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.     

Three new elemanolides from the seeds of Vernonia anthelmintica

Three new elemanolides, named vernonilides D (1), E (2), and F (3), along with four known sesquiterpenoids, including two elemanolides (4, 5), a guaianolide (6), and a germacranolide (7) were isolated from the seeds of Vernonia anthelmintica. The structures of them were elucidated based on 1D and 2D NMR experiments and comparison with published data. Cytotoxicity of the compounds against four human tumor cell lines was assayed. 6 showed strongly inhibitory effect against HCT-15 and PC-3 cell lines with IC₅₀ values of 0.56 and 0.69 μM, respectively. The new compounds showed moderate cytotoxicity against four cell lines with IC₅₀ values ranging from 9.1 to 28.1 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).     

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.     

Diarylpentanol constituents from the aerial part of Stelleropsis tianschanica

Five diarylpentanol derivatives including two new compounds stellerasme A (1), stellerasme B (2) were isolated from the aerial parts of Stelleropsis tianschanica. Their structures were elucidated by various spectroscopic techniques (UV, IR, MS, CD, 1D and 2D NMR). All compounds were evaluated for their cytotoxicity activity against HeLa and KB cell lines, and compound 1 showed selective activities against HeLa cell line with an IC₅₀ value of 7.4 μM.     

Cytotoxic ent-kaurane diterpenoids from Isodon macrophyllus

Two new ent-kaurane diterpenoids, dayecrystals D–E (1–2), together with nine known compounds, isojaponin A (3), rabdosin A (4), lushanrubescensin J (5), wikstroemioidin B (6), maoyecrystal C (7), rabdosin B (8), isodonal (9), shikokianin (10), and effusanin A (11), were isolated from the leaves of Isodon macrophyllus. The structures of the new compounds were elucidated using 1D and 2D NMR spectroscopy. The ¹³C-NMR spectral data of compound 4 are reported for the first time. All of the compounds were tested for their cytotoxicities against DU145 and LoVo human tumor cells. Compounds 4, 10, and 11 showed inhibitory effects on DU145 cells with IC₅₀ values 5.90, 4.24, and 3.16 μM, and LoVo cells with IC₅₀ values 14.20, 17.55, and 3.02 μM, respectively.     

Antioxidant and cytotoxic lignans from the roots of Bupleurum chinense

In the search for biologically active compounds from the roots of Bupleurum chinense D C., phytochemical investigation of its ethanol extract led to the isolation and identification of a new 8-O-4′ neolignan glucoside, saikolignanoside A (1), along with eight known lignans (2–9). Their structures were determined on the basis of IR, UV, HRESIMS, and NMR spectroscopic analyses. The antioxidant and cytotoxic effects of isolated compounds were evaluated in vitro. The isolated compounds (IC₅₀ > 200 μM) did not display 2, 2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activity. Whereas compounds 1–2, 5, 7, and 9 exhibited potent 2, 2′-azinobis(3-ethyl-benzothiazoline-6-sulfonic acid) (ABTS) free radical scavenging properties with IC₅₀ values ranging from 8.34 to 15.24 μM, while compounds 3–4, 6, 8 showed moderate properties. In addition, all compounds were evaluated for cytotoxicities against A549, HepG2, U251, Bcap-37, and MCF-7 cell lines. Compounds 5 and 9 (IC_50?相似文献   

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.     

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.     

Cytotoxic gelsedine-type indole alkaloids from Gelsemium elegans

The ethanol extract of the leaves and branches of Gelsemium elegans afforded three new gelsedine-type indole alkaloids, 11-methoxy-14,15-dihydroxyhumantenmine (1), 11-methoxy-14,15-dihydroxy-19-oxogelsenicine (2), and 11-methoxy-14-hydroxygelsedilam (3), along with one known alkaloid 11-methoxy-14-hydroxyhumantenmine (4). The structures of isolated compounds were established based on 1D and 2D (¹H-¹H COSY, HMQC, and HMBC) NMR spectroscopy, in addition to high-resolution mass spectrometry. The isolated alkaloids were tested in vitro for cytotoxic potential against four laryngeal tumor cell lines including Hep-2, LSC-1, TR-LCC-1, and FD-LSC-1. As a result, compounds 1 and 4 exhibited some cytotoxic activities against all tested tumor cell lines with IC₅₀ values of 10.9–12.1 μM and 9.2–10.8 μM, respectively.     

Three minor valepotriate isomers from Valeriana jatamansi and their cytotoxicity

Three new minor valepotriate isomers, jatamanvaltrates Z1 (1), Z2 (2), and Z3 (3), have been isolated from the whole plants of Valeriana jatamansi (syn. Valeriana wallichii.). Their structures were elucidated by extensive spectroscopic analysis, especially 2D NMR and ESI-MS/MSⁿ. All isolated compounds displayed moderate cytotoxicity against the lung adenocarcinoma (A549), metastatic prostate cancer (PC-3 M), colon cancer (HCT-8), and hepatoma (Bel7402) cell lines with IC₅₀ values of 2.8–8.3 μM.     

