New benzoate derivatives and hirsutane type sesquiterpenoids with antimicrobial activity and cytotoxicity from the solid-state fermented rice by the medicinal mushroom Stereum hirsutum
•The edible and medicinal mushroom Stereum hirsutum was fermented on rice.•Two new benzoate esters and three new sesquiterpenes were purified and identified.•The absolute configuration of compound 3 was assigned by X-ray.•New benzoate esters (1 and 2) showed moderate antimicrobial activity.•New sesq...
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Published in | Food chemistry Vol. 143; pp. 239 - 245 |
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Main Authors | , , , , , , , , , |
Format | Journal Article |
Language | English |
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15.01.2014
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Abstract | •The edible and medicinal mushroom Stereum hirsutum was fermented on rice.•Two new benzoate esters and three new sesquiterpenes were purified and identified.•The absolute configuration of compound 3 was assigned by X-ray.•New benzoate esters (1 and 2) showed moderate antimicrobial activity.•New sesquiterenes (1 and 3) presented strong NO inhibitory activity and cytotoxicity.
In addition to the fruiting bodies, mushroom mycelia can be used as functional foods and nutraceutical materials. In this study, two new benzoate derivatives (1 and 2) and three new sesquiterpenoids (3–5) were isolated from the mycelia of Stereum hirsutum. Their chemical structures were elucidated by NMR experiments. The absolute configuration in 3 was assigned by X-ray crystallographic analysis. In bioactivities evaluation, compounds 1 and 2 showed antimicrobial effects against methicillin-resistant Staphylococcusaureus, and S. aureus with the MIC values of 25.0μg/mL; compounds 1 and 3 inhibited the NO overproduction in the LPS-induced macrophages with the IC50 values of 19.17 and 15.44μM, and also displayed cytotoxicity against A549 and HepG2 with IC50 in the range of 10–50μM. These results support the usage of the mycelia of S. hirsutum as a good functional food. |
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AbstractList | In addition to the fruiting bodies, mushroom mycelia can be used as functional foods and nutraceutical materials. In this study, two new benzoate derivatives (1 and 2) and three new sesquiterpenoids (3-5) were isolated from the mycelia of Stereum hirsutum. Their chemical structures were elucidated by NMR experiments. The absolute configuration in 3 was assigned by X-ray crystallographic analysis. In bioactivities evaluation, compounds 1 and 2 showed antimicrobial effects against methicillin-resistant Staphylococcusaureus, and S. aureus with the MIC values of 25.0μg/mL; compounds 1 and 3 inhibited the NO overproduction in the LPS-induced macrophages with the IC50 values of 19.17 and 15.44μM, and also displayed cytotoxicity against A549 and HepG2 with IC50 in the range of 10-50μM. These results support the usage of the mycelia of S. hirsutum as a good functional food. •The edible and medicinal mushroom Stereum hirsutum was fermented on rice.•Two new benzoate esters and three new sesquiterpenes were purified and identified.•The absolute configuration of compound 3 was assigned by X-ray.•New benzoate esters (1 and 2) showed moderate antimicrobial activity.•New sesquiterenes (1 and 3) presented strong NO inhibitory activity and cytotoxicity. In addition to the fruiting bodies, mushroom mycelia can be used as functional foods and nutraceutical materials. In this study, two new benzoate derivatives (1 and 2) and three new sesquiterpenoids (3–5) were isolated from the mycelia of Stereum hirsutum. Their chemical structures were elucidated by NMR experiments. The absolute configuration in 3 was assigned by X-ray crystallographic analysis. In bioactivities evaluation, compounds 1 and 2 showed antimicrobial effects against methicillin-resistant Staphylococcusaureus, and S. aureus with the MIC values of 25.0μg/mL; compounds 1 and 3 inhibited the NO overproduction in the LPS-induced macrophages with the IC50 values of 19.17 and 15.44μM, and also displayed cytotoxicity against A549 and HepG2 with IC50 in the range of 10–50μM. These results support the usage of the mycelia of S. hirsutum as a good functional food. In addition to the fruiting bodies, mushroom mycelia can be used as functional foods and nutraceutical materials. In this study, two new benzoate derivatives (1 and 2) and three new sesquiterpenoids (3a5) were isolated from the mycelia of Stereum hirsutum. Their chemical structures were elucidated by NMR experiments. The absolute configuration in 3 was assigned by X-ray crystallographic analysis. In bioactivities evaluation, compounds 1 and 2 showed antimicrobial effects against methicillin-resistant Staphylococcusaureus, and S. aureus with the MIC values of 25.0 mu g/mL; compounds 1 and 3 inhibited the NO overproduction in the LPS-induced macrophages with the IC50 values of 19.17 and 15.44 mu M, and also displayed cytotoxicity against A549 and HepG2 with IC50 in the range of 10a50 mu M. These results support the usage of the mycelia of S. hirsutum as a good functional food. |
