A new dihydrofurocoumarin from the fruits of Pandanus tectorius Parkinson ex Du Roi

From the fruit of Pandanus tectorius Parkinson ex Du Roi, one new dihydrofurocoumarin, named pandanusin A (1) and 15 known compounds, including one furanocoumarin (2), two coumarins (3, 4), four lignans (5–8), one neolignan (9), two flavonoids (10, 11), three phenolics (12–14), one monoglyceride (15) and one monosaccharide (16) were isolated by various chromatography methods. Among them, compounds (3–5) were obtained from the Pandanus genus for the first time and compounds (9–14, 16) were reported from this species for the first time. Their structures were elucidated by HR–ESI–MS, NMR 1D and 2D experiments and comparison with previous reported data. The α-glucosidase inhibitory activity of all compounds was measured. The isolated compounds (1–12, 14) showed better α-glucosidase inhibitory activity (IC₅₀ = 42.2, 36.5, 84.7, 73.2, 40.8, 26.7, 76.5, 33.8, 68.1, 14.4, 22.1, 81.5, 43.8 μM, respectively) than the standard drug acarbose (IC₅₀ = 214.5 μM).     

A new sesquiterpene from the entomogenous fungus Phomopsis amygdali

A new sesquiterpene, (+)-S-1-methyl-abscisic-6-acid (1), together with five known compounds, (+)-S-abscisic acid (2), fusicoccin J (3), 3α-hydroxyfusicoccin J (4), (R)-5-hydroxymethylmellein (5) and 4-hydroxyphenethyl acetate (6) was isolated from the fermentation extract of Phomopsis amygdali, an entomogenous fungus isolated from Call midge. Their structures were determined mainly by analysis of MS and NMR spectroscopic data. Compounds 1–6 were tested for antimicrobial activity against three plant pathogenic fungi: Gibberella zeae, Verticillium albo-atrum, and Fusarium nivale, and two bacteria: Escherichia coli and Pseudomonas aeruginosa 2033E. As a result, compounds 1–4 displayed antibacterial activity against Gram-negative P. aeruginosa 2033E, and the minimum inhibition concentration (MIC value) of 1–4 is 30 μg/mL, 58 μg/mL, 26 μg/mL, and 26 μg/mL, respectively.     

Acetylcholinesterase inhibitory active metabolites from the endophytic fungus Colletotrichum sp. YMF432

An endophytic fungus, Chaetomium sp. YMF432, was isolated from Huperzia serrata (Thunb. ex Murray) Trev. and subjected to phytochemical investigation based on its special environment. From the extracts of fermentation solid of strain YMF 432, eight compounds including 1-O-methylemodin (1), 5-methoxy-2-methyl-3-tricosyl-1,4-benzoquinone (2), 4,8-dihydroxy-1-tetralone (3), (3β,5α,6α, 22E)-3-hydroxy-5,6-epoxy-7-one-8(14),22-dien-ergosta (4), ergosta-4,6,8(14),22-tetraen-3-one (5), β-sitostenone (6), β-sitosterol (7) and (22E,24R)-ergosta-5,7,22 -trien-3β-ol (8) were obtained. Their structures were elucidated on the basis of their spectroscopic data. These compounds were evaluated for acetylcholinesterase inhibitory activities in vitro. Compounds 1, 2, and 4 showed moderate acetylcholinesterase inhibitory activities (IC₅₀ from 37.7 ± 1.5 to 370.0 ± 2.9 μM).     

A bioactive cycloartane triterpene from Garcinia hombroniana

The dichloromethane bark extract of Garcinia hombroniana yielded one new cycloartane triterpene; (22Z,24E)-3β-hydroxycycloart-14,22,24-trien-26-oic acid (1) together with five known compounds: garcihombronane G (2), garcihombronane J (3), 3β acetoxy-9α-hydroxy-17,14-friedolanostan-14,24-dien-26-oic acid (4), (22Z, 24E)-3β, 9α-dihydroxy-17,14-friedolanostan-14,22,24-trien-26-oic acid (5) and 3β, 23α-dihydroxy-17,14-friedolanostan-8,14,24-trien-26-oic acid (6). Their structures were established by the spectral techniques of NMR and ESI-MS. These compounds together with some previously isolated compounds; garcihombronane B (7), garcihombronane D (8) 2,3’,4,5’-tetrahydroxy-6-methoxybenzophenone (9), volkensiflavone (10), 4’’-O-methyll-volkensiflavone (11), volkensiflavone-7-O-glucopyranoside (12), volkensiflavone-7-O-rhamnopyranoside (13), Morelloflavone (14), 3’’-O-methyl-morelloflavone (15) and morelloflavone-7-O-glucopyranoside (16) were evaluated for cholinesterase enzymes inhibitory activities using acetylcholinesterase and butyrylcholinesterase. In these activities, compounds 1–9 showed good dual inhibition on both the enzymes while compounds 10–16 did not reasonably contribute to both the cholinesterases inhibitory effects.     

