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New derivatives of the iridoid specioside from fungal biotransformation

Abstract

Iridoids are widely found from species of Bignoniaceae family and exhibit several biological activities, such as anti-inflammatory, antimicrobial, antioxidant, and antitumor. Specioside is an iridoid found from Tabebuia species, mainly in Tabebuia aurea. Thus, here fungus-mediated biotransformation of the iridoid specioside was investigated by seven fungi. The fungus-mediated biotransformation reactions resulted in a total of nineteen different analogs by fungus Aspergillus niger, Aspergillus flavus, Aspergillus japonicus, Aspergillus terreus, Aspergillus niveus, Penicillium crustosum, and Thermoascus aurantiacus. Non-glycosylated specioside was the main metabolite observed. The other analogs were yielded from ester hydrolysis, hydroxylation, methylation, and hydrogenation reactions. The non-glycosylated specioside and coumaric acid were yielded by all fungi-mediated biotransformation. Thus, fungus applied in this study showed the ability to perform hydroxylation and glycosidic, as well as ester hydrolysis reactions from glycosylated iridoid.

Key points

The biotransformation of specioside by seven fungi yielded nineteen analogs.

The non-glycosylated specioside was the main analog obtained.

Ester hydrolysis, hydroxylation, methylation, and hydrogenation reactions were observe

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Data availability

The strains are deposited in the library URM (University Recife Mycology) of Federal University of Pernambuco (UFPE) and MMBF (Micoteca Mario Barreto Figueiredo). The data can be found at http://www3.ufpe.br/micoteca/nova/fazerBusca.php and http://www.biologico.sp.gov.br/page/colecoes/fungos-fitopatogenicos.All MS/MS data obtained in this study is summarized in Table 1, and the spectra are illustrated in the Supplementary Information.

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Acknowledgements

The authors thank INAU (Instituto Nacional de Áreas Úmidas), CNPq (Conselho Nacional de Desenvolvimento Científico e Tecnológico), FUNDECT (Fundação de Apoio ao Desenvolvimento do Ensino, Ciência e Tecnologia do Estado de Mato Grosso do Sul), and CAPES (Coordenação de Aperfeiçoamento de Pessoal de Nível Superior).

Funding

DBS is supported by productive fellowship from CNPq (grant number 313047/2020–0).

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Authors and Affiliations

Authors

Contributions

NSC, JCPM, and DBS conceived and designed research. ESA supplied the strains of the fungi. NNK and CAC collected the plant and isolated the specioside iridoid. NSC, NNK, and LBS conducted experiments. RR analyzed the ITS sequence and identified the microorganisms. NSC, CAC, ESA, and DBS analyzed the chemical data. NSC and DBS wrote the manuscript. All authors read and approved the manuscript.

Corresponding author

Correspondence to Denise Brentan Silva.

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This article does not contain any studies with human participants or animals performed by any of the authors.

Conflict of Interest

All authors declare no competing interests.

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Supplementary Information

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Supplementary file1 (PDF 294 KB)

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Cassemiro, N.S., Sanches, L.B., Kato, N.N. et al. New derivatives of the iridoid specioside from fungal biotransformation. Appl Microbiol Biotechnol 105, 7731–7741 (2021). https://doi.org/10.1007/s00253-021-11504-7

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  • DOI: https://doi.org/10.1007/s00253-021-11504-7

Keywords

  • Non-glycosylated specioside
  • Aspergillus niger
  • Ester hydrolysis
  • Methylation
  • Hydroxylation