ABSTRACT
Seven novel norcycloartane glycosides, maryloside A-G (1-7), were isolated from the leaves of Cymbidium Great Flower 'Marylaurencin', along with a known norcycloartane glycoside, cymbidoside (8). These structures were determined on the basis of mainly NMR experiments as well as chemical degradation and X-ray crystallographic analysis. The isolated compounds (1-6 and 8) were evaluated for the inhibitory activity on lipopolysaccharide (LPS) and interferon-γ (IFN-γ)-stimulated nitric oxide (NO) production in RAW 264.7 cells. Consequently, 1 and 3 exhibited moderate activity.
Subject(s)
Flowers/chemistry , Glycosides/chemistry , Orchidaceae/chemistry , Plant Leaves/chemistry , Cell Survival , Flowers/metabolism , Glycosides/isolation & purification , Magnetic Resonance Spectroscopy , Models, Molecular , Molecular Structure , Nitric Oxide/biosynthesis , Orchidaceae/metabolism , Plant Extracts/chemistry , Plant Extracts/isolation & purification , Plant Leaves/metabolismABSTRACT
During the search for new antitrypanosomal drug leads, four antitrypanosomal compounds, of three depsipeptides and one nortriterpenoid, were isolated from cultures of the mutant strain IU-3 of the insect pathogenic fungus Ophiocordyceps coccidiicola NBRC 100683. Their structures were identified by the analysis of high resolution-electron ionization (HR-EI)-MS and HR-FAB-MS, and (1)H- and (13)C-NMR spectra, including extensive two dimensional (2D)-heteronuclear NMR experiments, and comparison with literature data for destruxin A (1), destruxin B (2), destruxin E chlorohydrin (3) and helvolic acid (4). Compounds 1-4 showed in vitro antitrypanosomal activity against Trypanosoma brucei brucei GUTat3.1 with IC50 values of 0.33, 0.16, 0.061 and 5.08 µg/mL, respectively.
Subject(s)
Antiprotozoal Agents/pharmacology , Ascomycota/chemistry , Trypanosoma brucei brucei/drug effects , Antiprotozoal Agents/chemistry , Antiprotozoal Agents/metabolism , Ascomycota/metabolism , Dose-Response Relationship, Drug , Molecular Conformation , Parasitic Sensitivity Tests , Structure-Activity RelationshipABSTRACT
During the search for secondary metabolites with antiproliferative activity, six new lanostane triterpenoids, tyrosamic acids A-F (1-6) together with ten known compounds (7-16), were isolated from the fruiting body of Tyromyces sambuceus. Their structures were elucidated using MS analyses, extensive 2D-heteronuclear NMR data interpretation and the structure of 3 was further confirmed by single-crystal X-ray data analyses. All lanostane triterpenoids (1-16) possesses a carboxy group at C-20 position and their strength of antiproliferative activity was affected by the presence or absence of a hydroxy group at C-15 position and at the side chain. Four of the compounds (1, 6, 10, 14) showed antiproliferative activities against human cancer cell lines with IC50 values of 16.8-48.3 µM (HL-60).
Subject(s)
Antineoplastic Agents/pharmacology , Fruiting Bodies, Fungal/chemistry , Polyporaceae/chemistry , Triterpenes/chemistry , Antineoplastic Agents/chemistry , Cell Line, Tumor , Humans , Triterpenes/classificationABSTRACT
During the search for bioactive secondary metabolites, thelepalmatins A and B (1 and 2) were isolated from the fresh fruiting bodies of Thelephra palmata, together with four known compounds (3-6). Their structures were elucidated using MS analyses, and extensive 2D-heteronuclear NMR data interpretation. Compounds 3, 4 and 6 showed antimicrobial activities against Staphylococcus aureus and Bacillus subtilis with MIC values of 21.7-70.4 µM.
Subject(s)
Basidiomycota/chemistry , Fruiting Bodies, Fungal/chemistry , Phenols/chemistry , Molecular StructureABSTRACT
Two new phenanthrenes, and one new phenylpropanoid, named ephemeranthoquinone C (1), and marylaurencinols C (2) and D (3), were isolated from the roots of Cymbidium Great Flower 'Marylaurencin', respectively. These structures were determined on the basis of 2D NMR experiments. The compounds were tested for antimicrobial activity against Bacillus subtilis, Klebsiella pneumoniae, and Trichophyton rubrum.