New chalcanonol glycoside from the seeds of saw palmetto: antiproliferative and antioxidant effects

A new chalcanonol glycoside dimer, bis-O-[(I-4′) → (II-6′)]-α-hydroxyphloretin-2′-O-β-glucoside (1), in addition to six known compounds, namely ( ? )-epicatechin (2) and ( ? )-epiafzelechin (3), 4-hydroxybenzoic acid (4), protocatechuic acid (5), methylgallate (6), β-sitosterol (7) and β-sitosterol-3-O-glucoside (8), was isolated from the seeds of saw palmetto. The structures of the isolated compounds were established from the analysis of their MS and 1D and 2D NMR spectroscopic data. The antiproliferative activities of the isolated compounds towards PC3, the human prostate cancer cells were investigated. Amongst the isolated compounds, the new compound and the sterolic derivatives showed antiproliferative effects. Screening of the antioxidant effects of the isolated compounds by 2,2′-azino-bis-(3-ethylbenzthiazoline-6-sulfonic acid radical assay revealed that the isolated phenolics were active free radical scavengers.     

Pheophytin analogues from the medicinal lichen Usnea diffracta

A new pheophytin, (13²S, 17S, 18S)-13²-hydroxy-20-chloro-ethylpheophorbide a (3), along with two known analogues (1–2) were isolated from the lichen Usnea diffracta Vainio (Parmeliaceae). Among them, compound 3 was a rare C-20-chloro type pheophytin obtained from lichens. Their structures were elucidated by extensive spectroscopic analysis, and all the compounds were obtained for the first time from U. diffracta. Compounds (1–3) were evaluated for their xanthine oxidase (XO) inhibitory activities in vitro, and the results showed that 1–3 possessed significant enzyme inhibitory actions with IC₅₀ values of 46.9 ± 3.8, 75.9 ± 7.4 and 42.1 ± 1.7 μg/mL, respectively.     

A new triterpenoid bearing octacosanoate from the stems and roots of Clerodendrum philippinum var. simplex (Verbenaceae)

A new triterpenoid bearing octacosanoate, named taraxer-3β-yl octacosanoate (1), together with 13 known compounds (2–14), was isolated from the ethanol extract of the stems and roots of Clerodendrum philippinum var. simplex. The structure of taraxer-3β-yl octacosanoate (1) was elucidated by extensive spectroscopic analysis. Uncinatone (8) and clerodenone A (10) exhibited inhibition of lipopolysaccharide-induced nitric oxide production in RAW 264.7 macrophages with IC₅₀ values of 12.50 and 3.18 μM, respectively.     

A new flavane acid from the fruits of Illicium verum

A new compound, illiciumflavane acid (1), along with 13 known compounds (2–14), were isolated from the fruits of Illicium verum Hook. F. Their structures were elucidated through various spectroscopic methods, including 1D NMR (¹H NMR, ¹³C NMR), 2D NMR (HMQC, HMBC and NOESY) and HRMS. The stereochemistry at the chiral centres was determined using CD spectrum as well as analyses of coupling constants and optical rotation data. Cytotoxicity evaluation of four compounds showed that illiciumflavane acid and (E)-1,2-bis(4-methoxyphenyl)ethene exhibited potential against A549 activities with IC₅₀ values of 4.63 μM and 9.17 μM, respectively.     

A new fatty acid ester from Nigella sativa var. hispidula Boiss showing potent anti-protein tyrosine phosphatase 1B activity

A new fatty acid ester (1) and seven known phenolic compounds, i.e. salfredin B₁₁ (2), nigephenol C (3), nigephenol B (4), acetovanillion (5), p-hydroxybenzoic acid (6), p-hydroxy-acetophenone (7) and p-hydroxybenzaldehyde (8), were isolated from the seeds of Nigella sativa var. hispidula. Among them, compounds 5, 7 and 8 were isolated from Nigella for the first time. Their structures were elucidated with HR-ESI-MS, 1D and 2D NMR spectra. Evaluation of the isolated compounds on protein tyrosine phosphatase (PTP1B) assay indicated that although compounds 2–8 show no promising anti-PTP1B activities, compound 1 possess anti-PTP1B activity with an IC₅₀ value of 7.38 ± 0.14 μM in vitro.     

