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

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.

Two new daphnane diterpenes from the roots of Stelleropsis tianschanica.

Two new daphnane diterpenes named tianchaterpenes A and B were isolated from the roots of Stelleropsis tianschanica. Their structures were elucidated on the basis of chemical and spectral analysis, including 1D, 2D NMR analyses and HRESIMS. Compounds 1 and 2 were evaluated for their cytotoxic activities against HeLa and HCT-8 cell lines. The results showed that all compounds displayed weak cytotoxicities to the HeLa cells and were inactive to the HCT-8 cells.

Triterpenoid saponins from Clinopodium chinense (Benth.) O. Kuntze and their biological activity.

Four new ursane-type triterpenoid saponins, clinopoursaponins A-D (1-4), six new oleanane-type triterpenoid saponins, clinopodiside VII-XII (5-10), as well as eight known triterpene analogues (11-18), were isolated from the aerial parts of Clinopodium chinense (Benth.) O. Kuntze. The structures of the new compounds were determined based on extensive spectral analyses, including 1D (1H and 13C) and 2D NMR experiments (COSY, NOESY, HSQC, 2D TOCSY, HSQC-TOCSY and HMBC), HR-ESI-MS and chemical methods. Compounds 1-18 were evaluated for their protective effects against anoxia/reoxygenation-induced apoptosis in H9c2 cells and cytotoxicities against murine mammary carcinoma cell line 4T1. Compounds 8, 9 and 18 exhibited significant protective effects, while compound 1 exhibited cytotoxic activity with IC50 value of 7.4 µm compared to 7.6 µm for the positive control 10-hydroxycamptothecin.

Cassane-type diterpenes from Caesalpinia minax induce apoptosis in pituitary adenoma: structure-activity relationship, ER stress and Wnt/ß-catenin pathways.

Plant-derived natural products have been the highly significant sources of novel antitumor agents. The cassane-type diterpenes of genus Caesalpinia have been reported to bear antiproliferative activities toward different types of cancer cells. In this study, we evaluated the antineoplasmic activities of 16 natural origin cassane-type diterpenes isolated from the CHCl3 extract of the seeds of C. minax in pituitary adenomas cells and identified caesalpin G (CAG) showed the strongest cytotoxicity. Moreover, we further investigated the structure-activity relationship and molecular mechanism of these derivatives systematically. The results confirmed the unsaturated lactone-type ring, hydroxyl at C-7, and alkenyl at C-11 or C-14 functionality as critical for anticancer activity in this family of natural products. In addition, the mechanism experiments also demonstrated unfolded protein response and ER stress and Wnt/ß-catenin pathway were involved in the CAG-induced apoptosis.

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.

The new steroidal glycosides from the aerial parts of Lepidogrammitis drymoglossoides.

Two new steroidal glycosides ponasteroside C (1) and ponasteroside D (2) were isolated from the aerial parts of Lepidogrammitis drymoglossoides. Their structures were elucidated by various spectroscopic techniques (IR, HRESIMS, 1D and 2D NMR). All compounds were evaluated for their cytotoxicity against HeLa and HCT-8 cell lines, and compounds 1 and 2 showed mild activity against all the test cell lines.

A new sesquiterpenoid quinone with cytotoxicity from Abelmoschus sagittifolius.

A new sesquiterpenoid quinone, Acyl hibiscone B (1), together with five known compounds, (R)-lasiodiplodin (2), (R)-de-O-methyllasiodiplodin, (3) dibutyl phthalate (4), (R)-9-phenylnonan-2-ol (5) and hibiscone B (6), was obtained from the stem tuber of Abelmoschus sagittifolius. The structure of compound 1 was elucidated by analysing its (1)H and (13)C NMR, (1)H-(1)H COSY, HSQC, HMBC, NOESY and HR-ESI-MS values. Compound 1 showed significant cytotoxicity against Hela and HepG-2 human cancer cell lines.

A new drimane sesquiterpenoid and a new triterpene lactone from fungus of Fomes officinalis.

A new sesquiterpenoid fomeffic acid (1) and a new triterpene lactone fomefficinin (2) were isolated from the fungus Fomes officinalis, together with another six known compounds fomitopsin C (3), dehydrosulfurenic acid (4), dehydroeburiconic acid (5), dehydroeburicoic acid (6), 3-keto-dehydrosulfurenic acid (7), and laricinolic acid (8). The structures and stereochemistry of 1 and 2 were determined by NMR and X-ray diffraction analyses. The sesquiterpenoid and five triterpenes were tested for cytotoxicity against HL-60, Bel-7402, and KB cancer lines in vitro, and they appeared to be modestly active.

Norcassane- and cassane-type furanoditerpenoids from the seeds of Caesalpinia sappan.

Three novel furanoditerpenoids, norcaesalpinin J (1) featuring an unusual 20-norcassane hydroperoxide and phangininoxys B (2) and C (3) possessing cassane hemiketal skeletons, were isolated from the seeds of Caesalpinia sappan. Their structures were elucidated by extensive spectroscopic methods. All isolates were evaluated for the cytotoxic activities on three human cancer cell lines.

A new ursane-type triterpene, cymosic acid from Rosa cymosa.

