Isolation of two triterpenoids from Phlomis purpurea, one of them with anti-oomycete activity against Phytophthora cinnamomi, and insights into its biosynthetic pathway
Phytophthora cinnamomi is an important plant pathogen responsible for dieback diseases in plant genera including Quercus, Fagus, Castanea, Eucalyptus, and Pinus, among others, all over the world. P. cinnamomi infection exerts tremendous ecological and economic losses. Several strategies have been de...
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| Format: | Article |
| Language: | English |
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Frontiers Media S.A.
2023-08-01
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| Series: | Frontiers in Plant Science |
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| Online Access: | https://www.frontiersin.org/articles/10.3389/fpls.2023.1180808/full |
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| author | L. Fernández-Calleja L. Fernández-Calleja L. Fernández-Calleja M. García-Domínguez M. García-Domínguez M. García-Domínguez B. Isabel Redondo J. L. Gómez Martín C. J. Villar C. J. Villar C. J. Villar F. Lombó F. Lombó F. Lombó |
| author_facet | L. Fernández-Calleja L. Fernández-Calleja L. Fernández-Calleja M. García-Domínguez M. García-Domínguez M. García-Domínguez B. Isabel Redondo J. L. Gómez Martín C. J. Villar C. J. Villar C. J. Villar F. Lombó F. Lombó F. Lombó |
| author_sort | L. Fernández-Calleja |
| collection | DOAJ |
| description | Phytophthora cinnamomi is an important plant pathogen responsible for dieback diseases in plant genera including Quercus, Fagus, Castanea, Eucalyptus, and Pinus, among others, all over the world. P. cinnamomi infection exerts tremendous ecological and economic losses. Several strategies have been developed to combat this pathogenic oomycete, including the search for novel anti-oomycete compounds. In this work, a Mediterranean vascular plant, Phlomis purpurea, has been screened for secondary bioactivity against this pathogen. The genus Phlomis includes a group of herbaceous plants and shrubs described as producers of many different bioactive compounds, including several triterpenoids. Triterpenoids are well-known molecules synthesized by plants and microorganisms with potent antioxidant, antitumoral, and antimicrobial activities. We have isolated by HPLC-DAD and characterized by HPLC-MS and NMR two nortriterpenoid compounds (phlomispentaol A and phlomispurtetraolone) from the root extracts of P. purpurea. One of them (phlomispentaol A) is active against the plant pathogenic oomycete P. cinnamomi (based on in vitro inhibition bioassays). Based on their chemical structure and their relationship to other plant triterpenoids, oleanolic acid is proposed to be the common precursor for these molecules. The anti-oomycete activity shown by phlomispentaol A represents a promising alternative to counteract the worldwide-scale damage caused to forest ecosystems by this pathogen. |
| first_indexed | 2024-03-12T13:23:45Z |
| format | Article |
| id | doaj.art-de2a50be5c9f4029b671a8f5aa6dbfa7 |
| institution | Directory Open Access Journal |
| issn | 1664-462X |
| language | English |
| last_indexed | 2024-03-12T13:23:45Z |
| publishDate | 2023-08-01 |
| publisher | Frontiers Media S.A. |
| record_format | Article |
| series | Frontiers in Plant Science |
| spelling | doaj.art-de2a50be5c9f4029b671a8f5aa6dbfa72023-08-25T12:51:58ZengFrontiers Media S.A.Frontiers in Plant Science1664-462X2023-08-011410.3389/fpls.2023.11808081180808Isolation of two triterpenoids from Phlomis purpurea, one of them with anti-oomycete activity against Phytophthora cinnamomi, and insights into its biosynthetic pathwayL. Fernández-Calleja0L. Fernández-Calleja1L. Fernández-Calleja2M. García-Domínguez3M. García-Domínguez4M. García-Domínguez5B. Isabel Redondo6J. L. Gómez Martín7C. J. Villar8C. J. Villar9C. J. Villar10F. Lombó11F. Lombó12F. Lombó13Research Unit “Biotechnology in Nutraceuticals and Bioactive Compounds-BIONUC”, Departamento de Biología Funcional, Área de Microbiología, Universidad de Oviedo, Oviedo, SpainInstituto Universitario de Oncología del Principado de Asturias, Oviedo, SpainInstituto de Investigación Sanitaria del Principado de Asturias, Oviedo, SpainResearch Unit “Biotechnology in Nutraceuticals and Bioactive Compounds-BIONUC”, Departamento de Biología Funcional, Área de Microbiología, Universidad de Oviedo, Oviedo, SpainInstituto