Two new compounds from Atractylodes macrocephala with neuroprotective activity

In the present study, two new compounds, together with six known compounds, were isolated from rhizome of Atractylodes macrocephala Koidz by a series of silica gel, ODS column chromatography, and preparative HPLC. Their structures were characterized as atractylenolide II (1), atractylenolide I (2), biepiasterolid (3), isoatractylenolide I (4), atractylenolide III (5), 3β-acetoxyl atractylenolide I (6), (4E,6E,12E)-tetradeca-4,6,12-triene-8,10-diyne-13,14-triol (7), (3S,4E,6E,12E)-1-acetoxy-tetradeca-4,6,12-triene-8,10-diyne-3,14-diol (8) on the basis of 1D, 2D NMR, and circular dichroism analyses. Among them, compounds 6 and 8 were novel compounds. In addition, their neuroprotective activity against MPP⁺-induced SH-SY5Y cells was evaluated by MTT colorimetry. The results showed that all these compounds have definite protective effect on MPP⁺-induced SH-SY5Y cells.     

Metabolites from endophytic fungus S20 of Cephalotaxus hainanensis

Three new C-methylated acetogenins, (2E,6Z)-9,10-dihydroxy-4-hydroxymethyl-2,6-decadiene (1), (2E,6Z)-8,9,10-trihydroxy-4-hydroxymethyl-2,6-decadiene (2), and (2E,6Z)-9-hydroxy-4-hydroxymethyl-2,6-nonadiene (3), together with two known compounds, p-hydroxybenzyl alcohol (4) and indolyl-3-carboxylic acid (5), were isolated from endophytic fungus S20 of Cephalotaxus hainanensis Li. Their structures were determined based on HR-ESI-MS and spectroscopic techniques (IR, UV, 1D, and 2D NMR). Compound 5 showed inhibitory effects on Staphylococcus aureus and methicillin-resistant S. aureus by the filter paper disc agar diffusion method.     

New anthraquinone dimer from the root bark of Cassia artemisioides (Gaudich. Ex. DC) Randell

The phytochemical investigation of the root bark of Cassia artemisioides (Gaudich. Ex. DC) Randell resulted in the isolation of one new anthraquinone 1,1′-dihydroxy-3,3′-dimethyl-8,8′-dimethoxy-6,6′-O-bianthraquinone (1) along with four known anthraquinones 1,6-dihydroxy-8-methoxy-3-methylanthraquinone (2), 1-hydroxy-8-methoxy-3-methylanthraquinone (3), 1,8-dihydroxy-6-methoxy-3-methylanthraquinone (4), and 1,6,8-trihydroxy-3-methylanthraquinone (5). The structures of the compounds were elucidated using spectroscopic techniques including 1D and 2D NMR. The compounds were evaluated for antioxidant activity. 1,6,8-Trihydroxy-3-methyl anthraquinone (5) showed good activity among the tested compounds.     

Three new amides from Microlepia pilosissima

Phytochemical investigation of 70% EtOH extract of the dry fronds of Microlepia pilosissima has resulted in isolation of three new amides, (7E)-N-(3′-hydroxyl-4′-methoxy)-phenylethyl-4-hydroxyl-cinnamamide (1), (7E)-N-(3′,4′,5′-trihydroxyl)-phenylethyl-4-hydroxyl-cinnamamide (2), and (7E)-N-(3′,4′,5′-trihydroxyl)-phenylethyl-4-methoxy-cinnamamide (3). Their structures were characterized by spectroscopic analysis and chemical method, including 1D NMR, 2D NMR, and HR-ESI-MS.     

Two new compounds from a marine-derived Streptomyces sp.

Two new long-chain unsaturated compounds, (2E, 6E)-10-methoxy-3,7-dimethyl-10-oxodeca-2,6-dienoic acid (1) and (2E, 6E)-3,7,11-trimethyldodeca-2,6-dienedioic acid (2), together with seven known compounds were isolated from a marine-derived Streptomyces sp. Their structures were determined by spectroscopic methods, including 2D NMR techniques. Compounds 1 and 2 were investigated for their antibacterial activities.     

