Monohexosylceramides from Rhizopus Species Isolated from Brazilian Caatinga: Chemical Characterization and Evaluation of Their Anti-Biofilm and Antibacterial Activities
Monohexosylceramides (CMHs) are highly conserved fungal glycosphingolipids playing a role in several cellular processes such as growth, differentiation and morphological transition. In this study, we report the isolation, purification and chemical characterization of CMHs from and . Using positive i...
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| Published in: | Molecules (Basel, Switzerland) Vol. 23; no. 6; p. 1331 |
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| Abstract | Monohexosylceramides (CMHs) are highly conserved fungal glycosphingolipids playing a role in several cellular processes such as growth, differentiation and morphological transition. In this study, we report the isolation, purification and chemical characterization of CMHs from
and
. Using positive ion mode ESI-MS, two major ion species were observed at
/
750 and
/
766, respectively. Both ion species consisted of a glucose/galactose residue attached to a ceramide moiety containing 9-methyl-4,8-sphingadienine with an amidic linkage to a hydroxylated C16:0 fatty acid. The antimicrobial activity of CMH was evaluated against Gram positive and Gram negative bacteria using the agar diffusion assay. CMH from both
species inhibited the growth of
,
(
) and
(
) with a MIC
of 6.25, 6.25 and 3.13 mg/mL, respectively. The bactericidal effect was detected only for
and
, with MBC values of 25 and 6.25 mg/mL, respectively. Furthermore, the action of CMH on the biofilm produced by methicillin-resistant
(MRSA) was analyzed using 12.5 and 25 mg/mL of CMH from
. Total biofilm biomass, biofilm matrix and viability of the cells that form the biofilm structure were evaluated. CMH from
was able to inhibit the MRSA biofilm formation in all parameters tested. |
|---|---|
| AbstractList | Monohexosylceramides (CMHs) are highly conserved fungal glycosphingolipids playing a role in several cellular processes such as growth, differentiation and morphological transition. In this study, we report the isolation, purification and chemical characterization of CMHs from
and
. Using positive ion mode ESI-MS, two major ion species were observed at
/
750 and
/
766, respectively. Both ion species consisted of a glucose/galactose residue attached to a ceramide moiety containing 9-methyl-4,8-sphingadienine with an amidic linkage to a hydroxylated C16:0 fatty acid. The antimicrobial activity of CMH was evaluated against Gram positive and Gram negative bacteria using the agar diffusion assay. CMH from both
species inhibited the growth of
,
(
) and
(
) with a MIC
of 6.25, 6.25 and 3.13 mg/mL, respectively. The bactericidal effect was detected only for
and
, with MBC values of 25 and 6.25 mg/mL, respectively. Furthermore, the action of CMH on the biofilm produced by methicillin-resistant
(MRSA) was analyzed using 12.5 and 25 mg/mL of CMH from
. Total biofilm biomass, biofilm matrix and viability of the cells that form the biofilm structure were evaluated. CMH from
was able to inhibit the MRSA biofilm formation in all parameters tested. Monohexosylceramides (CMHs) are highly conserved fungal glycosphingolipids playing a role in several cellular processes such as growth, differentiation and morphological transition. In this study, we report the isolation, purification and chemical characterization of CMHs from Rhizopus stolonifer and R. microspores. Using positive ion mode ESI-MS, two major ion species were observed at m/z 750 and m/z 766, respectively. Both ion species consisted of a glucose/galactose residue attached to a ceramide moiety containing 9-methyl-4,8-sphingadienine with an amidic linkage to a hydroxylated C16:0 fatty acid. The antimicrobial activity of CMH was evaluated against Gram positive