Phenylpropanol Derivatives from Morina chinensis

Abstract

Seven new phenylpropanol derivatives, named morinins A-G (1-7), along with five known compounds, 4-O-methylcinnamyl alcohol, 4-O-methylcinnamyl methyl ether, 4-O-methylcinnamyl acetate, p-methoxybenzaldehyde, and 4-O-methyl-(E)-coniferyl alcohol, have been isolated from the roots of the medicinal Chinese plant, Morina chinensis. Their structures were determined on the basis of spectral data, especially 2D NMR and HRMS.

Morinins H−K, Four Novel Phenylpropanol Ester Lipid Metabolites from Morina chinensis

“…The HREIMS of 1 gave an intense parent ion at m / z 522.3324, corresponding to a molecular formula of C 33 H 46 O 5 , which required 11 degrees of unsaturation. Similar to morinins D and F, the 1 H NMR spectral data of 1 showed a cinnamyl alcohol, a methoxyl group at δ H 3.82 (3H, s), and an oxygenated angeloyl group at δ H 6.44 (1H, br q, J = 7.2 Hz, H-3‘), 2.12 (3H, d, J = 7.2 Hz, H-4‘), and 4.77 (2H, br s, H-5‘). Similarly to morinins D and F, in compound 1 the C-5‘ position of the angeloyl group was esterified, but in this case the moiety seemed to be an unsaturated fatty ester group, after careful analysis of the other signals of 1 H NMR spectrum.…”

“…General Experimental Procedures and Plant Material. These were as described in a previous contribution …”

“…In a previous paper, we reported seven new phenylpropanol derivatives, morinins A−G, as well as five other known phenolic compounds from Morina chinensis (Dipsacaceae) . In a continued study on the chemical constituents of this traditional Chinese medicinal herb, we now wish to report the isolation and structure elucidation of four other novel phenylpropanol ester lipid metabolites, morinins H−K ( 1 − 4 ) (Chart ).…”

Phenylpropenoids from Bupleurum fruticosum as Anti-Human Rhinovirus Species A Selective Capsid Binders

“…The spectroscopic ( 1 H and 13 C NMR, UV, and MS) and physical data (melting point, optical rotation) of the known compounds cis -9,17-octadecadiene-12,14-diyne-1,16-diol ( 2 ), ( E )-3-(4-methoxyphenyl)-2-propen-1-yl ( Z )-2-[( Z )-2-methyl-2-butenoyloxymethyl)­butenoate ( 3 ), ( E )-3-(3,4-dimethoxyphenyl)-2-propen-1-yl ( Z )-2-[( Z )-2-methyl-2-butenoyloxymethyl)­butenoate ( 4 ), 4- O -methylcinnamyl angelic acid ester ( 5 ), 4- O -methyl-( E )-coniferyl angelic acid ester ( 6 ), cinnamyl isovalerate ( 7 ), 4-methoxycinnamyl alcohol ( 8 ), and 3,4-dimethoxycinnamyl alcohol ( 9 ) were in agreement with the literature data.…”

“…The spectroscopic ( 1 H and 13 C NMR, UV, and MS) and physical data (melting point, optical rotation) of the known compounds cis-9,17-octadecadiene-12,14-diyne-1,16-diol (2), 18 4), 11 4-O-methylcinnamyl angelic acid ester (5), 19 4-O-methyl-(E)-coniferyl angelic acid ester (6), 19 cinnamyl isovalerate (7), 20 4-methoxycinnamyl alcohol (8), 21 and 3,4-dimethoxycinnamyl alcohol (9) 22 were in agreement with the literature data.…”