Abstract
Eleven new furostanol saponins, typaspidosides B-L (1–11), one new spirostanol saponin, typaspidoside M (12), and five known spirostanol saponins, 25S-atropuroside (13), neoaspidistrin (14), (25S)-pratioside D1 (15), 25S-aspidistrin (16) and 25S-neosibiricoside (17) were isolated from the rhizomes of Aspidistra typica Baill. The structures of the new compounds were established using 1D and 2D NMR (1H-1H COSY, HMQC, HMBC and ROESY) spectroscopy, high resolution mass spectrometry, and chemical methods. The aglycones of 1–3 (unusual furostanol saponins with opened E ring type), 9 and 10 (the methoxyl substituent at C-23 position) were found, identified from natural products for the first time. Moreover, the anti-HIV activities of the isolated steroidal glycosides were assessed, and compounds 13, 14, 16 and 17 exhibited high active against HIV-1.
Highlights
Aspidistra typica Baill is a perennial herbaceous plant which belongs to the family Convallariaceae [1]
A wide range of steroidal saponins have been extracted from the family Convallariaceae, but no more than 30 compounds were reported from the genus Aspidistra [3,4,5,6,7]
In order to characterize the chemical composition and active steroidal saponins of A. typical, systemic phytochemical analysis on the ethanol extract of the rhizomes of A. typica was carried out, which led to the isolation and identification of twelve new steroidal saponins, including eleven furostanol saponins (1–11) and one spirostanol saponin (12), along with five known spirostanol saponins, 25S-atropuroside H (13) [8], neoaspidistrin (14) [9], (25S)-pratioside D1 (15) [10,11], 25S-aspidistrin (16) [2,3] and 25S-neosibiricoside D (17) [12,13] (Fig 1)
Summary
Aspidistra typica Baill is a perennial herbaceous plant which belongs to the family Convallariaceae [1]. Tubes 50–67 was purified by semi-preparative HPLC with MeOH-H2O (9:11, v/v) to Steroidal Saponins from the Rhizomes of Aspidistra typica yield 5 (38.1 mg). Compound 2, a white amorphous powder, showed an [M–H]−ion peak at m/z 1227.5659 in the negative HRESIMS, corresponding to the molecular formula C56H92O29.
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