Lentinulactam, a hirsutane sesquiterpene with an unprecedented lactam modification

Helaly, Soleiman E.; Richter, Christian; Thongbai, Benjarong; Hyde, Kevin D.; Stadler, Marc

doi:10.1016/j.tetlet.2016.11.075

Cited by 15 publications

(10 citation statements)

References 16 publications

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“…1D and 2D NMR spectra were recorded on a Bruker Avance III 700 spectrometer with a 5 mm TXI cryoprobe ( 1 H 700 MHz, 13 C 175 MHz) and a Bruker Avance III 500 ( 1 H 500 MHz, 13 C 125 MHz) spectrometer; optical rotations were measured on a Perkin-Elmer 241 polarimeter, IR spectra were measured with a Nicolet Spectrum 100 FTIR spectrometer (Perkin-Elmer, Waltham, MA, USA). All HPLC-MS analyses were performed on Agilent 1260 Infinity Systems with a diode array detector and C 18 Acquity UPLC BEH column (2.1 × 50 mm, 1.7 μm) from Waters with the gradient described by Helaly et al [ 22 ] combined with ion trap MS (amazon speed, Bruker, Bremen, Germany), and HR-ESIMS spectra on a time-of-flight (TOF) MS (Maxis, Bruker). Chemicals and solvents were obtained from AppliChem GmbH (Darmstadt, Germany), Avantor Performance Materials (Deventor, The Netherlands), Carl Roth GmbH & Co. KG (Karlsruhe, Germany), and Merck KGaA (Darmstadt, Germany) in analytical and HPLC grade.…”

Section: Methodsmentioning

confidence: 99%

Five Unprecedented Secondary Metabolites from the Spider Parasitic Fungus Akanthomyces novoguineensis

et al. 2017

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Five new compounds including the glycosylated β-naphthol (1, akanthol), a glycosylated pyrazine (2, akanthozine), and three amide derivatives including a hydroxamic acid derivative (3–5) were isolated from the spider-associated fungus Akanthomyces novoguineensis (Cordycipitaceae, Ascomycota). Their structures were elucidated by using high resolution mass spectrometry (HRMS) and NMR spectroscopy. In this study, the antimicrobial, cytotoxic, anti-biofilm, and nematicidal activities of the new compounds were evaluated. The distribution pattern of secondary metabolites in the species was also revealed in which more isolates of A. novoguineensis were encountered and their secondary metabolite profiles were examined using analytical HPLC with diode array and mass spectrometric detection (HPLC-DAD/MS). Remarkably, all isolated compounds are specifically produced by A. novoguineensis.

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Section: Methodsmentioning

confidence: 99%

Five Unprecedented Secondary Metabolites from the Spider Parasitic Fungus Akanthomyces novoguineensis

et al. 2017

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“…The biological activities of the pure compounds were conducted in accordance with literature descriptions; the MICs toward bacteria, yeast, and filamentous fungi were determined by a serial dilution technique using 96-well microtiter plates [21].…”

Section: Biological Activities Of the Pure Compoundsmentioning

confidence: 99%

Bacillus methylotrophicus ASWU-C2, a strain inhabiting hot desert soil, a new source for antibacterial bacillopyrone, pyrophen, and cyclopeptides

Helaly

Hamad

El‐Sayed

et al. 2018

Zeitschrift Für Naturforschung C

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A strain of Bacillus methylotrophicus was isolated from a soil sample collected in Aswan eastern desert, which is known for its extremely arid climate. After fermentation of the strain in liquid culture and subsequent extraction, a bioassay-guided isolation procedure yielded five compounds: 2-benzyl-4H-pyran-4-one, named bacillopyrone (1), pyrophen (2), macrolactin A (3) and the cyclopeptides malformin A1 (4), and bacillopeptin A (5). The structures were determined by interpretation of nuclear magnetic resonance (NMR) spectroscopy and high resolution mass spectrometry (HR-MS) data. This is the first report on the isolation of compounds 1 and 2 from Bacillus species; compound 1 was reported previously as synthetic product. Bacillopyrone (1) exhibited moderate activity against the Gram-negative Chromobacterium violaceum with minimum inhibitory concentration 266.6 μg/mL, while macrolactin A (3) and malformin A1 (4) inhibited Staphylococcus aureus (minimum inhibitory concentrations 13.3 and 133.3 μg/mL, respectively).

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“…Many compounds displayed a wide range of biological activities, such as cytotoxic, antimicrobial, and anti-inflammatory activities [ 4 , 5 , 6 , 7 ]. Hirsutanes and capnellenes are the most common scaffolds of the linear triquinane sesquiterpenoids ( Figure 1 b,c) [ 8 ]. However, many compounds cannot be simply classified into these two types.…”

Section: Introductionmentioning

confidence: 99%

Linear Triquinane Sesquiterpenoids: Their Isolation, Structures, Biological Activities, and Chemical Synthesis

Qiu

Lan

et al. 2018

Molecules

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Linear triquinane sesquiterpenoids represent an important class of natural products. Most of these compounds were isolated from fungi, sponges, and soft corals, and many of them displayed a wide range of biological activities. On account of their structural diversity and complexity, linear triquinane sesquiterpenoids present new challenges for chemical structure identification and total synthesis. 118 linear triquinane sesquiterpenoids were classified into 8 types, named types I–VIII, based on the carbon skeleton and the position of carbon substituents. Their isolation, structure elucidations, biological activities, and chemical synthesis were reviewed. This paper cited 102 articles from 1947 to 2018.

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Lentinulactam, a hirsutane sesquiterpene with an unprecedented lactam modification

Abstract: CitationLentinulactam, a hirsutane sesquiterpene with an unprecedented lactam modification 2016, 57 (52):5911 Tetrahedron Letters

Cited by 15 publications

References 16 publications

Five Unprecedented Secondary Metabolites from the Spider Parasitic Fungus Akanthomyces novoguineensis

Five Unprecedented Secondary Metabolites from the Spider Parasitic Fungus Akanthomyces novoguineensis

Bacillus methylotrophicus ASWU-C2, a strain inhabiting hot desert soil, a new source for antibacterial bacillopyrone, pyrophen, and cyclopeptides

Linear Triquinane Sesquiterpenoids: Their Isolation, Structures, Biological Activities, and Chemical Synthesis

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