A new rearranged cholestane glycoside from Ornithogalum saundersiae bulbs exhibiting potent cytostatic activities on leukemia HL-60 and MOLT-4 cells

Bioorganic and Medicinal Chemistry Letters

Volumn 6, Issue 22, 1996, Pages 2635-2638

  Mimaki, Yoshihiro ^a   Kuroda, Minpei ^a   Kameyama, Aiko ^a   Sashida, Yutaka ^a   Hirano, Toshihiko ^a   Oka, Kitaro ^a   Dobashi, Akira ^a   Koike, Kazuo ^b   Nikaido, Tamotsu ^b  

^a TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

^b TOHO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; CHOLESTANE DERIVATIVE; DOXORUBICIN; ETOPOSIDE; GLYCOSIDE; METHOTREXATE;

ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; CELL PROLIFERATION; CONTROLLED STUDY; DRUG IDENTIFICATION; DRUG ISOLATION; HUMAN; HUMAN CELL; LEUKEMIA CELL; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; PLANT; TUMOR CELL; ULTRAVIOLET SPECTROPHOTOMETRY;

ORNITHOGALUM; ORNITHOGALUM SAUNDERSIAE;

EID: 0030593872     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(96)00486-6     Document Type: Article

References (12)

1. 1. Fresh bulbs of O. saundersiae (16.2 kg) were purchased from Heiwaen, Japan. The plant specimen is on file in our laboratory.
2. 2. The assay was carried out according to a modified method of Sargent and Tayler. Sargent, J. M.; Tayler, C. G. Br. J. Cancer, 1989, 60, 206.
3. 4 (11:1) to remove exchangeable protons and minimize signal overlap.
4. 4. The monosaccharides were identified by converting them to the 1-[(S)-N-acetyl-α-methylbenzylamino]-1-deoxyalditol acetate derivatives followed by HPLC analysis. Oshima, R.; Yamauchi, Y.; Kumanotani, J. Carbohydr. Res. 1982, 107, 169.
5. 13C NMR of 1: δ 37.4, 30.2, 78.0, 39.4, 141.4, 121.9, 32.6, 32.7, 50.1, 37.5, 23.0, 34.6, 57.7, 51.1, 29.8, 77.3, 53.3, 108.8, 19.8, 86.0, 27.8, 50.8, 90.9, 122.9, 134.8, 26.6 and 19.1 (C-1 - C-27), 55.5 (OMe), 100.5, 77.6, 79.7, 71.8, 78.5 and 62.7 (C-1′ - C-6′), 101.8, 72.6, 70.5, 76.8, 67.2 and 18.3 (C-1″ - C-6″), and 123.8, 132.5, 114.3, 164.0, 114.3, 132.5, 166.6 and 55.6 (C-1‴ - C-7‴, OMe).
6. 6. Kuroda, M.; Mimaki, Y.; Sashida, Y.; Nikaido, T.; Ohmoto, T. Tetrahedron Lett. 1993, 34, 6073.
7. 7. Haasnoot, C. A. G.; Leeuw, F. A. A. M. De; Altona C. Tetrahedron 1980, 36, 2783.
8. 8. Kuroda, M.; Mimaki, Y.; Sashida, Y.; Hirano, T.; Oka, K.; Dobashi, A. Chem. Pharm. Bull. 1995, 43, 1257.
9. C,H=5 Hz and 8 Hz. The 4″-H proton of the rhamnose, however, was shifted downfield by 1.91 ppm in comparison of that of a steroidal saponin bearing the same saccharide sequence as 1 isolated by us from an Allium plant. This is believed to be a confirmative evidence for the ester linkage position.
10. 10. Compound 1 efficiently induced morphological changes characteristic of apoptosis in HL-60 cells. Untreated cells exhibited typical non-adherent, fairly round morphology. Wright, S. C.; Kumar, P.; Tam, A. W.; Shen, N.; Varma, M.; Larrick, J. W. J. Cellular Biochem. 1992, 48, 344.
11. 11. DNA fragmentation has been known as a characteristic feature of apoptosis. Wyllie, A. H.; Kerr, J. F.; Currie, A. R. Int. Rev. Cytol., 1980, 68, 251.
12. 2+ inhibits the enzyme activities which results in blocks of apoptosis. Duke, R. C.; Chervenak, R.; Cohen, J. J. Proc. Natl. Acad. Sci. 1983, 80, 6361.