Novel and enantioselective total synthesis of drimane type sesquiterpenes

Shishido, Kozo; Omodani, Tomoki; Shibuya, Masayuki

doi:10.1039/p19910002285

Cited by 25 publications

(12 citation statements)

References 9 publications

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“…This sesquiterpene compound has been isolated from A. oryzae strains that also produce sporogen AO1 and similar compounds, but very little is known on the bioactivity of this compound (Wada et al 1983 ; Leite et al 1986 ; Domíngues et al 1991 ; Shishido et al 1991 ; Armstrong et al 1996 ; Jansen and de Groot 1990 ; 2004 ).…”

Section: Secondary Metabolite Potentialmentioning

confidence: 99%

Safety of the fungal workhorses of industrial biotechnology: update on the mycotoxin and secondary metabolite potential of Aspergillus niger, Aspergillus oryzae, and Trichoderma reesei

Frisvad

Møller

Larsen

et al. 2018

Appl Microbiol Biotechnol

238

269

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This review presents an update on the current knowledge of the secondary metabolite potential of the major fungal species used in industrial biotechnology, i.e., Aspergillus niger, Aspergillus oryzae, and Trichoderma reesei. These species have a long history of safe use for enzyme production. Like most microorganisms that exist in a challenging environment in nature, these fungi can produce a large variety and number of secondary metabolites. Many of these compounds present several properties that make them attractive for different industrial and medical applications. A description of all known secondary metabolites produced by these species is presented here. Mycotoxins are a very limited group of secondary metabolites that can be produced by fungi and that pose health hazards in humans and other vertebrates when ingested in small amounts. Some mycotoxins are species-specific. Here, we present scientific basis for (1) the definition of mycotoxins including an update on their toxicity and (2) the clarity on misclassification of species and their mycotoxin potential reported in literature, e.g., A. oryzae has been wrongly reported as an aflatoxin producer, due to misclassification of Aspergillus flavus strains. It is therefore of paramount importance to accurately describe the mycotoxins that can potentially be produced by a fungal species that is to be used as a production organism and to ensure that production strains are not capable of producing mycotoxins during enzyme production. This review is intended as a reference paper for authorities, companies, and researchers dealing with secondary metabolite assessment, risk evaluation for food or feed enzyme production, or considerations on the use of these species as production hosts.

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Section: Secondary Metabolite Potentialmentioning

confidence: 99%

Safety of the fungal workhorses of industrial biotechnology: update on the mycotoxin and secondary metabolite potential of Aspergillus niger, Aspergillus oryzae, and Trichoderma reesei

Frisvad

Møller

Larsen

et al. 2018

Appl Microbiol Biotechnol

238

269

View full text Add to dashboard Cite

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“…The structure of 4 matched that of a synthesis intermediate without any data reported. 14 The molecular formula of compound 5 was established as C 15 Na, 261.1830) with three indices of hydrogen deficiency. Its 1 H and 13 C NMR and HSQC data ( Table 2) showed that it was a drimane sesquiterpenoid.…”

mentioning

confidence: 99%

Sesquiterpenoids from the Mangrove-Derived Endophytic Fungus Diaporthe sp.

et al. 2012

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A new sesquiterpenoid, diaporol A (1), possessing a unique tricyclic lactone framework, eight new drimane sesquiterpenoids, diaporols B-I (2-9), and the known compounds 10 and 11 were isolated from a culture of the mangrove-derived endophyte Diaporthe sp. The absolute configurations of 1-5 were determined by low-temperature (100 K) single-crystal X-ray diffraction with Cu Kα radiation. The compounds were evaluated for cytotoxic activity; however, no compound showed significant cytotoxicity against the tested cell lines at a concentration of 20 μM.

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“…The AB ring was constructed by an intramolecular Diels–Alder reaction. Heating triene 13 in toluene at 180 °C afforded trans ‐ and cis ‐fused tetracyclic keto‐acetate 14 in 2:1 ratio based on 1 H NMR spectroscopic studies 10. Variation of the reaction temperature (140–220 °C), reaction time (48–150 h), and solvent (benzene and benzonitrile) did not affect the ratio of trans and cis isomers.…”

Section: Methodsmentioning

confidence: 98%