New Azulene-Type Sesquiterpenoids from the Fruiting Bodies of Lactarius deliciosus

ABSTRACT: In the (1)H NMR-guided fractionation of extracts from the edible mushroom Lactarius deliciosus, two new azulene-type sesquiterpenoids, 7-isopropenyl-4-methyl-azulene-1-carboxylic acid (1) and 15-hydroxy-3,6-dihydrolactarazulene (2), together with seven known compounds were characterized. T...

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Autores principales: Feussi Tala, Michel, Qin, Jianchun, Ndongo, Joseph T., Laatsch, Hartmut
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Springer Singapore 2017
Materias:
Original Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5481275/
https://www.ncbi.nlm.nih.gov/pubmed/28493207
http://dx.doi.org/10.1007/s13659-017-0130-1
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author Feussi Tala, Michel
Qin, Jianchun
Ndongo, Joseph T.
Laatsch, Hartmut
author_facet Feussi Tala, Michel
Qin, Jianchun
Ndongo, Joseph T.
Laatsch, Hartmut
author_sort Feussi Tala, Michel
collection PubMed
description ABSTRACT: In the (1)H NMR-guided fractionation of extracts from the edible mushroom Lactarius deliciosus, two new azulene-type sesquiterpenoids, 7-isopropenyl-4-methyl-azulene-1-carboxylic acid (1) and 15-hydroxy-3,6-dihydrolactarazulene (2), together with seven known compounds were characterized. Their structures were determined on basis of spectroscopic evidence, as well as by comparing with literature data. Amongst the known metabolites, the (13)C NMR assignment of 15-hydroxy-6,7-dihydrolactarazulene (3) is reported here for the first time. Moreover, 7-acetyl-4-methylazulene-1-carbaldehyde (5) displayed a moderate antibacterial activity against Staphylococcus aureus. GRAPHICAL ABSTRACT: *Digital image of L. deliciosus. Retrieved March 17, 2017 from https://upload.wikimedia.org/wikipedia/commons/e/e3/Lactarius_deliciosus_1_(1).jpg [Image: see text]. ELECTRONIC SUPPLEMENTARY MATERIAL: The online version of this article (doi:10.1007/s13659-017-0130-1) contains supplementary material, which is available to authorized users.
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spelling pubmed-54812752017-07-07 New Azulene-Type Sesquiterpenoids from the Fruiting Bodies of Lactarius deliciosus Feussi Tala, Michel Qin, Jianchun Ndongo, Joseph T. Laatsch, Hartmut Nat Prod Bioprospect Original Article ABSTRACT: In the (1)H NMR-guided fractionation of extracts from the edible mushroom Lactarius deliciosus, two new azulene-type sesquiterpenoids, 7-isopropenyl-4-methyl-azulene-1-carboxylic acid (1) and 15-hydroxy-3,6-dihydrolactarazulene (2), together with seven known compounds were characterized. Their structures were determined on basis of spectroscopic evidence, as well as by comparing with literature data. Amongst the known metabolites, the (13)C NMR assignment of 15-hydroxy-6,7-dihydrolactarazulene (3) is reported here for the first time. Moreover, 7-acetyl-4-methylazulene-1-carbaldehyde (5) displayed a moderate antibacterial activity against Staphylococcus aureus. GRAPHICAL ABSTRACT: *Digital image of L. deliciosus. Retrieved March 17, 2017 from https://upload.wikimedia.org/wikipedia/commons/e/e3/Lactarius_deliciosus_1_(1).jpg [Image: see text]. ELECTRONIC SUPPLEMENTARY MATERIAL: The online version of this article (doi:10.1007/s13659-017-0130-1) contains supplementary material, which is available to authorized users. Springer Singapore 2017-05-11 /pmc/articles/PMC5481275/ /pubmed/28493207 http://dx.doi.org/10.1007/s13659-017-0130-1 Text en © The Author(s) 2017 Open AccessThis article is distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution, and reproduction in any medium, provided you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made.
spellingShingle Original Article
Feussi Tala, Michel
Qin, Jianchun
Ndongo, Joseph T.
Laatsch, Hartmut
New Azulene-Type Sesquiterpenoids from the Fruiting Bodies of Lactarius deliciosus
title New Azulene-Type Sesquiterpenoids from the Fruiting Bodies of Lactarius deliciosus
title_full New Azulene-Type Sesquiterpenoids from the Fruiting Bodies of Lactarius deliciosus
title_fullStr New Azulene-Type Sesquiterpenoids from the Fruiting Bodies of Lactarius deliciosus
title_full_unstemmed New Azulene-Type Sesquiterpenoids from the Fruiting Bodies of Lactarius deliciosus
title_short New Azulene-Type Sesquiterpenoids from the Fruiting Bodies of Lactarius deliciosus
title_sort new azulene-type sesquiterpenoids from the fruiting bodies of lactarius deliciosus
topic Original Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5481275/
https://www.ncbi.nlm.nih.gov/pubmed/28493207
http://dx.doi.org/10.1007/s13659-017-0130-1
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