Spiroketones and a Biphenyl Analog from Stems and Leaves of Larrea nitida and Their Inhibitory Activity against IL-6 Production
Bioactivity-guided fractionation for the stems of leaves of Larrea nitida Cav., using interleukin-6 (IL-6) inhibitory assay in human mast cells (HMC-1), led to the isolation of three new compounds with an unprecedented skeleton in nature (1–3) and three known compounds (4–6). Their structures were e...
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| Format: | Article |
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MDPI AG
2018-01-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/23/2/302 |
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| author | Jongmin Ahn Yihua Pei Hee-Sung Chae Seong-Hwan Kim Young-Mi Kim Young Hee Choi Joongku Lee Minsun Chang Yun Seon Song Roberto Rodriguez Dong-Chan Oh Jinwoong Kim Sangho Choi Sang Hoon Joo Young-Won Chin |
| author_facet | Jongmin Ahn Yihua Pei Hee-Sung Chae Seong-Hwan Kim Young-Mi Kim Young Hee Choi Joongku Lee Minsun Chang Yun Seon Song Roberto Rodriguez Dong-Chan Oh Jinwoong Kim Sangho Choi Sang Hoon Joo Young-Won Chin |
| author_sort | Jongmin Ahn |
| collection | DOAJ |
| description | Bioactivity-guided fractionation for the stems of leaves of Larrea nitida Cav., using interleukin-6 (IL-6) inhibitory assay in human mast cells (HMC-1), led to the isolation of three new compounds with an unprecedented skeleton in nature (1–3) and three known compounds (4–6). Their structures were elucidated through extensive spectroscopic analysis. The three new compounds were elucidated as two new spiroketones, nitidaones A (1), and B (2) and one new biphenyl analog, nitidaol (3). The known compounds were identified as nordihydroguaiaretic acid (4), 7,3′,4′-tri-O-methylquercetin (5) and ayanin (6). All the isolates were tested for their inhibitory activity against IL-6 production in HMC-1 cells. Of them, compounds 1, 3–6 showed potent anti-inflammatory activity, with IC50 values of 12.8, 17.5, 14.9, 22.9, and 17.8 µM, respectively. |
| first_indexed | 2024-12-13T08:34:32Z |
| format | Article |
| id | doaj.art-2b194e259d01468ab4a824007e753ac4 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-13T08:34:32Z |
| publishDate | 2018-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-2b194e259d01468ab4a824007e753ac42022-12-21T23:53:41ZengMDPI AGMolecules1420-30492018-01-0123230210.3390/molecules23020302molecules23020302Spiroketones and a Biphenyl Analog from Stems and Leaves of Larrea nitida and Their Inhibitory Activity against IL-6 ProductionJongmin Ahn0Yihua Pei1Hee-Sung Chae2Seong-Hwan Kim3Young-Mi Kim4Young Hee Choi5Joongku Lee6Minsun Chang7Yun Seon Song8Roberto Rodriguez9Dong-Chan Oh10Jinwoong Kim11Sangho Choi12Sang Hoon Joo13Young-Won Chin14College of Pharmacy and Research Institute of Pharmaceutical Sciences, Seoul National University, Seoul 08826, KoreaCollege of Pharmacy and Integrated Research Institute for Drug Development, Dongguk University-Seoul, Gyeonggi-do 10326, KoreaCollege of Pharmacy and Integrated Research Institute for Drug Development, Dongguk University-Seoul, Gyeonggi-do 10326, KoreaCollege of Pharmacy and Research Institute of Pharmaceutical Sciences, Seoul National University, Seoul 08826, KoreaCollege of Pharmacy and Integrated Research Institute for Drug Development, Dongguk University-Seoul, Gyeonggi-do 10326, KoreaCollege of Pharmacy and Integrated Research Institute for Drug Development, Dongguk University-Seoul, Gyeonggi-do 10326, KoreaDepartment of Environment and Forest Resources, College of Agriculture and Life Sciences, Chungnam National University, Daejeon 34134, KoreaDepartment of Biological Sciences, College of Science, Sookmyung Women’s University, Seoul 04310, KoreaCollege of Pharmacy, Sookmyung Women's University, Seoul 04310, KoreaDepartment of Botany, University of Concepcion, Casilla 160C, Concepcion 4080871, ChileCollege of Pharmacy and Research Institute of Pharmaceutical Sciences, Seoul National University, Seoul 08826, KoreaCollege of Pharmacy and Research Institute of Pharmaceutical Sciences, Seoul National University, Seoul 08826, KoreaInternational Biological Material Research Center, KRIBB, Daejeon 34141, KoreaCollege of Pharmacy, Daegu Catholic University, Gyeongbuk 38430, KoreaCollege of Pharmacy and Integrated Research Institute for Drug Development, Dongguk University-Seoul, Gyeonggi-do 10326, KoreaBioactivity-guided fractionation for the stems of leaves of Larrea nitida Cav., using interleukin-6 (IL-6) inhibitory assay in human mast cells (HMC-1), led to the isolation of three new compounds with an unprecedented skeleton in nature (1–3) and three known compounds (4–6). Their structures were elucidated through extensive spectroscopic analysis. The three new compounds were elucidated as two new spiroketones, nitidaones A (1), and B (2) and one new biphenyl analog, nitidaol (3). The known compounds were identified as nordihydroguaiaretic acid (4), 7,3′,4′-tri-O-methylquercetin (5) and ayanin (6). All the isolates were tested for their inhibitory activity against IL-6 production in HMC-1 cells. Of them, compounds 1, 3–6 showed potent anti-inflammatory activity, with IC50 values of 12.8, 17.5, 14.9, 22.9, and 17.8 µM, respectively.http://www.mdpi.com/1420-3049/23/2/302Larrea nitidaspiroketonesbiphenyl analogHMC-1IL-6 |
| spellingShingle | Jongmin Ahn Yihua Pei Hee-Sung Chae Seong-Hwan Kim Young-Mi Kim Young Hee Choi Joongku Lee Minsun Chang Yun Seon Song Roberto Rodriguez Dong-Chan Oh Jinwoong Kim Sangho Choi Sang Hoon Joo Young-Won Chin Spiroketones and a Biphenyl Analog from Stems and Leaves of Larrea nitida and Their Inhibitory Activity against IL-6 Production Molecules Larrea nitida spiroketones biphenyl analog HMC-1 IL-6 |
| title | Spiroketones and a Biphenyl Analog from Stems and Leaves of Larrea nitida and Their Inhibitory Activity against IL-6 Production |
| title_full | Spiroketones and a Biphenyl Analog from Stems and Leaves of Larrea nitida and Their Inhibitory Activity against IL-6 Production |
| title_fullStr | Spiroketones and a Biphenyl Analog from Stems and Leaves of Larrea nitida and Their Inhibitory Activity against IL-6 Production |
| title_full_unstemmed | Spiroketones and a Biphenyl Analog from Stems and Leaves of Larrea nitida and Their Inhibitory Activity against IL-6 Production |
| title_short | Spiroketones and a Biphenyl Analog from Stems and Leaves of Larrea nitida and Their Inhibitory Activity against IL-6 Production |
| title_sort | spiroketones and a biphenyl analog from stems and leaves of larrea nitida and their inhibitory activity against il 6 production |
| topic | Larrea nitida spiroketones biphenyl analog HMC-1 IL-6 |
| url | http://www.mdpi.com/1420-3049/23/2/302 |
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