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Article ; Online: Proposal for structural revision of several disubstituted tricycloalternarenes.

Fraga, Braulio M / Díaz, Carmen E

2022 Volume 201, Page(s) 113289

Abstract: Mono- and di-substituted tricycloalternarenes form a group of meroterpenes isolated from epiphytic fungi. In this work, we have made thirteen proposals to correct erroneous structures of disubstituted tricycloalternarenes, also known as guignardones. ... ...

Abstract	Mono- and di-substituted tricycloalternarenes form a group of meroterpenes isolated from epiphytic fungi. In this work, we have made thirteen proposals to correct erroneous structures of disubstituted tricycloalternarenes, also known as guignardones. Thus, in this group of compounds, structures of guignardones K, L
MeSH term(s)	Fungi ; Molecular Structure
Language	English
Publishing date	2022-06-20
Publishing country	England
Document type	Journal Article
ZDB-ID	208884-8
ISSN	1873-3700 ; 0031-9422
ISSN (online)	1873-3700
ISSN	0031-9422
DOI	10.1016/j.phytochem.2022.113289
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Article ; Online: Proposal for structural revision of several monosubstituted tricycloalternarenes.

Fraga, Braulio M / Díaz, Carmen E

Phytochemistry

2022 Volume 198, Page(s) 113141

Abstract: Cycloalternarenes are a group of meroterpenes isolated from epiphytic fungi with a mono-, bi, tri- or tetracyclic skeleton. We have detected in the bibliography a series of monosubstituted tricycloalternarenes with erroneous structures. Thus, in this ... ...

Abstract	Cycloalternarenes are a group of meroterpenes isolated from epiphytic fungi with a mono-, bi, tri- or tetracyclic skeleton. We have detected in the bibliography a series of monosubstituted tricycloalternarenes with erroneous structures. Thus, in this work we make several proposals to correct the structures of nineteen 4-hydroxy-tricycloalternarenes, TCA 6a, TCA 11a
MeSH term(s)	Fungi ; Molecular Structure
Language	English
Publishing date	2022-03-01
Publishing country	England
Document type	Journal Article
ZDB-ID	208884-8
ISSN	1873-3700 ; 0031-9422
ISSN (online)	1873-3700
ISSN	0031-9422
DOI	10.1016/j.phytochem.2022.113141
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Article: Proposal for structural revision of several disubstituted tricycloalternarenes

Fraga, Braulio M. / Díaz, Carmen E.

Phytochemistry. 2022 June 13,

2022

Abstract: ... tricycloalternarenes, also known as guignardones. Thus, in this group of compounds, structures of guignardones K, L₃, M ...

Abstract	and di-substituted tricycloalternarenes form a group of meroterpenes isolated from epiphytic fungi. In this work, we have made thirteen proposals to correct erroneous structures of disubstituted tricycloalternarenes, also known as guignardones. Thus, in this group of compounds, structures of guignardones K, L₃, M, W, tricycloalternarene B₂, 15-hydroxy-tricycloalternarene 5 b, guignardiaene D, magnardones F–H and coibanols A-C, have been revised. Moreover, we have also explained why there are only two types of disubstituted tricycloalternarenes in nature, one with a –CH₂-O- β-bridge between C-6 and C-4 (6R,4S-configuration), and the other with a –CH₂-O- α-bridge between C-4 and C-6 (4R,6S-configuration). Finally, the relative and absolute configurations of phyllostictone A and the absolute structure of phyllostictone D have been established by comparison with those of magnardones I and D, respectively.
Keywords	epiphytes ; meroterpenoids ; plant biochemistry
Language	English
Dates of publication	2022-0613
Publishing place	Elsevier Ltd
Document type	Article
Note	Pre-press version
ZDB-ID	208884-8
ISSN	1873-3700 ; 0031-9422
ISSN (online)	1873-3700
ISSN	0031-9422
DOI	10.1016/j.phytochem.2022.113289
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Article: Biotransformation of the diterpene 15β-hydroxy-18(4→3)-abeo-ent-kaur-4(19),16-diene by the fungus Fusarium fujikuroi

Fraga, Braulio M. / Hernández, Melchor G. / Guillermo, Ricardo

Phytochemical Society of Europe Phytochemistry letters. 2022 Aug., v. 50

2022

Abstract: 15β-Hydroxy-18(4→3)-abeo-ent-kaur-4(19),16-diene (4) was biotransformed by the fungus Fusarium fujikuroi into 3α,11β,15β-trihydroxy-18(4→3)-abeo-ent-kaur-4(19),16-diene (5). The hydroxylation at C-3(α) in this diterpene reminds a similar reaction that ... ...

