Two new sesquiterpenoids from cultures of the basidiomycete Tremella foliacea

Two new sesquiterpenoids, trefoliol B (1) and trefoliol C (2), together with known echinocidin A (3), were isolated from cultures of the basidiomycetes Tremella foliacea. The new structures were elucidated on the basis of extensive spectroscopic methods. At the same time, trefoliol B (1) and echinocidin A (3) were tested for their cytotoxicities against five human cancer cell lines and for their inhibitory activities against isozymes of 11β-hydroxysteroid dehydrogenases (11β-HSD). No compound showed significant activity (IC₅₀ > 40 μM). Compound 1 showed moderate inhibitory activities against 11β-HSD1 (human IC₅₀ = 13.1 μM; mouse IC₅₀ = 91.8 μM).     

Chemical constituents of the red alga Laurencia tristicha

Six new sesquiterpenes, 10-hydroxy-epiaplysin (1), 10-hydroxy-aplysin (2), 10-hydroxy-debromoepiaplysin (3), aplysin-9-ene (4), epiaplysinol (5) and debromoepiaplysinol (6), together with 13 known compounds (7–19), have been isolated from the red alga Laurencia tristicha. The structures of 1–6 were determined by spectroscopic methods including IR, EI-MS, HREI-MS, and 1D and 2D NMR techniques. All compounds were obtained from this species for the first time and were tested for cytotoxic activities against several human cancer cell lines including lung adenocarcinoma (A549), stomach cancer (BGC-823), hepatoma (Bel 7402), colon cancer (HCT-8) and HeLa cell lines. Compound 6 showed selective cytotoxicity against HeLa cell line with IC₅₀ 15.5 μM, cholest-5-en-3β,7α-diol (14) was toxic to all tested cell lines with IC₅₀ values of 16.8, 5.1, 0.5, 0.5, and 0.3 μM, respectively, and other compounds were inactive (IC₅₀>10 μg/ml).     

Isoflavanones from Desmodium oxyphyllum and their cytotoxicity

Two new isoflavanones, (3R)-7-hydroxy-4′-methoxy-5-methoxycarbonyl-isoflavanone (1) and (3R)-8-hydroxy-4′-methoxy-7-methoxycarbonyl-isoflavanone (2), together with seven known isoflavanones (3–9) were isolated from Desmodium oxyphyllum of the Leguminosae family. Their structures were elucidated by spectroscopic methods, including extensive 1D and 2D NMR techniques. Compound 1 showed good cytotoxicity against NB4 and SHSY5Y cell lines with IC₅₀ values of 3.1 and 2.5 μM; compound 2 exhibited cytotoxicity against PC3 cell lines with a IC₅₀ value of 3.6 μM; compound 4 showed cytotoxicity against A549 and SHSY5Y cell lines with IC₅₀ values of 3.6 and 2.8 μM; and compound 5 displayed cytotoxicity against NB4, SHSY5Y, and MCF7 cell lines with IC₅₀ values of 2.6, 3.8, and 2.8 μM, respectively. Other compounds also showed moderate cytotoxicity for some tested cell lines with IC₅₀ values between 5.4 and 8.8 μM.     

Rhobupcyanoside B,A new cyanoside from Rhodiola bupleuroides

One new cyanoside, rhobupcyanoside B (1), together with 7 known ones, was isolated from the 70% ethanol extract of the roots and rhizomes of Rhodiola bupleuroides. Their structures were determined by spectroscopic methods, including 2D NMR techniques. Compound 1 was evaluated for its inhibitory activity against α-glucosidase with IC₅₀ value of 278.28 ± 0.55 μM by comparing with the positive control (acarbose) at 210.40 ± 0.32 μM.     

Brominated polyunsaturated lipids with protein tyrosine phosphatase-1B inhibitory activity from Chinese marine sponge Xestospongia testudinaria

A new brominated polyunsaturated lipid, methyl (E,E)-14,14-dibromo-4,6,13-tetradecatrienoate (1), along with three known related analogues (2–4), were isolated from the Et₂O-soluble portion of the acetone extract of Chinese marine sponge Xestospongia testudinaria treated with diazomethane. The structure of the new compound was elucidated by detailed spectroscopic analysis and by comparison with literature data. Compound 3 exhibited significant inhibitory activity against protein tyrosine phosphatase 1B (PTP1B), a key target for the treatment of type II diabetes and obesity, with an IC₅₀ value of 5.30 ± 0.61 μM, when compared to the positive control oleanolic acid (IC₅₀ = 2.39 ± 0.26 μM).     

Chemical constituents from rhizome of Anemone amurensis

Phytochemical investigation of the 70% EtOH extract of the rhizome of Anemone amurensis led to the isolation of two new oleanane-type triterpenoid saponins 1 and 2. Their structures were elucidated on the basis of chemical and spectral analysis, including 1D, 2D NMR data, and HR–ESI–MS. Compounds 1 and 2 were tested for cytotoxicities against two human cancer cell lines (A549 and Hep-G2). Compound 2 showed potent cytotoxicity with IC₅₀ values of 38.53 and 66.17 μM, respectively, while compound 1 with IC_50?>?100 μM.     