Author | Ma, Ke Liu, Hongwei Bao, Li Song, Fuhang Liu, Miaomiao Zhao, Feng Jin, Tao Yang, Xiaoli Li, Shaifei Han, Junjie |
Author_xml | – sequence: 1 givenname: Ke surname: Ma fullname: Ma, Ke organization: State Key Laboratory of Mycology, Institute of Microbiology, Chinese Academy of Sciences, No. 9 Beiertiao, Zhongguancun, Haidian District, Beijing 100090, PR China – sequence: 2 givenname: Li surname: Bao fullname: Bao, Li organization: State Key Laboratory of Mycology, Institute of Microbiology, Chinese Academy of Sciences, No. 9 Beiertiao, Zhongguancun, Haidian District, Beijing 100090, PR China – sequence: 3 givenname: Junjie surname: Han fullname: Han, Junjie organization: State Key Laboratory of Mycology, Institute of Microbiology, Chinese Academy of Sciences, No. 9 Beiertiao, Zhongguancun, Haidian District, Beijing 100090, PR China – sequence: 4 givenname: Tao surname: Jin fullname: Jin, Tao email: 13766969566@163.com organization: Laboratory of Microbiology, College of Life Science, Heilongjiang University, Harbin 150080, PR China – sequence: 5 givenname: Xiaoli surname: Yang fullname: Yang, Xiaoli organization: State Key Laboratory of Mycology, Institute of Microbiology, Chinese Academy of Sciences, No. 9 Beiertiao, Zhongguancun, Haidian District, Beijing 100090, PR China – sequence: 6 givenname: Feng surname: Zhao fullname: Zhao, Feng organization: School of Pharmacy, Yantai University, No. 32 QingQuan Road, Laishan District, Yantai 264005, PR China – sequence: 7 givenname: Shaifei surname: Li fullname: Li, Shaifei organization: State Key Laboratory of Mycology, Institute of Microbiology, Chinese Academy of Sciences, No. 9 Beiertiao, Zhongguancun, Haidian District, Beijing 100090, PR China – sequence: 8 givenname: Fuhang surname: Song fullname: Song, Fuhang organization: CAS Key Laboratory of Pathogenic Microbiology and Immunology, Institute of Microbiology, Chinese Academy of Sciences, No. 9 Beiertiao, Zhongguancun, Haidian District, Beijing 100090, PR China – sequence: 9 givenname: Miaomiao surname: Liu fullname: Liu, Miaomiao organization: CAS Key Laboratory of Pathogenic Microbiology and Immunology, Institute of Microbiology, Chinese Academy of Sciences, No. 9 Beiertiao, Zhongguancun, Haidian District, Beijing 100090, PR China – sequence: 10 givenname: Hongwei surname: Liu fullname: Liu, Hongwei email: liuhw@im.ac.cn organization: State Key Laboratory of Mycology, Institute of Microbiology, Chinese Academy of Sciences, No. 9 Beiertiao, Zhongguancun, Haidian District, Beijing 100090, PR China |
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Keywords | Hirsutane sesquiterpenoids Cytotoxicity NO inhibition Stereum hirsutum Benzoate esters Antimicrobial agent Basidiomycota Fungi Ester Cereal Inhibition Antibacterial agent Food Rice |
Language | English |
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Snippet | •The edible and medicinal mushroom Stereum hirsutum was fermented on rice.•Two new benzoate esters and three new sesquiterpenes were purified and... In addition to the fruiting bodies, mushroom mycelia can be used as functional foods and nutraceutical materials. In this study, two new benzoate derivatives... |
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SubjectTerms | Agaricales - chemistry Agaricales - metabolism Anti-Bacterial Agents - chemistry Anti-Bacterial Agents - metabolism Anti-Bacterial Agents - pharmacology Antibacterial agents Antibiotics. Antiinfectious agents. Antiparasitic agents Benzoate esters Benzoates - chemistry Benzoates - metabolism Benzoates - pharmacology Biological and medical sciences Cell Line Cytotoxicity Cytotoxins - chemistry Cytotoxins - metabolism Cytotoxins - pharmacology Fermentation Functional Food - analysis Hirsutane sesquiterpenoids Humans Medical sciences Molecular Structure NO inhibition Oryza - metabolism Oryza - microbiology Oryza sativa Pharmacology. Drug treatments Sesquiterpenes - chemistry Sesquiterpenes - metabolism Sesquiterpenes - pharmacology Staphylococcus - drug effects Stereum hirsutum |
Title | New benzoate derivatives and hirsutane type sesquiterpenoids with antimicrobial activity and cytotoxicity from the solid-state fermented rice by the medicinal mushroom Stereum hirsutum |
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