Aim To obtain more valuable derivatives for the further structural modification of 6β-santonin (1) via biotransformation by using cell suspension cultures of Phytolacca acinosa. Methods The substrate 1 was incubated with cell suspension cultures of P.acinosa, the products were obtained by chromatography, and identified on the basis of their physical and spectral data (HRMS, 1D NMR, 2D NMR, NOE and IR). Results After incubation with cell suspension cultures of P.acinosa, 1 was converted into five products (2-6). Among them, 3 is a new compound. Conclusion 6β-santonin could be selectively reduced and hydroxylated by the cell suspension cultures of P.acinosa, which would provide valuable intermediates for its further structural modification.

Object To investigate the biotransformation of cantharidin by cell suspension cultures of Platycodon grandiflorus (Jacq ) A DC Methods Cantharidin was added into cell suspension cultures of P grandiflorus and incubated for another six days The culture supernatant was extracted with EtOAc and then subjected to silica gel chromatography Results Two products were isolated as a mixture in a molar ratio of about 2∶1 Their structures were identified on the basis of spectroscopic data as 1? OH cantharidin (Ⅱa) and 1? OH cantharidin (Ⅱb) The relative configuration was elucidated according to NOESY spectrum Conclusion The two products were new cantharidin derivatives

Aim To investigate the anti-neuroinflam-matory activities of dehydromiltirone and the underlying mechanisms in LPS-stimulated microglial cell line BV2 cells. Methods BV2 cells were pre-treated with de-hydromiltirone, then stimulated by LPS. The levels of nitric oxide( NO) were measured by Griess assay, and the concentrations of pro-inflammatory cytokines were measured by ELISA assay. Confocal fluorescence mi-croscopy was used to measure the expression of MAC-1, the biomarker of activated BV2 cells. The levels of-inducible nitric oxide synthase ( iNOS ) , cyclooxygen-ase-2 ( COX-2 ) , NF-κB and PI3 K/Akt were deter-mined by Western blot analysis. Results The treat-ment of dehydromiltirone significantly inhibited the pro-duction of NO, TNF-α and IL-6, attenuated the ex-pression of iNOS and COX-2 protein, and dampened the microglial activation in LPS-stimulated BV2 cells. The mechanistic study revealed that dehydromiltirone inhibited the phosphorylation of PI3 K and Akt in LPS-stimulated BV2 cells, and decreased NF-κB activation by suppressing the degradation of IκB. Conclusion dehydromiltirone shows significant anti-neuroinflamma-tory effects through inhibiting PI3 K/Akt phosphoryla-tion and then inhibiting NF-κB signaling pathway.

Seven meroterpenoids and five small-molecular precursors were isolated from Penicillium sp., an endophytic fungus from Dysosma versipellis. The structures of new compounds, 11beta-acetoxyisoaustinone (1) and isoberkedienolactone (2) were elucidated based on analysis of the spectral data, and the absolute configuration of 2 was established by TDDFT ECD calculation with satisfactory match to its experimental ECD data. Meroterpenoids originated tetraketide and pentaketide precursors, resepectively, were found to be simultaneously produced in specific fungus of Penicillium species. These compounds showed weak cytotoxicity in vitro against HCT-116, HepG2, BGC-823, NCI-H1650, and A2780 cell lines with IC 50 > 10 micromol x L(-1).

The prenylation of aromatic compounds plays an important role in the natural product research because it not only gives rise to an astounding diversity of primary and secondary metabolites in plants, fungi and bacteria but also enhances the bioactivities and bioavailabilities of these compounds. However, further investigation of prenylated aromatic compounds is frequently hindered due to their low content in nature and difficulties in chemical synthesis. Cloning aromatic prenyltransferase genes followed by heterologous expression would be attractive tools for the chemoenzymatic synthesis of bioactive molecules. This review summarizes the classifications, structural investigations, enzymatic catalysis and other progress in aromatic prenyltransferases originated from microorganisms.

The tumor multidrug resistance reversal effect of NPB304, a novel taxane, was studied. MTT assay was used to determine the IC50 of chemotherapy drugs. Western blotting assay was applied to analyze the expression of P-glycoprotein (P-gp). The effect of compounds on the P-gp function and P-gp ATPase activity was determined by rhodamine 123 (Rh123) accumulation assay and analysis kit, respectively. Molecular docking was employed to predict the binding force between compounds and P-gp. Transmembrane transport of NPB304 was analyzed using MDCK II and MDR1-MDCK II cell model. NPB304 displayed multidrug resistance reversal effect on KBV cells and MCF-7/paclitaxel cells, NPB304 collaborative with P-glycoprotein (P-gp) inhibitors verapamil enhanced the reversal activity, specifically, 10 μmol x L(-1) verapamil in combination with paclitaxel reversed resistance by 56.5-fold, while combined with NPB304 increased the reversal fold; NPB304 synergistically increased Rh123 accumulation in the resistant cells when combined with verapamil, and NPB304 at 0-1 μmol x L(-1) enhanced the ATPase activity activated by verapamil was observed. NPB304 existed the hydrophobic interactions with the TM regions of P-gp, and the binding force between NPB304 and the A chain of the TM region was stronger. P-gp ATPase activity assay demonstrated NPB304 at lower concentrations (0-1.5 μmol x L(-1)) could activate the P-gp ATPase, playing a role on inhibition of P-gp function. However, NPB304 did not have an obvious feature of P-gp substrate. NPB304 exerted itself and synergy with verapamil activity on reversing tumor resistance via inhibiting the P-gp function.

