta parvifolia were determined by detailed GC-MS analysis, spectroscopic and spectrometric data. Eighty-four compounds were identified, revealing a furoquinoline alkaloid-rich composition. The phytochemical analysis of the extracts allowed the isolation of eigth furoquinoline alkaloids. Retention indices in GC-MS for six of this alkaloids are reported for the first time. Furoquinoline alkaloids are acethylcholinesterase inhibitors. Thus, the essential oil and extracts were submitted to this in vitro assay. The EtOAc and BuOH extracts showed potent activity, with IC₅₀ of 9.7 and 12.9 μg mL^?1, respectively. Additionaly, a correlation of their chemical constituents, established by principal component analysis (PCA) demostrated a similar profile and a high content of alkaloids. It is for these reasons that we can assume that the alkaloid content in these extracts could be responsible for their anticholinesterase activity.     

A new triterpenoid glucoside from Leucas zeylanica

Abstract

A new triterpenoid glucoside, leuctriterpencoside (1), along with two known compounds (2–3) were isolated from Leucas zeylanica. The structure of the new compound was elucidated using comprehensive spectroscopic methods. Compound 1 showed significant inhibitory activity against α-glucosidase (IC₅₀ value of 0.85?±?0.12?μM).     

Two new hirsutane-type sesquiterpenoids chondrosterins N and O from the marine fungus Chondrostereum sp.

The marine fungus Chondrostereum sp. was collected from a soft coral Sarcophyton tortuosum from the South China Sea. This fungus was cultured in glucose-peptone-yeast (GPY) medium and the culture broth was extracted with EtOAc. By the method of ¹H NMR pre-screening and tracing the diagnostic proton signals of the methyl groups, two new hirsutane-type sesquiterpenoids, chondrosterins N and O (1 and 2) were isolated from the metabolite extracts. Their structures were elucidated on the basis of MS, 1D and 2D NMR data.     

New glycosylsphingolipids from Psychotria serpens L

Abstract

In clinical, Psychotria serpens L. was often substitute for Caulis trachelospermi to treat cancer in China. Meanwhile, EtOAc and n-BuOH fractions of MeOH extract of P. serpens L. show power activity against H460, HepG2, Hela, and PC9/GR cell lines, and no toxic effects against normal 16HBE cell lines. In our ongoing search for bioactive novel compounds from Chinese material medica, one new type of glycosylsphingolipids Psychotramide (1a–1c) were isolated from P. serpens L., and their structures were identified through spectroscopic techniques including NMR (1D and 2D) and MS (LC-MS, and GC-MS).     

The One Step Synthesis of 2-(2-Bromo-5- methoxyphenyl)-5-(3-arylidene)-1,3-thiazolo[3,2-b]- 1,2,4-triazol-6-(5H)-ones and the Evaluation of the Anticonvulsant Activity

A smooth one-step synthesis of 2-(2-bromo-5-methoxyphenyl)-5-(3-arylidene)-1,3-thiazolo[3,2-b]-1,2,4-triazol-6-(5H)-ones (4a–n) is described. The newly prepared compounds are characterized by analytical and IR, ¹ H NMR, ¹³ C NMR, and FABMS spectral analysis. A few compounds are screened for anticonvulsant activity. Compounds 4i and 4n exhibit promising anticonvulsant activity and are recommended for further studies.     

Chemical constituents and biological activities of Dianthus elegans var. elegans

Chemical investigation of the aerial parts of Dianthus elegans var. elegans afforded two previously undescribed saponins, named dianosides M-N (1–2), together with four oleanane-type triterpenoid glycosides (3–6). Their structures were elucidated as 3-O-α-L-arabinofuranosyl-16α-hydroxyolean-12-ene-23α, 28β-dioic acid (1) and 3-O-α-L-arabinofuranosyl-(1 → 3)-β-D-glucopyranosyl 16α-hydroxyolean-12-ene-23α-oic acid, 28-O-β-D-glucopyranosyl-(1 → 6)-β-D-glycosyl ester (2) by chemical and extensive spectroscopic methods including IR, 1D, 2D NMR and HRESIMS. Both of the saponins were evaluated for their cytotoxicities against HEK-293, A-549 and HeLa human cancer cells using the MTT method. All compounds showed no substantial cytotoxic activity against tested cell lines. However, dianosides M-N and the n-butanol fraction exhibited considerable haemolysis in human erythrocyte cells. The immunomodulatory properties of dianosides M-N were also evaluated in activated whole blood cells by PMA plus ionomycin. Dianosides M-N increased IL-1β concentration significantly whereas the n-butanol fraction slightly augmented IL-1β secretion. All compounds did not change IL-2 and IFN-γ levels considerably.     

Three new acyltyramines from Anisodus luridus Link et Otto (Solanaceae)

Three new acyltyramines, N-[2-(4-hydroxyphenyl)ethyl]hentriacontanamide (1), N-[2-(4-hydroxyphenyl)ethyl]nonacosanamide (2) and N-[2-(4-hydroxyphenyl)ethyl]heneicosanamide (3) have been isolated from n-hexane extract of leaves of Anisodus luridus (Solanaceae). Successive extraction of defatted leaves of A. luridus with methanol afforded a residue on removal of solvent under reduced pressure. Residue was partitioned by means of chloroform and n-butanol. Chromatographic resolution of n-BuOH extract afforded six known compounds, apigenin (4), luteolin (5), quercetin (6), quercetin 3-O-α-l-rhamnoside (7), kaempferol 3-O-α-rhamnoside (8) and quercetin 3-O-α-l-rhamnopyranosyl-(1→6)-β-d-glucopyranoside (9). The structures of the isolated compounds were assigned with the help of spectroscopic techniques. This is the first report of isolation of these compounds from this plant.     

Heliotropium bacciferum Forssk. (Boraginaceae) extracts: chemical constituents,antioxidant activity and cytotoxic effect in human cancer cell lines

Heliotropium bacciferum (Boraginaceae) is a perennial herb, growing in the Bechar region of Algeria, where it is traditionally used for skin diseases and tonsillitis. Herein, we report the isolation and characterization of sixteen secondary metabolites from the aerial part extracts. They include a sterol (1), megastigman type nor-isoprenoids (2, 3, 4, 6, 8, 10), C-11 terpene lactones (5 and 9), and a monoterpene (7) from the chloroform extract (HB-C); monoterpene glucoside (14), and phenolic compounds (11–13, 15, 16) from the methanol one (HB-M). Their structures were elucidated by spectroscopic methods including 1D and 2D NMR experiments, and ESIMS analysis. HB-M showed a significant and concentration dependent scavenging activity in vitro against the radicals DPPH and ABTS, related to the phenol derivatives (11–13, and 15–16), and HB-C inhibited the growth of colon cancer cell lines, mainly for the presence of the antiproliferative C-11 terpene lactones (5 and 9).     

Chemical composition,antioxidant and antibacterial properties of Pteranthus dichotomus from Algerian Sahara

The phytochemical study of ethyl acetate and n-butanol extracts of Pteranthus dichotomus Forssk. led to the isolation and identification of 11 compounds, including three glycolipids 1–3, one lignan 4, three flavonoids 5–7 and four phytosterols 8–11. Structures of the isolated compounds have been elucidated by analysis of 1D and 2D NMR data, and mass spectrometry EI-MS and ESI-MS and by comparison with literature data. Furthermore, the ethyl acetate and n-butanol extracts were examined for their antioxidant and antibacterial activities. The results showed that both extracts (PDAC and PDBU) had a moderate antioxidant activity (IC50 = 375.514 μg/mL and 691.333 μg/mL) respectively.