Sclerodin and related compounds from a plant disease causing fungus. Scleroderris yellow

1989 ◽  
Vol 67 (12) ◽  
pp. 2089-2094 ◽  
Author(s):  
William A. Ayer ◽  
Masayuki Kamada ◽  
Yu-Ting Ma
Keyword(s):  
Methyl Oleate ◽  
Stearic Acid ◽  
Causative Agent ◽  
Plant Disease ◽  
Culture Medium ◽  
Optical Purity ◽  
Lettuce Seeds ◽  
Shoot Blight ◽  
Optically Pure ◽  
Related Compounds

The metabolites of several strains of a fungus that gives rise to the disease of conifers known as Sirococcus shoot blight have been studied. The metabolites are similar to those isolated from Gremmeniellaabietina, the causative agent of Scleroderris canker of pine. Sclerodin (1), scleroderolide (2), and Scleroderris blue (3) have been isolated, along with the known lactone 4, trypethelone (6), and a new purple compound named scleroquinone (12). Another new compound, related to Scleroderris blue (3) and Scleroderris green (7); which we have named Scleroderris yellow, is shown to possess structure 8. The sclerodin (1) isolated in these studies is not optically pure, in some cases being nearly racemic. It is noted that the optical purity may be a function of the culture medium employed. Scleroderolide (2) strongly inhibits the germination of lettuce seeds. In addition to the metabolites noted, squalene, methyl oleate, stearic acid, ergosta-4,6,8(14),22-tetraene-3-one, and ergosterol endoperoxide were also isolated from the cultures. Keywords: Sirococcus, phenalenones, Scleroderris yellow, scleroquinone, sclerodin.

scholarly journals A Comprehensive Analysis Using Colorimetry, Liquid Chromatography-Tandem Mass Spectrometry and Bioassays for the Assessment of Indole Related Compounds Produced by Endophytes of Selected Wheat Cultivars

Molecules ◽  
2021 ◽  
Vol 26 (5) ◽  
pp. 1394
Author(s):  
Agnieszka Kuźniar ◽  
Kinga Włodarczyk ◽  
Ilona Sadok ◽  
Magdalena Staniszewska ◽  
Małgorzata Woźniak ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Liquid Chromatography ◽  
Tandem Mass Spectrometry ◽  
Endophytic Bacteria ◽  
Culture Medium ◽  
Tandem Mass ◽  
Wheat Cultivars ◽  
Chromatography Tandem Mass Spectrometry ◽  
Liquid Chromatography Tandem Mass ◽  
Related Compounds

Liquid chromatography–tandem mass spectrometry (LC–MS/MS), colorimetry, and bioassays were employed for the evaluation of the ability of endophytic bacterial strains to synthesize indole-related compounds (IRCs) and in particular indole-3-acetic acid (IAA). A total of 54 endophytic strains belonging to seven bacterial genera isolated from tissues of common and spelt wheat cultivars were studied. The endophytic bacteria isolated from different tissues of the tested wheat types were capable of IRCs production, including IAA, which constituted from 1.75% to 52.68% of all IRCs, in in vitro conditions via the tryptophan dependent pathway. The selected post-culture medium was also examined using a plant bioassay. Substantial growth of wheat coleoptile segments treated with the bacterial post-culture medium was observed in several cases. Our data suggest that the studied endophytic bacteria produce auxin-type compounds to support plant development. Summarizing, our approach to use three complementary methods for estimation of IRCs in different endophytic strains provides a comprehensive picture of their effect on wheat growth.

ChemInform Abstract: Synthesis of Optically Pure Bisphosphine Oxides and Related Compounds.

ChemInform ◽  
2010 ◽  
Vol 31 (27) ◽  
pp. no-no
Author(s):  
Masashi Sugiya ◽  
Hiroyuki Nohira
Keyword(s):  
Optically Pure ◽  
Related Compounds

New and Improved Synthesis of Optically Pure (R)-and (S)-2,2′-Dimethyl-1, 1′-binaphthyl and Related Compounds

Synthesis ◽  
1985 ◽  
Vol 1985 (03) ◽  
pp. 317-320 ◽  
Author(s):  
Nicole Maigrot ◽  
Jean-Paul Mazaleyrat
Keyword(s):  
Optically Pure ◽  
Related Compounds

Preparation of secondary alcohols of high optical purity

1986 ◽  
Vol 51 (2) ◽  
pp. 401-403 ◽  
Author(s):  
Otakar Červinka ◽  
Anna Fábryová ◽  
Irina Sablukova
Keyword(s):  
Nmr Spectroscopy ◽  
Optical Purity ◽  
Optically Active ◽  
Secondary Alcohols ◽  
Lithium Aluminium Hydride ◽  
Enantioselective Reduction ◽  
H Nmr ◽  
Lithium Aluminium ◽  
High Optical Purity ◽  
Optically Pure

Partially resolved enantiomers of optically active alcohols I-V, obtained by enantioselective reduction of the corresponding ketones with lithium aluminium hydride in the presence of (-)-quinine, were converted into crystalline 3,5-dinitrobenzoates or phenylcarbamates. The esters of the nearly optically pure enantiomers were separated by crystallization from the generally more soluble esters of the racemates. Optical purity of the hydrolytically liberated alcohols was determined by 1H NMR spectroscopy in the presence of chiral shifting agents.

Synthesis of Optically Active N6-Alkyl Derivatives of (R)-3-(Adenin-9-yl)-2-hydroxypropanoic Acid and Related Compounds

2003 ◽  
Vol 68 (5) ◽  
pp. 931-950 ◽  
Author(s):  
Marcela Krečmerová ◽  
Miloš Buděšínský ◽  
Milena Masojídková ◽  
Antonín Holý
Keyword(s):  
Nmr Spectra ◽  
Enantiomeric Purity ◽  
Optically Active ◽  
Secondary Amines ◽  
H Nmr ◽  
Alkyl Derivatives ◽  
Optically Pure ◽  
Derivatives Of ◽  
Related Compounds

Reaction of ethyl (R)-oxiranecarboxylate (2a) with various nucleobases (adenine, 6-chloropurine, thymine, cytosine, N6-benzoyladenine, 4-methoxy-5-methylpyrimidin-2(1H)-one and 4-methoxypyrimidin-2(1H)-one) afforded ethyl 3-substituted-2-hydroxypropanoates 4-10. Enantioselectivity of this reaction is dependent on the type of the base: 6-chloropurine, N6-benzoyladenine, 4-methoxy-5-methylpyrimidin-2(1H)-one, thymine and cytosine gave optically pure R enantiomers. In other cases, partial or complete racemization occurred. Optically pure ethyl (R)-3-(6-chloropurin-9-yl)-2-hydroxypropanoate (5a) was hydrolyzed to give (R)-3-(6-chloropurin-9-yl)-2-hydroxypropanoic acid (11). Reactions of 11 with various primary or secondary amines led to N6-substituted (R)-3-(adenin-9-yl)-2-hydroxypropanoic acids 14-19. Enantiomeric purity was determined from 1H NMR spectra measured in the presence of (-)-(R)-1-(9-anthryl)-2,2,2-trifluoroethan-1-ol.

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