Kaemtakols A–D, highly oxidized pimarane diterpenoids with potent anti-inflammatory activity from Kaempferia takensis

doi:10.1007/s13659-023-00420-0

Natural Products and Bioprospecting ›› 2023, Vol. 13 ›› Issue (6): 55-55.DOI: 10.1007/s13659-023-00420-0

• ORIGINAL ARTICLES • Previous Articles

Kaemtakols A–D, highly oxidized pimarane diterpenoids with potent anti-inflammatory activity from Kaempferia takensis

Orawan Jongsomjainuk¹, Jutatip Boonsombat^1,4, Sanit Thongnest^1,4, Hunsa Prawat^1,4, Paratchata Batsomboon², Sitthivut Charoensutthivarakul⁵, Saroj Ruchisansakun⁶, Kittipong Chainok⁷, Jitnapa Sirirak⁸, Chulabhorn Mahidol^1,3, Somsak Ruchirawat^2,3,4

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

Received:2023-10-06 Online:2023-12-26 Published:2023-12-24
Contact: Sanit Thongnest,E-mail:sanit@cri.or.th
Supported by:
Thailand Science Research and Innovation, 36824/4274394, Sanit Thongnest, 36827/4274406, Sanit Thongnest.

Kaemtakols A–D, highly oxidized pimarane diterpenoids with potent anti-inflammatory activity from Kaempferia takensis

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

通讯作者: Sanit Thongnest,E-mail:sanit@cri.or.th
基金资助:
Thailand Science Research and Innovation, 36824/4274394, Sanit Thongnest, 36827/4274406, Sanit Thongnest.

Abstract

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[3.2.1.0^2,7]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.

Key words: Kaempferia takensis, Diterpenoid, Structure elucidation, Anti-inflammatory, DP4+, Molecular docking

摘要： 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[3.2.1.0^2,7]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.

关键词: Kaempferia takensis, Diterpenoid, Structure elucidation, Anti-inflammatory, DP4+, Molecular docking

Orawan Jongsomjainuk, Jutatip Boonsombat, Sanit Thongnest, Hunsa Prawat, Paratchata Batsomboon, Sitthivut Charoensutthivarakul, Saroj Ruchisansakun, Kittipong Chainok, Jitnapa Sirirak, Chulabhorn Mahidol, Somsak Ruchirawat. Kaemtakols A–D, highly oxidized pimarane diterpenoids with potent anti-inflammatory activity from Kaempferia takensis[J]. Natural Products and Bioprospecting, 2023, 13(6): 55-55.

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Kaemtakols A–D, highly oxidized pimarane diterpenoids with potent anti-inflammatory activity from Kaempferia takensis

Kaemtakols A–D, highly oxidized pimarane diterpenoids with potent anti-inflammatory activity from Kaempferia takensis

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