and Gram negative bacteria using the agar diffusion assay. CMH from both Rhizopus species inhibited the growth of Bacillus terrae, Micrococcus luteus (M. luteus) and Pseudomonas stutzeri (P. stutzeri) with a MIC50 of 6.25, 6.25 and 3.13 mg/mL, respectively. The bactericidal effect was detected only for M. luteus and P. stutzeri, with MBC values of 25 and 6.25 mg/mL, respectively. Furthermore, the action of CMH on the biofilm produced by methicillin-resistant Staphylococcus aureus (MRSA) was analyzed using 12.5 and 25 mg/mL of CMH from R. microsporus. Total biofilm biomass, biofilm matrix and viability of the cells that form the biofilm structure were evaluated. CMH from R. microsporus was able to inhibit the MRSA biofilm formation in all parameters tested. Monohexosylceramides (CMHs) are highly conserved fungal glycosphingolipids playing a role in several cellular processes such as growth, differentiation and morphological transition. In this study, we report the isolation, purification and chemical characterization of CMHs from Rhizopus stolonifer and R. microspores . Using positive ion mode ESI-MS, two major ion species were observed at m / z 750 and m / z 766, respectively. Both ion species consisted of a glucose/galactose residue attached to a ceramide moiety containing 9-methyl-4,8-sphingadienine with an amidic linkage to a hydroxylated C16:0 fatty acid. The antimicrobial activity of CMH was evaluated against Gram positive and Gram negative bacteria using the agar diffusion assay. CMH from both Rhizopus species inhibited the growth of Bacillus terrae , Micrococcus luteus ( M. luteus ) and Pseudomonas stutzeri ( P. stutzeri ) with a MIC 50 of 6.25, 6.25 and 3.13 mg/mL, respectively. The bactericidal effect was detected only for M. luteus and P. stutzeri , with MBC values of 25 and 6.25 mg/mL, respectively. Furthermore, the action of CMH on the biofilm produced by methicillin-resistant Staphylococcus aureus (MRSA) was analyzed using 12.5 and 25 mg/mL of CMH from R. microsporus . Total biofilm biomass, biofilm matrix and viability of the cells that form the biofilm structure were evaluated. CMH from R. microsporus was able to inhibit the MRSA biofilm formation in all parameters tested. |
| Author | Barreto-Bergter, Eliana Alviano, Daniela Sales de Campos-Takaki, Galba Maria Vieira, Edson Rodrigues Xisto, Mariana Ingrid Dutra da Silva Pele, Milagre Américo Alviano, Celuta Sales |
| AuthorAffiliation | 2 Laboratório de Química Biológica de Microrganismos, Instituto de Microbiologia Paulo de Góes, Centro de Ciências da Saúde, Universidade Federal do Rio de Janeiro, Ilha do Fundão, Rio de Janeiro 21941-902, RJ, Brazil; marylanax@gmail.com 3 Laboratório de Estrutura de Microrganismos, Instituto de Microbiologia Paulo de Góes, Centro de Ciências da Saúde, Universidade Federal do Rio de Janeiro, Ilha do Fundão, Rio de Janeiro 21941-902, RJ, Brazil; danialviano@micro.ufrj.br (D.S.A.); alviano@micro.ufrj.br (C.S.A.) 1 Núcleo de Pesquisa em Ciências Ambientais e Biotecnologia, Universidade Católica de Pernambuco, Recife 50050-590, PE, Brazil; edsonipubi@gmail.com (E.R.V.); phelema1@gmail.com (M.A.P.); galba_takaki@yahoo.com.br (G.M.d.C.-T.) |
| AuthorAffiliation_xml | – name: 2 Laboratório de Química Biológica de Microrganismos, Instituto de Microbiologia Paulo de Góes, Centro de Ciências da Saúde, Universidade Federal do Rio de Janeiro, Ilha do Fundão, Rio de Janeiro 21941-902, RJ, Brazil; marylanax@gmail.com – name: 3 Laboratório de Estrutura de Microrganismos, Instituto de Microbiologia Paulo de Góes, Centro de Ciências da Saúde, Universidade Federal do Rio de Janeiro, Ilha do Fundão, Rio de Janeiro 21941-902, RJ, Brazil; danialviano@micro.ufrj.br (D.S.A.); alviano@micro.ufrj.br (C.S.A.) – name: 1 Núcleo de Pesquisa em Ciências Ambientais e Biotecnologia, Universidade Católica de Pernambuco, Recife 50050-590, PE, Brazil; edsonipubi@gmail.com (E.R.V.); phelema1@gmail.com (M.A.P.); galba_takaki@yahoo.com.br (G.M.d.C.-T.) |
