Eremophilenolides and Other Constituents from the Roots of<i>Ligularia sagitta</i>

Li, Xuqin; Gao, Kun; Jia, Zhong‐Jian

doi:10.1055/s-2003-38872

Cited by 37 publications

(33 citation statements)

References 7 publications

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“…(Verbenaceae) [65] and Ligularia sagitta (Astraceae) [66]. Similarly, no antibacterial activity against MRSA was found for UA isolated from Rosa nutkana (Rosaceae) [67].…”

Section: Vitex Negundomentioning

confidence: 99%

Antibacterial activity of oleanolic and ursolic acids and their derivatives

et al. 2010

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Bacterial resistance to antibiotics is increasing at an alarming rate and many commonly used antibiotics are no longer effective.Thus, there is considerable interest in investigating novel antibacterial compounds, such as the plant-derived pentacyclic triterpenoids, including oleanolic acid (OA), ursolic acid (UA) and their derivatives. These compounds can be isolated from many medicinal and crop plants and their antibacterial, antiviral, antiulcer and anti-inflammatory effects are well documented. OA and UA are active against many bacterial species, particularly Gram-positive species, including mycobacteria. They inhibit bacterial growth and survival, and the spectrum of minimal inhibitory concentration (MIC) values is very broad. In addition, OA, UA and their derivatives display potent antimutagenic activity. Studies to identify the cellular targets and molecular mechanisms of OA and UA action were initiated a few years ago and it has already been demonstrated that both acids influence bacterial gene expression, the formation and maintenance of biofilms, cell autolysis and peptidoglycan turnover. Before these compounds can be used clinically as antimicrobial agents, further extensive studies are required to determine their cytotoxicity and the optimum mode of their application.

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“…(Verbenaceae) [65] and Ligularia sagitta (Astraceae) [66]. Similarly, no antibacterial activity against MRSA was found for UA isolated from Rosa nutkana (Rosaceae) [67].…”

Section: Vitex Negundomentioning

confidence: 99%

Antibacterial activity of oleanolic and ursolic acids and their derivatives

et al. 2010

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However, the chemical constituents of this plant have not been reported up until now.

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confidence: 99%

Sesquiterpenes, Nortriterpenes and Other Constituents from Ligularia tongolensis

Han

Pan

Gao

et al. 2005

CHEMICAL & PHARMACEUTICAL BULLETIN

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In our ongoing investigation into bioactive compounds from the genus Ligularia (Compositae) plants [1][2][3][4][5][6][7] we have studied the roots of Ligularia tongolensis (FRANCH) HAND-MAZZ collected in mountainous areas (altitude: 3600 m) in southwestern China. Ligularia tongolensis is used as a traditional folk medicine in China and its roots can reduce phlegm, relieve coughing and cure pulmonary tuberculosis, urinary track blockages, common cold, and pharyngitis. 8)However, the chemical constituents of this plant have not been reported up until now. In this paper, we report the isolation and structural elucidation of four new compounds (1, 2, 7, 8) and nine known compounds 3, 9) 4, 10) 5, 11) 6, 6) 9, 12) 10, 13) 11, 14) 12 15) and 13 14) from its roots. In addition, the cytotoxic activity in vitro of compounds 1, 2, 3, 7 and 8 were tested against human hepatoma (SMMC-7721), human embryo liver (L-02) and human leukemia (HL-60) cell lines with 10-hydroxycamptothecine as a standard. Results and DiscussionCompound 1 , and the other 15 carbon signals suggested that 1 was an eremophilenolide-type sesquiterpene and its NMR data were similar to those of the known compound, 3b-angeloyloxy-8bH-eremophil-7(11)-ene-12,8a (14,6a)-diolide, 3) except for the presence of a 2-methylbutanoyloxy group in 1 instead of an angeloyloxy group in the known compound. The localization of the 2-methylbutanoyloxy group moiety at C-3 was deduced from the heteronuclear multiple bond correlation (HMBC) spectrum, in which H-3 (d H 5.47) gave a long-range coupling with C-1Ј (d C 175.5). Stereochemically, Me-14 and Me-15 are biogenetically b-orientated.16) The positive nuclear Overhauser effect spectrometry (NOEs) between Me-15 and H-10 (5.30%) showed a cis-fused eremophilane. The coupling pattern observed for H-3 (d H 5.47 q, 3.0 Hz) implied that H-3 was an equatorial proton and should be a-orientated.17,18) H-6 and H-8 were identified as b-orientated from the evidence of positive NOEs between H-6 and H-15 (7.73%), between H-6 and H-8 (4.35%). Therefore, compound 1 was assigned as 3b -(2Ј-methylbutanoyloxy)-8b H-eremophil-7(11)-ene-12,8a (14,6a)-diolide.The molecular formula of compound 2, C 15 H 16 O 4 , was determined by the HR-SI-MS, 13 C-NMR and DEPT (distortionless enhancement by polarization transfer) data. The NMR and IR data were similar to those of compound 1 except for the presence of a double bond at C-3 in 2 instead of the 2-methylbutanoyloxy group in 1. The signals of H-3 and C-3 as well as the adjacent C-4 were shifted downfield [H-3 at d H 6.85, C-3 at d C 136.9 and C-4 at d C 129.6], which indicated that a double bond was between C-3 and C-4. In combination with the other NMR data (Tables 1, 2) and HMBC spectrum, compound 2 was confirmed as 8bH-eremophil-3,7(11)-dien-12,8a (14,6a)-diolide. The molecular formula C 29 H 48 O 3 for compound 7 was determined by the high resolution electrospray ionization mass spectrometry (HR-ESI-MS) and the data of 13 C-NMR and DEPT. Its IR spectrum showed strong hydroxyl bands at * To whom cor...

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“…The structure of 1 was finally concluded to be as shown in Fig. 1 by the HMBC spectrum, in which the two and three bond heteronuclear correlations from H 3 -12 to C-2, C-10 and C-11, from H 2 -11 to C-2, C-10 and C-7Ј, from H-3 to C-2, C-4 and C-9, from H-6Ј to C-1Ј, C-4Ј, C-5Ј and C-7Ј, and from H-3Ј to C-1Ј, C-2Ј, C-4Ј and C-5Ј were observed and the correlations of OCH 3 The absolute configuration of 1 was elucidated by CD excition chirality method. 17,18) The sign of the first Cotton effect was negative [l max 244.1 nm (De Ϫ25.3)], while that of the second one [l max 240.5 nm (De ϩ18.5)] was positive, indicating that the chirality between 5,6-dimethoxybenzofuran ring and benzene ring at C-10 should be unclockwise.…”

Section: Resultsmentioning

confidence: 86%

“…1) As part of our program to systematically assess the chemical and biological diversity of Ligularia species in China, we have previously reported several new eremophilane-type sesquiterpenes, bisabolane-type sesquiterpenes and nortriperpenes obtained from some species of the genus Ligularia. [2][3][4][5][6][7] Continuing our investigation into this genus, we report here the isolation and structural elucidation of a novel benzofuran derivative (R)-(ϩ)-Ligulaodonin A (1) and a new olean-12-ene triterpene (5) along with 10 known compounds from the whole plant of Ligularia odontomanes HAND.-MAZZ. No report has been found about the constituents of this plant to date.…”

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confidence: 97%