In the current work, the production of dioxolanone and meroterpene type secondary metabolites under different fermentation conditions by the endophytic fungus Phyllosticta capitalensis (isolate YCC4) isolated from the leaves of the endemic plant Persea indica has been evaluated. Different techniques, such as microparticle-enhanced culture (MPEC: bentonite, talcum powder) and surface adhesion fermentation (SAF: metallic mesh and glass wool) were applied to the culture medium. Ethyl acetate extracts from different fermentations of the isolate YCC4 were analyzed for their content and revealed the following dioxolanone derivatives: metguignardic acid (1), guignardianone C (2), ethyl guignardate (3), guignardianone D (4) and phenguignardic acid methyl ester (5), and meroterpenes: guignardone A (6) and B (7), guignarenone C (8), guignarenone B (9) and guignardone I (10).
View Article and Find Full Text PDFEndolichenic fungi represent an important ecological group of microorganisms that form associations with photobionts in the lichen thallus. These endofungi that live in and coevolve with lichens are known for synthesizing secondary metabolites with novel structures and diverse chemical skeletons making them an unexplored microbial community of great interest. As part of our search for new phytoprotectants, in this work, we studied the endolichenic fungus sp.
View Article and Find Full Text PDFThe search for natural product-based biopesticides from endophytic fungi is an effective tool to find new solutions. In this study, we studied a pre-selected fungal endophyte, isolate YCC4, from the paleoendemism , along with compounds present in the extract and the identification of the insect antifeedant and nematicidal ones. The endophyte YCC4 was identified as sp.
View Article and Find Full Text PDFThe continuous search for natural product-based biopesticides from fungi isolated from untapped sources is an effective tool. In this study, we studied a pre-selected fungal endophyte, isolate Aa22, from the medicinal plant Artemisia absinthium, along with the antifungal, insect antifeedant and nematicidal compounds present in the extract. The endophyte Aa22 was identified as Stemphylium solani by molecular analysis.
View Article and Find Full Text PDFBioresour Bioprocess
March 2024
The endophytic fungus Aspergillus sp. SPH2 was isolated from the stems of the endemic plant Bethencourtia palmensis and its extracts were found to have strong fungicidal effects against Botrytis cinerea and ixodicidal effects against Hyalomma lusitanicum at different fermentation times. In this study, the fungus was grown using three different culture media and two methodologies, Microparticulate Enhancement Cultivation (MPEC) and Semi-Solid-State Fermentation (Semi-SSF), to increase the production of secondary metabolites during submerged fermentation.
View Article and Find Full Text PDFIn this work, we have studied the benzofurans of (aerial parts and transformed roots), (aerial parts and transformed roots), (aerial parts), and (aerial parts and roots). This work has permitted the isolation of the new benzofurans 10-ethoxy-11-hydroxy-10,11-dihydroeuparin (), (-)-eupachinin A ethyl ether (), 11,15-didehydro-eupachinin A (), 10,12-dihydroxy-11-angelyloxy-10,11-dihydroeuparin (), 2,4-dihydroxy-5-formyl-acetophenone () isolated for the first time as a natural product, 11-angelyloxy-10,11-dihydroeuparin (), and 12-angelyloxyeuparone (), along with several known ones (-). In addition, the incubation of the abundant component, 6-hydroxytremetone (), with the fungus has been studied.
View Article and Find Full Text PDFThe chemical composition of essential oils (EOs) from ten Peruvian Piper species (Piper coruscans, Pc; P. tuberculatum, Pt; P. casapiense, Pcs; P.
View Article and Find Full Text PDFPhytochemistry
September 2022
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, M, W, tricycloalternarene B, 15-hydroxy-tricycloalternarene 5 b, guignardiaene D, magnardones F-H and coibanols A-C, have been revised.
View Article and Find Full Text PDFPhytochemistry
June 2022
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, (2E)- and (2Z)-TCA 12a, 2H-(2E)-TCA 12a, TCAs 9a and F methyl nor-tricycloalternarate, TCAs K, L, S-W, X and tricycloalterfurenes A-C, and four 6-hydroxy-tricycloalternarenes, TCA 12b, TCA 13b, tricycloalterfurene D and TCA F.
View Article and Find Full Text PDFPlants (Basel)
February 2022
Three new compounds, the sesquiterpenes absilactone and hansonlactone and the acetophenone derivative ajenjol, have been isolated from a cultivated variety of . In addition, the major lactone isolated, 3α-hydroxypelenolide, was biotransformed by the fungus affording the corresponding 1β, 10α-epoxide. A cadinane derivative was formed by an acid rearrangement produced in the culture medium, but not by the enzymatic system of the fungus.
View Article and Find Full Text PDFThis work presents the study of the roots of the Macaronesian paleoendemism Persea indica (L.) Spreng. The root biomass of this protected tree species has been produced by soil-less aeroponic culture under controlled environment.
View Article and Find Full Text PDFBotanical and fungal biopesticides, including endophytes, are in high demand given the current restrictive legislations on the use of chemical pesticides. As part of an ongoing search for new biopesticides, a series of fungal endophytes have been isolated from selected medicinal plants including species. In the current study, an extract from the endophytic fungus sp.
View Article and Find Full Text PDFGiven the importance of the genus as a source of valuable natural products, the rare plant subspecies endemic to the Iberian Peninsula, has been experimentally cultivated in the greenhouse and aeroponically, to produce biomass for essential oil (EO) extraction. The chemical composition of the EOs was analyzed, and their plant protection (insects: , and ; plants: and ; fungi: and nematode: ) and antiparasitic (, and antiplasmodial by the ferriprotoporphyrin biocrystallization inhibition test) properties were studied, in addition to the hydrolate by-product. The EOs showed a 1,8-cineole and camphor profile, with quantitative and qualitative chemical differences between the cultivation methods.
