A new flavanone glycoside isolated from Tournefortia sibirica

A new flavanone glycoside, (2S)-dihydrooroxylin A 7-O-[β-D-apiosyl(1→2)]-β-D-glucoside (1), and four known compounds (2–5) were isolated from Tournefortia sibirica L. The chemical structures of these compounds were determined by 1?D and 2?D NMR and HR-ESI-MS spectra, and results were compared with data from the literature. These five compounds (1–5) were isolated from the family Boraginaceae for the first time. Anti-inflammatory effects of compounds (1–5) were evaluated in terms of inhibition of production of NO, TNF-α, and IL-6 in LPS-induced RAW 264.7 cells.     

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.     

Three new sesquiterpenes from Ainsliaea glabra

Three new sesquiterpenes: 4-acrylic-6-methyl-α-tetralone (1), ainsliaea acid A (2) and ainsliaea acid B (3), together with 8 known compounds (4-11) were isolated from the whole herb of Ainsliaea glabra and their structures were established by means of 1D and 2D NMR spectroscopy and HR-ESIMS. Compounds 1–6 were tested for the inhibition of nuclear factor kappa B (NF-κB) in the 293-NF-κB-luciferase reporter cell line induced by lipopolysaccharide (LPS), and compound 2 was further tested for the production of tumor necrosis factor-α (TNF-α), interleukin-1β (IL-1β), IL-6 and IL-10 in RAW264.7 macrophages induced by LPS. The isolated compound 2 exhibited significant anti-inflammatory activity.     

A new C-glycosyl flavone and a new neolignan glycoside from Passiflora edulis Sims peel

A new C-glycosyl flavone, Chrysin-8-C-(2″-O-β-6-deoxy-glucopyranosyl)-β-D-glucopyranoside (1), a new neolignan glycoside, citrusin G (2), as well as 15 known compounds (3–17) were isolated from the peel of Passiflora edulis Sims. The structure determinations were primarily based on comprehensive spectroscopic analyses, and the absolute configuration of 2 were unequivocally determined by the CD experiment and chemical transformation. Compound 1 represents the rare examples of the flavonoid featuring a deoxy glucose sugar moiety. Compounds 5, 7 and 9 exhibited moderate inhibitory effects on nitric oxide (NO) production stimulated by lipopolysaccharide (LPS) in RAW 264.7 cells, with IC₅₀ values of 34.92, 16.12 and 26.67 μM, 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.     

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.     

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 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.     

A new natural nucleotide and other antibacterial metabolites from an endophytic Nocardia sp.

Nine compounds were isolated from Nocardia sp. YIM 64630, and their structures were elucidated as 5′-O-acetyl-2′-deoxyuridine (1), 22E,24R-5α,6α-epoxyergosta-8(14),22-diene-3β,7α-diol (2), 22E,24R-5α,6α-epoxyergosta-8,22-diene-3β,7α-diol (3), 22E,24R-ergosta-7,22-diene-3β,5α,6β-triol (4), 5α,8α-epidioxyergosta-6,22-dien-3β-ol (5), 4′,5,6-trihydroxy-7-methoxyisoflavone (6), 2,4,4′-trihydroxy-deoxybenzoin (7), methyl [4-hydroxyphenyl]acetate (8) and daidzein by extensive spectroscopic analyses. Compound 1 was isolated from natural resources for the first time. The antimicrobial and antioxidant activities of compounds 1–8 were investigated.     

Two new triterpenoid glycosides from the stems of Camellia oleifera Abel

Two new oleanane-type triterpenoid glycosides, 3-O-β-D-xylopyranosyl-(1→2)-α-L-arabinopyranosyl-(1→3)-[β-D-glucuronopyranosyl-(1→2)]-β-D-glucuronopyranosyl-22α-angeloyloxyolean-12-ene-15α,16α,28-triol(1) and 3-O-β-D-xylopyranosyl-(1→2)-α-L-arabinopyranosyl-(1→3)-[β-D-glucuronopyranosyl-(1→2)]-β-D-glucuronopyranosyl-21β-acetyl-22α-angeloyloxyolean-12-ene-16α,28-diol (2) were isolated from the stems of Camellia oleifera Abel. Their structures were elucidated by means of spectroscopic methods and chemical evidence. The cytotoxic activities of compounds 1–2 were evaluated against five human tumour cell lines (HCT-8, BGC-823, A5049, and A2780). Compounds 1–2 showed cytotoxic activity against five human cancer cell lines, with IC₅₀ values ranging from 3.15 to 7.32 μM.     