Two new ent-kaurane diterpenes from the stems of Eurya chinensis

Abstract

Two new ent-kaurane diterpenes (1–2), together with five known analogs, were isolated from the stems of Eurya chinensis. The structures of new compounds were established by extensive analysis of mass spectrometric and 1D and 2D NMR spectroscopic data. Compound 3 exhibited noticeable anti-inflammatory activity as denoted by inhibiting LPS-induced nitric oxide (NO) production in RAW264.7 cells with an IC₅₀ value of 7.82 μM. Compound 4 showed potent cytotoxic activity against human cancer cell lines NCI-H46, HepG2 and SW480 with IC₅₀ values ranging from 7.45 to 8.54 μM.     

A new bioactive steroidal ketone from the South China Sea sponge Xestospongia testudinaria

A new steroidal ketone (1), with an ergosta-22,25-diene side chain, was obtained from the South China Sea marine sponge Xestospongia testudinaria. The structure of 1 was determined on the basis of detailed spectroscopic analysis and by comparison with literature. Compound 1 exhibited significant inhibitory activity against protein tyrosine phosphatase 1B (PTP1B), a key target for the treatment of type II diabetes and obesity, with an IC₅₀ value of 4.27 ± 0.55 μM, which is comparable with the positive control oleanolic acid (IC₅₀ = 2.63 ± 0.22 μM).     

Two new sesquiterpenoid glycosides from the leaves of Lycium barbarum

Two new sesquiterpenoid glycosides, lyciumionosides A–B (1–2), together with four known compounds (3–6), were isolated from the leaves of Lycium barbarum. Their structures were mainly established on the basis of MS, 1D and 2D NMR spectroscopic techniques. The antiproliferative activities of compounds 1–5 were evaluated. Compound 1 showed highest inhibitory activity against A549 cells with IC₅₀ value of 32.6 ± 2.6 μM, compound 3 showed highest inhibitory activity against PC-3 cells with IC₅₀ value of 36.0 ± 2.9 μM, and compound 5 exhibited highest inhibitory activity against HeLa cells with IC₅₀ value of 32.3 ± 4.2 μM.     

Selective cytotoxic eremophilane-type sesquiterpenes from Penicillium citreonigrum

Abstract

One new eremophilane-type sesquiterpene (1, citreopenin) was isolated from Penicillium citreonigrum (HQ738282), and the structure was elucidated by a combination of spectroscopic data interpretation and single-crystal X-ray diffraction analysis using Cu Kα radiation (CCDC 1030588). Compound 1 showed weak activity against KB-VIN (IC₅₀ = 11.0 ± 0.156 μM), while the known compound 3 exhibited selective cytotoxicity against MDA-MB-231 triple-negative breast cancer (TNBC) (IC₅₀ = 5.42 ± 0.167 μM).     

Further brominated polyacetylenes with pancreatic lipase inhibitory activity from Chinese marine sponge Xestospongia testudinaria

A new brominated polyacetylene, xestonariene I (1), along with three known related analogues (2–4), was obtained from Chinese marine sponge Xestospongia testudinaria. Its structure was determined on the basis of detailed spectroscopic analysis and by comparison with literature data. Compound 4 exhibited significant inhibitory activity against pancreatic lipase, which plays a key role in preventing obesity, with an IC₅₀ value of 0.61 μM, being comparable to that of the positive control orlistat (IC₅₀ = 0.78 μM).     

A new N-methoxyl-carbonyl benzylisoquinoline from Litsea cubeba

A new benzylisoquinoline alkaloid (?)-N-methoxycarbonyl-norjuziphine (1) was isolated from Litsea cubeba. Its structure was identified by extensively spectroscopic techniques and confirmed by the single-crystal X-ray diffraction analysis. Compound 1 showed cytotoxicity against HL-60 and MCF-7 cells, with IC₅₀ values of 18.1 and 15.0 μM, respectively, comparable to 3.1 and 17.5 μM of the cisplatin (positive control).     

A new labdane-type diterpenoid from Leonurus japonicus

Five fractions prepared from the crude extract of Leonurus japonicus were examined in order to determine their cytotoxic potential. Under the bioassay guidance, a new labdane-type diterpenoid (1), and nine known ones (2–10) along with a seco-labdane (11) were isolated from the aerial parts of Leonurus japonicus. The structure elucidation was primarily based on comprehensive spectroscopic analyses, including HRESIMS, IR, and 1D and 2D NMR methods. Compound 4 (6β-hydroxy-15,16-epoxylabda-8,13(16),14-trien-7-one) exhibited potential cytotoxicity against HeLa cell line (IC₅₀ = 23.75 μM).     