Triterpene saponins with α-glucosidase inhibition and cytotoxic activity from the leaves of Schefflera sessiliflora

From the leaves of Schefflera sessiliflora De P. V., two new triterpene saponins including one oleanane-type saponin, named scheffleraside C (1) and one lupane-type saponin scheffleraside D (2), together with six known triterpene saponins (3–8), were isolated by various chromatography methods. Among them, 3 was found for the first time from natural sources, while 6–8 were isolated for the first time from the genus Schefflera. Their structures were elucidated by IR, UV, HR-ESI-MS, NMR 1D and 2D experiments, and comparison of their NMR data with previously reported data. Their α-glucosidase inhibition and cytotoxic activity against MCF-7 human breast cancer cell lines were evaluated. The isolates (1, 3–5, 8) showed stronger α-glucosidase inhibitory activity (IC₅₀ = 5.99–76.58 μM) than the standard drug acarbose (IC₅₀ = 214.50 μM). At the concentration of 100 μg/ml, the isolates (1, 2) showed appreciable cytotoxic activity (67.92, 63.83%, respectively).     

Lanostane triterpenoids and ergostane-type steroids from the cultured mycelia of Ganoderma capense

Abstract

Two new lanostane triterpenoids (1 and 2), two new ergostane-type steroids (3 and 4) together with two known lanostane triterpenoids (5 and 6) and one known steroid (7) were isolated from the cultured mycelia of Ganoderma capense (CGMCC 5.71). Their structures were determined on the basis of extensive spectroscopic (HRESIMS, 1D NMR, 2D NMR) data analyses. Compound 1 exhibited moderate cytotoxic activity against the human cancer cell line NCI-H1650 with an IC₅₀ value of 22.3 μM, and 7 displayed cytotoxic activity against the human cancer cell line HCT116 with an IC₅₀ value of 17.4 μM. In addition, compounds 2, 3, 5, and 6 displayed weak anti-HIV activity with IC₅₀ values of 23.5, 46.7, 21.6, and 30.1 μM, respectively.     

Adlumiceine methyl ester,a new alkaloid from Fumaria vaillantii

A new alkaloid, adlumiceine methyl ester (1), together with two known alkaloids, parfumine (2) and N-methylhydrastine methyl ester (3), was isolated from aerial parts of Fumaria vaillantii. The structures of compounds were determined by 1D/2D NMR and MS data. All three compounds were tested for cytotoxic activity against PC3 and MCF7 cell lines using Alamar blue assay. The tested compounds showed no significant cytotoxic activity (IC₅₀>50 μM) against PC3 and MCF7 cell lines.     

Prenylated isoflavones from Cudrania tricuspidata inhibit NO production in RAW 264.7 macrophages and suppress HL-60 cells proliferation

Inhibitory effects of NO production in RAW 264.7 macrophages guided the isolation of nine prenylated isoflavones, including a new cudraisoflavone L (1) and eight known metabolites furowanin B (2), erysubin A (3), wighteone (4), lupalbigenin (5), laburnetin (6), isolupalbigenin (7), 6,8-diprenylorobol (8), millewanin H (9) from the leaves of Cudrania tricuspidata. At the concentration of 10 μM, compounds 1, 2, and 4 significantly inhibited NO production with the inhibitory values of 72.5 ± 2.4, 66.9 ± 1.8, and 55.4 ± 2.7%, respectively. In addition, all of isolated compounds 1–9 showed promising cytotoxic effects toward HL-60 cells (IC₅₀ 4.3 ± 0.7 to 18.0 ± 1.7 μM).     

2H-Pyranone and isocoumarin derivatives isolated from the plant pathogenic fungus Leptosphaena maculans

Abstract

Two new 2H-pyranones and two new isocoumarin derivatives, maculanslines A-D (1–4), together with seven known compounds (5–11), were isolated from the plant pathogenic fungus Leptosphaena maculans. Their planar structures and absolute configuration were elucidated by comprehensive spectroscopic techniques including high-resolution electrospray ionization mass spectrum, 1D and 2D nuclear magnetic resonance, as well as electronic circular dichroism. All 11 compounds were tested for their inhibitory activity against α-glucosidase. Compound 1 showed moderate inhibitory activity against α-glucosidase with IC₅₀ of 74.35 μM.     

Acylphloroglucinol derivatives from Decaspermum gracilentum and their antiradical and cytotoxic activities

Two new acylphloroglucinol derivatives, 1-(hexanoyl)phloroglucinol-α-d-arabinopyranoside (1) and 1-(hexanoyl)phloroglucinol-β-d-glucopyranoside (2), along with two known ones, 1-(acetyl)phloroglucinol-β-d-glucopyranoside (3) and ethyl 2,4,6-trihydroxybenzoate (4), were isolated from the EtOAc soluble fraction of EtOH extract of Decaspermum gracilentum. The structures of the new compounds were determined by extensive spectroscopic analyses including HRESIMS, 1D and 2D NMR data. Interestingly, all of the compounds showed ABTS^·+ radical scavenging activity with the IC₅₀ values less than 10 μM. Furthermore, compounds 3 and 4 displayed moderate cytotoxicity on human non-small-cell lung carcinoma cell line A549 (IC₅₀ = 50.9 μΜ) and human renal carcinoma cell line 786-O (IC₅₀ = 38.6 μΜ), respectively.     

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.     

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.     

New polyacetylenes glycoside from Eclipta prostrate with DGAT inhibitory activity

One new polyacetylene glycoside eprostrata Ⅰ (1), together with seven known compounds (2–8), were isolated from Eclipta prostrata. Their structures were elucidated on the basis of spectroscopic and physico-chemical analyses. All the isolates were evaluated inhibitory activity on DGAT in an in vitro assay. Compounds 1–8 were found to exhibit inhibitory activity of DGAT1 with IC₅₀ values ranging from 74.4 ± 1.3 to 101.1 ± 1.1 μM.