| Author_xml | – sequence: 1 givenname: Edson Rodrigues surname: Vieira fullname: Vieira, Edson Rodrigues email: edsonipubi@gmail.com organization: Núcleo de Pesquisa em Ciências Ambientais e Biotecnologia, Universidade Católica de Pernambuco, Recife 50050-590, PE, Brazil. edsonipubi@gmail.com – sequence: 2 givenname: Mariana Ingrid Dutra da Silva surname: Xisto fullname: Xisto, Mariana Ingrid Dutra da Silva email: marylanax@gmail.com organization: Laboratório de Química Biológica de Microrganismos, Instituto de Microbiologia Paulo de Góes, Centro de Ciências da Saúde, Universidade Federal do Rio de Janeiro, Ilha do Fundão, Rio de Janeiro 21941-902, RJ, Brazil. marylanax@gmail.com – sequence: 3 givenname: Milagre Américo surname: Pele fullname: Pele, Milagre Américo email: phelema1@gmail.com organization: Núcleo de Pesquisa em Ciências Ambientais e Biotecnologia, Universidade Católica de Pernambuco, Recife 50050-590, PE, Brazil. phelema1@gmail.com – sequence: 4 givenname: Daniela Sales surname: Alviano fullname: Alviano, Daniela Sales email: danialviano@micro.ufrj.br organization: Laboratório de Estrutura de Microrganismos, Instituto de Microbiologia Paulo de Góes, Centro de Ciências da Saúde, Universidade Federal do Rio de Janeiro, Ilha do Fundão, Rio de Janeiro 21941-902, RJ, Brazil. danialviano@micro.ufrj.br – sequence: 5 givenname: Celuta Sales surname: Alviano fullname: Alviano, Celuta Sales email: alviano@micro.ufrj.br organization: Laboratório de Estrutura de Microrganismos, Instituto de Microbiologia Paulo de Góes, Centro de Ciências da Saúde, Universidade Federal do Rio de Janeiro, Ilha do Fundão, Rio de Janeiro 21941-902, RJ, Brazil. alviano@micro.ufrj.br – sequence: 6 givenname: Eliana surname: Barreto-Bergter fullname: Barreto-Bergter, Eliana email: eliana.bergter@micro.ufrj.br organization: Laboratório de Química Biológica de Microrganismos, Instituto de Microbiologia Paulo de Góes, Centro de Ciências da Saúde, Universidade Federal do Rio de Janeiro, Ilha do Fundão, Rio de Janeiro 21941-902, RJ, Brazil. eliana.bergter@micro.ufrj.br – sequence: 7 givenname: Galba Maria surname: de Campos-Takaki fullname: de Campos-Takaki, Galba Maria email: galba_takaki@yahoo.com.br organization: Núcleo de Pesquisa em Ciências Ambientais e Biotecnologia, Universidade Católica de Pernambuco, Recife 50050-590, PE, Brazil. galba_takaki@yahoo.com.br |
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| CitedBy_id | crossref_primary_10_3389_fcimb_2020_598823 crossref_primary_10_3390_jof6040345 crossref_primary_10_3390_jof8101012 crossref_primary_10_3390_md19100553 crossref_primary_10_1371_journal_pone_0242887 |
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| Keywords | monohexosylceramides antibacterial activities Rhizopus biofilm |
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| References | ref13 ref35 ref12 ref34 ref15 ref37 ref14 ref36 ref31 ref30 ref11 ref33 ref10 ref32 ref2 ref1 ref17 ref16 ref38 ref19 ref18 Folch (ref39) 1957; 226 ref24 ref23 ref45 ref26 ref25 ref20 ref42 ref41 ref22 ref44 ref21 ref43 ref28 ref27 ref29 ref8 ref7 ref9 ref4 ref3 ref6 ref5 ref40 |
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| SubjectTerms | antibacterial activities Antimicrobial activity biofilm Biofilms Ceramide Drug resistance Galactose Glycosphingolipids Gram-negative bacteria Methicillin Microspores monohexosylceramides Organic chemistry Positive ions Purification Rhizopus Staphylococcus aureus Staphylococcus infections |
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| Title | Monohexosylceramides from Rhizopus Species Isolated from Brazilian Caatinga: Chemical Characterization and Evaluation of Their Anti-Biofilm and Antibacterial Activities |
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