The isolation, identification, and bioassay of the antifungal metabolites produced by Monocillium nordinii

1980 ◽  
Vol 26 (7) ◽  
pp. 766-773 ◽  
Author(s):  
William A. Ayer ◽  
Sing Ping Lee ◽  
Akihiko Tsuneda ◽  
Yasuyuki Hiratsuka
Keyword(s):  
Absolute Configuration ◽  
Liquid Culture ◽  
Dutch Elm Disease ◽  
Antifungal Metabolites ◽  
The Absolute ◽  
New Compounds

The metabolites produced when Monocillium nordinii (Bourchier) W. Gams, a destructive mycoparasite of pine stem rusts, is grown in liquid culture have been separated and identified. The metabolites include the known compound monorden (1) and five new substances, monocillin I (2), monocillin II (4), monocillin III (3), monocillin IV (5), and monocillin V (6). Structural assignments and chemical correlations of the five new compounds are reported and the absolute configuration of monorden is assigned. The antifungal spectra of the three major metabolites are reported. Monorden and monocillin I show pronounced activity against a wide variety of fungi, including Ceratocystis ulmi, the cause of Dutch elm disease. Extraction of the mycelium yielded averufin (13), along with a pigment C18H12O6, as yet unidentified.

scholarly journals Massiliamide, a cyclic tetrapeptide with potent tyrosinase inhibitory properties from the Gram-negative bacterium Massilia albidiflava DSM 17472T

2020 ◽  
Author(s):  
Andri Frediansyah ◽  
Jan Straetener ◽  
Heike Brötz-Oesterhelt ◽  
Harald Gross
Keyword(s):  
Absolute Configuration ◽  
Inhibitory Activity ◽  
Liquid Culture ◽  
Spectroscopic Analysis ◽  
2D Nmr ◽  
Negative Bacterium ◽  
Gram Negative ◽  
The Absolute ◽  
Potent Inhibitory Activity ◽  
Cyclic Tetrapeptide

AbstractA cyclic tetrapeptide, designated massiliamide, was isolated from the liquid culture of the Gram-negative bacterium Massilia albidiflava DSM 17472T. The structure was elucidated through extensive spectroscopic analysis, including HR-MS and 1D and 2D NMR experiments. The absolute configuration was determined using the Marfey´s method. Massiliamide showed potent inhibitory activity towards tyrosinase with an IC50 value of 1.15 µM and no cytotoxicity.

scholarly journals Novel Bisabolane Sesquiterpenes from the Marine-derived Fungus Verticillium tenerum

2010 ◽  
Vol 5 (4) ◽  
pp. 1934578X1000500 ◽  
Author(s):  
Celso Almeida ◽  
Somaia Elsaedi ◽  
Stefan Kehraus ◽  
Gabriele M. König
Keyword(s):  
Absolute Configuration ◽  
Cd Spectroscopy ◽  
Mass Spectrometric ◽  
Planar Structures ◽  
The Absolute ◽  
New Compounds ◽  
Mass Spectrometric Techniques

Chemical investigations of the marine-derived fungus Verticillium tenerum yielded two new hydroxylated bisabolane-type sesquiterpenes verticinol A (1) and B (2). The planar structures of the new compounds were elucidated by employing spectroscopic (NMR, UV, and IR) and mass spectrometric techniques. The absolute configuration of the cyclohexenyl moiety was deduced by a combination of CD spectroscopy and NOESY measurements.

scholarly journals New Isochromane Derivatives from the Mangrove Fungus Aspergillus ustus 094102

2015 ◽  
Vol 10 (12) ◽  
pp. 1934578X1501001 ◽  
Author(s):  
Peipei Liu ◽  
Cong Wang ◽  
Zhenyu Lu ◽  
Tonghan Zhu ◽  
Kui Hong ◽  
...  
Keyword(s):  
Absolute Configuration ◽  
Spectroscopic Analysis ◽  
Fermentation Broth ◽  
Dpph Radical ◽  
Etoac Extract ◽  
Aspergillus Ustus ◽  
The Absolute ◽  
New Compounds

Four new isochromane derivatives (1–4) along with the known peniciphenol (5) and ( R)-2-(hydroxymethyl)-3-(2-hydroxypropyl)phenol (6) were isolated from the EtOAc extract of the fermentation broth of the mangrove fungus, Aspergillus ustus 094102. The structures of the new compounds including the absolute configuration were elucidated on the basis of spectroscopic analysis, CD and ECD calculation. Compounds 1 and 2 exhibited α-glucosidase inhibition and anti-oxidation against DPPH radical with IC50 values of 1.4 mM and 25.7 μM, respectively.