Secoiridoids and other chemotaxonomically relevant compounds in Pedicularis: phytochemical analysis and comparison of Pedicularis rostratocapitata Crantz and Pedicularis verticillata L. from Dolomites

We compared the respective metabolite patterns of two Pedicularis species from Dolomites. Seven phenylethanoid glycosides, i.e., verbascoside (1), echinacoside (2), angoroside A (3), cistantubuloside B1 (4), wiedemannioside C (5), campneoside II (11) and cistantubuloside C1 (12), together with several iridoid glucosides as aucubin (6), euphroside (7), monomelittoside (8), mussaenosidic acid (9) and 8-epiloganic acid (13) were identified. Pedicularis verticillata showed also the presence of greatly unexpected secoiridoids, ligustroside (14) and excelside B (15), very rare compounds in Lamiales. Both PhGs and iridoids are considered of taxonomical relevance in the Asteridae and their occurrence in Pedicularis was discussed. In particular, the exclusive presence of several compounds such as 8-epiloganic acid (13), campneoside II (11), cistantubuloside C1 (12), ligustroside (14) and excelside B (15) in Pedicularis rostratocapitata, and angoroside A (3), cistantubuloside B1 (4) and wiedemannioside C (5) in P. verticillata could be considered specific markers for the two botanical entities.     

Chemical constituents and biological activities of Viburnum macrocephalum f. keteleeri

Three new compounds (1–3) and seven known compounds (4–10) have been isolated from the ethanolic extract of Viburnum macrocephalum f. keteleeri using bioactivity-guided fractionation and identified as methyl (2-α-L-rhamnopyranosyloxy)acetate (1), methyl (2R-3-α-L-rhamnopyranosyloxy)glycerate (2), methyl (3R-4-α-L-rhamnopyranosyloxy-3-hydroxy)butanoate (3), bridelionoside B (4), (6S,7E,9R)-roseoside (5), linarionoside A (6), 3,7,11-trimethyl-1,6-dodecadien-3,10,11-triol (7), (+)-8-hydroxylinalool (8), β-sitosterol (9) and daucosterol (10). The structures of 1–3, including absolute configurations, were determined by spectroscopic data (¹H and ¹³C NMR, HSQC, HMBC and ORD) and chemical methods. In addition, compounds 1–8 were assayed for their insecticidal and antimicrobial activities. Compounds 7 and 8 exhibited moderately insecticidal effects against Mythimna separata with LD₅₀ values of 180 and 230 μg g^?1, respectively. Compounds 2, 3, 7 and 8 showed varying antimicrobial activities with IC₅₀ values ranging from 125 to 529 μM.     

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.     

Chemical constituents and biological activities from branches of Colubrina asiatica

Sixteen compounds were isolated from a Thai medicinal plant, Colubrina asiatica. The isolated compounds were elucidated on the basis of spectroscopic methods (IR, 1D and 2D NMR) as six triterpene acids (1–6), five steroids (7–11), one benzoic acid derivative (12), two peptides (13 and 14), one sesquiterpenoid (15) and one jujubogenin (16). Compounds 3 and 10 showed antimalarial activity against Plasmodium falciparum. Compound 5 showed antimycobacterial activity. Moreover, compounds 3, 5, 6, 10 and 14 exhibited weak cytotoxicity against cancer cell lines. Compounds 1–15 have been isolated for the first time from this plant.     

A new benzofuran from Artemisia halodendron Turcz. ex Bess.

A new benzofuran, methyl (2S,2″S,3′E)-[2-(1″-acetoxypropan-2-yl)-2,3-dihydrobenzofuran-5-yl]acrylate (1), and 13 known compounds (2–14) were isolated from an ethanol extract of Artemisia halodendron Turcz. ex Bess. The chemical structures of these compounds were determined by 1D and 2D NMR (¹H-¹H COSY, HMBC, HMQC and NOESY) and HR-ESI-MS spectra, and results were compared with data from the literature. The effects of compounds 1–14 were measured on NF-κB activation, with compounds 2 and 3 exhibiting inhibitory activities against TNF-α-induced NF-κB reporter gene expression in HeLa cells from 10 to 100 μM.     

