Novel ceramides and a new glucoceramide from the roots of Incarvillea arguta

Abstract

Novel ceramides, rel-(3S,4S,5S)-3-[(2R)-2-hydroxy- (2) were isolated from the aqueous ethanolic extract of the roots of Incarvillea arguta, together with eight known compounds: β-sitosterol (3), oleanolic acid (4), ursolic acid (5), piperin (6), maslinic acid (7), β-sitosterol 6′-O-acyl-β-D-glucopyranoside (8), 8-epideoxyloganic acid (9), and plantarenaloside (10). Their structures were elucidated on the basis of spectral data including IR, MS, NMR [ 1 H NMR, 13 C NMR (distortionless enhancement by polarization transfer), 1 H-1 H COSY, heteronuclear multiplequantum coherence, and heteronuclear multiple-bond coherence correlations]. The relative configurations were established by nuclear Overhauser effect spectroscopy experiments and by comparison of the NMR spectral data and coupling constants with those already reported in the literature.

Novel ceramides from aerial parts of Saussurea involucrata Kar. et. Kir.

“…Besides, there existed one oxygenated methine (δ C 72.5) in the structure. Above on data, compounds 1a-g were suspected to be the ceramide derivatives with a tetrahydrofuran ring, which showed similar signal pattern to 3-[2-hydroxycosanoyl~hexacosanoylamino]-4-hydroxy-5-[(4Z)-tetradecane-4-ene]-2, 3, 4, 5-tetrahydrofuran (A) (Luo et al, 2004) and 1a-g in this paper were the second example of this kind of skeleton. The connections between protons and carbons were identified by its HMQC, 1 H-1 H COSY NMR, HMBC spectral correlations (see Table I).…”

Clinically useful anticancer, antitumor, and antiwrinkle agent, ursolic acid and related derivatives as medicinally important natural product

“…Ursolic acid could significantly inhibit the proliferation of HepG2 and its drug-resistance strain, R-HepG2 cells, but had no inhibitory effect on primarily cultured normal mouse hepatocytes whereas all the six derivatives of ursolic acid (52)(53)(54)(55)(56)(57) could not inhibit the growth of all tested cell lines. Further study on mechanism demonstrated that apoptosis and G0/G1 arrest were involved in the cytotoxicity and cleavage of poly-(ADPribose) -polymerase.…”

Four New Sesquiterpenoids from the Roots of Incarvillea arguta and Their Inhibitory Activities against Lipopolysaccharide-Induced Nitric Oxide Production

“…The relative configuration of 4 was confirmed by careful analysis of NOESY data. C-3 and C-4 of the rigid spiro [4,5]deca skeleton were determined to be aorientation, when C-1 was randomly assigned to be b-orientation. The strong NOESY correlations of Me-13 to H-14a and H-14b, H-2 to Me-15 and H-12 suggested that Me-13 would be close to H 2 -14, and H 2 -12 would be close to Me-15, giving a relative configuration of 4 as shown in Fig.…”

“…The specific rotation of 4 was positive. Thus, the structure of 4 was elucidated to be (ϩ)-2-isopropenyl-6-hydroxymethyl-10-methylspiro [4,5]deca-6,9-dien-8-one with as yet unknown absolute configuration, and named argutosine D.…”

“…[4][5][6][7] Recently, we have reported the isolation and structure elucidation of two monoterpene alkaloid dimers and two biphenyls from the roots of I. arguta. 8,9) Further investigation of this plant led us to isolate four new sesquiterpenoids, argutosines A-D (1-4) (Fig.…”