2016
DOI: 10.3390/molecules21091121
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Three Novel Triterpenoids from Taraxacum officinale Roots

Abstract: Three novel lupane-, bauerane-, and euphane-type triterpenoids (1-3), in addition to seven known triterpenoids (4-10)-18β,19β-epoxy-21β-hydroxylupan-3β-yl acetate (4), 21-oxolup-18-en-3β-yl acetate (5), betulin (6), officinatrione (7), 11α-methoxyolean-12-en-3-one (8), eupha-7,24-dien-3-one (9), and 24-oxoeupha-7,24-dien-3β-yl acetate (10)-were isolated from the roots of Taraxacum officinale. Their structures were elucidated on the basis of spectroscopic analyses using 1D and 2D-NMR spectra and electron ioniza… Show more

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Cited by 18 publications
(14 citation statements)
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“…Recently, other authors have determined from ethanol extract three novel lupane-, bauerane-, and euphane-type triterpenoids and other known triterpenes present in dandelion roots, using spectroscopic analysis, which have potential anti-inflammatory activity [ 32 , 33 ]. Dandelion leaves in this study were found to be rich in triterpenes such as betulin, lupeol acetate, lupeol, α -Amyrin, and β -sitosterol from both extracts with potential antibacterial activity against pathogens that infect the urinary tract.…”
Section: Resultsmentioning
confidence: 99%
“…Recently, other authors have determined from ethanol extract three novel lupane-, bauerane-, and euphane-type triterpenoids and other known triterpenes present in dandelion roots, using spectroscopic analysis, which have potential anti-inflammatory activity [ 32 , 33 ]. Dandelion leaves in this study were found to be rich in triterpenes such as betulin, lupeol acetate, lupeol, α -Amyrin, and β -sitosterol from both extracts with potential antibacterial activity against pathogens that infect the urinary tract.…”
Section: Resultsmentioning
confidence: 99%
“…The UV band at λ max 252 (log ε 3.42) supported the presence of the enone moiety, similar to compound 2 . The 1 H- and 13 C-NMR spectra (in CDCl 3 ) of 3 almost resembled those of 2 exhibiting signals at δ H 0.84 (s), 0.87 (s), 0.91 (d), 0.95 (s), 0.99 (brs), 1.01 (s), 1.06 (s) and 1.22 (s), and at δ C 38.1 (CH 3 ), 29.6 (CH 3 ), 27.1 (CH 3 ), 22.5 (CH 3 ), 21.7 (CH 3 ), 18.5 (CH 3 ), 16.0 (CH 3 ), and 15.4 (CH 3 ) ( Table 1 ), that were attributed to six tertiary and two secondary methyls in agreement with the bauerane architecture [ 34 , 35 , 36 , 37 , 38 , 39 , 40 ]. The 3-oxo functionality in the structure of 2 was replaced in 3 by an acetoxy moiety as revealed by the additional methyl singlet at δ H 2.07 and the 1H double doublet at δ H 4.52 in the proton spectrum, and by signals at δ C 170.9 (C, Ac- CO ), 79.8 (CH, C-3) and 21.3 (CH 3 , Ac- CH 3 ) in the carbon spectrum ( Table 1 ).…”
Section: Resultsmentioning
confidence: 89%
“…The 1 H- and 13 C-NMR data of 2 indicated six tertiary methyls [δ H 1.01, δ C 18.1 (H 3 -27); δ H 1.08, δ C 21.8 (H 3 -24); δ H 1.09, δ C 38.3 (H 3 -28); δ H 1.11, δ C 27.6 (H 3 -23); δ H 1.16, δ C 22.0 (H 3 -26); δ H 1.27, δ C 19.8 (H 3 -25)] and two secondary methyls [δ H 0.90, δ C 23.1 (H 3 -30); δ H 1.03, δ C 25.7 (H 3 -29)] ( Table 1 ), suggesting a pentacyclic triterpenoid structure with an ursane-type or rearranged ursane skeleton [ 27 ]. In particular, the presence of a bauerane framework [ 34 , 35 , 36 ], in which the methyl group at C-14 of ursane skeleton is migrated to C-13 and the methyl group at C-8 is migrated to C-14 by 1,2 shifts from isoursyl cation ( II ) ( Figure 5 ) [ 27 ], was strongly suspected due to the characteristic carbon value of H 3 -28 appearing abnormally deshielded [ 37 ] in triterpenes with this skeleton (i.e., [ 38 , 39 , 40 ]).…”
Section: Resultsmentioning
confidence: 99%
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“…Phytochemical studies have reported the presence of diverse constituents from leaves, roots and flowers of Taraxacum species. Sesquiterpene lactones together with phenylpropanoids and terpenoids are known to be responsible for the diverse biological activities of dandelion [ 7 , 8 , 9 , 10 , 11 ].…”
Section: Introductionmentioning
confidence: 99%