A New Lupane Glycoside from the Leaves of Acanthopanax koreanum

Abstract

Acanthopanax genus is a shrub indigenous to Northeast Asia. Its bark, known as Acanthopanis Cortex, is used to treat sinew and bone pains in traditional oriental medicine. Several studies on the triterpenoid constituents of Acanthopanax koreanum NAKAI, have been reported. [1][2][3] As a results of an in-going search for the phytochemical constituents in Acanthopanax genus, [4][5][6][7][8][9] we report on the isolation of a new lupane triterpene glycoside, acankoreosideester from the leaves of Acanthopanax koreanum and describe the determination of its structure.The methanolic extract of A. koreanum leaves gave acankoreoside E (1) by the various chromatographic techniques. Acankoreoside E (1) was obtained as a white amorphous powder of molecular formula C 48 H 76 O 20 , as determined by HR-FAB-MS (molecular ion peak at m/z 995.4828 due to [MϩNa] ϩ ). Its 13 C-NMR and DEPT spectra revealed 48 carbons signals, 30 of which were assigned to a triterpenoid sapogenol moiety, and 18 to three monosaccharide moieties. Relevant 1 H-NMR data showed the following; four tertiary methyl groups [d 0.85, 0.96, 1.19

LC‐UV Assay Method and UPLC/Q‐TOF‐MS Characterisation of Saponins from Ilex Paraguariensis A. St. Hil. (Mate) Unripe Fruits

“…Nevertheless, saponins assay also presents difficulty because of the absence of chromophoric groups with absorption above 210–215 nm and structural similarity. Evaporative light scattering and mass spectrometry detection are examples of feasible methods used for saponin detection (Park et al , ; Nord and Kenne, ; Young and Doran, ; Park et al , ; Dini et al , ), nevertheless the wider access to LC‐UV probably makes it a more sensible and accessible approach for routine measurements. Two LC‐UV methods were previously described for mate saponins assay.…”

Lupane Glycosides from the Leaves of Acanthopanax koreanum

“…The assignment of the ahydroxyl group at C-3 was performed by comparing spectral data to literature values. [14][15][16] In the NOESY spectrum, the presence of cross-peaks between H-24 and H-25 as well as H-3 indicated that the methyl group (H-24) was axial, which in turn suggested that the carboxyl group at C-4 was a-positioned. In the HMBC spectrum, the carbonyl carbon signal at d 175.1 (C-28) showed a The three isolates (1-3) were assessed for anti-inflammatory activity by examining their effects on nitric oxide (NO) and prostaglandin E 2 (PGE 2 ) by lipopolysaccharide (LPS)-induced in RAW 264.7 cells.…”

Lupane-Type Triterpene Glycosides from the Leaves ofAcanthopanax koreanumand TheirIn VitroCytotoxicity

“…This evidence suggested that the carboxy group was at C-23, confirmed by the HMBCs between the proton signal at δ = 1.11 (H-24) and carbons C-3 (δ = 73.49), C-4 (δ = 52.24), C-5 (δ = 46.69), and C-23 (δ = 183.40). The carbon signals of the sugar moiety were superimposable on those of the characteristic triterpene glycosides isolated from the Acanthopanax species [3][4][5][6][7]. In addition, acid hydrolysis of 1 (see Materials and Methods) provided the monosaccharide components of rhamnose and glucose (identified as TMS derivatives).…”

“…Its roots and stem barks have been traditionally used by practitioners of oriental medicine as a tonic, as a prophylactic, and to treat rheumatism, paralysis, hepatitis, and diabetes [1,2]. Previous phytochemical and biological investigations of A. koreanum have yielded a number of triterpenes [3][4][5][6][7]. Of these, lupane triterpenoids are major components of A. koreanum.…”