Column chromatography on silica gel, Sephadex LH-20, semi-preparative HPLC were used to separate and purify the compounds from the petroleum ether and ethanol extract of Chinese eaglewood. Nine compounds were isolated. On the basis of their spectroscopic data, their structures were identified as dehydroabietic acid (1), methyl dehydroabietate (2), methyl 7-oxodehydroabietate (3), 7alpha, 15-dihydroxydehydroabietic acid (4), 7alpha-hydroxypodocarpen-8(14)-en-13-on-18-oic acid (5), pimaric acid (6), pimarol (7), 18-norpimara-8 (14), and 15-dien-4alpha-ol (8), 18-norisopimara-8 (14), 15-dien-4beta-ol (9). All of the compounds were isolated from this plant for the first time, and compounds 5, 8 and 9 are norditerpenoids.
Diterpenes ; chemistry ; isolation & purification ; Drugs, Chinese Herbal ; chemistry ; isolation & purification ; Plants, Medicinal ; chemistry ; Thymelaeaceae ; chemistry

The column chromatography on silica gel, semi-preparative HPLC were used to separate and purify the compounds from the petroleum ether and ethanol extract of Aquilaria sinensis. Nine compounds were isolated. On the basis of their spectroscopic data, the structures were identified as 3, 3, 7-trimethyltricycloundecan-8-one (1), longifolene (2), norlongilactone (3), caryophyllenol-II (4), humulene diepoxide A (5), kobusone (6), (-)-bornyl ferulate (7), (24R) -24-ethylcholesta-4, 22-dien-3-one (8), (24R)-24-3-ono-4-en-sitosterone (9). Compounds 2-9 were isolated from this plant for the first time. compounds 1-6 are sesquiterpenes, compound 7 is a monoterpene derivative, compound 8 and 9 are steroids.
Chromatography ; methods ; Drugs, Chinese Herbal ; chemistry ; isolation & purification ; Medicine, Chinese Traditional ; Monoterpenes ; chemistry ; isolation & purification ; Sesquiterpenes ; chemistry ; isolation & purification ; Thymelaeaceae ; chemistry

OBJECTIVETo search for new antitumor active lead compounds from marine microorganism.

METHODA marine strain, Aspergillus terreus, was cultured and up-scaled in artificial seawater media, from which the metabolites were isolated and elucidated by using modern spectroscopy techniques.

RESULTTwelve compounds were isolated from mycelia and fermentation broth of A. terreus.

CONCLUSIONCompounds 1-4 were steroids, compounds 5-8 were organic acids and esters, compound 9 was an alkaloid, compound 10 was an isocoumarin, compound 11 was ceramide, compound 12 was propenyl cyclic pentanediol.

Alkaloids ; chemistry ; isolation & purification ; metabolism ; Aspergillus ; chemistry ; metabolism ; Ceramides ; chemistry ; isolation & purification ; metabolism ; Culture Media ; chemistry ; metabolism ; Esters ; chemistry ; isolation & purification ; metabolism ; Isocoumarins ; chemistry ; isolation & purification ; metabolism ; Mycelium ; chemistry ; metabolism ; Propylene Glycols ; chemistry ; isolation & purification ; metabolism ; Rhizophoraceae ; microbiology ; Steroids ; chemistry ; isolation & purification ; metabolism

From callus cultures of Stellera chamaejasme, 17 compounds were isolated. Based on their physical and chemical data and spectroscopic analysis, they were identified as syringaresinol (1), medioresinol (2), pinoresinol (3), (1R, 2S, 5R, 6S)- 2-(4- hydroxyphenyl)-6-(3-methoxy-4-hydroxyphenyl)-3, 7-dioxabicyclo [3, 3, 0] octane (4), epipinoresinol (5), caruilignan D (6), 3-oxo-guai-4-ene-11, 12-diol (7), (-) -lariciresinol (8), tetrahydro-2-(4-hydroxy-3-methoxyphenyl)-4-[(4-hydroxyphenyl) methyl]-3-furanmethanol (9), 5'-methoxylariciresinol (10), vladinol D (11), cyclo (L-Pro-L-Val) (12), oxomatairesinol (13), (+) -guayarol (14); acutissimalignan B (15), isolariciresinol (16), and beta-sitosterol (17), respectively. Among these compounds, 12 was a cyclodipeptide, 7 was a sesquiterpene, and the others except 17 were lignans. All compounds were first isolated from callus cultures of S. chamaejasme.
Lignans ; analysis ; Thymelaeaceae ; chemistry