Study on chemical constituents of an edible mushroom Volvariella volvacea and their antitumor activity in vitro

Abstract

Phytochemical investigation of the fruiting body of Volvariella volvacea led to the isolation of a new furanone, 2(5H)-furanone-4-propionic acid named volvafuranone A (1), together with twelve known compounds (2–13). Compounds 2–7, 9–11 were isolated from this mushroom for the first time. The isolated compounds were assessed for their cytotoxicity against four human tumour lines (SGC-7901, PC-3M, MCF-7, HepG-2), and the results showed that compound 2, 3, 12, 13 have significant cytotoxicity with IC₅₀ values of 5.90?μM (HepG-2), 20.72?μM (HepG-2), 27.98?μM (PC-3M) and 23.15?μM (PC-3M), respectively.     

Abeliaside,a new phenolic glucoside from Abelia triflora

A new phenolic glucoside, abeliaside, along with four known compounds, 5,6,7,4′-tetrahydroxy flavones, caffeic acid, 4-O-caffeoylquinic acid and caffeic acid glucoside, was isolated from the leaves of Abelia triflora R. Br. (Caprifoliaceae). The structure of the new compound was elucidated by different spectroscopic techniques. Compounds 1–5 were assayed for their anticancer activities against two cancerous human cell lines, MCF-7 and PC-3 cells, and normal Vero cell line using the crystal violet staining method. From the results it could be seen that caffeic acid possessed the highest anticancer effect against MCF-7 (IC₅₀: 17 μg/mL) and PC-3 (IC₅₀: 20.1 μg/mL) compared to vinblastine sulphate as reference drug (IC₅₀: 4.6, 2.8 μg/mL). The other compounds showed weak anticancer activity on both cell lines.     

Two new 5,6-epoxysterols from calcareous marine sponge Leucetta chagosensis

Chemical investigation on CH₂Cl₂ extract of the marine sponge Leucetta chagosensis, collected from the South China Sea, afforded two new 5,6-epoxysterols, 5α,6α-epoxycholesta-8(14),22(E)-diene-3β,7α-diol (1) and (24R)-24-ethyl-5α,6α-epoxycholesta-8(14),22(E)-diene-3β,7α-diol (2) along with ten known related steroid analogs (3–12). Their structures were elucidated on the basis of NMR spectroscopic analyses, and comparison with the literature. All isolates were tested for cytotoxicity against three tumor cell lines only known compounds 11 and 12 exhibited notable cytotoxic activity against A549 (IC₅₀: 3.0 and 5.6?μM), PC9 (2.0 and 15.6?μM), and MCF-7 (9.4 and 11.8?μM) cell lines, respectively.     

New sesquiterpenoid glycoside from the rhizomes of Atractylodes lancea

Abstract

Six sesquiterpenoids and four lignans (1–10) were isolated from the n-BuOH extract of the rhizomes of Atractylodes lancea. Among them, the new sesquiterpenoid glycoside named (4?R, 5S, 7R)-hinesolone-11-O-β-?-glucopyranoside (1), along with three known compounds (2–4) were first obtained from this genus. All the isolates were elucidated by spectroscopic analyses and chemical methods, and the absolute configurations were assigned by electronic circular dichroism spectroscopy technique. In addition, the cytotoxic bioassay of compound 1 was evaluated and results showed it had no significant antitumor activity against human cancer cell lines MCF-7, HepG-2 and Hela.     

Neoclerodane diterpenoids from Scutellaria barbata with cytotoxic activities

Abstract

Two new neoclerodane diterpenoids, barbatin F (1), barbatin G (2) together with four known compounds, scutebata A (3), scutebata B (4), scutebata C (5) and scutebata P (6) were isolated from the whole plant of Scutellaria barbata D.Don. Their structures were elucidated on the basis of spectroscopic studies. In vitro cytotoxicity of selected compounds against cancer cell lines LoVo, SMMC-7721, HCT-116, and MCF-7 were evaluated, compound 1 and 2 showed weak cytotoxic activities against HCT-116 colon cancer cell lines with IC₅₀ value of 44.3, 32.3?μM, respectively, while compound 3 and 4 exhibited moderate cytotoxic activities against four tested human cancer cell lines with IC₅₀ values of 5.31～28.5?μM.     

Two new ent-atisanes from the root of Euphorbia fischeriana Steud.

Two new ent-atisanes ent-1β,3β,16β,17-tetrahydroxyatisane (1), ent-1β,3α,16β,17-tetrahydroxyatisane (2) together with 11 known diterpenes were isolated from the anti-tumour activity fraction of Euphorbia fischeriana Steud. The compounds were identified by detailed spectroscopic analysis, including extensive 2D-NMR experiments. X-ray analysis was applied to determine the structure of compound 2. All 13 compounds were screened for cytotoxicity in vitro against human tumour MCF-7, HepG-2 and SGC-7901 cell lines. Compounds 1 and 2 showed the inhibitory effects against MCF-7 with IC₅₀ levels of 23.21 and 15.42 μM; simultaneously, compounds 4, 6, 8 and 11 also had definite inhibitory effect against different cell lines.     