View Article and Find Full Text PDFSince 1980, many species and different strains from endophytic genera of Phomopsis, Fusarium, Pestaliopsis and Aspergillus have been studied because of their ability to produce medicinal compounds found in their host plants. Some of these medicinal agents such as Taxol, Brefeldine A, Camptothecin and Podophyllotoxin are being produced in large-scale after an optimization process. However, the potential of fungal endophytes to produce host-like medicinal compounds remains largely unexplored.
View Article and Find Full Text PDFThe aim of this research was to determine the cytotoxic action of sixteen structurally-related eremophilane-type sesquiterpenes, isolated from several species of Senecio, against a panel of cancer cell lines. The cytotoxic activities were evaluated by WST-I test and the ICso values calculated. The investigated compounds exerted dose-dependent cytotoxic actions against selected cancer cell lines and no-tumoral HS5 cell line.
View Article and Find Full Text PDFA phytochemical study of an extract from transformed root cultures of Nepeta teydea, induced by Agrobacterium rhizogenes, led to the isolation of the following new compounds: the sesquiterpene (-)-cinalbicol, the diterpene teydeadione (6,11,14-trihydroxy-12-methoxy-abieta-5,8,11,13,15-penten-7-one), a degraded C23-triterpene (teydealdehyde) and three fatty acid esters of lanosta-7,24-dien-3β-ol. The propyl ester of rosmarinic acid was also isolated for the first time from a natural source. In addition, two dehydroabietane diterpenes, eight triterpenes and eighteen known phenolic compounds were obtained.
View Article and Find Full Text PDFBiotransformation of 8β-hydroxy-african-4(5)-en-3-one angelate by the fungus Mucor plumbeus afforded as main products 6α,8β-dihydroxy-african-4(5)-en-3-one 8β-angelate and 1α,8β-dihydroxy-african-4(5)-en-3-one 8β-angelate, which had been obtained, together with the substrate, from transformed root cultures of Bethencourtia hermosae. This fact shows that the enzyme system involved in these hydroxylations in both organisms, the fungus and the plant, acts with the same regio- and stereospecificity. In addition another twelve derivatives were isolated in the incubation of the substrate, which were identified as the (2'R,3'R)- and (2'S,3'S)-epoxy derivatives of the substrate and of the 6α- and 1α-hydroxy alcohols, the 8β-(2'R,3'R)- and 8β-(2'S,3'S)-epoxyangelate of 8β,15-dihydroxy-african-4(5)-en-3-one, the hydrolysis product of the substrate, and three isomers of 8β-hydroxy-african-4(5)-en-3-one 2ξ,3ξ-dihydroxy-2-methylbutanoate.
View Article and Find Full Text PDFSeveral preparations were obtained from the aerial parts of predomesticated Lavandula luisieri, including the essential oil and ethanolic, hexane, and ethyl acetate extractives. Additionally, pilot plant vapor pressure extraction was carried out at a pressure range of 0.5-1.
View Article and Find Full Text PDFPhytochemistry
December 2014
A chemical study of Bethencourtia hermosae, aerial parts and in vitro root cultures, transformed by Agrobacterium rhizogenes, afforded the hitherto unreported sesquiterpenes ceratopicanol angelate (1), 8β-hydroxy-african-4(5)-en-3-one tiglate (4), 8β-hydroxy-african-4(5)-en-3-one 3'-angeloxy-2'-methylbutanoate (5), 1α,8β-dihydroxy-african-4(5)-en-3-one 8β-angelate (7) and 6α,8β-dihydroxy-african-4(5)-en-3-one 8β-angelate (8). In addition, 8β-hydroxy-african-4(5)-en-3-one (6) was isolated for the first time from a natural source, along with the rare sesquiterpenoid senecrassidiol (10) and two jacaranone derivatives 14 and 16. Known pyrrolizidine alkaloids, together with previously unreported hermosine (23), have also been isolated from this plant.
View Article and Find Full Text PDFArtemisia granatensis, an endemic endangered plant species from Sierra Nevada (Spain) has been successfully cultivated in artificial systems (plants in artificial soil and transformed in vitro roots) to generate enough plant biomass (aerial and root) to allow for its chemical and biological study and at the same time to provide with methods for the sustainable production of the plant and its metabolites. A eudesmanolide (17) along with six sesquiterpenes (11-16), nine monoterpenes (2-10), one nor-monoterpene (1), three acetylenic spiroacetal enoleters (18-20) and one coumarin (21) have been identified from the aerial plant ethanolic extract. Acetylenic spiroacetal enoleters 18-19 and coumarins 21-23 have been isolated from the transformed root ethanolic extract.
View Article and Find Full Text PDFFive new and 15 known anthraquinones have been isolated from Plocama pendula root cultures transformed by Agrobacterium rhizogenes. The new anthraquinones were named balonone, balonone methyl ether, and plocamanones A, B, and C. Moreover, lucidin dimethyl ether was obtained for the first time as a natural compound.
View Article and Find Full Text PDFThis study evaluated the internal consistency of a Spanish version of the short form of the Francis Scale of Attitude Toward Christianity based on responses of 405 Colombian adolescent students ages 13 to 17 years. This translated short-form version of the scale had an internal consistency of .80.
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