Chemical structure of hyoscyamosides D and D1 - spirostanol glycosides from the seeds of Hyoscyamus niger L

Hyoscyamus niger L. (black henbane), occurring in Central and Southern Europe and in Western Asia, belongs to the family Solonaceae [1]. This plant is known in medicine due to its toxic properties as it contains alkaloids [2]. To our knowledge, it has never been studied before on steroidal glycosides [3], which are biological active compounds.

Two spirostanol glycosides, named by us hyoscyamosides D (1) and D₁ (2), were isolated from the ethanolic extract of Hyoscyamus niger L. seeds using gel filtration on Sephadex and High Perfomance Liquid Chromatography. After full acid hydrolysis by physical and chemical techniques tigogenin was identified as aglycone for each glycoside. In the hydrolyzate of the previously obtained acetates of aldonitryl derivatives of monosaccharides, galactose and glucose in ratio 1:3 for each compound were identified by paper and gas-liquid chromatography.

By chemical and spectroscopic evidence including 2D-NMR, DQF-COSY as well as ESI-MS analyses, the chemical structures of hyoscyamosides D (1) and D₁ were elucidated as 3-Î-{[β-D-glucopyranosyl-(1→2)]-[β-D- glucopyranosyl -(1→2)-β-D- glucopyranosyl -(1→3)]-β-D – galactopyranoside} – (25R)-5α-spirostan-3β-ol and 3–Î–β– D – glucopyranosyl – (1→2) –β– D – glucopyranosyl – (1→2) –β– D – glucopyranosyl – (1→4) –β– D – galactopyranoside – (25R) –5α– spirostan –3β-ol, respectively.

Biological tests revealed that these steroidal glycosides possess antifungal and growth stimulating activity.

Acknolegements: University of Salerno, Salerno, Italy; INTAS, Balashova, N.

References: 1. Kirtikar, K. Basu, B. (1975) Indian Medicinal Plants, 3:1794–1795.

2. Hashimoto, T. Yamada, Y. (1987) European J. of Biochem., .164(2):277–285.

3. Nohara, T. et al. (1998) Nat. Prod. Sciences,4:203–214.