1989
DOI: 10.1016/0031-9422(89)80136-0
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Phenolic compounds from Coix lachryma-jobi var. Ma-yuen

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Cited by 121 publications
(72 citation statements)
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“…Esta conclusão também pôde ser confirmada pela ordem de eluição destes dois compostos na separação por cromatografia líquida de alta eficiência em fase reversa, onde isômeros eritro com estruturas semelhantes à de 4 apresentam tempo de retenção menor que os dos isômeros treo correspondentes. 14,15 As diferenças observadas nos valores de deslocamento químico de C-7, C-8 e C-9 em 3 e 4 também estão de acordo com as relatadas para fenilpropanóides diastereoisoméricos contendo hidroxilas em C-7 e C-8. 14 Os diastereoisômeros 3 e 4 foram descritos anteriormente apenas como produtos de metabolismo de alquenilbenzenos em ratos 16 e 4 (na forma dos enantiômeros 7R,8R e 7S,8S) também como produto de síntese.…”
Section: Resultsunclassified
“…Esta conclusão também pôde ser confirmada pela ordem de eluição destes dois compostos na separação por cromatografia líquida de alta eficiência em fase reversa, onde isômeros eritro com estruturas semelhantes à de 4 apresentam tempo de retenção menor que os dos isômeros treo correspondentes. 14,15 As diferenças observadas nos valores de deslocamento químico de C-7, C-8 e C-9 em 3 e 4 também estão de acordo com as relatadas para fenilpropanóides diastereoisoméricos contendo hidroxilas em C-7 e C-8. 14 Os diastereoisômeros 3 e 4 foram descritos anteriormente apenas como produtos de metabolismo de alquenilbenzenos em ratos 16 e 4 (na forma dos enantiômeros 7R,8R e 7S,8S) também como produto de síntese.…”
Section: Resultsunclassified
“…The aqueous solution was partitioned with CHCl 3 and EtOAc, successively. The obtained CHCl 3 and EtOAc soluble fractions were individually separated by silica gel column chromatography to afford fifty-six compounds, including five new compounds: hibicuslide A (1), hibicuslide B (2), hibicuslide C (3), hibicutaiwanin (4), hibicusin (5), and fifty-one known compounds: hibicuwanin A (6), 3) hibicuwanin B (7), 3) (7S,8S)-demethylcarolignan E (8), 3) threo-carolignan E (9), 4) erythro-carolignan E (10), 4) threo-1-C-syringylglycerol (11), 5) 9,9Ј-O-feruloyl-(Ϫ)-secoisolaricinresinol (12), 6) dihydrodehydrodiconiferyl alcohol (13), 7) boehmenan (14), 4) (Ϫ)-syringaresinol (15), 8) cleomiscosin A (16), 9) cleomiscosin C (17), 9) mansonone E (18), 10) mansonone H (19), 11) hibiscone C (20), 12) isohemigossypol-1-methyl ether (21), 13) gossyvertin (22), 14) N-trans-feruloyltyramine (23), 15) N-cis-feruloyltyramine (24), 16) 2-(2-hydroxytricosanoylamino)-1,3,4-hexadecanetriol (25), 17) myricerol (26), 18) myriceric acid A (27), 18) myriceric acid B (28), 18) myriceric acid C (29), 18) uncarinic acid A (30), 19) uncarinic acid B (31), 19) 3-oxo-olean-12-en-28-oic acid (32), 20) scopoletin (33), 21) scoparone (34), 22) 4-hydroxybenzoic acid (35), 15) ferulic acid (36), 15) methyl trans-ferulate (37), 23) methyl cis-ferulate (38), 24) lignocerylferulate (39), 25) caffeic acid (...…”
mentioning
confidence: 99%
“…It was found that the differences of the The OH configurations of two stereogenic centers in 1 and 2 were determined by comparison with the 13 C NMR data of the structural similar compounds, erythro-and threo-honokitriol 16 and erythro-and threo-1-C-syringylglycerol. 17 The difference of 13 C NMR chemical shifts of C-7 (δ C 76.0) and C-8 (δ C 76.2) in erythro-honokitriol is δ C-8-C-7 0.2, which is smaller than that in threo-honokitriol ( δ C-8(77.8)-C-7(74.6) 3.2). 16 In addition, the difference of 13 C NMR chemical shifts of C-7 (δ C 74.1) and C-8 (δ C 75.3) in erythro-1-C-syringylglycerol is δ C-8-C-7 1.2, which is also smaller than that in its threo-isomer ( δ C-8(75.8)-C-7(72.9) 2.9).…”
Section: Resultsmentioning
confidence: 98%
“…16 In addition, the difference of 13 C NMR chemical shifts of C-7 (δ C 74.1) and C-8 (δ C 75.3) in erythro-1-C-syringylglycerol is δ C-8-C-7 1.2, which is also smaller than that in its threo-isomer ( δ C-8(75.8)-C-7(72.9) 2.9). 17 Therefore,the relative configurations of 1 and 2 could also be determined base on the rules as mentioned in the above cases. 16,17 In compound 2, the difference of the carbon signals of C-7 (δ C 75.8) and C-8 (δ C 76.5) is δ C-8-C-7 0.7, which is smaller than that in 1 ( δ C-8(76.9)-C-7(75.4) 1.5).…”
Section: Resultsmentioning
confidence: 99%
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