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Eight drimane-type sesquiterpenes, including six undescribed ones named spinulactones A-F (-), together with two known labdane-type diterpenoids ( and ) and a sterol (), were isolated from the endophytic fungus 9-1. The structures and absolute configurations of the new compounds were characterized by extensive spectroscopic data, X-ray diffraction analysis, and electronic circular dichroism calculations. Compounds - feature a rare spiro β-lactone moiety, with and additionally incorporating a distinctive nicotinic acid structural motif. Biological evaluation revealed that compounds , , , , and exhibited antifungal activity against the phytopathogen with MIC values ranging from 6.25 to 25 μg/mL. Additionally, compounds , , , and demonstrated significant proangiogenic activity in transgenic zebrafish. Compound also displayed obvious antigastric aging effect . This study expanded the structural diversity of drimane-type sesquiterpenes and provided potential leads for agricultural and pharmaceutical applications.
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http://dx.doi.org/10.1021/acs.jnatprod.5c00431 | DOI Listing |
Chem Sci
August 2025
Natural Product Biosynthesis Research Unit, RIKEN Center for Sustainable Resource Science Wako Saitama 351-0198 Japan
Terpene cyclases (TCs), consisting of various combinations of α, β, and γ domains, have been extensively studied. Recently, non-canonical enzymes comprising a TCβ domain and a haloacid dehalogenase (HAD)-like domain (referred to as HAD-TCβ) have been discovered. However, their overall structure remains unclear.
View Article and Find Full Text PDFJ Nat Prod
July 2025
Department of Microbial Drugs, Helmholtz Centre for Infection Research (HZI), Inhoffenstrasse 7, 38124 Braunschweig, Germany.
Eight unprecedented terpenoids were isolated from submerged cultures of a polyporoid basidiomycete originating from Thailand (which had been referred to as " sp." in a previous publication) by preparative chromatography. Their chemical structures were elucidated by extensive two-dimensional nuclear magnetic resonance (NMR) spectroscopy and high-resolution mass spectrometry.
View Article and Find Full Text PDFJ Nat Prod
June 2025
Institute of Pharmaceutical Biology and Biotechnology, Heinrich-Heine-Universität Düsseldorf, Düsseldorf 40225, Germany.
Eight drimane-type sesquiterpenes, including six undescribed ones named spinulactones A-F (-), together with two known labdane-type diterpenoids ( and ) and a sterol (), were isolated from the endophytic fungus 9-1. The structures and absolute configurations of the new compounds were characterized by extensive spectroscopic data, X-ray diffraction analysis, and electronic circular dichroism calculations. Compounds - feature a rare spiro β-lactone moiety, with and additionally incorporating a distinctive nicotinic acid structural motif.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
February 2025
State Key Laboratory of Natural Medicines, School of Traditional Chinese Pharmacy, China Pharmaceutical University, Nanjing, 211198, China.
Drimane-type merosesquiterpenoids (DMT) are a class of natural products with diverse structures and broad biological activity. Classical DMT synthesis relies on atom-inefficient plant-derived chiral pool building blocks, while alternative drimane-type building blocks such as drimenol and albicanol offer more direct routes but face production challenges. In this study, we engineered a microbial platform for efficient production of these building blocks.
View Article and Find Full Text PDFNat Prod Rep
January 2025
State Key Laboratory of Green Pesticide, Center for R&D of Fine Chemicals of Guizhou University, Guiyang, 550025, China.
Covering: 1962 to 2023Drimane (hydro)quinones biosynthetically arise from the combination of drimane-type terpenoids with phenols or equivalents. Since the isolation of siccanin in 1962 (structure identified in 1967), over 200 natural drimane (hydro)quinones have been reported. They are widespread with remarkably diverse architectures and biological functions, which are achieved by varying either the drimane subunit, hydroquinone segment, or the fusion types of drimane and hydroquinone segment both of them.
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