ChemInform Abstract: Aculeoside A, a Novel Steroidal Saponin Containing a Deoxyaldoketose from Ruscus aculeatus.

Abstract

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Ruscus Genus: A Rich Source of Bioactive Steroidal Saponins

“…Since 1971, from the underground parts of R. aculeatus, several spirostane derivatives have been isolated (9-28) (l " Fig. 3) [25,[27][28][29][30][31][32]. All isolated neoruscogenin derivatives are characterized by the presence of a sugar chain only at C-1.…”

“…Aculeoside A (17) represents an unusual bisdesmosidic spirostanol saponin, having 6-deoxy-D-glycero-L-threo-4-hexosulose linked to the C-24 hydroxyl group of the aglycone. Aculeoside A was active as a cyclic AMP phosphodiesterase inhibitor [30]. Other unusual structures are spilacleosides A and B (18 and 19) having spiro 1,3-dioxolan-4-one structures, made up of aculeoside A and (2R,3S)-2,3-dihydroxy-3-methylpentanoic acid [32].…”

Steroidal Saponins from the Rhizomes of Ruscus Hypophyllum

“…These spectral features of 4 were similar to those of 3. The presence of an acetyl group in the molecule of 4 was shown by the IR (1749 cm -1 ), 1 Treatment of 4 with 3% NaOMe in MeOH gave 3. Therefore, 4 was found to be a monoacetate of 3.…”

“…Plants of the genus Ruscus in the family Liliaceae are composed of about six species and are known to be rich sources of steroidal saponins. The representative species of the genus Ruscus, R. aculeatus, has been shown to contain a variety of steroidal saponins based upon spirost-5-ene-1β,3β-diol (ruscogenin) [1][2][3][4][5][6]. Previously, we have made a phytochemical screening of the rhizomes of Ruscus hypophyllum L., which is distributed from the Madeira Island to the Caucasian mountains, and isolated a series of cholestane glycosides [7].…”

“…Furthermore, long-range correlations were observed between the carbonyl carbon at δ 170.5 and the unequivalent H 2 -6 methylene protons of the galactosyl residue at δ 4.93 (dd, J = 11.2, 7.7 Hz) and 4.49 (dd, J = 11.2, 4.2 Hz) in the HMBC spectrum of 4. Thus, the acetyl moiety was revealed to be linked to the galactose C-6 hydroxy position, and the structure of 4 was determined to be (25R)-3β- The fundamental structure of 9 was shown to be a 22-methoxyfurostanol saponin by a positive color reaction with Ehrlich's reagent, and by the 1 In addition, a longrange correlation was observed between the anomeric proton of the terminal glucosyl unit at δ 4.80 and the C-26 methylene carbon at δ 75.1. Thus, 9 was revealed to be the corresponding 22-methoxyfurostanol saponin of 3 with a glucosyl unit at C-26.…”