New cyclopeptide alkaloid and lignan glycoside from Justicia procumbens

This study reported a new cyclopeptide alkaloid, justicianene A (1), and a new lignan glycoside, procumbenoside H (2), isolated from Justicia procumbens. The structures of the new compounds were elucidated by means of spectroscopic analysis, including extensive 2D NMR studies and mass spectrometry. Cyclopeptide alkaloids were first observed from the genus Justicia. Compound 2 was cytotoxic against human LoVo colon carcinoma cells with an IC₅₀ value of 17.908 ± 1.949 μM.     

Two new triterpenoid saponins from rhizome of Anemone amurensis

Two new triterpenoid saponins were isolated from the 70% ethanol extract of the rhizome of Anemone amurensis, they are oleanolic acid 28-O-β-d-glucopyranosyl-(1 → 3)-α-l-rhamnopyranosyl-(1 → 4)-β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranosyl ester (1) and 23,27-dihydroxy oleanolic acid 3-O-α-l-arabinopyranoside (2). The structures of 1 and 2 were elucidated on the basis of chemical and spectral analysis, including 1D and 2D NMR data and HR-ESI-MS. Compounds 1 and 2 were tested for cytotoxicities against three human cancer cell lines (A549, Hep-G2, and MCF-7). Compound 1 showed potent cytotoxicity with IC₅₀ values of 34.76, 41.17, and 28.92 μM, respectively, while compound 2 with IC₅₀>100 μM.     

Two new morphinane alkaloids from Sinomenium acutum

Two new morphinane alkaloids, 1-hydroxy-10-oxo-sinomenine (1) and 4,5-epoxy-14-hydroxy sinomenine N-oxide (2), have been isolated from the stems of Sinomenium acutum. Their structures were established by various spectral analyses, especially 2D NMR experiments. The structure of 2 was confirmed by single crystal X-ray diffraction. The absolute configurations of 1 and 2 were deduced by comparison of CD spectra with the known alkaloid sinomenine (3). Compound 1 was tested for DPPH inhibition and gave IC(50) of 27.9?μM. Compound 2 was tested for neuroprotective effect and showed significant activity against β-amyloid(25-35)-induced oxidative injury (*P?相似文献   

Three new C-alkylated flavonoids from Desmodium oblongum

Three new C-alkylated flavonoids, 4′-hydroxy-8-isobutyryl-7-methoxy-6-methyl-flavone (1), 4′,7-dimethoxy-8-isobutyryl-6-methyl-flavone (2), and 4′,7-dimethoxy-8-isobutyryl-flavone (3), together with three know ones luteolin (4), kaemferol (5), and quercetin (6), were isolated from Desmodium oblongum. Their structures were elucidated by spectroscopic methods, including extensive 1D- and 2D-NMR techniques. Compound 1 showed cytotoxicity against NB4, SHSY5Y, and MCF7 cell lines with IC₅₀ values of 8.5, 6.5, and 7.8 μM; compound 2 showed cytotoxicity against SHSY5Y and PC3 cell lines with IC₅₀ values of 5.0 and 6.8 μM; compound 3 displayed cytotoxicity against SHSY5Y and MCF7 cell lines with IC₅₀ values of 6.4 and 9.4 μM, respectively.     

Noralashinol B,a norlignan with cytotoxicity from stem barks of Syringa pinnatifolia

One new norlignan, noralashinol B (1), and one new natural product, proposed noralashinol C (2), were isolated in a continuous phytochemical investigation on the stem barks of Syringa pinnatifolia. Their structures were elucidated based on the analysis of spectroscopic data, including mass spectrometry and 1D and 2D NMR spectroscopies, and the absolute configuration was determined by experimental and calculated electronic circular dichroism. Compound 1 showed a weak cytotoxicity against HepG2 hepatic cancer cells with its IC₅₀ value of 31.7 μM. Furthermore, 1 induced apoptosis of HepG2 cells in a dose-dependent manner at concentrations of 0–80.0 μM.     

Anti-inflammatory amide alkaloids from the stems of Clausena emarginata

Two new amide alkaloids, clauemaramide A (1) and clauemaramide B (2), and three known analogs were isolated from the stems of Clausena emarginata. Their structures were determined on the basis of spectroscopic analyses. The absolute configurations of 1 and 2 were confirmed by CD spectroscopy. Compound 3 showed moderate inhibitory effects on LPS-induced NO production (IC₅₀ value = 4.9 μM).     

Anti-inflammatory and antimicrobial coumarins from the stems of Eurya chinensis

Two new coumarins, named (±)-euryacoumarin A (1) and 6-demethylobtusinin (2), and one new natural coumarin, named euryacoumarin B (3), along with two known compounds, scopoletin (4) and obtusinol (5), were isolated from the stems of Eurya chinensis. Their structures were elucidated by means of extensive spectroscopic methods and comparison with data reported in the literatures. Compound 1 exhibited significant inhibition of LPS-induced nitric oxide (NO) production in RAW264.7 cells with IC₅₀ value of 35.64 ± 1.73 μM, and showed marginal antibacterial activities against Bacillus subtilis and B. cereus with MIC values of 50.59 ± 2.12 and 35.42 ± 0.96 μM, respectively.