Cytotoxic oplopane sesquiterpenoids from Arnoglossum atriplicifolium

Pale Indian plantain (Arnoglossum atriplicifolium (L.) H. Rob.) is a plant with traditional medicinal usage among the Cherokee Native American tribe for treating cancer. Two oplopane sesquiterpenoids were isolated from an extract of A. atriplicifolium from Western North Carolina. The compounds were isolated by bioassay-guided fractionation using an MCF-7 breast tumour cell line assay. The known compound (1S,6R,7R,8R)-1-acetoxy-6,7-diangeloxy-8,10-epoxy-2-oxo-oplopa-3,14Z,11,12-dien-13-al (1) had an EC₅₀ value of 9.0 μM against MCF-7 cells, while the new compound (1S,3R,6R,7R,8R,11S)-1-acetoxy-6,7-diangeloxy-8,10,11,13-bisepoxyoplopan-2-one (2) had an EC₅₀ value of 96 μM. The compounds were characterised by 1D and 2D NMR spectroscopy and by comparison with literature values in the case for 1. Based on NOESY analysis, a correction of the relative configuration for 1 is presented. The presence of these compounds may help to explain the folk remedy usage of this plant as an anticancer agent.     

Synthesis and biological evaluation of 1,2,4-oxadiazole linked 1,3,4-oxadiazole derivatives as tubulin binding agents

As an aspect of our ongoing research in search of new anticancer agents, a series of novel analogs of 1,3,4-oxadiazole embedded with 1,2,4-oxadiazole moieties (11a–j) were synthesized. The structure of the final compounds was confirmed by ¹H NMR, ¹³CNMR and mass spectroscopic techniques and evaluated for their in vitro anticancer activity against three human cancer cell lines (lung, breast). Among the synthesized compounds, 11?b, 11?g, 11?h, and 11i showed potent anticancer activity with IC₅₀ values within the range of 0.34?±?0.025 to 2.45?±?0.23?μM against three human cancer cell lines. Further, these compounds (11a–j) were investigated for molecular docking studies. Among them, compound 11?h showed strong binding affinity on binding sites of target protein EGFR (PDB ID: 4hjo) with highest docking score (-7.028). It revealed that 11?h was a strong tubulin binding agent.     

Chemical constituents of the fermentative extracts of marine fungi Phoma sp. CZD-F11 and Aspergillus sp. CZD-F18 from Zhoushan Archipelago,China

A new diphenyl ether (1) as well as 20 other compounds were identified from the fermentative extracts of marine-derived fungi Phoma sp. CZD-F11 (Compounds 1–8) and Aspergillus sp. CZD-F18(Compounds 9–21). Their structures were elucidated on the basis of extensive spectroscopic analysis. The broth extracts of the fungi exhibited very good anticancer activity against H1975 cells with 5.62 and 25.8% viability at concentration of 10 μg/mL for Phoma sp. CZD-F11 and Aspergillus sp. CZD-F18, respectively. The inhibitory activity of all compounds against PC-3 cell lines, BRD4 and aromatase were evaluated. The results showed compound 7 exhibited moderate anticancer activity with 66.1% inhibition against PC-3 cell lines at the concentration of 10 μg/mL. Compound 7 and 8 exhibited favourable BRD4 inhibitory activity with 78.5 and 76.4% inhibition at the concentration of 10 μg/mL.     

Two new bioactive triterpenoids from the roots of Colubrina asiatica

Abstract

Two new ceanothane triterpenes, 3,7-O,O-dibenzoyl ceanothic acid methylester (1) and 3-O-acetyl-7-O-benzoyl ceanothic acid methylester (2), along with nine known compounds (3–11), were isolated from the roots of Colubrina asiatica. The isolated compounds were identified by spectroscopic evidence. Compounds 1 and 2 showed antimalarial activity against Plasmodium falciparum with IC₅₀ values of 4.67 and 3.07?µg/mL, respectively. Compound 2 also showed antimycobacterial activity against Mycobacterium tuberculosis (MIC 6.25?µg/mL). In addition, compounds 1, 2, 10 and 11 showed cytotoxicity against three cancer cell lines (KB, NCI-H187 and MCF-7) with IC₅₀ values ranging from 8.32 to 46.72?µg/mL.     

