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Kaemtakols A–D, highly oxidized pimarane diterpenoids with potent anti-inflammatory activity from Kaempferia takensis |
| Orawan Jongsomjainuk1, Jutatip Boonsombat1,4, Sanit Thongnest1,4, Hunsa Prawat1,4, Paratchata Batsomboon2, Sitthivut Charoensutthivarakul5, Saroj Ruchisansakun6, Kittipong Chainok7, Jitnapa Sirirak8, Chulabhorn Mahidol1,3, Somsak Ruchirawat2,3,4 |
1. Laboratory of Natural Products, Chulabhorn Research Institute, Bangkok, Thailand;
2. Laboratory of Medicinal Chemistry, Chulabhorn Research Institute, Bangkok, Thailand;
3. Program in Chemical Sciences, Chulabhorn Graduate Institute, Chulabhorn Royal Academy, Bangkok, Thailand;
4. Center of Excellence on Environmental Health and Toxicology (EHT), OPS, MHESI, Bangkok, Thailand;
5. Excellent Center for Drug Discovery (ECDD), School of Bioinnovation and Bio-Based Product Intelligence, and Center for Neuroscience, Faculty of Science, Mahidol University, Bangkok, Thailand;
6. Department of Plant Science, Faculty of Science, Mahidol University, Bangkok, Thailand;
7. Thammasat University Research Unit in Multifunctional Crystalline Materials and Applications (TU-MCMA), Faculty of Science and Technology, Thammasat University, Pathum Thani, Thailand;
8. Department of Chemistry, Faculty of Science, Silpakorn University, Nakhon Pathom, Thailand |
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Abstract Four highly oxidized pimarane diterpenoids were isolated from Kaempferia takensis rhizomes. Kaemtakols A–C possess a tetracyclic ring with either a fused tetrahydropyran or tetrahydrofuran motif. Kaemtakol D has an unusual rearranged A/B ring spiro-bridged pimarane framework with a C-10 spirocyclic junction and an adjacent 1-methyltricyclo[3.2.1.02,7]octene ring. Structural characterization was achieved using spectroscopic analysis, DP4+ and ECD calculations, as well as X-ray crystallography, and their putative biosynthetic pathways have been proposed. Kaemtakol B showed significant potency in inhibiting nitric oxide production with an IC50 value of 0.69 μM. Molecular docking provided some perspectives on the action of kaemtakol B on iNOS protein.
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| Keywords
Kaempferia takensis
Diterpenoid
Structure elucidation
Anti-inflammatory
DP4+
Molecular docking
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| Fund:Thailand Science Research and Innovation, 36824/4274394, Sanit Thongnest, 36827/4274406, Sanit Thongnest. |
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Corresponding Authors:
Sanit Thongnest,E-mail:sanit@cri.or.th
E-mail: sanit@cri.or.th
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Issue Date: 26 December 2023
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