A new ursane-type triterpene, cymosic acid (1) together with two known compounds, 3ß,19α-dihydroxy-2-oxo-12-ursen-28-oic acid (2) and 2α,19α-dihydroxy-3-oxo-12-ursen-28-oic acid (3), were isolated from Rosa cymosa Tratt. The structure of compound 1 was elucidated by analyzing its ¹H and ¹³C NMR, ¹H-¹H COSY, HSQC, HMBC, NOESY, and HR-ESI-MS values. The three compounds were found to display moderate inhibitory activities against nitric oxide production in lipopolysaccharide-activated macrophage cell lines, RAW 264.7 cells.

Novel dinorcassane- and cassane-type diterpenes from the seeds of Caesalpinia minax.

Two novel diterpenes, norcaesalpinin I (1) featuring an unusual ring C-contracted dinorcassane and caesalpinin U (2) possessing a highly oxygenated furanocassane skeleton were isolated from the seeds of Caesalpinia minax. Their structures were determined by different spectroscopic methods. A plausible biosynthetic pathway of 1 was proposed. The cytotoxic activity of compounds 1 and 2 against HepG2 and HeLa human tumor cell lines was evaluated.

Four new diterpenes from Aphanamixis polystachya.

Four novel diterpenes possessing rare five-membered peroxide ring, aphanaperoxides E-H (1-4), were isolated from stem bark of Aphanamixis polystachya. Their structures including the absolute configuration were elucidated by spectroscopic data and CD analysis. The cytotoxicities of the isolated compounds against a panel of human cancer cell lines were evaluated.

A new sesquiterpene lactone from Sarcandra glabra.

A new eudesmanolide sesquiterpene, atractylenolide IV (1), together with seven known compounds were isolated from the 70% aqueous acetonic extract of the whole plant of Sarcandra glabra (Chloranthaceae). Their structures were established by spectral analysis, mainly UV, IR, HRESI-MS, 1D and 2D-NMR experiments (HSQC, HMBC and NOESY). Compounds 1-4 showed no remarkable cytotoxic activity against Hela, HCT-8 and MCF-7 cancer cell lines with IC50 > 50 µg mL(-1).

Two new diterpenes from Caesalpinia minax Hance.

Two new cassane-type diterpenes, Caesalpinolide F (1) and Caesalpinolide G (2) were isolated from Caesalpinia minax Hance. Their structures were elucidated on the basis of 1D and 2D NMR, MS and CD analysis. Compounds 1 and 2 were tested against colon carcinoma (HCT-8) and breast cancer (MCF-7) human cancer cell lines, and showed mild cytotoxicity activities.

Two new diterpenes, neocaesalpin MR and minaxin C, from Caesalpinia minax.

Two new cassane-type diterpenes, neocaesalpin MR and minaxin C, were isolated from Caesalpinia minax HANCE. The structures of these compounds were elucidated by means of spectroscopic analysis. Among these isolated compounds, neocaesalpin MR showed mild activities toward HeLa and colon cancer (HCT-8) human cancer cell lines.

Cassane-type diterpenes from the seeds of Caesalpinia minax with their antineoplastic activity.

Five new cassane-type diterpenes, neocaesalpin AA (1), neocaesalpin AB (2), neocaesalpin AC (3), neocaesalpin AD (4) and neocaesalpin AE (5), were isolated from Caesalpinia minax together with three known compounds, 12α-methoxyl,5α,14ß-dihydroxy-1α,6α,7ß-triacetoxycass-13(15)-en-16,12-olide (6), spirocaesalmin (7) and magnicaesalpin (8). Their structures were elucidated based on 1D and 2D NMR, MS and CD analyses. Compounds 1-6 were tested against Hela, HCT-8, HepG-2, MCF-7 and A549 cancer cells and showed moderate cytotoxicity with IC50 values from 18.4 to 83.9 µM.

The new cassane-type diterpenes from Caesalpinia minax.

Four new cassane-type diterpenes, Neocaesalpin S (1), Neocaesalpin T (2), Neocaesalpin U (3), and Neocaesalpin V (4) were isolated from Caesalpinia minax HANCE together with seven known compounds Neocaesalpin A (5), Neocaesalpin K (6), Neocaesalpin L (7), Neocaesalpin M (8), Neocaesalpin O (9), Neocaesalpin MP (10), and Magnicaesalpin (11). Their structures were elucidated on the basis of 1D- and 2D-NMR, MS, and circular dichroism (CD) analysis. Compounds 1-4 were tested against liver cancer (HepG-2) and breast cancer (MCF-7), and showed mild antiproliferative activity.

Laevigatbenzoate from Croton laevigatus Vahl.

A new trans-clerodane diterpenoid, laevigatbenzoate (1), was isolated from the leaves of Croton laevigatus Vahl. Its structure was established on the basis of spectroscopic analysis, and the absolute configuration was determined by application of the CD excitation chirality method. This compound showed weak cytotoxicity against HeLa cells, with an IC(50) value of 45.4 µM.

Lactonecembranoids from Croton laevigatus.

Six new cembranoids, laevigatlactones A-F (1-6), and the known compound neocrotocembraneic acid (7) were isolated from leaves of Croton laevigatus. Their structures were elucidated on the basis of spectroscopic analysis, and that of 1 was confirmed by X-ray crystallography. Compound 2 exhibited modest cytotoxicity against HeLa cells, with an IC(50) value of 38.4 microM.