A Sulfated Saponin from Bupleurum rigidum

Abstract

A new sulfated triterpene glycoside with the sulfate group located in an unusual position in the carbohydrate moiety, was isolated from the MeOH extract of the aerial parts of Bupleurum rigidum. This compound was identified by a combination of chemical degradation and spectral methods as 3beta,16beta,23-trihydroxy-13, 28-epoxyolean-11-en-3beta-yl-beta-D-glucopyranosyl-(1-->2)[4-sulfate- beta-D-glucopyranosyl-(1-->3)]-beta-D-fucopyranoside (sandrosaponin I) (1). In addition, the known compound 3beta,16beta, 23-trihydroxy-13, 28-epoxyolean-11-en-3beta-yl-beta-D-glucopyranosyl-(1-->2)[beta-D-glu copyranosyl-(1-->3)]beta-D-fucopyranoside (2) was isolated in the present investigation.

Four New Triterpenoid Saponins from the Roots of Bupleurum rigidum

“…The methanol extract was dried and partitioned between H 2 O and n -butanol, and the butanol extract was subjected to Si gel column chromatography to afford compounds 1 − 4 and a previously known saponin. The 1 H and 13 C NMR spectra of this substance were identical to those published data, and comparison with an authentic sample demonstrated that it was 3β,16β,23-trihydroxy-13,28-epoxyolean-11-en-3β-yl β- d -glucopyranosyl-(1→2)-[β- d -glucopyranosyl-(1→3)]-β- d -fucopyranoside (buddlejasaponin IV). , …”

Digging Deep for New Compounds from the Compass Plant, Silphium laciniatum

“…The chemical shift of H-4′ (δ H 4.17) was unusually high for glucose, suggesting that the sulfate group was attached at this position. The chemical shift of H-4′ is consistent with literature values. − Thus, compound 22 was identified as a new sulfated analogue of ginsenoside Ro ( 21 ).…”

Antiviral Activity of Seven Iridoids, Three Saikosaponins and One Phenylpropanoid Glycoside Extracted from Bupleurum rigidum and Scrophularia scorodonia

“…Saikosaponins were isolated from S. scorodonia and B. rigidum, and identified as buddlejasaponin I and IV and sandrosaponin 1 (see Fig. 3 for structures) as described in detail elsewhere [4]. Chromatographic analysis (TLC) and NMR spectra showed the purity of compounds.…”

“…Many studies have reported on the chemical and pharmacological activities of B. falcatum, whose roots are an officinal drug cited in the Japanese Pharmacopoeia. The active constitu-ents of these drugs have been proved to be saikosaponins, which are oleanane derivatives found in other Bupleurum species, such as in B. gibraltaricum and B. rigidum growing in Spain [3], [4]. Saponins in general are known to have a wide range of biological properties, including antiviral activity [5], [6], [7], [8], [9].…”