Abstract	15β-Hydroxy-18(4→3)-abeo-ent-kaur-4(19),16-diene (4) was biotransformed by the fungus Fusarium fujikuroi into 3α,11β,15β-trihydroxy-18(4→3)-abeo-ent-kaur-4(19),16-diene (5). The hydroxylation at C-3(α) in this diterpene reminds a similar reaction that occurs at C-13 in the biosynthesis of gibberellic acid in this fungus. The presence of the 15β-alcohol in the substrate directs the second hydroxylation at C-11(β), which had been observed in the incubation of ent-kaur-16-ene derivatives with this fungus when the C-19 hydroxylation was inhibited by the existence in the molecule of a 3α-OH or 3-oxo group. We also show that the angelate of the substrate is an undescribed natural product now identified as a component of the plant Distichoselinum tenuifolium.
Keywords	Fusarium fujikuroi ; biosynthesis ; biotransformation ; diterpenoids ; fungi ; gibberellic acid ; hydroxylation
Language	English
Dates of publication	2022-08
Size	p. 36-39.
Publishing place	Elsevier Ltd
Document type	Article
ISSN	1874-3900
DOI	10.1016/j.phytol.2022.05.003
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Article: Proposal for structural revision of several monosubstituted tricycloalternarenes

Fraga, Braulio M. / Díaz, Carmen E.

Phytochemistry. 2022 June, v. 198

2022

Abstract	Cycloalternarenes are a group of meroterpenes isolated from epiphytic fungi with a mono-, bi, tri- or tetracyclic skeleton. We have detected in the bibliography a series of monosubstituted tricycloalternarenes with erroneous structures. Thus, in this work we make several proposals to correct the structures of nineteen 4-hydroxy-tricycloalternarenes, TCA 6a, TCA 11a₂, (2E)- and (2Z)-TCA 12a, 2H-(2E)-TCA 12a, TCAs 9a and F₂, methyl nor-tricycloalternarate, TCAs K, L, S–W, X₂ and tricycloalterfurenes A-C, and four 6-hydroxy-tricycloalternarenes, TCA 12b, TCA 13b, tricycloalterfurene D and TCA F₃. Moreover, the graphic representation of TCA 14b and TCAs 15b–18b had been corrected. In addition, we have suggested that mono-hydroxylated tricycloalternarenes can only exist in nature substituted at the 4α- or 6β-position (4R- or 6R-configuration), which could also be explained considering biogenetic reasons. We have also determined the C-4 and C-6 configuration of several monosubstituted tricycloalternarenes, whose planar structure had been previously determined. Thus, compounds of the “series a” such as TCAs 1a-8a, 11a and ACTG-toxin H have a 4R-configuration, whilst in the “series b” TCAs 3b–7b and TCAs 9b–11b possess a 6R-configuration.
Keywords	chemical structure ; epiphytes ; meroterpenoids ; plant biochemistry
Language	English
Dates of publication	2022-06
Publishing place	Elsevier Ltd
Document type	Article
ZDB-ID	208884-8
ISSN	1873-3700 ; 0031-9422
ISSN (online)	1873-3700
ISSN	0031-9422
DOI	10.1016/j.phytochem.2022.113141
Database	NAL-Catalogue (AGRICOLA)

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Article: Sesquiterpene Lactones from

Fraga, Braulio M / Díaz, Carmen E / Bailén, María / González-Coloma, Azucena

Plants (Basel, Switzerland)

2021 Volume 10, Issue 5

Abstract: Three new compounds, the sesquiterpenes absilactone and hansonlactone and the acetophenone derivative ajenjol, have been isolated from a cultivated variety ... ...

Abstract	Three new compounds, the sesquiterpenes absilactone and hansonlactone and the acetophenone derivative ajenjol, have been isolated from a cultivated variety of
Language	English
Publishing date	2021-04-28
Publishing country	Switzerland
Document type	Journal Article
ZDB-ID	2704341-1
ISSN	2223-7747
ISSN	2223-7747
DOI	10.3390/plants10050891
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Article ; Online: Insect Antifeedant Benzofurans from

Díaz, Carmen E / Fraga, Braulio M / G Portero, Adriana / Brito, Iván / López-Balboa, Carmen / Ruiz-Vásquez, Liliana / González-Coloma, Azucena

Molecules (Basel, Switzerland)

2023 Volume 28, Issue 3

Abstract: In this work, we have studied the benzofurans ... ...

Abstract	In this work, we have studied the benzofurans of
MeSH term(s)	Animals ; Insecta ; Mucor ; Larva ; Benzofurans/pharmacology ; Spodoptera ; Insecticides/pharmacology
Chemical Substances	Benzofurans ; Insecticides
Language	English
Publishing date	2023-01-18
Publishing country	Switzerland
Document type	Journal Article
ZDB-ID	1413402-0
ISSN	1420-3049 ; 1431-5165 ; 1420-3049
ISSN (online)	1420-3049
ISSN	1431-5165 ; 1420-3049
DOI	10.3390/molecules28030975
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Article: The Dimerization of Precocene I.

Fraga, Braulio M / Cabrera, Inmaculada

Natural product communications

2018 Volume 12, Issue 5, Page(s) 691–694

Abstract: In an earlier work we reported that treatment of precocene I with Brönsted and Lewis acids produces its oligomerization, giving dimers, trimers, tetramers, etc. Now, in this article we show that bromination of precocene I with phenyltrimethylammonium ... ...

