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.

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.

No abstract

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). (Cancer Sci 2010; 101: 2110-2114 V accine therapies have long been used for the prevention of infectious diseases. However, recent advances in immunology and molecular pathology have led to the use of vaccines not only for the prevention but also for the treatment of allergies, (1,2) autoimmune diseases, (3)(4)(5) cancer, (6,7) Alzheimer disease, (8) and hypertension. (9) At the same time, the antigens in the vaccine formulas have expanded from whole microorganisms to fine molecules such as epitope peptides. There is, thus, a need for new adjuvants to be used in these new applications.Incomplete Freund's adjuvant (IFA) is one of the most famous adjuvants and is widely used for protein and peptide antigens to induce both humoral and cellular immunity in animals and humans. There are currently only two IFA formulas commercially available for clinical use: Montanide ISA51(VG) and ISA720 (products of Seppic, Paris, France).(10,11) Both Montanide ISA51(VG) and the original formula of IFA, consist of mineral oil and mannide monooleate.(10) Although pharmaceutical-grade (i.e. meeting the requirements of pharmacopeia such as the Japanese pharmacopeia and US pharmacopeia) mineral oil is commercially available, pharmaceutical-grade formulas of mannide monooleate, such as Montanide 80 (Seppic), are difficult to obtain, particularly for academic researchers. A highpurity oleic acid derivative, sorbitan monooleate (NOFABLE SO-991), has recently been made available, and its regulatory status meets the requirements of the Japanese pharmaceutical excipients. Therefore, we attempted to develop a new oil adjuvant formula for clinical use using a pharmaceutical grade mineral oil and sorbitan monooleate. In this paper, we investigated the effects of the new adjuvant on peptide vaccination at both the pre-clinical and clinical levels. Materials and ...

A new diphenyl ether glycoside, xylosmaloside (1), was isolated from the MeOH extract of Xylosma longifolium Clos. The structure of xylosmaloside (1) was elucidated using MS analyses, extensive 2D-homo and heteronuclear NMR data interpretation and the chemical conversions. Xylosmaloside (1) showed stronger antioxidant activity than ascorbic acid.