Two new casbane diterpenoids from the roots of Euphorbia pekinensis

From the roots of Euphorbia pekinensis, two new casbane diterpenoids, named pekinenins A (1) and B (2), were isolated. Their structures were elucidated as 18-hydroxy-1βH,2αH-casba-3E,7E,11E-trien-5-one (1), 5α-methoxy-1βH,2αH-casba-3Z,7E,11E-trien-18-oic acid (2) by a combination of 1D and 2D NMR spectroscopy and mass spectrometry. In the cytotoxicity assay of the two new compounds against Hela, MCF-7, and C6 human cancer cell lines, compound 1 showed moderate cytotoxic activity against two human cancer cell lines, Hela and C6, with IC₅₀ values of 42.97 and 50.00 μM, respectively.     

New long-chain hydroxyalkyl ferulates from the root bark of Lycium chinense Mill.

Two new long-chain hydroxyalkyl ferulates, (E)-22-hydroxydocosyl 3-(4-hydroxy-3-methoxyphenyl)acrylate (lyciumol A, 1) and (E)-20-hydroxyeicosyl 3-(4-hydroxy-3-methoxyphenyl)acrylate (lyciumol B, 2), together with eight known compounds, were isolated from the root bark of Lycium chinense Mill. Their structures were elucidated by spectroscopic methods, including 1D, 2D NMR, and HR-ESI-MS analysis.     

New acylated flavonoid glycosides from flowers of Aerva javanica

Chromatographic purification of ethyl acetate soluble fraction of the methanolic extract of the flowers of Aerva javanica yielded three new acylated flavone glycosides: kaempferol-3-O-β-d-[4?-E-p-coumaroyl-α-l-rhamnosyl(1 → 6)]-galactoside (1), kaempferol-3-O-β-d-[4?-E-p-coumaroyl-α-l-rhamnosyl(1 → 6)]-(3″-E-p-coumaroyl)galactoside (2), and kaempferol-3-O-β-d-[4?-E-p-coumaroyl-α-l-rhamnosyl(1 → 6)]-(4″-E-p-coumaroyl)galactoside (3), along with p-coumaric acid (4), caffeic acid (5), gallic acid (6), eicosanyl-trans-p-coumarate (7), hexadecyl ferulate (8), and hexacosyl ferulate (9). The compounds 1–9 were characterized using 1D (¹H, ¹³C) and 2D NMR (HMQC, HMBC, and COSY) spectroscopy and mass spectrometry (EI-MS, HR-EI-MS, FAB-MS, and HR-FAB-MS) and in comparison with the reported data in the literature. Compound 1 showed weak inhibitory activity against enzymes, such as acetylcholinesterase, butyrylcholinesterase, and lipoxygenase with IC₅₀ values 205.1, 304.1, and 212.3 μM, respectively, whereas compounds 2 and 3 were only weakly active against the enzyme acetylcholinesterase.     

Caragasinin C: a new oligostilbene from the roots of Caragana sinica

A new oligostilbene, caragasinin C (1), and seven known compounds, betulinic acid (2), 4-hydroxybenzaldehyde (3), (?)-medicarpin (4), wistin (5), (2E,4S)-4-hydroxy-2-nonenoic acid (6), pallidol (7), and (+)-α-viniferin (8), were isolated from the roots of Caragana sinica. The structure of caragasinin C was established on the basis of spectroscopic techniques, including HRESIMS, 1D and 2D-NMR.     

New glycosides from <Emphasis Type="Italic">Dracocephalum tanguticum</Emphasis> maxim

Four new glycosides, luteolin-7-methoxy-3′-O-(3″-O-acetyl)-β-D-gluco pyranuronic acid-6″-methyl ester (1), benzyl-6-[(2E)-2-butenoate]-β-D-glucopyranoside (2), 2-methoxy-4-(2-propen-1-yl)penyl-6-acetate-β-D-glucopyranoside (3), and 2-methoxy-4-(2-propen-1-yl)penyl-6-[(2E)-2-butenoate]-β-D-glucopyranoside (4), along with benzyl-β-D-glucopyranoside (5), 2-methoxy-4-(2-propen-1-yl)penyl-β-D-glucopyranoside (6), and pectolarigenin (7), were isolated from the whole plant of Dracocephalum tanguticum Maxim. The structures of 1-4 were elucidated by detailed spectroscopic analyses, including HR-ESI-MS and 2D NMR spectroscopic data. The inhibitory effects against nitric oxide production in LPS-stimulated RAW264.7 cells of all seven compounds were also evaluated.     

