Penigequinolones A and B, pollen-growth inhibitors produced by Penicilium sp., No. 410

Kimura, Yasuo; Kusano, Miyako; Koshino, Hiroyuki; Uzawa, Jun; Fujioka, Shozo; Tani, K.

doi:10.1016/0040-4039(96)00978-1

Cited by 43 publications

(30 citation statements)

References 6 publications

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“…7–9 HMBC correlations from the H-12/H-16 signal for the phenyl group to C-4; from the isolated oxymethine H-3 to C-2, C-4, C-5, and C-11; and from the amide NH to C-5 and C-10 were consistent with the corresponding features of the structure of aspoquinolone C, albeit without the para -methoxy group on the aromatic ring substituent. 8 …”

Section: Resultssupporting

confidence: 65%

Aflaquinolones A–G: Secondary Metabolites from Marine and Fungicolous Isolates of Aspergillus spp.

et al. 2012

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Seven new compounds (aflaquinolones A – G; 1 – 7) containing dihydroquinolin-2-one and terpenoid units have been isolated from two different fungal sources. Two of these metabolites (1 and 2) were obtained from a Hawaiian fungicolous isolate of Aspergillus sp. (section Flavipedes; MYC-2048 = NRRL 58570), while the others were obtained from a marine Aspergillus isolate (SF-5044) collected in Korea. The structures of these compounds were determined mainly by analysis of NMR and MS data. Relative and absolute configurations were assigned on the basis of NOESY data and 1H NMR J-values, comparison of calculated and experimental ECD spectra, and analysis of a Mosher’s ester derivative of 2. Several known compounds, including alantrypinone, aspochalasins I and J, methyl-3,4,5-trimethoxy-2((2-((3-pyridinylcarbonyl)amino) benzoyl)amino) benzoate, and trans-dehydrocurvularin were also encountered in the extract of the Hawaiian isolate.

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Section: Resultssupporting

confidence: 65%

Aflaquinolones A–G: Secondary Metabolites from Marine and Fungicolous Isolates of Aspergillus spp.

et al. 2012

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“…315 Compared with other natural pollen inhibitors, the mixture's effects were stronger than those of emeniveol, but weaker than those of hericerin and isofunicone. 315…”

Section: Herbicidal Activitymentioning

confidence: 93%

“…It inhibited the germination of representative monocot and dicot seeds, impeded the growth of aquatic duckweed, and reduced cell division in onion . A mixture of two highly substituted 4‐phenyl 2‐quinolone alkaloids penigequinolones A ( 148 ) and B ( 149 ) inhibited the growth of tea pollen tubes by 40% at 10 mg/L and 100% at 100 mg/L . Compared with other natural pollen inhibitors, the mixture's effects were stronger than those of emeniveol, but weaker than those of hericerin and isofunicone …”

Section: Bioactivities Of Quinoline and Quinazoline Alkaloidsmentioning

confidence: 99%

Biologically active quinoline and quinazoline alkaloids part I

Shang

Morris‐Natschke

Liu

et al. 2017

Medicinal Research Reviews

307

175

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Quinoline and quinazoline alkaloids, two important classes of N-based heterocyclic compounds, have attracted tremendous attention from researchers worldwide since the 19th century. Over the past 200 years, many compounds from these two classes were isolated from natural sources, and most of them and their modified analogs possess significant bioactivities. Quinine and camptothecin are two of the most famous and important quinoline alkaloids, and their discoveries opened new areas in antimalarial and anticancer drug development, respectively. In this review, we survey the literature on bioactive alkaloids from these two classes and highlight research achievements prior to the year 2008 (Part I). Over 200 molecules with a broad range of bioactivities, including antitumor, antimalarial, antibacterial and antifungal, antiparasitic and insecticidal, antiviral, antiplatelet, anti-inflammatory, herbicidal, antioxidant and other activities, were reviewed. This survey should provide new clues or possibilities for the discovery of new and better drugs from the original naturally occurring quinoline and quinazoline alkaloids.

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“…Dihydroquinolin-2-ones can exist as isolated ring systems, as in the penigquinolones,2 pinolinone,3 α 2 β 3 integrin antagonists4 (see 1 , Figure 1), and a class of HIV reverse transcriptase inhibitors 5. Or, they can be conjoined with other rings, as in scandine and the related meloscine alkaloids (see 2 , Figure 1).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Highly Enantioenriched 3,4-Dihydroquinolin-2-ones by 6-Exo-trigRadical Cyclizations of Axially Chiral α-Halo-ortho-alkenyl Anilides

2009

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Radical cyclizations (Bu 3 SnH, Et 3 B/air, rt) of racemic α-halo-ortho-alkenyl anilides provide 3,4-dihydroquinolin-2-ones in high yield. Cyclizations of enantioenriched precursors occur in similarly high yields and with transfer of axial chirality to the new stereocenter of the products with exceptionally high fidelity (often > 95%). Single and tandem cyclizations of α-halo-ortho-alkenyl anilides bearing an additional substituent on the α-carbon occur with high chirality transfer and high diastereoselectivity. Straightforward models are proposed to interpret both the chirality transfer and diastereoselectivity aspects. These first examples of an approach for axial chiral transfer from a reactive species in the amide to an acceptor suggest broad potential for extension both within and beyond radical reactions.

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Penigequinolones A and B, pollen-growth inhibitors produced by Penicilium sp., No. 410

Cited by 43 publications

References 6 publications

Aflaquinolones A–G: Secondary Metabolites from Marine and Fungicolous Isolates of Aspergillus spp.

Aflaquinolones A–G: Secondary Metabolites from Marine and Fungicolous Isolates of Aspergillus spp.

Biologically active quinoline and quinazoline alkaloids part I

Synthesis of Highly Enantioenriched 3,4-Dihydroquinolin-2-ones by 6-Exo-trigRadical Cyclizations of Axially Chiral α-Halo-ortho-alkenyl Anilides

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