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.     

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.     

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).     

Six new C-21 steroidal glycosides from Dregea sinensis Hemsl

Six new C-21 steroidal glycosides (1–6) were separated from the root of Dregea sinensis Hemsl. and their structures were elucidated using extensive nuclear magnetic resonance, mass spectrometry, and infrared spectral analyses. Isolated compounds were evaluated for antitumor activity, which showed that compound 3 had moderate activity in Jurkat cells (IC₅₀ 19.54 ± 0.91 μM), and compounds 1–4 had significant effects against IL-2R and TNFR2 (IC₅₀ 1.518 ± 0.06 μM to 5.9 ± 0.07 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.     

Two new triterpenes from Euphorbia alatavica

A phytochemical investigation on Euphorbia alatavica Boiss resulted in the isolation of nine compounds, including two new ones, alatavolide and alatavoic acid (1–2). Chemical structures of these compounds were established on the basis of 1D, 2D NMR, and HR-MS techniques, and by comparison with data reported in the literature. Compounds 1, 2, 4, 6, 8, and 9 were screened for cytotoxicity using the MTT assay. Among these compounds, the new compound 2 showed moderate cytotoxicity against Hela, MCF-7 and A549 cell lines (IC₅₀ values of 16.4 ± 3.2, 14.5 ± 2.8, 22.3 ± 3.1 μM, respectively), while the known compound 8 exhibited the most potent cytotoxicity with the IC₅₀ values of 6.5 ± 3.1, 1.9 ± 0.9, 8.6 ± 3.5 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   

Cytotoxic triterpene saponins from Clematis mandshurica

Two new triterpene saponins, mandshunosides A and B (1 and 2), were isolated from the roots and rhizomes of Clematis mandshurica. Their structures were elucidated on the basis of spectroscopic evidence and hydrolysis products. Compounds 1 and 2 showed inhibitory activities against two colorectal human cancer cells HCT 116 (IC₅₀ 2.1 μM for 1 and 2.5 μM for 2) and HT-29 (IC₅₀ 3.7 μM for 1 and 3.3 μM for 2).     

Selective dual cholinesterase inhibitors from Aconitum laeve

New lycoctonine-type dual cholinesterase inhibitor, swatinine-C (1), along with three known norditerpenoid alkaloids, hohenackerine (2), aconorine (5) and lappaconitine (6) and two synthetically known but phytochemically new benzene derivatives, methyl 2-acetamidobenzoate (3) and methyl 4-[2-(methoxycarbonyl)anilino]-4-oxobutanoate (4), was isolated from the roots of A. laeve. Structures of new and known compounds (1–6) were established on the basis of latest spectroscopic techniques and by close comparison with the data available in literature. In vitro, compounds (1–6) were tested against AChE and BChE inhibitory activities. Compounds 1 and 2 showed competitive inhibition against AChE (IC_50?=?3.7 μM, 4.53 μM) and BChE (IC_50?=?12.23 μM, 9.94 μM), respectively. Compounds 5 and 6 showed promising noncompetitive type of inhibitory profile against AChE (IC_50?=?2.51 and 6.13 μM) only. Compounds 3 and 4 showed weak inhibitory profile against both AChE and BChE.     

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.     

Quinones and coumarins from Ajania salicifolia and their radical scavenging and cytotoxic activity

Abstract

1,4-Naphthoquinone (1) and a new coumarin (3) were isolated from Ajania salicifolia, together with two known compounds (2, 4). The structures and stereochemistry of new compounds were elucidated using spectroscopic methods. Two compounds exhibited potent ABTS cation radical scavenging activities with IC₅₀ values ranging 7.97–8.44 μM. Two quinones (1, 2) exhibited moderate cytotoxic activity against the human cancer cell lines (Hela, HepG2, and K562) with IC₅₀ values of 11.24–35.15 μM in vitro. This is the first report of naphthoquinone in the genus Ajania.     

Phorbol ester-type diterpenoids from the twigs and leaves of Croton tiglium

Phytochemical investigation of the ethanol extract from the twigs and leaves of Croton tiglium led to the isolation of two new phorbol esters (1–2) and seven known ones (3–9). Their structures were elucidated by the analyses of extensive spectroscopic data (IR, MS, and 1D and 2D NMR) and comparing with related compounds. Meanwhile, compounds 1–9 were determined for their cytotoxic activities on human lung cancer cell line A549. Among them, 1–2 were inactive against the cell line A549 (IC₅₀ > 100 μM), but compounds 3 and 7 showed weak activities.     

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).     

Synthesis and cytotoxic activity of two steroids: icogenin aglycone analogs

During the process of icogenin analog research, we obtained two cytotoxic steroids: compound 4 and compound 6 casually. Their in vitro antitumor activities were tested by the standard MTT assay. The results disclosed that compound 4 (IC₅₀ = 3.65–6.90 μM) showed potential antitumor activities against HELA, KB cell lines and compound 6 (IC₅₀ = 2.40–9.05 μM) showed potential antitumor activities against HELA, BGC-823, KB, A549, HCT-8 cell lines.     

Synthesis of piscidinol A derivatives and their ability to inhibit HIV-1 protease

Four types of piscidinol A derivatives were synthesized and evaluated their ability to inhibit HIV-1 protease to understand their structure-activity relationships. Of these tirucallane-type triterpene derivatives, an A-seco derivative (1b) moderately inhibited human immunodeficiency virus (HIV) protease (IC₅₀ 38.2 μM). The 2,2-dimethyl succinic acid (DMS) acylated tirucallane derivatives (4b, 6a, and 7b, 50 < IC₅₀ < 100 μM) were more inhibitory against HIV-1 PR than the others (PA, 2a, 4a, 4c–4d, 5a, 6b–6d, and 7a, IC₅₀ > 100 μM). These findings indicated that the 2,3-seco-2,3-dioic acid (1b) and DMS-acylated tirucallane-type derivatives preferably inhibited HIV viral protease.     

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.     

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).     

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.     

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).     

(±) Cochlearoids N–P: three pairs of phenolic meroterpenoids from the fungus Ganoderma cochlear and their bioactivities

Three pairs of meroterpenoids (±) cochlearoids N–P (1–3) were isolated from the fruiting bodies of Ganoderma cochlear. Their structures including absolute configurations were assigned by spectroscopic techniques. All the isolated compounds were tested for their inhibitory activities toward BRD4, human cancer cells, and micro-organisms. The results show that the enantiomers of (±)-1 are BRD4 inhibitors, (?)-1 and (+)-3 are cytotoxic against human cancer cells (K562) with IC₅₀ values of 7.68 and 6.68 μM, respectively. Besides compounds (±)-2 and (±)-3 exhibit potent inhibitory activity against Staphylococcus aureus with IC₅₀ values in the range of 5.43–17.99 μM.