Universitario de Oncología del Principado de Asturias, Oviedo, SpainInstituto de Investigación Sanitaria del Principado de Asturias, Oviedo, SpainDepartment Animal Science, Faculty of Veterinary Medicine, Universidad Complutense de Madrid, Madrid, SpainResearch and Development Department, Campojerez SL, Jerez de los Caballeros, Badajoz, SpainResearch Unit “Biotechnology in Nutraceuticals and Bioactive Compounds-BIONUC”, Departamento de Biología Funcional, Área de Microbiología, Universidad de Oviedo, Oviedo, SpainInstituto Universitario de Oncología del Principado de Asturias, Oviedo, SpainInstituto de Investigación Sanitaria del Principado de Asturias, Oviedo, SpainResearch Unit “Biotechnology in Nutraceuticals and Bioactive Compounds-BIONUC”, Departamento de Biología Funcional, Área de Microbiología, Universidad de Oviedo, Oviedo, SpainInstituto Universitario de Oncología del Principado de Asturias, Oviedo, SpainInstituto de Investigación Sanitaria del Principado de Asturias, Oviedo, SpainPhytophthora cinnamomi is an important plant pathogen responsible for dieback diseases in plant genera including Quercus, Fagus, Castanea, Eucalyptus, and Pinus, among others, all over the world. P. cinnamomi infection exerts tremendous ecological and economic losses. Several strategies have been developed to combat this pathogenic oomycete, including the search for novel anti-oomycete compounds. In this work, a Mediterranean vascular plant, Phlomis purpurea, has been screened for secondary bioactivity against this pathogen. The genus Phlomis includes a group of herbaceous plants and shrubs described as producers of many different bioactive compounds, including several triterpenoids. Triterpenoids are well-known molecules synthesized by plants and microorganisms with potent antioxidant, antitumoral, and antimicrobial activities. We have isolated by HPLC-DAD and characterized by HPLC-MS and NMR two nortriterpenoid compounds (phlomispentaol A and phlomispurtetraolone) from the root extracts of P. purpurea. One of them (phlomispentaol A) is active against the plant pathogenic oomycete P. cinnamomi (based on in vitro inhibition bioassays). Based on their chemical structure and their relationship to other plant triterpenoids, oleanolic acid is proposed to be the common precursor for these molecules. The anti-oomycete activity shown by phlomispentaol A represents a promising alternative to counteract the worldwide-scale damage caused to forest ecosystems by this pathogen.https://www.frontiersin.org/articles/10.3389/fpls.2023.1180808/fullanti-oomyceteroot rotnatural compoundoomycetedieback |
| spellingShingle | L. Fernández-Calleja L. Fernández-Calleja L. Fernández-Calleja M. García-Domínguez M. García-Domínguez M. García-Domínguez B. Isabel Redondo J. L. Gómez Martín C. J. Villar C. J. Villar C. J. Villar F. Lombó F. Lombó F. Lombó Isolation of two triterpenoids from Phlomis purpurea, one of them with anti-oomycete activity against Phytophthora cinnamomi, and insights into its biosynthetic pathway Frontiers in Plant Science anti-oomycete root rot natural compound oomycete dieback |
| title | Isolation of two triterpenoids from Phlomis purpurea, one of them with anti-oomycete activity against Phytophthora cinnamomi, and insights into its biosynthetic pathway |
| title_full | Isolation of two triterpenoids from Phlomis purpurea, one of them with anti-oomycete activity against Phytophthora cinnamomi, and insights into its biosynthetic pathway |
| title_fullStr | Isolation of two triterpenoids from Phlomis purpurea, one of them with anti-oomycete activity against Phytophthora cinnamomi, and insights into its biosynthetic pathway |
| title_full_unstemmed | Isolation of two triterpenoids from Phlomis purpurea, one of them with anti-oomycete activity against Phytophthora cinnamomi, and insights into its biosynthetic pathway |
| title_short | Isolation of two triterpenoids from Phlomis purpurea, one of them with anti-oomycete activity against Phytophthora cinnamomi, and insights into its biosynthetic pathway |
| title_sort | isolation of two triterpenoids from phlomis purpurea one of them with anti oomycete activity against phytophthora cinnamomi and insights into its biosynthetic pathway |
| topic | anti-oomycete root rot natural compound oomycete dieback |
| url | https://www.frontiersin.org/articles/10.3389/fpls.2023.1180808/full |
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