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

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...

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Autores principales: Jongsomjainuk, Orawan, Boonsombat, Jutatip, Thongnest, Sanit, Prawat, Hunsa, Batsomboon, Paratchata, Charoensutthivarakul, Sitthivut, Ruchisansakun, Saroj, Chainok, Kittipong, Sirirak, Jitnapa, Mahidol, Chulabhorn, Ruchirawat, Somsak
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Springer Nature Singapore 2023
Materias:
Original Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10689700/
https://www.ncbi.nlm.nih.gov/pubmed/38036688
http://dx.doi.org/10.1007/s13659-023-00420-0
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author Jongsomjainuk, Orawan
Boonsombat, Jutatip
Thongnest, Sanit
Prawat, Hunsa
Batsomboon, Paratchata
Charoensutthivarakul, Sitthivut
Ruchisansakun, Saroj
Chainok, Kittipong
Sirirak, Jitnapa
Mahidol, Chulabhorn
Ruchirawat, Somsak
author_facet Jongsomjainuk, Orawan
Boonsombat, Jutatip
Thongnest, Sanit
Prawat, Hunsa
Batsomboon, Paratchata
Charoensutthivarakul, Sitthivut
Ruchisansakun, Saroj
Chainok, Kittipong
Sirirak, Jitnapa
Mahidol, Chulabhorn
Ruchirawat, Somsak
author_sort Jongsomjainuk, Orawan
collection PubMed
description 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 IC(50) value of 0.69 μM. Molecular docking provided some perspectives on the action of kaemtakol B on iNOS protein. GRAPHICAL ABSTRACT: [Image: see text] SUPPLEMENTARY INFORMATION: The online version contains supplementary material available at 10.1007/s13659-023-00420-0.
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spelling pubmed-106897002023-12-02 Kaemtakols A–D, highly oxidized pimarane diterpenoids with potent anti-inflammatory activity from Kaempferia takensis Jongsomjainuk, Orawan Boonsombat, Jutatip Thongnest, Sanit Prawat, Hunsa Batsomboon, Paratchata Charoensutthivarakul, Sitthivut Ruchisansakun, Saroj Chainok, Kittipong Sirirak, Jitnapa Mahidol, Chulabhorn Ruchirawat, Somsak Nat Prod Bioprospect Original Article 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 IC(50) value of 0.69 μM. Molecular docking provided some perspectives on the action of kaemtakol B on iNOS protein. GRAPHICAL ABSTRACT: [Image: see text] SUPPLEMENTARY INFORMATION: The online version contains supplementary material available at 10.1007/s13659-023-00420-0. Springer Nature Singapore 2023-12-01 /pmc/articles/PMC10689700/ /pubmed/38036688 http://dx.doi.org/10.1007/s13659-023-00420-0 Text en © The Author(s) 2023 https://creativecommons.org/licenses/by/4.0/Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if changes were made. The images or other third party material in this article are included in the article's Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article's Creative Commons licence and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this licence, visit http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) .
spellingShingle Original Article
Jongsomjainuk, Orawan
Boonsombat, Jutatip
Thongnest, Sanit
Prawat, Hunsa
Batsomboon, Paratchata
Charoensutthivarakul, Sitthivut
Ruchisansakun, Saroj
Chainok, Kittipong
Sirirak, Jitnapa
Mahidol, Chulabhorn
Ruchirawat, Somsak
Kaemtakols A–D, highly oxidized pimarane diterpenoids with potent anti-inflammatory activity from Kaempferia takensis
title Kaemtakols A–D, highly oxidized pimarane diterpenoids with potent anti-inflammatory activity from Kaempferia takensis
title_full Kaemtakols A–D, highly oxidized pimarane diterpenoids with potent anti-inflammatory activity from Kaempferia takensis
title_fullStr Kaemtakols A–D, highly oxidized pimarane diterpenoids with potent anti-inflammatory activity from Kaempferia takensis
title_full_unstemmed Kaemtakols A–D, highly oxidized pimarane diterpenoids with potent anti-inflammatory activity from Kaempferia takensis
title_short Kaemtakols A–D, highly oxidized pimarane diterpenoids with potent anti-inflammatory activity from Kaempferia takensis
title_sort kaemtakols a–d, highly oxidized pimarane diterpenoids with potent anti-inflammatory activity from kaempferia takensis
topic Original Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10689700/
https://www.ncbi.nlm.nih.gov/pubmed/38036688
http://dx.doi.org/10.1007/s13659-023-00420-0
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