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2006
DOI: 10.1016/j.tet.2006.01.019
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Cinnamic acid amides and lignanamides from Aptenia cordifolia

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Cited by 49 publications
(35 citation statements)
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References 15 publications
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“…The 1 H NMR spectrum of 30 and 31 showed the presence of two tyramine moieties, five aromatic and one olefinic protons, two methoxy signals and two methenyl protons signals, which were coupled with each other. The 1 H and 13 C NMR data of 30 and 31 were almost similar with dihydro-naphthalene lignin: 7-Hydroxy-1-(4-hydroxyl-3-methoxyphenyl)-N 2 ,N 3 -bis (4-hydroxyphenethyl)-6-methoxy-1,2-dihydro-naphthalene-2,3-dicarboxamide reported by DellaGreca et al (2006) [24]. On the basis of HMBC correlations (Table 4), the singlet signals at δ H 3.75 (3H, s, 3′-OCH 3 ) and δ H 3.89 (3H, s, 4′-OCH 3 ), which typically represent methoxy protons, showed correlations with 149.0 (C-3′) and 146.4 (C-4′), thus confirming the assignment of the methoxy groups at C-3′ and C-4′, respectively.…”
Section: Resultssupporting
confidence: 67%
See 1 more Smart Citation
“…The 1 H NMR spectrum of 30 and 31 showed the presence of two tyramine moieties, five aromatic and one olefinic protons, two methoxy signals and two methenyl protons signals, which were coupled with each other. The 1 H and 13 C NMR data of 30 and 31 were almost similar with dihydro-naphthalene lignin: 7-Hydroxy-1-(4-hydroxyl-3-methoxyphenyl)-N 2 ,N 3 -bis (4-hydroxyphenethyl)-6-methoxy-1,2-dihydro-naphthalene-2,3-dicarboxamide reported by DellaGreca et al (2006) [24]. On the basis of HMBC correlations (Table 4), the singlet signals at δ H 3.75 (3H, s, 3′-OCH 3 ) and δ H 3.89 (3H, s, 4′-OCH 3 ), which typically represent methoxy protons, showed correlations with 149.0 (C-3′) and 146.4 (C-4′), thus confirming the assignment of the methoxy groups at C-3′ and C-4′, respectively.…”
Section: Resultssupporting
confidence: 67%
“…45°. The minimized structure obtained by MM2 calculation [22] was used to generate dihedral angles and an angle of 52°w as measured, which is compatible with a cis configuration [24]. The absolute configuration of C-1 and C-2 of 30 and 31 was further established to be (1R, 2R) and (1S, 2S), since there is no Cotton effect in the CD spectrum.…”
Section: Resultsmentioning
confidence: 99%
“…The known isolates were readily identified by a comparison of physical and spectroscopic data (UV, IR, 1 H NMR, [D] D , and MS) with corresponding authentic samples or literature values, and this included two amides, N-trans-feruloyltyramine (2) [13] and N-trans-feruloyloctopamine (3) [14], a benzenoid, vanillin (4) [15], a benzoquinone, D-tocopheryl quinone (5) [16], and three steroids, E-sitostenone (6) [17], E-sitosterol (7) [18], and 6D-hydroxystigmast-4-en-3-one (8) [8].…”
mentioning
confidence: 99%
“…Previously, pharmacological research has shown that Portulaca oleracea L. produces a wide range of pharmacological effects such as anti-inflammatory [3], antibacterial [4], skeletal muscle relaxant [5], wound-healing [6], and in vitro antitumor [7] activities. In the search for biologically active compounds from this species, we isolated 12 nitrogen-containing compounds (1-12): aurantiamide acetate (1) [8], aurantiamide (2) [9], cyclo(L-tyrosinyl-L-tyrosinyl) (3) [10], cyclo(L-leucinyl-L-tyrosinyl) (4), oleracein B (5), 3-hydroxy-2-pyridone-6-carboxylic acid (6), trollisine (7), 1H-pyrrole-2,5-dicarboxylic acid (8), 5-hydroxy-2-pyridine carboxylic acid (9), N-feruloyl normetanephrine (10) [11], N-trans-feruloyl tyramine (11) [12], and aminobenzoic acid (12); nine flavonoids (13-21): liquiritin (13) [13], isoliquiritoside (14) [13], oroxyloside (15) [14], luteolin-7-O-glucoside (16) [15], kaempferol-3-O-E-D-glucopyranoside (17) [16], vitexin (18), baicalin (19) [15], puerarin (20) [17], and scutellarin (21) [15]); eight triterpenoids (22-29): glycyrrhetinic acid (22) [18], 3-acetylaleuritolic acid (23), friedelin (24), betulinic acid (25) [19], ursolic acid (26) [19], lupeol (27), oleanolic acid (28) [20], and 4D-methyl-3E-hydroxylfriedelan (29); four anthraquinones (30-33): chrysophanol (30) [21], emodin (31) [22], aloeemodin (32) [23], and rhein (33) [24]); and five common compounds (34-38): dieugenol (34) [25], syringaresinol (35) [26], o-hydroxybenzoic acid (36), 3-hydroxycoumarin (37) [27], and vanillic acid (38). All the compounds isolated from the genus Portulaca L. for the first time were confirmed by comparison of their 1 H NMR and 13 C NMR data with those reported in the literature.…”
mentioning
confidence: 99%