Two new coumarins from the seeds of Solanum indicum

Two new coumarins, (E)-2-(4-hydroxy-3-methoxybenzylidene)-5-methoxy-2H-[1,4]dioxino[2,3-h]chromene-3,9-dione (indicumin E, 1) and 7-hydroxy-6,8-dimethoxy-3-(4′-hydroxy-3′-methoxyphenyl)-coumarin (2), together with two known coumarins isofraxidin (3) and fraxetin (4), were isolated from the Solanum indicum seeds. Their structures were established on the basis of 1D and 2D spectroscopic data. Compound 1 was the rarest coumarinolignoid known to date.     

New cycloartanes and new iridoids from Dolichandrone spathacea collected in the mangrove forest of Soc Trang province,Vietnam

Abstract

Two new cycloartanes, named dolichandrone A (1) and dolichandrone B (2), as well as two new iridoids, named [6-O-[(E)-4-methoxycinnamoyl]-1β-hydroxy-dihydrocatalpolgenin (3) and 6-O-[(E)-4-methoxycinnamoyl]-1α-hydroxy-dihydrocatalpolgenin (4), together with four known iridoids (5–8), were isolated from the leaves and barks of Dolichandrone spathacea. Their structures were elucidated by means of extensive analysis of their HRESIMS, 1D and 2D NMR spectroscopic data. All of these compounds have been isolated for the first time from this plant. Compounds 1, 2, 5, and 7 were evaluated for their cytotoxic activity in vitro against four human cancer cell lines KB, Lu, HepG2, and MCF7. The results showed that only compound 2 exhibited a good cytotoxicity against KB cell line with IC₅₀ of 18.77 μM.     

Two new compounds from the fruiting bodies of Ganoderma philippii

Two new compounds, philippin (1) and 3β,9α,14α-trihydroxy-(22E,24R)-ergost-22-en-7-one (2), were isolated from the fruiting bodies of Ganoderma philippii. Their structures were elucidated on the basis of the spectroscopic technologies, including 1D and 2D NMR as well as MS. The bioassay of inhibitory activity against acetylcholinesterase (AChE) showed compound 1 exhibited weak inhibitory activity against AChE.     

Microwave-assisted synthesis and evaluation of naphthalimides derivatives as free radical scavengers

A facile and efficient microwave-assisted reaction of 1,8-naphthalic anhydride derivatives with primary amines, leading to the synthesis of 1,8-naphthalimides, has been developed. Subsequently, the free radical scavenging properties of the 1,8-naphthalimide derivatives were evaluated against 2,2-diphenyl-1-picrylhydrazyl (DPPH^•). The results showed that the scavenging activities of compounds 2a, NBNA, 3b, and 3c were more efficient than that of the common synthetic antioxidant 2,6-diter-butyl-4-methylphenol (BHT), with IC₅₀ values of 61.9, 54.0, 42.2, and 43.1 μM, respectively. The imide groups introduced at position 4 as well as the nitro functionality at position 3 of the naphthalene moiety were the major contributors to the free radical scavenging activities.     

One pair of new cyclopentaisochromenone enantiomer from Alternaria sp. TNXY-P-1 and their cytotoxic activity

One pair of new cyclopentaisochromenone derivatives, (+)-(S)-6-hydroxy-1,8-dimethoxy-3a-methyl-3,3a-dihydrocyclopenta[c]isochromene-2,5-dione (1a) and (-)-(R)-6-hydroxy-1,8-dimethoxy-3a-methyl-3,3a-dihydrocyclopenta[c]isochromene-2,5-dione (1b), together with seven known analog 2?8, were isolated from a rice solid culture of the endophytic fungus Alternaria sp. TNXY-P-1, obtained from fresh leaf of Arisaema heterophyllum. Their structures were elucidated on the basis of detailed 1D, 2D NMR, and HRESIMS analysis. Among them, compounds 1a and 1b were enantiomers separated from 1 by chiral HPLC. The absolute configurations of 1a and 1b were assigned by quantum chemical calculations of the electronic circular dichroic spectra. All isolated compounds were evaluated for cytotoxic activities. Interestingly, enantiomers (+)-1a and (?)-1b showed distinct selective antitumor activities against HL-60 cell lines with IC₅₀ values of >200, 75.3 μM, respectively.     