Subject(s)
Anti-Infective Agents/chemistry , Orchidaceae/chemistry , Phenanthrenes/chemistry , Phenylpropionates/chemistry , Anti-Infective Agents/isolation & purification , Anti-Infective Agents/pharmacology , Flowers/chemistry , Phenanthrenes/isolation & purification , Phenanthrenes/pharmacology , Phenylpropionates/isolation & purification , Phenylpropionates/pharmacology , Plant Roots/chemistry , Quinones/chemistryABSTRACT
Two novel aromatic glucosides, named marylaurencinosides D (1) and E (2), were isolated from the fresh flowers of Cymbidium Great Flower 'Marylaurencin'. In addition, eight known aromatic compounds (3-10) were isolated. These structures were determined on the basis of NMR experiments as well as chemical evidence.
Subject(s)
Glucosides/chemistry , Orchidaceae/chemistry , Flowers/chemistry , Glucosides/isolation & purificationABSTRACT
Two new compounds named caryocanolide (1), and caryocanoside A (2), together with nine known compounds (3-11) were isolated from the whole plant of Caryopteris incana. These structures were determined mainly on the basis of 2D nuclear magnetic resonance and high resolution fast atom bombardment mass spectroscopy data. Furthermore, the isolated compounds (1, 2, 4-11) were tested for their antibacterial activity. Compound 1 exhibited moderate antimicrobial activity against Bacillus subtilis with a minimum inhibitory concentration value of 35.7 µM.
Subject(s)
Anti-Bacterial Agents/pharmacology , Plant Extracts/pharmacology , Verbenaceae , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/isolation & purification , Bacillus subtilis/drug effects , Bacillus subtilis/growth & development , Magnetic Resonance Spectroscopy , Microbial Sensitivity Tests , Models, Molecular , Molecular Structure , Phytotherapy , Plant Extracts/chemistry , Plant Extracts/isolation & purification , Plants, Medicinal , Spectrometry, Mass, Fast Atom Bombardment , Verbenaceae/chemistryABSTRACT
A new phenanthrendione, ephemeranthoquinone B (1), two phenanthrenes, marylaurencinols A (2) and B (3), and a phenanthrene glucoside, marylaurencinoside A (4), were isolated from the roots of Cymbidium Great Flower Marie Laurencin, along with six known phenanthrenes, 5-10. The structures of these compounds were established by a combination of extensive NMR spectroscopy and/or X-ray crystallographic analysis and chemical degradation. The compounds were tested for antibacterial activities against Bacillus subtilis and Klebsiella pneumoniae and for cytotoxic activity against the human promyelocytic leukemia (HL-60) cell line. Compounds 1, 3, and 6 showed antibacterial activities with minimum inhibitory concentration (MIC) values in the range of 4.88 to 65.10 µM. Notably, ephemeranthoquinone B (1) had a strong antibacterial effect on B. subtilis. Furthermore, 1 exhibited moderate cytotoxic activity (IC(50) 2.8 µM) against HL-60 cells. Compounds 4-9 also showed weak cytotoxic activity against the HL-60 cell line with IC(50) values of 19.3-52.4 µM.
Subject(s)
Antineoplastic Agents, Phytogenic/isolation & purification , Antineoplastic Agents, Phytogenic/pharmacology , Orchidaceae/chemistry , Phenanthrenes/isolation & purification , Phenanthrenes/pharmacology , Antineoplastic Agents, Phytogenic/chemistry , Crystallography, X-Ray , Drug Screening Assays, Antitumor , HL-60 Cells , Humans , Inhibitory Concentration 50 , Japan , Molecular Conformation , Molecular Structure , Phenanthrenes/chemistry , Plant Roots/chemistryABSTRACT
Vaccine therapies are increasingly being used for the treatment of various diseases, and the antigen molecules themselves are being expanded from whole microorganisms to fine molecules such as peptides. Accordingly, there is a need for new adjuvants to support these new applications. In this paper, we used pharmaceutical grade mineral oil and sorbitan monooleate to develop a new oil adjuvant formula, NH(2) , and investigated its effects on peptide vaccination at both the pre-clinical and clinical levels. The adjuvant effect of NH(2) on peptide-induced cellular immunity in mice was superior to that of Montanide ISA51VG, a commercially available incomplete Freund's adjuvant for clinical use, although no significant difference was observed between the two adjuvants on peptide-induced humoral immunity. The adjuvant effects of NH(2) were also confirmed in a Phase-I clinical trial of peptide vaccines for patients with advanced cancers. These results suggest that NH(2) is a suitable adjuvant for peptide vaccination, particularly for cancer vaccines (Phase-I clinical trial of pan-HLA type personalized peptide vaccine for advanced cancer patients, UMIN clinical trial registry number: UMIN 000000619).
