Characterization of Eight Novel Spiroleptosphols from Fusarium avenaceum

Westphal, Klaus Ringsborg; Werner, Manuela Ilse Helga; Nielsen, Katrine Amalie Hamborg; Sørensen, Jens Laurids; Andrushchenko, Valery; Winde, Jacob; Hertz, Morten; Jensen, Mikkel Astrup; Mortensen, Mathilde Lauge; Bouř, Petr; Søndergaard, Teis Esben; Wimmer, Reinhard

doi:10.3390/molecules24193498

Cited by 7 publications

(3 citation statements)

References 28 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

Section: Resultsmentioning

confidence: 99%

“…The relative stereochemistry was assigned using 1 H NMR coupling constants, NOESY, and ROESY experiments, while the AC was established as (6R,9S,10R,11R,12R,1 3S)−188 by VCD. 90 VCDEC was used to determine the (2R,2'R,3S) absolute stereochemistry at C-2' in 189 ( Figure 50) using the mono (S)-MTPA ester of chaetophenol G isolated from Chaetomium cancroideum. 91 The structure of (-)-aloesaponol III 8-methyl ether (190) (Figure 51), isolated from the roots of Eremurus persicus, was elucidated by IR and NMR experiments and the AC was assigned through VCD and ECD spectroscopies as (R).…”

Section: Polyketidesmentioning

confidence: 99%

See 1 more Smart Citation

Vibrational Circular Dichroism Absolute Configuration of Natural Products From 2015 to 2019

Río

Joseph‐Nathan

2021

Natural Product Communications

View full text Add to dashboard Cite

Although demonstrated in 1975, vibrational circular dichroism (VCD) finally started to popularize during this century as a reliable tool to determine the absolute configuration (AC) of organic molecules. This research field continues to be a very dynamic one, in particular for the study of natural products which are a unlimited source of chiral molecules. It therefore turns of interest to summarize the accomplishments published in recent years and to comment on some eventual difficulties that emerged in rare cases to complete the AC determination task. Therefore the aim of this review is to update VCD results for the AC assignment of natural products published from 2015 to 2019, a period in which VCD was reported in some 126 publications involving almost 300 molecules. They are organized according the type of studied metabolite allowing an easily search. The molecules correspond to 28 monoterpenes concerning 17 papers, to 42 sesquiterpenes in 14 papers, to 51 diterpenes in 19 publications, to 5 other terpenoids in three papers, to 48 aromatic molecules in 15 reports, to 20 polyketides in 10 publications, to 27 miscellaneous formulas also in 10 papers, and to 76 nitrogen containing compounds, which include alkaloids and their synthetic analogs, in 38 articles. The landscape of reviewed molecules is quite wide as it goes from simple monoterpenes, like borneol or camphor, to very relevant biological molecules like the alkaloid cocaine or tadalafil samples to distinguish genuine and counterfeit Cialis®. In addition, 5 natural products and a simple derivative published outside the reviewed period, were used to illustrate some aspects of density functional theory calculations.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Polyketidesmentioning

confidence: 99%

Vibrational Circular Dichroism Absolute Configuration of Natural Products From 2015 to 2019

Río

Joseph‐Nathan

2021

Natural Product Communications

View full text Add to dashboard Cite

show abstract

“…Gunatilaka et al employed this mechanism to explain the reasons behind the inseparable diastereomers of oxaspirol B . Furthermore, Wimmer et al reported the ring-opened analog spiroleptosphol V from Fusarium avenaceum , corresponding to the right structure in Scheme . We assumed that this mechanism contributes to the generation of C-6 diastereomers 1 and 2 , as described in the next section.…”

Section: Resultsmentioning

confidence: 99%

Pseudo-Enantiomeric Paraphaeolactones and Their Biosynthetic Derivatives from Paraphaeosphaeria sp. KT4192: A Proposition of a Favorskii Rearrangement for Their Biosynthesis

Kanehara,

Oinuma,

Maeda

et al. 2023

J. Nat. Prod.

View full text Add to dashboard Cite

Paraphaeolactones A1, A2, B1, and B2 (1–4, respectively), known arthropsadiol D (5), massariphenone (6) and its positional isomer 7, and massarilactones E (8) and G (9) were isolated from the culture broth of Paraphaeosphaeria sp. KT4192. Although the structural resemblance between 1 and 2 implies that these comprised a diastereomeric pair at the C-2 stereogenic center, electronic circular dichroism (ECD) spectral analyses revealed that they were pseudo-enantiomers possessing the common (2R)-configuration. Paraphaeolactones B1 and B2 (3 and 4) were the derivatives of 2, which equipped the 3-(1-hydroxy-2-oxopropyl)-4-methylcatechol moiety via an acetal bond at C-10. The relative configurations of their acetal carbons were elucidated by NOE experiments, and those of C-8′ were deduced independently by ECD spectral analysis. The present study disclosed that 1–5, 8, and 9 contain a methylcyclohexene substructure with the same absolute configuration. This prompted us to reinvestigate the absolute configurations of known structurally related fungal metabolites, allowing us to conclude that the methylcyclohexene moieties of these natural products have the same absolute configuration despite the variety of configurations of other stereogenic centers. The plausible biosynthetic routes for 1–9 are discussed on the basis of the above conclusion. We propose a Favorskii rearrangement as the key transformation for biosyntheses of 1–4.

show abstract

Final piece to the Fusarium pigmentation puzzle – Unraveling of the phenalenone biosynthetic pathway responsible for perithecial pigmentation in the Fusarium solani species complex

Nielsen,

Sørensen,

Pedersen

et al. 2024

Fungal Genetics and Biology

View full text Add to dashboard Cite

Characterization of Eight Novel Spiroleptosphols from Fusarium avenaceum

Cited by 7 publications

References 28 publications

Vibrational Circular Dichroism Absolute Configuration of Natural Products From 2015 to 2019

Vibrational Circular Dichroism Absolute Configuration of Natural Products From 2015 to 2019

Pseudo-Enantiomeric Paraphaeolactones and Their Biosynthetic Derivatives from Paraphaeosphaeria sp. KT4192: A Proposition of a Favorskii Rearrangement for Their Biosynthesis

Final piece to the Fusarium pigmentation puzzle – Unraveling of the phenalenone biosynthetic pathway responsible for perithecial pigmentation in the Fusarium solani species complex

Contact Info

Product

Resources

About