Atalantums H-K from the peels of Atalantia monophylla and their cytotoxicity

Abstract

Four new benzoyltyramines, atalantums H-K (1–4) and seven known compounds were isolated from the peels of Atalantia monophylla. All compounds were tested for cytotoxicity against HeLa, HCT116 and MCF-7 cell lines, as well as normal cells (Vero cells). Compound 5 showed cytotoxicity against HeLa, HCT116 and MCF-7 cell lines with IC₅₀ values ranging from 16-25?μg/mL but was inactive against Vero cells. Compound 6 also showed interesting results as compound 5 with IC₅₀ values ranging from 15-18?μg/mL and an IC₅₀ value of 80.20?μg/mL against Vero cells. This means compounds 5 and 6 can be used as lead compounds for anticancer agents.     

A new abietane diterpenoid glycoside from ajuga ovalifolia var. calantha

A new abietane diterpenoid glycoside, ajugaside B (1), along with three known compounds (2–4), were isolated from the whole plants of Ajuga ovalifolia var. calantha. The structure of the new compound (1) was elucidated by means of spectroscopic analyses (HRESIMS, IR, NMR and ECD). All of the isolated compounds were evaluated for their antitumor activities against MGC803, MCF-7, A549, HT29 and HepG2 cell lines. Compounds 3–4 showed moderate cytotoxicity against all tested cell lines with IC₅₀ values of 1.8–7.3?μM.     

A new phenolic glycoside from Saprosma merrillii

A new phenolic glycoside derivative, saproglucoside (1), along with five known phenolic glycoside derivatives (2–6) were isolated from the stems of Saprosma merrillii. The structure of the new compound 1 was determined by 1D and 2D NMR as well as by HRESIMS and hydrolysis. The inhibitory activities of all compounds against seven pathogenic bacteria and two cancer cell lines were evaluated.     

Cytotoxic triquinane-type sesquiterpenoids from the endophytic fungus Cerrena sp. A593

Abstract

The culture broth of Cerrena sp. A593, which was isolated from Pogostemon cablin, showed potent cytotoxicity against several human tumor cell lines. The following chemical study resulted in the isolation of two new triquinane-type sesquiterpenoids, named cerrenins D (1) and E (2), along with two known compounds plerocybellone A (3) and chloriolin B (4). Their structures were fully assigned with the aid of extensive spectroscopic analysis (¹H and ¹³C NMR, HSQC, HMBC, ¹H-¹H COSY, HRESIMS, and IR) and data from the literature. Moreover, cytotoxic activity in vitro of compounds 1–4 were evaluated against SF-268, MCF-7, NCI-H460, and HepG-2 tumor cell lines. The new compound 1 exhibited weak growth inhibitory activity against all the four tumor cell lines with IC₅₀ values of 41.01, 14.43, 29.67, 44.32?μM.     

Two novel prenylated kaempferol derivatives from fresh bud’s fur of Platanus acerifolia and their anti-proliferative activities

Two novel prenylated kaempferol derivatives (1, 2), together with seven known metabolites were isolated from ethanol extract of fresh Platanus acerifolia bud’s fur by multistep chromatographic processing. Structure of compounds 1 and 2 was confirmed by 1D, 2D NMR spectra and HR-ESI-MS. In addition, compound 1 was further analysed by X-ray crystallography. Anti-proliferative activities in vitro against human breast carcinoma (MCF-7) and human hepatocellular carcinoma (Hep-G2) cell lines for compound 1, 2 and 8 were evaluated. Compound 1 exhibited cytotoxic activity towards MCF-7 and Hep-G2 cell lines with the IC₅₀ values 38.2 and 39.5 μM, respectively. Moreover, compound 2 showed weak cytotoxic activities against the two cell lines.     

Insecticidal,cytotoxic and anti-phytopathogenic fungal activities of chemical constituents from the aerial parts of Ferula sinkiangensis

Abstract

A new rare monoterpene coumarin (1) and its two known analogues (2–3), together with two sesquiterpenes (6–7) and ferulic acid (8) were isolated from the aerial parts of Ferula sinkiangensis. The structure of new compound was established on the basis of 1D and 2D NMR data and HRESIMS data interpretation. Insecticidal, cytotoxic and anti-phytopathogenic fungal activities of isolated compounds were evaluated against third-instar larvae of Spodoptera exigua and its cell line, and three plant pathogenic fungi respectively. Compounds 1–3 and 6–7 were found to be more effective contact toxicity to S. exigua with the corrected mortality values of 38.89%-58.89% at 10?μg/larva doses for 24?h. Further studies showed that compounds 3 and 6 exhibited cell growth inhibitory activity against S. exigua cell line with the EC₅₀ values of 22.78 and 14.64?µM for 72?h. In addition, compound 6 exhibited potent antifungal activity with MICs?=?16–32?µg/mL.     