Two new triterpenoids from Gypsophila oldhamiana

Two new triterpenoids (1–2) were isolated and elucidated from the roots of Gypsophila oldhamiana, together with four known triterpenoids (3–6). Their structures were identified to be 3β-hydroxyolean-13(18)-ene-23, 28-dioic acid (1), 3β, 12α-dihydroxy-23-carboxyolean-28, 13β-olide (2), 3β, 16α-dihydroxy-23-oxoolean-13(18)-en-28-oic acid (3), gypsogenin (4), quillaic acid (5) and gypsogenic acid (6) by spectral methods. All compounds were tested for their cytotoxicities against human tumour cell lines (lung cancer H460 and gastric cancer SGC-7901) and for their antiangiogenic effects using a zebra fish model. All compounds showed interesting antiangiogenic activities and the significant cytotoxicities against H460.     

New C20-gibberellin diterpene from the leaves of Schefflera sessiliflora De P. V.

From the leaves of Schefflera sessiliflora De P. V., one new C₂₀-gibberellin diterpene 2β,12β-dihydroxygibberellin (12β-hydroxy-GA₁₁₀ or 2β-hydroxy-GA₁₁₂) (1), together with three known compounds, trans-tiliroside (2), kaempferol 3-O-β-d-glucuronopyranoside (3), 5-p-trans-coumaroylquinic acid (4), was isolated for the first time from the genus Schefflera by various chromatography methods. Their structures were elucidated by IR, UV, HR-ESI-MS, NMR 1D and 2D experiments and comparison with previous reported data. The α-glucosidase inhibitory activity of all compounds was measured. The isolates (2, 3) showed better α-glucosidase inhibitory activity (IC₅₀ = 134.60, 147.10 μM, respectively) than the standard drug acarbose (IC₅₀ = 214.50 μM).     

A new cytotoxic biflavonoid from the rhizome of Wikstroemia indica

One new chalcone-flavone biflavonoid, 3′-hydroxydaphnodorin A (1), together with 12 known biflavonoids (2–13), was isolated from the rhizome of Wikstroemia indica. Their structures were established on the basis of extensive spectroscopic methods. Eight isolated compounds 1–3, 6, 7, 9, 12 and 13 were evaluated for their cytotoxic activities against cancer-derived cell lines Hep3B, HepG2 and CNE2, and 1 was found to possess moderate cytotoxicity against HepG2 and CNE2 cell lines, with IC₅₀ values of 65.5 ± 11.4 and 53.6 ± 10.1 μM, respectively.     

A new caffeic acid tetramer from the Dracocephalum moldavica L.

A new caffeic acid tetramer compound, named (+) methyl rabdosiin (4), together with seven known caffeic acid multimers (1–3, 5–8) and one caffeic acid monomer (9), were isolated from the aerial parts of Dracocephalum moldavica L. The structures of these compounds were assigned on the basis of 1D and 2D NMR spectroscopic and mass spectrometry analyses. The protective effects of compounds 2–4 against hydrogen peroxide (H₂O₂)-induced apoptosis were evaluated in primary cardiomyocytes of SD neonatal rats in vitro by the MTT method. Three compounds exhibited potent protective activities at 12.5 μg/mL.     

Phenanthrenes from Arundina graminifolia and in vitro evaluation of their antibacterial and anti-haemolytic properties

Chemical investigation and activity test of Arundina graminifolia led to the isolation of six phenanthrenes: blestriarene A (1), shancidin (2), densiflorol B (3), ephemeranthoquinone (4), coelonin (5) and lusianthridin (6). The isolated compounds demonstrated antibacterial and anti-haemolytic activities. It was found that compounds 1 and 2 had medium antibacterial activity against Staphylococcus aureus, Bacillus subtilis and Escherichia coli, with MICs of 20–40 μg/mL and MBCs of 40–320 μg/mL. Bactericidal mechanisms were explored. Rupture of cell wall and membrane and leakage of nuclear mass were observed by transmission electron microscopy (TEM). Moreover, compounds 1–3 attenuated the erythrocyte damage. Compounds 1 and 2 showed significant anti-haemolytic activity with inhibition rate about 50% at 16 μg/mL.