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Planta Med 1997; 63(3): 258-262
DOI: 10.1055/s-2006-957667
Papers
Natural Product Chemistry
© Georg Thieme Verlag Stuttgart · New York

Steroidal Saponins from Asparagus officinalis and Their Cytotoxic Activity

Yu Shao1 , 2 , Onoomar Poobrasert3 , Edward J. Kennelly3 , Chee-Kok Chin1 , Chi-Tang Ho2 , Mou-Tuan Huang4 , Stephen A. Garrison1 , Geoffrey A. Cordell3 , 3
  • 1Department of Plant Science, Cook College, Rutgers, The State University of New Jersey, New Brunswick, NJ 08903, U.S.A.
  • 2Department of Food Science, Cook College, Rutgers, The State University of New Jersey, New Brunswick, NJ 08903, U.S.A.
  • 3Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The University of Illinois at Chicago, Chicago, IL 60612, U.S.A.
  • 4Department of Chemical Biology, Laboratory for Cancer Research, College of Pharmacy, Rutgers, The State University of New Jersey, Piscataway, NJ 08855, U.S.A
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Publication History

1996

1996

Publication Date:
04 January 2007 (online)

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Abstract

Two oligofurostanosides were isolated from the seeds of Asparagus officinalis L. and their structures characterized as 3-O-[α-L-rhamnopyranosyl-(1→2)-{α-L-rhamnopyranosyl-(1→4)}-β-D-glucopyranosyl]-26-O-[β-D-glucopyranosyl]-(25R)-22α-methoxyfurost-5-ene-3β,26-diol (methyl protodioscin) and its corresponding 22α-hydroxy analogue (protodioscin). The structural identification was performed using detailed analysis of 1H-and 13C-NMR spectra including two-dimensional NMR spectroscopy (COSY, HMQC, NOESY and HMBC), and chemical conversions. These two compounds have been shown to inhibit the growth of human leukemia HL-60 cells in culture and macro-molecular synthesis in a dose-dependent manner. The inhibitory effect on DNA synthesis was found to be irreversible.

key words

Asparagus officinalis - Liliaceae - steroidal saponins - furostanoside - methyl protodioscin - protodioscin - HL-60 cells - cytotoxic activity