Amide derivatives of 4-azaindole: Design,synthesis, and EGFR targeting anticancer agents

Abstract

A series of amide derivatives of azaindole-oxazoles (11a-n) were designed and synthesized and their structures were confirmed by ¹HNMR, ¹³CNMR and mass spectral analysis. Further, these derivatives were screened for their anticancer activity against human cancer cell lines viz; MCF7 (breast), A549 (lung) and A375 (melanoma). In vitro anticancer activity screening indicated that most of the hybrids exhibited potent inhibitory activities in a variety of cancer cell lines. Among the compounds 11d, 11e, 11f, 11j, 11k, 11l, 11m, and 11n were exhibited more potent activity than standard, in those mainly two compounds 11m and 11j were exhibited excellent activity in MCF-7 cell line with IC₅₀ values 0.034 and 0.036?µM. Moreover, all these compounds were carried out their molecular docking studies on EGFR receptor results indicated that two potent compounds 11m and 11j were strongly binds to protein EGFR (PDB ID: 4hjo). It was found that the energy calculations were in good agreement with the observed IC₅₀ values.     

Secondary metabolites from marine-derived Streptomyces antibioticus strain H74-21

A new secondary metabolite, (2S,3R)-l-threonine, N-[3-(formylamino)-2-hydroxybenzoyl]-ethyl ester (streptomyceamide C, 1), together with four known compounds 1, 4-dimethyl-3-isopropyl-2,5-piperidinedione (2), cyclo-((S)-Pro-8- hydroxy-(R)-Ile (3), cyclo-((S)-Pro-(R)-Leu (4), and seco-((S)-Pro-(R)-Val) (5), were isolated from the EtOH extract of the fermented mycelium of the marine-derived streptomycete strain H74-21, which was isolated from sea sediment in a mangrove site. The structure of the new compound was established on the basis of its spectroscopic data, including 1D and 2D NMR, HR-TOF-MS. Their antifungal activities against Candida albicans and cytotoxicities against human breast adenocarcinoma cell line MCF-7, human glioblastoma cell line SF-268 and human lung cancer cell line NCI-H460 were tested. Compounds 1 only displayed cytotoxicity against human breast adenocarcinoma cell line MCF-7 with the IC₅₀ value of 27.0 μg/mL. However, compounds 1–5 do not show antifungal activities at the test concentration of 1 mg/mL, and 2–5 have no cytotoxicities at the test concentration of 50 μg/mL.     

A new 5-alkylresorcinol glucoside derivative from Cybianthus magnus

One new 5-alkylresorcinol glucoside (1) was isolated from leaves of Cybianthus magnus, along with 12 known compounds, isolated from four plants belonging to Myrsinaceae family (2, 3 isolated from C. magnus; 4–7, 10 and 11 isolated from Myrsine latifolia; 4, 8 and 9 isolated from Myrsine sessiflora; 6, 7, 10, 12 and 13 isolated from Myrsine congesta). Their structures were determined on the basis of spectroscopic analysis and by comparison of their spectral data with those reported in the literature. So far, only nine 5-alkylresorcinol glucosides were isolated from leaves of Grevillea robusta. Since resorcinols are known to exhibit strong cytotoxic activity, compounds 1 and 2 were tested against cell lines 3T3, H460, DU145 and MCF-7 for cytotoxicity in vitro and compounds 3–13 were tested for their antileishmanial activity. Compound 2 displayed a strong cytotoxic activity with IC₅₀ values ranging between 22 and 100 μM for all tested cell lines. Compounds 3–13 were not active against Leishmania amazonensis amastigotes.     

Chemical characterization of constituents from Polygonatum cyrtonema Hua and their cytotoxic and antioxidant evaluation

Abstract

Twenty-four compounds were isolated from the roots of Polygonatum cyrtonema Hua, including a new octopamine dimer, named trans-bis(N-feruloyl)octopamine (1). The structure was established on the basis of spectroscopic and chemical methods. All the extracts and compounds were evaluated for cytotoxic and antioxidant activities by using MTT and chemiluminescence assay. The extracts showed activity against MCF-7 and HepG-2 cell lines from IC₅₀ 0.30 to 1.01 mg mL^?1. Compound 3 exhibited activity against HepG-2 cell lines with IC₅₀ 8.99?μM. Compound 7 exhibited activity against Hela cell lines with IC₅₀ 2.53?μM and BGC-823 cell lines with IC₅₀ 7.77?μM. Moreover, compound 7 showed antioxidant with IC₅₀ 12?µM compared to the positive control with IC₅₀ 77?µM. Compound 16 exhibited activity against HepG-2 cell lines with IC₅₀ 1.05?μM and MCF-7 cell lines with IC₅₀ 1.89?μM. These results indicated that this plant might be potential in natural medicine and healthy food.