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    Publicación
    DOI 10.1080/14786419.2021.1946534
    Synthesis, characterisation, crystal structure and antimicrobial evaluation of novel 6-alkoxyergosta-4,6,8(14),22-tetraen-3-one derived from natural ergosta-5,7,22-trien-3β-ol
    2023-01-02
    Bacho, Mitchell
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    Artigas, Vania
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    Araya-Contreras, Tiare
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    Bittner, Mauricio
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    Escobar, Carlos A.
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    Fuentealba, Mauricio
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    Becerra, Jose
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    ;
    In this study, we report a facile transformation starting from 5 alpha-hydroxyergosta-7,22-dien-3,6-dione (1) to afford two novel compounds: 6-methoxyergosta-4,6,8(14),22-tetraen-3-one (2) and 6-ethoxyergosta-4,6,8(14),22-tetraen-3-one (3) using alcoholic acid catalysis. Their structures were elucidated using NMR experiments, FT-IR, MS and X-ray analysis. These compounds were evaluated for antibacterial activity using the disk and broth diffusion test. In those tests, compound 3 was found to be the most significant antibacterial agent. In general, compounds 1-3 showed inhibition zone in the range of 7.00-12.3 mm for S. aureus and S. mutans, meanwhile for Gram-negative bacteria E. coli and Pseudomonas sp. was found to be in the range of 7.00-8.00 mm. For the most active, compound 3, MIC was significantly lower than that reported for ergosterol, in a value of 160 mu g/mL. Overall, these compounds were more active than their natural precursor.
  • Some of the metrics are blocked by your 
    Publicación
    DOI 10.1080/14786419.2021.1946534
    Synthesis, characterisation, crystal structure and antimicrobial evaluation of novel 6-alkoxyergosta-4,6,8(14),22-tetraen-3-one derived from natural ergosta-5,7,22-trien-3β-ol
    2023-01-02
    Bacho, Mitchell
    ;
    Artigas, Vania
    ;
    Araya-Contreras, Tiare
    ;
    Bittner, Mauricio
    ;
    Escobar, Carlos A.
    ;
    Fuentealba, Mauricio
    ;
    Becerra, Jose
    ;
    ;
    In this study, we report a facile transformation starting from 5 alpha-hydroxyergosta-7,22-dien-3,6-dione (1) to afford two novel compounds: 6-methoxyergosta-4,6,8(14),22-tetraen-3-one (2) and 6-ethoxyergosta-4,6,8(14),22-tetraen-3-one (3) using alcoholic acid catalysis. Their structures were elucidated using NMR experiments, FT-IR, MS and X-ray analysis. These compounds were evaluated for antibacterial activity using the disk and broth diffusion test. In those tests, compound 3 was found to be the most significant antibacterial agent. In general, compounds 1-3 showed inhibition zone in the range of 7.00-12.3 mm for S. aureus and S. mutans, meanwhile for Gram-negative bacteria E. coli and Pseudomonas sp. was found to be in the range of 7.00-8.00 mm. For the most active, compound 3, MIC was significantly lower than that reported for ergosterol, in a value of 160 mu g/mL. Overall, these compounds were more active than their natural precursor.
    ScopusĀ© Citations 2  2
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    Publicación
    DOI 10.4067/s0717-97072018000404200
    ANTIMICROBIAL ACTIVITIES OF DITERPENOWS AND SEMISYNTHETIC DERIVATIVES FROM AZORELLA COMPACTA
    2018-12
    The antibacterial activity of two natural diterpenoids isolated from Azorella compacta together with six semisynthetic derivatives, were evaluated against three bacteria: Staphylococcus aureus. Escherichia coli and Mycobacterium smegmatis. The synthesis of the semisynthetic derivatives 3-5 and 8 have not been previously reported with the methods described in this research. The structures of all diterpenoids were elucidated by NMR H-1,C- 13 and IR spectroscopy. The natural diterpenoids, mulinolic acid (1) and azorellanol (2) did not present antibacterial activity, but the six derivatives: 12-oxo-11,13-alpha,alpha-dihydroxymulin-20-oic acid (3), 11-oxo-12,13-alpha,alpha-dihydroxymulin-20-oic acid (4) 11,12-dioxo-13-alpha-hydroxymulin-20-oic acid (5). 7-acetoxymulin-9,12-diene (6). mulin-9,12-dien-7-ol (7) and 7-acetoxy-12,13-dihydroxymulin-9-en (8) were active against three tested bacteria. The antibacterial activity reported for six semisynthetic diterpenoids may not be comparable with positive control ampicillin but demonstrate the possibility of modification of the biological activity of diterpenoids.
    ScopusĀ© Citations 5  1
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    Publicación
    DOI 10.4067/s0717-97072018000304082
    A NOVEL NORMULINANE ISOLATED FROM Azorella compacta AND ASSESSMENT OF ITS ANTIBACTERIAL ACTIVITY
    2018
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    Bacho, M.
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    Núñez, S.
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    Rovirosa, J.
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    Soler, A.
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    Blanc, V.
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    León, R.
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    Olea, A. F.
    ABSTRACT Phytochemical analysis of Azorella compacta resulted in the isolation of six known diterpenes and one unknown norditerpene using chromatographic methods. The structure of this new compound was established by spectroscopic analysis. The bioactivity of the new compound was assessed against six oral bacteria using a drop test method. A high level of growth inhibition was observed against F. nucleatum and P. gingivalis; however, other species such as V. parvula and A. actinomycetemcomitans were not affected.
    ScopusĀ© Citations 7  1
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    Publicación
    DOI 10.37360/blacpma.21.20.5.33
    Phytochemistry and biological properties of Drimys winteri JR et G. Forster var chilensis (DC) A
    2021-9
    Drimys winteri JR et G. Forster var chilensis (DC) A. is a tree native to central and southern Chile. Also it found in part of Argentina. It is abundant in wet swampy localities from sea level to an altitude of 1700 m. This tree is sacred for the Mapuche culture; it is used in folk medicine in such as inflammatory and painful processes. Phytochemical studies have demonstrated that this plant contains mainly sesquiterpenes of the drimane type, flavonoids, essential oils, phytosterols and some lignans. These drimanes have attracted interest because of their antifeedant, plant growth regulation, cytotoxic, antimicrobial and insecticidal properties. The objective of this review is to establish clearly the phytochemistry and biological activity of Drimys winteri JR et G. Forster var chilensis (DC) A. Articles based on other varieties are not considered.
    ScopusĀ© Citations 7  2