New diterpenoids from Semiaquilegia adoxoides

Two new ent-kaurane-type diterpenoids, E-semiaquilegin (1) and Z-semiaquilegin (2), together with eight known compounds (3–10) were isolated from the dried roots of Semiaquilegia adoxoides (DC.) Makino. The structures of compounds 1 and 2 were elucidated mainly by 2D NMR techniques including ¹H–¹H COSY, HSQC, HMBC, NOESY as 16α-hydroxy-ent-kaurane-17,20-di-(3,4-dihydroxy-E-cinnamoyl) ester and its (Z)-isomer.     

Two new monoterpenes from Sibiraea laevigata

Two new monoterpenes, 3-(2-oxo-4-methyl-3-pentenyl)furan-5H-2-one (1) and 3-[(2E)-4-hydroxyl-4-methyl-2-pentenyl)]furan-5H-2-one (2), along with eight known compounds (3–10), were isolated from the stalks and infructescence of Sibiraea laevigata. Their structures were elucidated by spectroscopic methods including extensive 1D and 2D NMR techniques. In addition, all of these isolates were evaluated for their cytotoxic and antioxidant activities. The results showed that compounds 5–7 displayed cytotoxicity with IC₅₀ values ranging from 34.8 to 43.2 μg ml^?1 against tumor cell lines. Furthermore, 5 and 9 showed antioxidant activities.     

Constituents of the roots of <Emphasis Type="Italic">Ligularia dentata</Emphasis> Hara

Nine known compounds, butyrospermol (1), lupeol (2), stigmast-4-en-3-one (3), stigmast-4-ene-3,6-dione (4), (+)-methyl abscisate (5), methyl indole-3-carboxylate (6), vanillin (7), methyl (E)-caffeate (8), and methyl (E)-ferulate (9), and two new compounds, methyl (E)-feruloylglycolate (10), and methyl-7,8-dihydro-(S)-7-methoxyferulate (11), have been isolated from the roots of Ligularia dentata Hara (Compositae). The structures were elucidated on the basis of spectral data.     

Sesquiterpenoids from Ferula fukanensis and their inhibitory effects on nitric oxide production

Six sesquiterpene derivatives, 2,3-dihydro-7-methoxy-2S*, 3R*-dimethyl-2-[4,8-dimethyl-3(E),7-nonadienyl]furo[3,2-c]coumarin (1) and 2,3-dihydro-7-methoxy-2R*,3R*-dimethyl-2-[4,8-dimethyl-3(E),7-nonadienyl]furo[3,2-c]coumarin (2), nerolidol (3), 1-(2,4-dihydroxyphenyl)-3,7,11-trimethyl-3-ninyl-6(E),10-dodecadien-1-one (4), 1-(2,4-dihydroxyphenyl)-3,7-dimethyl-3-vinyl-8-(4-methyl-2-furyl)-6(E)-octen-1-one (5) and dshamirone (6) were isolated from an 80% aqueous methanol extract of the roots of Ferula fukanensis. The sesquiterpenoids inhibited nitric oxide (NO) production and inducible NO synthase gene expression by a murine macrophage-like cell line (RAW 264.7) [1], which was activated by lipopolysaccharide and recombinant mouse interferon-.     

New phenolic glycosides from Pilea cavaleriei

Five new phenolic glycosides, 2-hydroxy-(2′E)-prenyl benzoate-2,4′-di-O-β-d-glucopyranoside (1), 2-hydroxy-(2′E)-prenyl benzoate-2-O-α-l-arabinopyranosyl-(1 → 6)-β-d-glucopyranoside (2), 4-methylphenol-1-O-α-l-rhamnopyranosyl-(1 → 6)-β-d-glucopyranoside (3), 4-methylphenol-1-O-α-l-arabinopyranosyl-(1 → 6)-β-d-glucopyranoside (4), and 3,5-dimethoxyphenol-1-O-β-d-apiofuranosyl-(1 → 2)-β-d-glucopyranoside (5), together with six known glycosides (6–11), were isolated from the n-BuOH fraction of the EtOH extract of Pilea cavaleriei Levl subsp. cavaleriei. Their structures were elucidated by extensive spectroscopic analysis, including 1D and 2D NMR spectroscopy as well as HR-ESI-MS, and chemical evidences. All these compounds were isolated from the genus Pilea for the first time.