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Spiroketones and a Biphenyl Analog from Stems and Leaves of Larrea nitida and Their Inhibitory Activity against IL-6 Production

College of Pharmacy and Research Institute of Pharmaceutical Sciences, Seoul National University, Seoul 08826, Korea
College of Pharmacy and Integrated Research Institute for Drug Development, Dongguk University-Seoul, Gyeonggi-do 10326, Korea
Department of Environment and Forest Resources, College of Agriculture and Life Sciences, Chungnam National University, Daejeon 34134, Korea
Department of Biological Sciences, College of Science, Sookmyung Women’s University, Seoul 04310, Korea
College of Pharmacy, Sookmyung Women's University, Seoul 04310, Korea
Department of Botany, University of Concepcion, Casilla 160C, Concepcion 4080871, Chile
International Biological Material Research Center, KRIBB, Daejeon 34141, Korea
College of Pharmacy, Daegu Catholic University, Gyeongbuk 38430, Korea
Author to whom correspondence should be addressed.
These authors contributed equally to this work.
Molecules 2018, 23(2), 302;
Received: 17 January 2018 / Revised: 28 January 2018 / Accepted: 30 January 2018 / Published: 31 January 2018
(This article belongs to the Section Natural Products Chemistry)
PDF [739 KB, uploaded 31 January 2018]


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 (13) and three known compounds (46). 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, 36 showed potent anti-inflammatory activity, with IC50 values of 12.8, 17.5, 14.9, 22.9, and 17.8 µM, respectively. View Full-Text
Keywords: Larrea nitida; spiroketones; biphenyl analog; HMC-1; IL-6 Larrea nitida; spiroketones; biphenyl analog; HMC-1; IL-6

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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Ahn, J.; Pei, Y.; Chae, H.-S.; Kim, S.-H.; Kim, Y.-M.; Choi, Y.H.; Lee, J.; Chang, M.; Song, Y.S.; Rodriguez, R.; Oh, D.-C.; Kim, J.; Choi, S.; Joo, S.H.; Chin, Y.-W. Spiroketones and a Biphenyl Analog from Stems and Leaves of Larrea nitida and Their Inhibitory Activity against IL-6 Production. Molecules 2018, 23, 302.

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