2009
DOI: 10.1055/s-0029-1186194
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Terpene Glycosides and Cytotoxic Constituents from the Seeds ofAmomum xanthioides

Abstract: Column chromatographic isolation of the MeOH extract of the seeds of Amomum xanthioides afforded a new diterpene glycoside, amoxanthoside A (1), two new monoterpene glycosides, (1 S,4 S,5 S)-5- EXO-hydroxycamphor 5-O-beta-D-glucopyranoside (2) and (1 R,4 R,5 S)-5-ENDO-hydroxycamphor 5-O-beta-D-glucopyranoside (3), together with four known compounds, hedychiol A (4), pygmol (5), (1 S,4 R,6 R)-(+)-6- ENDO-hydroxycamphor (6), and dihydroyashabushiketol (7). The structures of the new compounds were determined thro… Show more

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Cited by 18 publications
(7 citation statements)
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“…HMBC correlations and NOESY cross-peaks ( Figure 2 ) reconfirmed the suggested structure of 1 . The enzymatic hydrolysis of 1 afforded d -glucose, which was identified by the sign of the specific rotation +48.2 ( c = 0.03, H 2 O) and by co-TLC (CHCl 3 :MeOH:H 2 O = 2:1:0.1; R f = 0.21) [ 20 ] and the aglycone 1a , which was identified by 1 H-NMR and MS data [ 17 ]. Thus, the structure of 1 was determined as (7 R , 8 S , 8′ S , 7″ S , 8″ R )-abiesol A 4″- O -β- d -glucopyranoside, and it was named capselloside.…”
Section: Resultsmentioning
confidence: 99%
“…HMBC correlations and NOESY cross-peaks ( Figure 2 ) reconfirmed the suggested structure of 1 . The enzymatic hydrolysis of 1 afforded d -glucose, which was identified by the sign of the specific rotation +48.2 ( c = 0.03, H 2 O) and by co-TLC (CHCl 3 :MeOH:H 2 O = 2:1:0.1; R f = 0.21) [ 20 ] and the aglycone 1a , which was identified by 1 H-NMR and MS data [ 17 ]. Thus, the structure of 1 was determined as (7 R , 8 S , 8′ S , 7″ S , 8″ R )-abiesol A 4″- O -β- d -glucopyranoside, and it was named capselloside.…”
Section: Resultsmentioning
confidence: 99%
“…The IR spectrum indicated that 1 possesses hydroxy (3383 cm −1 ), carbonyl (1666 cm −1 ), and C=C double bond (1642 cm −1 ) functional groups. The 1 H and 13 C NMR spectra of 1 (l " Tables 1 and 2) were similar to those of serratagenic acid [4] [5,6]. Comparison of the 13 C NMR data of 1 with that of serratagenic acid showed the downfield shift of C-3 (+ 11.5) and upfield shift of C-2 (− 2.5) in 1, indicating glycosylation at C-3.…”
mentioning
confidence: 90%
“…This evidence, together with the observation of the HMBC correlation between O-CH 3 (δ H 3.77) and C-6′ (δ C 169.9), suggested that compound 2 contains a 6′-O-methyl-β-glucuronopyranoside [8]. Acidic hydrolysis and spectral analysis of 2 confirmed the presence of the 6′-O-methyl-β-D-glucuronopyranoside from the 1 H NMR coupling constant (J = 8.0 Hz) and its optical rotation value [6][7][8]. The relative configuration of 2 was confirmed to be identical to that of 1 in the NOESY spectrum.…”
mentioning
confidence: 95%
“…MTT [17] and SRB [18] bioassays were used to determine the cytotoxicity of each compound against HL60 and A549 tumor cell lines, respectively. Doxorubicin (purity ≥ 99.5 %; Dalian Melone Pharmaceutical Co., Ltd.) was used as a positive control.…”
Section: Cytotoxicity Assaymentioning
confidence: 99%