Novel dammarane-type saponins from Gynostemma pentaphyllum and their neuroprotective effect

Abstract

Three novel dammarane-type saponins, 2α,3β,12β,20(S),24(S)-pentahydroxydammar-25-ene-3-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl-20-O-β-D-glucopyranoside (1, namely gypenoside J1), 2α,3β,12β,20(S),25-pentahydroxydammar-23-ene-3-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl-20-O-β-D-glucopyranoside (2, namely gypenoside J2) and 2α,3β,12β,20(S)-tetrahydroxydammar-25-en-24-one-3-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl-20-O-β-D-xylopyranosyl-(1→6)-β-D-glucopyranoside (3, namely gypenoside J3) along with one known gypenoside (gypenoside LVII) were isolated from the aerial parts of G. pentaphyllum using various chromatographic methods. Their structures were elucidated on the basis of IR, 1D- (¹H and ¹³C), 2D-NMR spectroscopy (HSQC, HMBC and COSY), and mass spectrometry (ESI-MS/MS). Their activity was tested using CCK-8 assay. These four compounds showed little anti-cancer activity with IC₅₀ values more than 100?μM against four types of human cancer lines. The effects of them against H₂O₂-induced oxidative stress in human neuroblastoma SH-SY5Y cells were evaluated and they all showed potential neuroprotective effects with 3.64–18.16% higher cell viability than the H₂O₂-induced model group.     

A new aromatic glucoside from stem bark of Illicium difengpi K.I.B. et K.I.M.

A new aromatic glucoside, namely 4-methoxyphenyl-(6-deoxy-α-L-mannopyranosyl)-β-D-glucopyranoside (1), together with six known aromatic glucosides (2–7) were isolated from the stem bark of Illicium difengpi. The structures of these compounds were established by spectroscopic methods. The isolated aromatic glucosides were tested for anti-inflammatory activity. Compounds 1, 3 and 6 showed significant inhibitory effect on nuclear factor kappa B (NF-κB) in RAW 264.7 macrophages induced by lipopolysaccharide.     

Microbial hydroxylation and glycosidation of oleanolic acid by Circinella muscae and their anti-inflammatory activities

Biotransformation of oleanolic acid (OA) by Circinella muscae AS 3.2695 was investigated. Nine hydroxylated and glycosylated metabolites (1–9) were obtained. Their structures were elucidated as 3β,7β-dihydroxyolean-12-en-28-oic acid (1), 3β,7β,21β-trihydroxyolean-12-en-28-oic acid (2), 3β,7α,21β-trihydroxyolean-12-en- 28-oic acid (3), 3β,7β,15α-trihydroxyolean-12-en-28-oic acid (4), 7β,15α-dihydroxy- 3-oxo-olean-12-en-28-oic acid (5), 7β-hydroxy-3-oxo-olean-12-en-28-oic acid (6), oleanolic acid-28-O-β-D-glucopyranosyl ester (7), 3β,21β-dihydroxyolean-12-en-28- oic acid-28-O-β-D-glucopyranosyl ester (8), and 3β,7β,15α-trihydroxyolean-12-en- 28-oic acid-28-O-β-D-glucopyranosyl ester (9) by spectroscopic analysis. Among them, compounds 4 and 9 were new compounds. In addition, anti-inflammatory activities were assayed and evaluated for the isolated metabolites. Most of the metabolites exhibited significant inhibitory activities on lipopolysaccharides-induced NO production in RAW 264.7 cells.     

A new β-tetralonyl glucoside from the Santalum album derived endophytic fungus Colletotrichum sp. GDMU-1

A new β-tetralonyl glucoside, methylberchemiaside (1), along with five known compounds (2–6) were isolated from a fungus Colletotrichum sp. GDMU-1 derived from the leaves of Santalum album. Their structures were determined by detailed analysis of spectroscopic data. All compounds were tested for the inhibitory effects on the nitric oxide (NO) production in lipopolysaccharide (LPS)-treated RAW264.7 cells. Among them, compounds 4 and 5 showed moderate anti-inflammatory activity with IC₅₀ value of 30.4 and 8.9 μM, respectively.     

Two new noroleanane-type triterpenoid saponins from the stems of Stauntonia chinensis

Two new noroleanane-type triterpenoid saponins, 3β,20α,24-trihydroxy-29-norolean-12-en-28-oic acid 24-O-β-L-fucopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucopyranoside (1) and 3β,20α,24-trihydroxy-29-norolean-12-en-28-oic acid 24-O-β-D-glucopyranosyl-(1→2)-[α-L-arabinopyranosyl-(1→3)]-β-D-glucopyranoside (2) were isolated from the stems of Stauntonia chinensis DC., together with three known compounds, brachyantheraoside B₂ (3), eupteleasaponin Ⅷ (4) and fargoside B (5). Their structures were elucidated by spectroscopic and chemical methods. The cytotoxic activities of compounds 1 and 2 were evaluated against five human tumor cell lines (HCT-116, HepG2, BGC-823, NCI-H1650, and A2780). Compounds 1 and 2 showed moderate cytotoxic activities toward the tested cell lines with IC₅₀ values ranging from 12.71 to 32.04 μM.     

