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Cyclohumulanoid Sesquiterpenes from the Culture Broth of the Basidiomycetous Fungus Daedaleopsis tricolor
- Source :
- Molecules, Volume 26, Issue 14, Molecules, Vol 26, Iss 4364, p 4364 (2021)
- Publication Year :
- 2021
- Publisher :
- MDPI AG, 2021.
-
Abstract
- A series of cyclohumulanoids, i.e., tricocerapicanols A–C (1a–1c), tricoprotoilludenes A (2a) and B (3), tricosterpurol (4), and tricoilludins A–C (5–7) were isolated along with known violascensol (2b) and omphadiol (8) from the culture broth of Daedaleopsis tricolor, an inedible but not toxic mushroom. The structures were fully elucidated on the basis of NMR spectroscopic analysis, and the suggested relative structures were confirmed via density functional theory (DFT)-based chemical shift calculations involving a DP4 probability analysis. In the present study, the 1H chemical shifts were more informative than the 13C chemical shifts to distinguish the diastereomers at C-11. The absolute configurations of 1–5 were determined by comparing the experimental and calculated electronic circular dichroism (ECD) spectra. For 6 and 7, the same chirality was assigned according to their biosynthetic similarities with the other compounds. The successful assignment of some Cotton effects was achieved by utilizing DFT calculations using simple model compounds. The plausible biosynthesis of 1–7 was also discussed on the basis of the structural commonality and general cyclohumulanoid biosynthesis. Compounds 2a and 5 were found to simultaneously induce hyphal swelling and branching at 5.0 μg/mL against a test fungus Cochliobolus miyabeanus.
- Subjects :
- Circular dichroism
Stereochemistry
Pharmaceutical Science
01 natural sciences
Analytical Chemistry
DFT-based chemical shift calculation
chemistry.chemical_compound
QD241-441
Biosynthesis
Drug Discovery
Cochliobolus miyabeanus
Physical and Theoretical Chemistry
Mushroom
biology
010405 organic chemistry
Chemistry
Chemical shift
Organic Chemistry
Diastereomer
biology.organism_classification
DFT-based ECD spectral calculation
0104 chemical sciences
010404 medicinal & biomolecular chemistry
Chemistry (miscellaneous)
Molecular Medicine
Density functional theory
cyclohumulanoid
Chirality (chemistry)
Subjects
Details
- ISSN :
- 14203049
- Volume :
- 26
- Database :
- OpenAIRE
- Journal :
- Molecules
- Accession number :
- edsair.doi.dedup.....30efb7588739b93520330ef3b40180c9