LC-ESI-IT-MS/MS and MALDI-TOF Approach: Identification of Natural Polymers from Rhizophora mangle Barks and Determination of Their Analgesic and Anti-inflammatory Properties

doi:10.1007/s13659-018-0192-8

应用天然产物 ›› 2019, Vol. 9 ›› Issue (1): 23-34.DOI: 10.1007/s13659-018-0192-8

LC-ESI-IT-MS/MS and MALDI-TOF Approach: Identification of Natural Polymers from Rhizophora mangle Barks and Determination of Their Analgesic and Anti-inflammatory Properties

Leonardo Mendes de Souza Mesquita¹, Caroline Fabri Bittencourt Rodrigues¹, Cláudia Quintino da Rocha^1,2, Mayara Silveira Bianchim¹, Clenilson Martins Rodrigues³, Vanda Maria de Oliveira³, Henrique Hessel Gaeta¹, Mariana Novo Belchor¹, Marcos Hikari Toyama¹, Wagner Vilegas¹

1 Laboratory of Bioprospection of Natural Products(LBPN), UNESP-Saõ Paulo State University/Coastal Campus of Saõ Vicente, Pça Infante Dom Henrique S/N, Saõ Vicente, Saõ Paulo CEP:11330-900, Brazil;
2 Laboratório de Estudos Avançados em Fitomedicamentos(LEAF), UFMA-Federal University of Maranhaõ, Av. dos Portugueses, 1966-Bacanga, Saõ Luís, Maranhaõ CEP:65080-805, Brazil;
3 Embrapa Agroenergy, Brazilian Agricultural Research Corporation, W3 Norte, PqEB, Brasília, DF 70770-901, Brazil

收稿日期:2018-08-20 出版日期:2019-02-24 发布日期:2019-01-28
通讯作者: Wagner Vilegas
基金资助:
This work was supported by Fundaçaõ de Amparo à Pesquisa do Estado de Saõ Paulo (FAPESP) (Grant 2009/52237-9 to WV, fellowship 2014/23951-3 to LMSM).

LC-ESI-IT-MS/MS and MALDI-TOF Approach: Identification of Natural Polymers from Rhizophora mangle Barks and Determination of Their Analgesic and Anti-inflammatory Properties

1 Laboratory of Bioprospection of Natural Products(LBPN), UNESP-Saõ Paulo State University/Coastal Campus of Saõ Vicente, Pça Infante Dom Henrique S/N, Saõ Vicente, Saõ Paulo CEP:11330-900, Brazil;
2 Laboratório de Estudos Avançados em Fitomedicamentos(LEAF), UFMA-Federal University of Maranhaõ, Av. dos Portugueses, 1966-Bacanga, Saõ Luís, Maranhaõ CEP:65080-805, Brazil;
3 Embrapa Agroenergy, Brazilian Agricultural Research Corporation, W3 Norte, PqEB, Brasília, DF 70770-901, Brazil

Received:2018-08-20 Online:2019-02-24 Published:2019-01-28
Contact: Wagner Vilegas
Supported by:
This work was supported by Fundaçaõ de Amparo à Pesquisa do Estado de Saõ Paulo (FAPESP) (Grant 2009/52237-9 to WV, fellowship 2014/23951-3 to LMSM).

摘要/Abstract

摘要： We recognize the chemical composition of the acetonic extract of Rhizophora mangle barks (AERM) using mass spectrometry analysis[liquid chromatography (LC)-ESI-IT-MS/MS and matrix-assisted laser desorption/ionization-time of flight-MS (MALDI-TOF)]. Analgesic activity was evaluated by formalin and tail-flick experimental assays. Anti-inflammatory activity was performed by paw edema test induced by carrageenan and 48/80 compounds. The first series of experiments involved[LC]-FIA-IT-MS/MS with 11 separated catechins derivatives until degree of polymerization 3 (DP3). The spectra obtained by MALDI-TOF analysis of the AERM presented two homologous series:one based on polymers of m/z 288 Da increments (up to DP12) and another series based on polymers of m/z[288 + 162] Da increments (up to DP11). In addition to these series of flavan-3-ol, each DP had a subset of masses with a variation of-16 Da (homologous series of afzelechins-m/z 873-3465 Da) and + 16 Da (homologous series of gallocatechins-m/z 905-3497 Da). A similar pattern with homologous series of gallocatechins and afzelechins could also be observed for a fifth and a sixth monohexoside series:glucogallocatechins (m/z 779-3371) and glucoafzelechins (m/z 747-3339). The intraperitoneal administration of different doses of AERM (50, 150 and 300 lg mL^-1) have a morphine-like effect and intense anti-inflammatory activity.

关键词: Catechins, Tannins, Morphine-like effect, Anti-inflammatory, Mangroves

Abstract: We recognize the chemical composition of the acetonic extract of Rhizophora mangle barks (AERM) using mass spectrometry analysis[liquid chromatography (LC)-ESI-IT-MS/MS and matrix-assisted laser desorption/ionization-time of flight-MS (MALDI-TOF)]. Analgesic activity was evaluated by formalin and tail-flick experimental assays. Anti-inflammatory activity was performed by paw edema test induced by carrageenan and 48/80 compounds. The first series of experiments involved[LC]-FIA-IT-MS/MS with 11 separated catechins derivatives until degree of polymerization 3 (DP3). The spectra obtained by MALDI-TOF analysis of the AERM presented two homologous series:one based on polymers of m/z 288 Da increments (up to DP12) and another series based on polymers of m/z[288 + 162] Da increments (up to DP11). In addition to these series of flavan-3-ol, each DP had a subset of masses with a variation of-16 Da (homologous series of afzelechins-m/z 873-3465 Da) and + 16 Da (homologous series of gallocatechins-m/z 905-3497 Da). A similar pattern with homologous series of gallocatechins and afzelechins could also be observed for a fifth and a sixth monohexoside series:glucogallocatechins (m/z 779-3371) and glucoafzelechins (m/z 747-3339). The intraperitoneal administration of different doses of AERM (50, 150 and 300 lg mL^-1) have a morphine-like effect and intense anti-inflammatory activity.

Key words: Catechins, Tannins, Morphine-like effect, Anti-inflammatory, Mangroves

Leonardo Mendes de Souza Mesquita, Caroline Fabri Bittencourt Rodrigues, Cláudia Quintino da Rocha, Mayara Silveira Bianchim, Clenilson Martins Rodrigues, Vanda Maria de Oliveira, Henrique Hessel Gaeta, Mariana Novo Belchor, Marcos Hikari Toyama, Wagner Vilegas. LC-ESI-IT-MS/MS and MALDI-TOF Approach: Identification of Natural Polymers from Rhizophora mangle Barks and Determination of Their Analgesic and Anti-inflammatory Properties[J]. 应用天然产物, 2019, 9(1): 23-34.

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LC-ESI-IT-MS/MS and MALDI-TOF Approach: Identification of Natural Polymers from Rhizophora mangle Barks and Determination of Their Analgesic and Anti-inflammatory Properties

LC-ESI-IT-MS/MS and MALDI-TOF Approach: Identification of Natural Polymers from Rhizophora mangle Barks and Determination of Their Analgesic and Anti-inflammatory Properties

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