Steroidal Saponins from Asparagus officinalis and Their Cytotoxic Activity

Yu Shao; Onoomar Poobrasert; Edward J. Kennelly; Chee-Kok Chin; Chi-Tang Ho; Mou-Tuan Huang; Stephen A. Garrison; Geoffrey A. Cordell

doi:10.1055/s-2006-957667

Planta Medica, Inhaltsverzeichnis

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

Abstract

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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

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