A new furostanol saponin from Dendrobium chrysanthum Lindl. with cytotoxic activity

A new furostanol saponin, (25R)-26-O-(α-d-glucopyranosyl)-(1→2)-α-l-rhamnopyranosyl-furost-5-ene-3β, 22α, 26-triol-3-O-α-d-glucopyranoside (1), together with four known compounds 2–5 were isolated from the ethanolic extract of the stems of Dendrobium chrysanthum Lindl. The structures of these new compounds were identified by extensive spectroscopic analysis including 1D and 2D NMR and HR-ESI-MS, as well as chemical methods. Compounds 1–3 were isolated from D. chrysanthum for the first time. Furthermore, the inhibitory effects of the compounds on tumor cells were evaluated, and compounds 1–2 exhibited significant cytotoxic activities potentially against SPC-A1, MCF-7 and HeLa human cancer cell lines. Compounds 3–5 showed inhibitory activity against the SPC-A1 and MCF-7.     

Bioactive triterpenoids from Sambucus javanica Blume

Abstract

A new triterpene, javablumine A (1) along with six known ones were isolated from the aerial parts of Sambucus javanica Blume. They were identified as 3β,23-dihydroxy-11α,12α-epoxy-urs-20(30)-en-28,13β-olide (1), ursolic acid (2), pomolic acid (3), oleanic acid (4), 2α-hydroxy-oleanolic acid (5), α-amyrin (6), and lupeol palmitate (7), respectively. Compounds 1 and 3 exhibited inhibitory effect against nitric oxide (NO) production in lipopolysaccharide (LPS)-activated RAW264.7 macrophage cell lines with IC₅₀ values of 17.4 and 26.2?μM, respectively.     

2-Deoxy-2-C-(2,3-dideoxy-α-d-erythro-hexopyranosyl)-β-d-glucopyranoses: Reinvestigation of Synthesis,Use in Glycosylation,and Conformational Analyses by NMR

Abstract

Conformational investigations using 1D TOCSY and ROESY ¹H NMR experiments on 1,3,4,6-tetra-O-acetyl-2-C-(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hexopyranosyl)-2-deoxy-β-D-glucopyranose (8) and related disaccharides showed that for steric reasons the C-linked hexopyranosyl ring occurs in the usually unfavoured ¹C₄ conformation and reconfirmed the structure of 1,3,4,6-tetra-O-acetyl-2-C-(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)-2-deoxy-β-D-glucopyranose (5). Glycosylation of 2,3,6-tri-O-benzyl-α-D-glucopyranosyl 2,3-di-O-benzyl-4,6-(R)-O-benzylidene-α-D-glucopyranoside (13) with acetate 8 using trimethylsilyl triflate as a catalyst afforded the α-D-linked tetrasaccharide 14. A remarkable side product in this reaction was the unsaturated tetrasaccharide 2,3,6-tri-O-benzyl-4-O-[4,6-di-O-acetyl-2,3-dideoxy-2-C-(4,6-di-O-acetyl-2,3-dideoxy-β-D-erythro-hexopyranosyl)-α-D-erythro-hex-2-enopyranosyl]-α-D-glucopyranosyl 2,3-di-O-benzyl-4,6-(R)-O-benzylidene-α-D-glucopyranoside (16) where in the C-linked hexopyranosyl ring an isomerization to the β-anomer had taken place to allow for the favoured ⁴C₁ conformation. The tetrasaccharide 14 was deacetylated and hydrogenolyzed to form the fully deprotected tetrasaccharide 18. The ¹ C ₄ conformation of the C-glycosidic pyranose of this tetrasaccharide was maintained as shown by an in depth NMR analysis of its peracetate 19.     

Anti-inflammatory spirobisnaphthalene natural products from a plant-derived endophytic fungus Edenia gomezpompae

Spirobisnaphthalenes comprise a relatively rare family of natural products that are normally isolated from fungi and occasionally from plants.Here we reported the discovery of seven new preussomerintype spirobisnaphthalenes,preussomerins YT1-YT7(1-7),and seven known ones(8-14),from the endophytic fungus Edenia gomezpompae,enriching the structural diversity of this family of natural products.Their structures were established by 1 D and 2 D NMR spectroscopy,HRESIMS analysis and comparison with previously reported compounds,with the absolute configurations of compounds 1 and2 being further confirmed by single-crystal X-ray diffraction using Cu Ka radiation.The antiinflammatory activities of all isolates were assessed by measuring the production of NO in LPS-induced RAW2 64.7 macrophage cells.Among them,compounds 8 and 13 exhibited potent inhibitory activities on the production of NO,with IC_(50) values of 2.61 and 1.32 μmol/L,respectively.