Omphaloprenol A: A new bioactive polyisoprenepolyol isolated from the mycelium of poisonous mushroom Omphalotus japonicus

2021 ◽  
Author(s):  
Satoki Aoki ◽  
Takako Aboshi ◽  
Takumu Onodera ◽  
Ken-ichi Kimura ◽  
Daisuke Arai ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
Secondary Metabolites ◽  
Bioactive Compounds ◽  
Chemical Structure ◽  
Lettuce Seeds ◽  
Illudin S ◽  
Poisonous Mushroom ◽  
Growth Promoting

Abstract Mushrooms of the Omphalotus genus are known to be rich in secondary metabolites. In the quest for new bioactive compounds, we analyzed the compounds isolated from the mycelium of the poisonous mushroom Omphalotus japonicus. As a result, a new polyisoprenepolyol, which was named omphaloprenol A, was identified, along with known substances such as hypsiziprenol A10 and A11, illudin S, and ergosterol. The chemical structure of omphaloprenol A was elucidated by nuclear magnetic resonance and infrared spectroscopies and mass spectrometry, and its bioactivity was investigated. Omphaloprenol A showed growth promoting activity against the root of lettuce seeds and cytotoxicity against HL60 cells. To the best of our knowledge, this is the first report on the isolation of a polyisoprenepolyol compound from Omphalotaceae mushrooms.

scholarly journals Chemical Structure of a Novel Aminophospholipid from Hydrogenobacter thermophilus Strain TK-6

2001 ◽  
Vol 183 (21) ◽  
pp. 6302-6304 ◽  
Author(s):  
Jun-ichiro Yoshino ◽  
Yasumasa Sugiyama ◽  
Shohei Sakuda ◽  
Tohru Kodama ◽  
Hiromichi Nagasawa ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
Chemical Structure ◽  
Fast Atom Bombardment ◽  
Phospholipid Composition ◽  
Methanospirillum Hungatei ◽  
Hydrogen Bacterium ◽  
Hydrogenobacter Thermophilus ◽  
Nuclear Magnetic

ABSTRACT The phospholipid composition of Hydrogenobacter thermophilus strain TK-6, an obligately chemolithoautotrophic, extremely thermophilic hydrogen bacterium, was analyzed. Two of four phospholipids detected from the strain were assumed to be phosphatidylinositol and phosphatidylglycerol. An aminophospholipid named PX, whose content among the phospholipids was 65%, was found to have a novel chemical structure by analysis of the dilyso form with nuclear magnetic resonance and fast atom bombardment-mass spectrometry (FAB-MS) and by analysis of the intact PX with FAB-MS as 1,2-diacyl-3-O-(phospho-2′-O-(1′-amino)-2′,3′,4′,5′-pentanetetrol)-sn-glycerol. Structurally similar phospholipids have been identified inMethanospirillum hungatei, Methanolacinia paynteri, and Methanogenium cariaci, which all belong to the Archaea.

Metabolomics: A High-throughput Screen for Biochemical and Bioactivity Diversity in Plants and Crops

2018 ◽  
Vol 24 (19) ◽  
pp. 2043-2054 ◽  
Author(s):  
Alexandre Foito ◽  
Derek Stewart
Keyword(s):  
Mass Spectrometry ◽  
Nuclear Magnetic Resonance ◽  
Natural Products ◽  
Drug Discovery ◽  
Magnetic Resonance ◽  
Bioactive Compounds ◽  
Modern Medicine ◽  
Plant Tissues ◽  
Technical Developments ◽  
Biological Sources

Plants and crops contain a staggering diversity of compounds, many of which have pharmacological activity towards a variety of diseases. These properties have been exploited by traditional and modern medicine providing important sources of healthcare to this day. The contribution of natural products (such as plant-derived) to the modern pharmacopeia is indeed significant; however, the process of identifying novel bioactive compounds from biological sources has been a central challenge in the discovery of natural products. The resolution of these challenges relied extensively on the use of hyphenated Mass Spectrometry (MS) and Nuclear Magnetic Resonance (NMR)-based analytical technologies for the structural elucidation and annotation of novel compounds. Technical developments in instrumentation and data processing have fostered the development of the field of metabolomics which provides a wealth of tools with the huge potential for application in the process of drug/bioactive discovery from plant tissues. This manuscript provides an overview of the metabolomics toolbox available for the discovery of novel bioactive compounds and the integration of these tools in the bioprospection and drug discovery workflows.

