ABSTRACT
Seven undescribed guaiane-type sesquiterpenoids named biscogniauxiaols A-G (1-7) were isolated from the endophytic fungus Biscogniauxia petrensis on Dendrobium orchids. Their structures were determined by extensive spectroscopic analyses, electronic circular dichroism (EC) and specific rotation (SR) calculations. Compound 1 represented a new family of guaiane-type sesquiterpenoids featuring an unprecedented [5/6/6/7] tetracyclic system. A plausible biosynthetic pathway for compounds 1-7 was proposed. The anti-fungal, anti-inflammatory and multidrug resistance reversal activities of the isolates were evaluated. Compounds 1, 2 and 7 exhibited potent inhibitory activities against Candida albicans with MIC values ranging from 1.60 to 6.30 µM, and suppressed nitric oxide (NO) production with IC50 ranging from 4.60 to 20.00 µM. Additionally, all compounds (100 µg/mL) enhanced the cytotoxicity of cisplatin in cisplatin-resistant non-small cell lung cancer cells (A549/DDP). This study opened up a new source for obtaining bioactive guaiane-type sesquiterpenoids and compounds 1, 2, and 7 were promising for further optimization as multifunctional inhibitors for anti-fungal (C. albicans) and anti-inflammatory purposes.
ABSTRACT
Induced water hyacinth with purple roots (PRWH) exerts a significant inhibitory effect on the growth of blue-green algae. Interestingly, its chemical constituents differ from those of wild-type water hyacinth and have not yet been reported. This study aimed to explore the chemical constituents of PRWH and its bioactive components serving as allelopathic agents against blue-green algae. Phytochemical investigation of the bioactive ethyl acetate fraction of a crude methanol extract from PRWH led to the isolation of 56 compounds, including 11 new phenylphenalene derivatives. The structures of these compounds were elucidated by comprehensive analyses through NMR, HRMS, and X-ray techniques. Bioactivity evaluation against Microcystis aeruginosa indicated that compounds 7, 12, 15, 37, 39, 45, and 47 potently inhibited blue-green algae growth.
Subject(s)
Allelopathy , Eichhornia/chemistry , Microcystis/drug effects , Plant Extracts/pharmacology , China , Molecular Structure , Phytochemicals/pharmacology , Plant Roots/chemistryABSTRACT
Two new pyrazinoquinazoline alkaloids, epi-fiscalin D (1) and epi-fiscalin E (2), as well as three known analogues, norquinadoline A (3), quinadoline A (4), and fiscalin C (5), were isolated from ethyl acetate extract of the fermentation broth of Stentrophomonas maltophilia QB-77. The structures of new compounds were elucidated on the basis of extensive spectroscopic data analysis including UV, HRESIMS, and 1D and 2D NMR experiments. All the isolated compounds were tested for their in vitro cytotoxicity against five human cancer cell lines (SMMC-7721, MCF-7, HL-60, SW480, and A-549) and antibacterial activities against Bacillus subtilis, Escherichia coli, and Staphylococcus aureus.
Subject(s)
Alkaloids/chemistry , Alkaloids/pharmacology , Anti-Bacterial Agents/pharmacology , Antineoplastic Agents/pharmacology , Stenotrophomonas maltophilia/chemistry , Alkaloids/isolation & purification , Anti-Bacterial Agents/chemistry , Antineoplastic Agents/chemistry , Bacillus subtilis/drug effects , Cell Line, Tumor , Drug Evaluation, Preclinical , Escherichia coli/drug effects , Fermentation , HL-60 Cells , Humans , Indoles/isolation & purification , Magnetic Resonance Spectroscopy , Molecular Structure , Quinazolines/isolation & purification , Spectrometry, Mass, Electrospray Ionization , Staphylococcus aureus/drug effects , Stenotrophomonas maltophilia/growth & developmentABSTRACT
Chemical investigation on the aqueous fraction of the stems of Epigynum cochinchinensis led to the isolation of a new pregnane glycoside named as epigycoside A (1) along with three known analogues (2-4). The structure of compound 1 was elucidated by means of spectroscopic techniques, including HRESIMS, and 1D and 2D NMR experiments. The immunosuppressive activity of 1 was evaluated by an in vitro model of concanavalin A-induced mice splenocytes proliferation. Compound 1 showed significant inhibitory activity in a dose-dependent manner, closer to the efficacy of positive control, dexamethasone, at a concentration of 50 µM.
Subject(s)
Apocynaceae/chemistry , Glycosides/isolation & purification , Immunosuppressive Agents/isolation & purification , Immunosuppressive Agents/pharmacology , Pregnanes/isolation & purification , Animals , Cell Proliferation/drug effects , Cells, Cultured , Dose-Response Relationship, Drug , Glycosides/chemistry , Glycosides/pharmacology , Immunosuppressive Agents/chemistry , Mice , Molecular Structure , Plant Stems/chemistry , Pregnanes/chemistry , Pregnanes/pharmacology , Spleen/cytologyABSTRACT
Seven new clerodane diterpenoids, dysoxydensins A-G (1-7), together with six known clerodanes, were isolated from Dysoxylum densiflorum. The structures of all the compounds were elucidated by extensive spectroscopic analysis. These compounds were evaluated for their cytotoxic activities against five human cancer cell lines, and compounds 2, 3, and 5 showed moderate cytotoxic activities.