Novel Bromo Metabolites From a Dictyoceratid Sponge of the Cacospongia Genus

1989 ◽  
Vol 42 (5) ◽  
pp. 611 ◽  
Author(s):  
MJ Garson ◽  
DC Manker ◽  
KE Maxwell ◽  
BW Skelton ◽  
AH White
Keyword(s):  
Structure Analysis ◽  
Absolute Configuration ◽  
Marine Sponge ◽  
Carbon Skeleton ◽  
Crystallographic Structure ◽  
X Ray ◽  
The Absolute ◽  
New Compounds

Two novel brominated metabolites, tribromocacoxanthene (3) and tetrabromocacoxanthene (4),have been isolated from a marine sponge of the Cacospongia genus (family Thorectidae ) along with 12-epideoxoscalarin (2). The structures of compounds (3), systematic name (2S,4aS,9aS)-2,7-dibromo-4a-bromomethyl-1,1-dimethyl-2,3,4,4a,9,9a-hexahydro-1H-xanthene, and (4), systematic name (2S,4aS,9aS)-2,5,7-tribromo-4a-bromomethyl-l,1-dimethyl-2,3,4,4a,9,9a-hexahydro-1H-xanthene , were deduced from analysis of 1H and 13C n.m.r. data and that of (3) was confirmed by X-ray crystallographic structure analysis which provided the absolute configuration. The two new compounds are the first tricyclic examples of a carbon skeleton previously isolated only from algae. The chemotaxonomic implication of the isolation of these new compounds is discussed.

scholarly journals A Unique Naphthone Derivative and a Rare 4,5-seco-Lanostane Triterpenoid from Poria cocos

Molecules ◽  
2018 ◽  
Vol 23 (10) ◽  
pp. 2508 ◽  
Author(s):  
Ting Chen ◽  
La Hua ◽  
Guixin Chou ◽  
Xudong Mao ◽  
Xianliang Zou
Keyword(s):  
Mass Spectroscopy ◽  
Absolute Configuration ◽  
Cytotoxic Activities ◽  
Electronic Circular Dichroism ◽  
Poria Cocos ◽  
Etoh Extract ◽  
The Absolute ◽  
Lanostane Triterpenoid ◽  
New Compounds ◽  
Circular Dichroïsm

A previously undescribed naphthalenone derivative, sohiracillinone (1), and a novel 4,5-seco-lanostane triterpenoid, 11β-ethoxydaedaleanic acid A (2) were isolated with two new lanostane triterpenoids, ceanphytamic acids A (3) and B (4), from the EtOH extract of Poria cocos along with 17 known compounds 5–21. The absolute configuration of sohiracillinone (1) was unambiguously identified by NMR and electronic circular dichroism (ECD) data. The structures of other new compounds were elucidated on the basis of NMR and mass spectroscopy (MS), and the cytotoxic activities of all the isolated components were evaluated.

A New Series of Diterpenes from Australian Spongia Species

1979 ◽  
Vol 32 (4) ◽  
pp. 867 ◽  
Author(s):  
R Kazlauskas ◽  
PT Murphy ◽  
RJ Wells ◽  
K Noack ◽  
WE Oberhansli ◽  
...  
Keyword(s):  
Great Barrier Reef ◽  
Single Crystal ◽  
Absolute Configuration ◽  
Spectral Methods ◽  
Barrier Reef ◽  
X Ray ◽  
The Absolute ◽  
New Compounds ◽  
The Relationship ◽  
Circular Dichroïsm

Great Barrier Reef sponges of the genus Spongia have yielded eight closely related tetracyclic furanoditerpenes. The structures, assigned on the basis of spectral methods, have been confirmed by a single-crystal X-ray analysis of one of the metabolites and the relative stereochemical features have been defined. The absolute configuration of this metabolite was determined by circular dichroism, which allowed the relationship between the eight new compounds to be determined.

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