Methods to Determine Phytopharmaceuticals in Tobacco and Tobacco Products. 4th Report: A Procedure to Determine Vamidothion and its Metabolites/Methoden zur Bestimmung von Phytopharmaka in Tabak und Tabakerzeugnissen: IV. Mitteilung: Ein Bestimmungsverfahren fuer Vamidothion und seine Metaboliten

1977 ◽  
Vol 9 (2) ◽  
Author(s):  
A.N. Sagredos ◽  
R. Moser
Keyword(s):  
Mass Spectrometry ◽  
Nuclear Magnetic Resonance ◽  
Acetic Acid ◽  
Magnetic Resonance ◽  
Aluminium Oxide ◽  
Nuclear Magnetic Resonance Data ◽  
Gas Chromatograph ◽  
Tobacco Products ◽  
Magnetic Resonance Data ◽  
Resonance Data

AbstractBased on previous work (7) a method to simultaneously determine vamidothion [I], vamidothion-sulfoxide [II] and vamidothion sulfone [III] in tobacco has been developed. The compounds are extracted with water/acetone/acetic acid from the tobacco, cleansed over an aluminium oxide column and then determined on the gas chromatograph with the specific sulphur detector. Rates of recovery are 70 % - 92 %, the determination level is 0.1 ppm. Mass spectrometry and nuclear magnetic resonance data of vamidothion [I], vamidothion-sulfoxide [ II ] and vamidothion-sulfone [III] are given.

scholarly journals N,N-Bis(Hexyl α-d-Acetylmannosyl) Acrylamide

Molbank ◽  
10.3390/m1255 ◽  
2021 ◽  
Vol 2021 (3) ◽  
pp. M1255
Author(s):  
Atsushi Miyagawa ◽  
Shinya Ohno ◽  
Hatsuo Yamamura
Keyword(s):  
Mass Spectrometry ◽  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
Magnetic Resonance Spectroscopy ◽  
Nuclear Magnetic Resonance Spectroscopy ◽  
Side Reaction ◽  
Resonance Spectroscopy ◽  
Biological Functions ◽  
Unknown Compound ◽  
Acrylamide Monomer

Glycosyl monomers for the assembly of multivalent ligands are typically synthesized using carbohydrates with biological functions and polymerizable functional groups such as acrylamide or styrene introduced into the carbohydrate aglycon, and monomers polymerized using a radical initiator. Herein, we report the acryloylation of 6-aminohexyl α-mannoside and its conversion into the glycosyl monomer bearing an acrylamide group. The general acryloylation procedure afforded the desired N-hexyl acetylmannosyl acrylamide monomer as well as an unexpected compound with a close Rf value. The compounds were separated and analyzed by nuclear magnetic resonance spectroscopy and mass spectrometry, which revealed the unknown compound to be the bivalent N,N-bis(hexyl α-d-acetylmannosyl) acrylamide monomer, which contains two hexyl mannose units and one acrylamide group. To the best of our knowledge, this side reaction has not previously been disclosed, and may be useful for the construction of multivalent sugar ligands.

scholarly journals Metabolomics in nutrition research–a powerful window into nutritional metabolism

2016 ◽  
Vol 60 (5) ◽  
pp. 451-458 ◽  
Author(s):  
Lorraine Brennan
Keyword(s):  
Mass Spectrometry ◽  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
Data Acquisition ◽  
Small Molecules ◽  
Biological Samples ◽  
Metabolic Pathways ◽  
Recent Trend ◽  
Disease States ◽  
Nutrition Research

Metabolomics is the study of small molecules present in biological samples. In recent years it has become evident that such small molecules, called metabolites, play a key role in the development of disease states. Furthermore, metabolomic applications can reveal information about alterations in certain metabolic pathways under different conditions. Data acquisition in metabolomics is usually performed using nuclear magnetic resonance (NMR)-based approaches or mass spectrometry (MS)-based approaches with a more recent trend including the application of multiple platforms in order to maximise the coverage in terms of metabolites measured. The application of metabolomics is rapidly increasing and the present review will highlight applications in nutrition research.

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