Norcarotenoids of Rehmannia glutinosa var. Hueichingensis☆
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Cited by (34)
Ionones and lignans from the fresh roots of Rehmannia glutinosa
2022, PhytochemistryCitation Excerpt :The 1D NMR data (Table 1) of 1 revealed the signals due to one carbonyl carbon [δC 201.3 (C-9)], one trans double bond [δH 7.40 (1H, d, J = 16.4 Hz, H-7), 6.30 (1H, d, J = 16.4 Hz, H-8); δC 152.8 (C-7), 131.5 (C-8)], two oxygenated quaternary carbons [δC 81.9 (C-6), 77.3 (C-5)], one oxymethine [δH 3.65 (1H, dd, J = 11.3, 4.5 Hz, H-4); δC 73.2 (C-4)], and four methyl groups [δH 2.30 (3H, s, CH3-10), 1.22 (3H, s, CH3-11), 1.14 (3H, s, CH3-13), 0.78 (3H, s, CH3-12); δC 27.0 (C-10), 26.9 (C-12), 25.5 (C-11), 22.5 (C-13)]. The 1H and 13C NMR data of 1 were similar to those of 5,6-dihydroxy-β-ionone (Sasaki et al., 1991) with a hydroxyl group instead of hydrogen at C-4, which was verified by the HMBC correlations from H-4 (δH 3.65) to C-5/C-2/C-3/C-13 (δC 77.3/36.2/27.7/22.5) (Fig. 2). The NOESY correlations between H-4 (δH 3.65) and H3-13 (δH 1.14), H3-12 (δH 0.78), as well as between H-7 (δH 7.40) and H3-11 (δH 1.22) (Fig. 2) suggested that the H-4, CH3-5, and 6-OH were co-facial.
Two new ionones from the fresh roots of Rehmannia glutinosa
2021, Phytochemistry LettersCitation Excerpt :The 13C NMR data revealed the presence of one carboxylic carbon [δC 170.7 (C-11)], four olefinic carbons[δC 153.8 (C-9), 139.5 (C-7), 134.8 (C-8), 119.6 (C-10)], two oxygenated sp3 quaternary carbons [δC 79.9 (C-6), 77.9 (C-5)], an oxygenated sp3 methine carbon [δC 65.2 (C-3)] and four methyl carbons [δC 27.6 (C-13), 27.2 (C-15), 26.3 (C-14), 14.2 (C-12)]. The 1H and 13C NMR data of compound 1 resembled those of aeginetic acid (5) (Sasaki et al., 1991), except for the hydroxyl group instead of hydrogen at C-3, which was confirmed by the 1H-1H COSY correlations between the oxygenated methine proton (δH 4.07) and methylene protons (δH1.77)/(δH1.65, 1.47) (Fig. 2). The NOESY correlations of H3-13/H3-15, H3-14/H-3, and H3-14/H-7 suggested that the hydroxy groups at C-3, C-5 and C-6 are β-, α- and β-oriented, respectively.
Nine new compounds from the whole plants of Rehmannia henryi
2019, Journal of Asian Natural Products ResearchThree new alkaloids and a new iridoid glycoside from the roots of Rehmannia glutinosa
2017, Phytochemistry LettersA novel strategy to evaluate the quality of traditional Chinese medicine based on the correlation analysis of chemical fingerprint and biological effect
2013, Journal of Pharmaceutical and Biomedical AnalysisCitation Excerpt :Chemical components in RG include iridoids glycosides, ionone glycosides, and phenylpropanoid glycosides [11–13]. Sixteen compounds were identified according to the method described above; the results are shown in Supplementary Table S1 [13–20]. Peak intensities of these compounds between the raw and processed RGs were analyzed by t-test (Table 2).
Monoterpenoids from the fruit of Gardenia jasminoides Ellis (Rubiaceae)
2013, Biochemical Systematics and EcologyCitation Excerpt :The structures of the isolated compounds were identified on the basis of spectral data (1H and 13C NMR, CD). They were elucidated as 6α-hydroxygeniposide (1) (Miyagoshi et al., 1987), 6-O-methylscandoside methyl ester (2) (Machida et al., 2003), 6-O-methyldeacetylasperulosidic acid methyl ester (3) (Machida et al., 2003), gardenoside (4) (Machida et al., 2003), 8-O-methylmonotropein methyl ester (5) (Machida et al., 2003), shanzhiside (6) (Inouye et al., 1970), gardoside (7) (Ronsted et al., 2000), 10-O-trans-sinapoylgeniposide (8)(Yu et al., 2012), 6″-O-trans-sinapoylgenipin gentiobioside (9) (Yu et al., 2009), 6″-O-trans-p-coumaroylgenipin gentiobioside (10) (Yu et al., 2009), rehmapicrogenin (11) (Sasaki et al., 1991), jasminoside C (12) (Machida et al., 1998), jasminoside B (13) (Machida et al., 1998), jasminoside G (14) (Chang et al., 2005), jasminoside K (15) (Yu et al., 2010), jasminoside I (16) (Chen et al., 2008), jasminoside H (17) (Chen et al., 2008), epijasminoside H (18) (Chen et al., 2008), 6′-O-sinapoyljasminoside C (19) (Chen et al., 2008), 6′-O-trans-sinapoyljasminoside L (20) (Yu et al., 2010) (Fig. 1). Plants of the genus Gardenia are known to be rich of monoterpenoids, including iridoids and pyronane monoterpenoids.
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Part 8 in the series ‘Chemical and Biological Studies on Rehmanniae Radix’. For Part 7 see ref. [7].