Abstract	In an earlier work we reported that treatment of precocene I with Brönsted and Lewis acids produces its oligomerization, giving dimers, trimers, tetramers, etc. Now, in this article we show that bromination of precocene I with phenyltrimethylammonium tribromide (PTT) blocks its oligomerization giving a dibromo- dimer, which was reduced with tri-n-butyl tin hydride affording the same dimer obtained in the reactions with acid, thus avoiding the oligomerization. Additionally, the oxidations of precocene I with Jones reagent afforded the corresponding 3-hydroxy-4-chromanone, 3,4-chromandione, 3,4-diacid, and two dimers.
MeSH term(s)	Benzopyrans/chemistry ; Dimerization ; Molecular Structure
Chemical Substances	Benzopyrans ; precocene I (25HLF91DGR)
Language	English
Publishing date	2018-11-29
Publishing country	United States
Document type	Journal Article
ISSN	1934-578X
ISSN	1934-578X
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Article ; Online: Natural sesquiterpenoids.

Fraga, Braulio M

Natural product reports

2013 Volume 30, Issue 9, Page(s) 1226–1264

Abstract: This review covers the isolation, structural determination, synthesis and chemical and microbiological transformations of natural sesquiterpenoids. The literature from January to December 2012 is reviewed, and 471 references are cited. ...

Abstract	This review covers the isolation, structural determination, synthesis and chemical and microbiological transformations of natural sesquiterpenoids. The literature from January to December 2012 is reviewed, and 471 references are cited.
MeSH term(s)	Animals ; Biological Products ; Humans ; Molecular Structure ; Porifera/chemistry ; Sesquiterpenes
Chemical Substances	Biological Products ; Sesquiterpenes
Language	English
Publishing date	2013-09
Publishing country	England
Document type	Journal Article ; Review
ZDB-ID	2002546-4
ISSN	1460-4752 ; 0265-0568
ISSN (online)	1460-4752
ISSN	0265-0568
DOI	10.1039/c3np70047j
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Article ; Online: Insect Antifeedant Benzofurans from Pericallis Species

Carmen E. Díaz / Braulio M. Fraga / Adriana G. Portero / Iván Brito / Carmen López-Balboa / Liliana Ruiz-Vásquez / Azucena González-Coloma

Molecules, Vol 28, Iss 975, p

2023 Volume 975

Abstract: In this work, we have studied the benzofurans of Pericallis echinata (aerial parts and transformed roots), P. steetzii (aerial parts and transformed roots), P. lanata (aerial parts), and P. murrayi (aerial parts and roots). This work has permitted the ... ...

Abstract	In this work, we have studied the benzofurans of Pericallis echinata (aerial parts and transformed roots), P. steetzii (aerial parts and transformed roots), P. lanata (aerial parts), and P. murrayi (aerial parts and roots). This work has permitted the isolation of the new benzofurans 10-ethoxy-11-hydroxy-10,11-dihydroeuparin ( 10 ), (-)-eupachinin A ethyl ether ( 12 ), 11,15-didehydro-eupachinin A ( 13 ), 10,12-dihydroxy-11-angelyloxy-10,11-dihydroeuparin ( 14 ), 2,4-dihydroxy-5-formyl-acetophenone ( 15 ) isolated for the first time as a natural product, 11-angelyloxy-10,11-dihydroeuparin ( 16 ), and 12-angelyloxyeuparone ( 17 ), along with several known ones ( 1 – 9, 11 ). In addition, the incubation of the abundant component, 6-hydroxytremetone ( 1 ), with the fungus Mucor plumbeus has been studied. Benzofurans in the tremetone series ( 1 , 1a , 2 – 5 , 18 , 18a ), the euparin series ( 6 , 7 , 7a , 8 – 10 , 14 , 16 ), and the eupachinin-type ( 11 , 12 ) were tested for antifeedant effects against the insect Spodoptera littoralis . The antifeedant compounds ( 1 , 4 , 6 , 11 , 12 ) were further tested for postingestive effects on S. littoralis larvae. The most antifeedant compounds were among the tremetone series, with 3-ethoxy-hydroxy-tremetone ( 4 ) being the strongest antifeedant. Glucosylation of 1 by its biotransformation with Mucor plumbeus gave inactive products. Among the euparin series, the dihydroxyangelate 14 was the most active, followed by euparin ( 6 ). The eupachinin-type compounds ( 11 , 12 ) were both antifeedants. Compounds 4, 11, and 12 showed antifeedant effects without postingestive toxicity to orally dosed S. littoralis larvae. Euparin ( 6) had postingestive toxicity that was enhanced by the synergist piperonyl butoxide.
Keywords	Pericallis ; aerial parts ; transformed roots ; benzofurans ; biotransformation ; antifeedant ; Organic chemistry ; QD241-441
Subject code	540
Language	English
Publishing date	2023-01-01T00:00:00Z
Publisher	MDPI AG
Document type	Article ; Online
Database	BASE - Bielefeld Academic Search Engine (life sciences selection)

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