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Chemical Constituents from the Rhizomes of Smilax glabra and Their Antimicrobial Activity
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, No. 38, Xueyuan Road, Beijing 100191, China
Key Laboratory of Carcinogenesis and Translational Research (Ministry of Education), Department of Biochemistry and Molecular Biology, Peking University Cancer Hospital & Institute, No. 52 Fucheng Road, Beijing 100142, China
* Authors to whom correspondence should be addressed.
Received: 10 April 2013; in revised form: 24 April 2013 / Accepted: 2 May 2013 / Published: 8 May 2013
Abstract: Six new phenolic compounds, named smiglabrone A (1), smiglabrone B (2), smilachromanone (3), smiglastilbene (4), smiglactone (5), smiglabrol (6), together with fifty-seven known ones 7–63 were isolated from the rhizomes of Smilax glabra. Their structures were elucidated on the basis of extensive spectroscopic analyses, as well as by comparison with literature data. Twenty-seven of these compounds were obtained from and identified in the genus Smilax for the first time. The absolute configuration of (2S)-1,2-O-di-trans-p-coumaroylglycerol (43) was determined for the first time using the exciton-coupled circular dichroism (ECCD) method. Thirty isolated compounds were evaluated for their antimicrobial activity against three Gram-negative bacteria, three Gram-positive bacteria and one fungus, and the corresponding structure-activity relationships were also discussed. Eighteen compounds were found to be antimicrobial against the microorganisms tested and the minimum inhibitory concentrations (MIC) were in the range of 0.0794–3.09 mM. Among them, compound 1 showed antimicrobial activity against Canidia albicans with MIC value of 0.146 mM, which was stronger than cinchonain Ia with an MIC of 0.332 mM. Compounds 3 and 4 exhibited inhibitory activity against Staphylococcus aureus with MIC values of 0.303 and 0.205 mM, respectively. The results indicated that these antimicrobial constituents of this crude drug might be responsible for its clinical antimicrobial effect.
Keywords: Smilax glabra; phenylpropanoid-substituted epicatechin; homoisoflavanone; stilbenes; antimicrobial activity
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Xu, S.; Shang, M.-Y.; Liu, G.-X.; Xu, F.; Wang, X.; Shou, C.-C.; Cai, S.-Q. Chemical Constituents from the Rhizomes of Smilax glabra and Their Antimicrobial Activity. Molecules 2013, 18, 5265-5287.
Xu S, Shang M-Y, Liu G-X, Xu F, Wang X, Shou C-C, Cai S-Q. Chemical Constituents from the Rhizomes of Smilax glabra and Their Antimicrobial Activity. Molecules. 2013; 18(5):5265-5287.
Xu, Shuo; Shang, Ming-Ying; Liu, Guang-Xue; Xu, Feng; Wang, Xuan; Shou, Cheng-Chao; Cai, Shao-Qing. 2013. "Chemical Constituents from the Rhizomes of Smilax glabra and Their Antimicrobial Activity." Molecules 18, no. 5: 5265-5287.