Identification and characterization of (+)-α-bisabolol and 7-epi-silphiperfol-5-ene synthases from Artemisia abrotanum

Muangphrom, Paskorn; Misaki, Momoka; Suzuki, Munenori; Shimomura, Masaru; Suzuki, Hideyuki; Seki, Hikaru; Muranaka, Toshiya

doi:10.1016/j.phytochem.2019.05.010

Cited by 15 publications

(15 citation statements)

References 67 publications

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“…dentata , also an Asteraceae, Zardi‐Bergaoui et al [41] . found two isomers of the sesquiterpene silphiperfol‐5‐ene (C 15 H 24 ), silphiperfol‐6‐ene and 7‐ epi‐ silphiperfol‐5‐ene, as well as silphiperfol‐4,7‐(13)‐diene (C 15 H 22 ) and silphiperfol‐6‐en‐5‐one (C 15 H 22 O) [42] …”

Section: Resultsmentioning

confidence: 99%

Inter‐Individual versus Inter‐Population Variability of Calendula suffruticosa subsp. algarbiensis Hexane Extracts

Ohse

Marques

Silveira

et al. 2021

Chemistry & Biodiversity

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Calendula suffruticosa subsp. algarbiensis (Boiss.) Nyman is very common on the Portuguese coast, but it has only recently begun to be studied chemically and belongs to a genus of difficult taxonomic classification. To improve the knowledge on the chemical variability of this taxon and evaluate the possible use of this tool for taxonomical purposes, the aim of this work was to determine the extent of chemical variation between individuals collected in the same geographic region, and to compare with samples mixing fragments of several individuals each (populations) from different local environments. Overall, hexane extract analysis by GC/MS allowed to identify 42 compounds, eight fatty acids, 24 terpenoids, three alcohols, five alkanes, and two pollutants. Greater chemical differences were found between individuals, grown in the same region, than were found between population samples from different regions. Additionally, 25 phytochemicals were identified for this taxon for the first time and may be used for taxonomic classification, even to distinguish between subspecies of C. suffruticosa. Furthermore, plants collected near urban areas accumulated pollutants, indicating the importance of controlling local environmental conditions when C. suffruticosa cultivation is for human consumption.

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Section: Resultsmentioning

confidence: 99%

Inter‐Individual versus Inter‐Population Variability of Calendula suffruticosa subsp. algarbiensis Hexane Extracts

Ohse

Marques

Silveira

et al. 2021

Chemistry & Biodiversity

View full text Add to dashboard Cite

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“…To strengthen the study on the cyclization enzymes of diterpenes and more complex or active terpenes, it is expected to further elucidate the regulation mechanism of enzymes on terpene cyclization. In recent years, aided with computational biology technologies, the methods for studying the structure and mechanism of cyclization enzymes become more diverse (Freud et al 2017;Muangphrom et al 2019;Szymczyk et al 2020;Van Rijn et al 2019). It is expected that more enzyme sources with novel structures and properties will be discovered, and more active terpenoid molecules will be synthesized through extensive or intensive exploration of these cyclases.…”

Section: Discussionmentioning

confidence: 99%

“…The terpene cyclases corresponding to the 4 isomers of α-Bisabolol have been discovered (Albertti et al, 2018;Attia et al 2012;Muangphrom et al 2019;Nakano et al 2011). Li et al (2013) obtained the crystal structure (PDB ID: 4FJQ) of an α-bisabolol synthase (AaBOS) from Artemisia annua.…”

Section: Sesquiterpene Cyclases α-Bisabolol Synthase (α-Bos)mentioning

confidence: 99%

Mining methods and typical structural mechanisms of terpene cyclases

Huang

et al. 2021

Bioresour. Bioprocess.

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Terpenoids, formed by cyclization and/or permutation of isoprenes, are the most diverse and abundant class of natural products with a broad range of significant functions. One family of the critical enzymes involved in terpenoid biosynthesis is terpene cyclases (TCs), also known as terpene synthases (TSs), which are responsible for forming the ring structure as a backbone of functionally diverse terpenoids. With the recent advances in biotechnology, the researches on terpene cyclases have gradually shifted from the genomic mining of novel enzyme resources to the analysis of their structures and mechanisms. In this review, we summarize both the new methods for genomic mining and the structural mechanisms of some typical terpene cyclases, which are helpful for the discovery, engineering and application of more and new TCs.

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“…antimicrobial production will facilitate natural product discovery and provide insight into this discrepancy (Zander et al, 2011). Interestingly, all of the library hits provided by GNPS analysis were mono-or sesquiterpene metabolites that have previously been considered plant metabolites (Schneider et al, 2001;Zhang et al, 2018;Muangphrom et al, 2019). Although production of α-bisabolol and characterization of the corresponding synthase (AB621339.1) from Streptomyces citricolor have been reported, no homology to this synthase was observed when comparing the six putative terpene synthases from A. sp.…”

Section: Discussionmentioning

confidence: 99%

Myxobacterial Response to Methyljasmonate Exposure Indicates Contribution to Plant Recruitment of Micropredators

et al. 2020

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Chemical exchanges between plants and microbes within rhizobiomes are critical to the development of community structure. Volatile root exudates such as the phytohormone methyljasmonate (MeJA) contribute to various plant stress responses and have been implicated to play a role in the maintenance of microbial communities. Myxobacteria are competent predators of plant pathogens and are generally considered beneficial to rhizobiomes. While plant recruitment of myxobacteria to stave off pathogens has been suggested, no involved chemical signaling processes are known. Herein we expose predatory myxobacteria to MeJA and employ untargeted mass spectrometry, motility assays, and RNA sequencing to monitor changes in features associated with predation such as specialized metabolism, swarm expansion, and production of lytic enzymes. From a panel of four myxobacteria, we observe the most robust metabolic response from plant-associated Archangium sp. strain Cb G35 with 10 µM MeJA impacting the production of at least 300 metabolites and inducing a ≥ fourfold change in transcription for 56 genes. We also observe that MeJA induces A. sp. motility supporting plant recruitment of a subset of the investigated micropredators. Provided the varying responses to MeJA exposure, our observations indicate that MeJA contributes to the recruitment of select predatory myxobacteria suggesting further efforts are required to explore the microbial impact of plant exudates associated with biotic stress.

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Identification and characterization of (+)-α-bisabolol and 7-epi-silphiperfol-5-ene synthases from Artemisia abrotanum

Cited by 15 publications

References 67 publications

Inter‐Individual versus Inter‐Population Variability of Calendula suffruticosa subsp. algarbiensis Hexane Extracts

Inter‐Individual versus Inter‐Population Variability of Calendula suffruticosa subsp. algarbiensis Hexane Extracts

Mining methods and typical structural mechanisms of terpene cyclases

Myxobacterial Response to Methyljasmonate Exposure Indicates Contribution to Plant Recruitment of Micropredators

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