Xenicane Natural Products: Biological Activity and Total Synthesis

Betschart, Leo; Altmann, Karl‐Heinz

doi:10.2174/1381612821666151002112607

Cited by 16 publications

(21 citation statements)

References 131 publications

(295 reference statements)

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“…Structurally, waixenicin A ( 1 ) belongs to the xenicin subclass of Xenia diterpenoids, a unique family of natural products that was first described in 1977 . Since then, several challenging structures have been isolated and identified from marine organisms . Their oxidized polycyclic framework, along with their diverse biological activities, has stimulated the chemical community to initiate several synthesis campaigns .…”

Section: Introductionmentioning

confidence: 99%

Total Syntheses of (+)-Waixenicin A, (+)-9-Deacetoxy-14,15-deepoxyxeniculin, and (−)-Xeniafaraunol A

Steinborn,

Huber,

Lichtenegger

et al. 2023

J. Am. Chem. Soc.

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The first asymmetric total synthesis of the Xenia diterpenoid waixenicin A, a potent and highly selective TRPM7 inhibitor, is reported. The characteristic trans-fused oxabicyclo[7.4.0]tridecane ring system was constructed via a diastereoselective conjugate addition/trapping sequence, followed by an intramolecular alkylation to forge the 9-membered ring. While a β-keto sulfone motif enabled efficient ring-closure, the subsequent radical desulfonylation suffered from (E)/(Z)-isomerization of the C7/C8-alkene. Conducting the sequence with a trimethylsilylethyl ester allowed for a fluoride-mediated decarboxylation that proceeded without detectable isomerization. The acid-labile enol acetal of the delicate dihydropyran core was introduced at an early stage and temporarily deactivated by a triflate function. The latter was critical for the introduction of the side chain. Diverting from a common late-stage intermediate provided access to waixenicin A and 9-deacetoxy-14,15-deepoxyxeniculin. A high-yielding base-mediated dihydropyran-cyclohexene rearrangement of 9-deacetoxy-14,15-deepoxyxeniculin led to xeniafaraunol A in one step.

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Section: Introductionmentioning

confidence: 99%

Total Syntheses of (+)-Waixenicin A, (+)-9-Deacetoxy-14,15-deepoxyxeniculin, and (−)-Xeniafaraunol A

Steinborn,

Huber,

Lichtenegger

et al. 2023

J. Am. Chem. Soc.

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“…15 a ,18 Potentially, the RuCl 2 (PPh 3 ) 3 /O 2 oxidation would provide a new useful direct synthetic protocol to connect the diols with a variety of lactone-containing natural products, 11 a such as xenicane diterpenoid xeniolide A. 19…”

Section: Resultsmentioning

confidence: 99%

Cytotoxic analogues of marine diterpenoid plumisclerin A by shifting the lipophilic branch on the characteristic tricyclic core

Gao

Chen

et al. 2022

Org. Biomol. Chem.

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“…The xenicanes are characterized by antiproliferative, anti-inflammatory, and antifungal effects. Information on their in vivo activity is still lacking [53]. As far as we know, compound 2 was isolated previously only from Dictyota plectens [50] and it was never detected in fungi.…”

Section: Structural Characterization Of Active Compoundsmentioning

confidence: 99%

Production and identification of two antifungal terpenoids from the Posidonia oceanica epiphytic Ascomycota Mariannaea humicola IG100

et al. 2020

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Background Marine fungi are an important repository of bioactive molecules with great potential in different technological fields, the annual number of new compounds isolated from marine fungi is impressive and the general trend indicates that it is still on the rise. In this context, the antifungal and antimicrobial activity of the marine strain Mariannaea humicola IG100 was evaluated and two active terpenoids were isolated and characterized. Methods Preliminary screening of activity of marine strain IG100 was carried out by agar plug diffusion methods against fungal (Penicillium griseofulvum TSF04) and bacterial (Bacillus pumilus KB66 and Escherichia coli JM109) strains. Subsequently, inhibition tests were done by using the cultural broth and the organic extract (ethyl acetate, EtOAc) by the agar well diffusion methods. The main active fractions were identified and tested for their antifungal activity against P. griseofulvum TSF04 in a 24 wells microplate at different concentrations (1000, 100, 10 and 1.0 µg/mL). Two active compounds were characterized and their relative MIC measured by the broth micro-dilution methods in a 96-well microplate against Aspergillus flavus IG133, P. griseofulvum TSF04, and Trichoderma pleuroticola IG137. Results Marine strain IG100 presented significant antifungal activity associated with two active compounds, the terpenoids terperstacin 1 and 19-acetyl-4-hydroxydictyodiol 2. Their MIC values were measured for A. flavus (MIC of 7.9 µg/mL and 31.3 µg/mL for 1 and 2, respectively), P. griseofulvum (MIC of 25 µg/mL and 100 µg/mL for 1 and 2, respectively) and T. pleuroticola (MIC > 500 µg/mL and 125 µg/mL for 1 and 2, respectively). They showed a rather good fungistatic effect. Conclusions In this study, the first marine strain of M. humicola (IG100) was investigated for the production of bioactive molecules. Strain IG100 produced significant amounts of two bioactive terpenoids, terperstacin 1 and 19-acetyl-4-hydroxydictyodiol 2. The two compounds showed significant antifungal activities against A. flavus IG133, T. pleuroticola IG137 and P. griseofulvum TSF04. Compound 2 was identified for the first time in fungi.

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Xenicane Natural Products: Biological Activity and Total Synthesis

Cited by 16 publications

References 131 publications

Total Syntheses of (+)-Waixenicin A, (+)-9-Deacetoxy-14,15-deepoxyxeniculin, and (−)-Xeniafaraunol A

Total Syntheses of (+)-Waixenicin A, (+)-9-Deacetoxy-14,15-deepoxyxeniculin, and (−)-Xeniafaraunol A

Cytotoxic analogues of marine diterpenoid plumisclerin A by shifting the lipophilic branch on the characteristic tricyclic core

Production and identification of two antifungal terpenoids from the Posidonia oceanica epiphytic Ascomycota Mariannaea humicola IG100

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