Peptaibol metabolites of Tolypocladium geodes

1996 ◽  
Vol 74 (2) ◽  
pp. 165-172 ◽  
Author(s):  
Youla S. Tsantrizos ◽  
Sotiria Pischos ◽  
Françoise Sauriol ◽  
Paul Widden
Keyword(s):  
Amino Acid ◽  
2D Nmr ◽  
Chemical Shift Assignments ◽  
Pentanoic Acid ◽  
2D Nmr Spectroscopy ◽  
New Members ◽  
The Common ◽  
Unusual Amino Acid ◽  
Acid Unit ◽  
C Nmr

Three antibiotic peptides, LP237-F8 (1), F5 (2), and F7 (3), were isolated from the liquid culture of the fungus Tolypocladium geodes. Chemical shift assignments of the 1H and 13C NMR resonances and sequencing of these metabolites were achieved by extensive high-field 2D NMR spectroscopy. The N-terminal of peptides 1 and 2 is protected with an octanoyl (Oc) fatty acid unit, whereas that of peptide 3 is protected with a decanoyl (Dec) unit. The C-terminal of all three peptides is protected with the amino alcohol leucinol (Lol). All three metabolites contain the common amino acids Ala, Phe or Tyr, Pro, and Gln, as well as the unusual amino acid α-aminoisobutyric acid (Aib). In addition, peptides 1 and 2 contain the amino acid α-amino-α-ethyl-n-pentanoic acid (α-ethylnorvaline, EtNor), which has not been previously reported as a constituent of a natural product. Metabolites 1, 2, and 3 are new members of the class of natural products known as peptaibols. Key words: Tolypocladium geodes, peptaibols, leucinol, α-amino-α-ethyl-n-pentanoic acid.

scholarly journals Chemical Constituents of Lecythis pisonis (Lecythidaceae) – A New Saponin and Complete 1H and 13C Chemical Shift Assignments

2015 ◽  
Vol 10 (6) ◽  
pp. 1934578X1501000
Author(s):  
Rennê C. Duarte ◽  
Carlos R. R. Matos ◽  
Raimundo Braz-Filho ◽  
Leda Mathias
Keyword(s):  
High Resolution Mass Spectrometry ◽  
Chemical Constituents ◽  
2D Nmr ◽  
Triterpenoid Saponin ◽  
Chemical Shift Assignments ◽  
2D Nmr Spectroscopy ◽  
13C Chemical Shift ◽  
Long Chain Alcohol ◽  
Long Chain ◽  
C Nmr

A novel triterpenoid saponin 3- O-β-D-glucuronopyranosyl-(1→3)-2α,19α-dihydroxyolean-12-en-28-oic acid [3- O-β-D-glucuronopyranosyl-(1′→3)-arjunic acid, 1], ten known compounds [six triterpenoids: α-amyrin (2), β-amyrin (3), germanicol (4), lupeol (5), friedelin (6), friedelanol (7); four steroids -campesterol (8), stigmasterol (9), sitosterol (10), cholesterol (11)], and a long chain alcohol n-eicosan-1-ol (12) were identified in the bark of Lecythis pisonis. The structures were established by 1D and 2D NMR spectroscopy (1H and 13C-NMR, DEPTQ, 1H-1H-COSY, NOESY, HSQC and HMBC), low (CG-MS) and high resolution mass spectrometry (HR-ESI-MS), and infrared (IR) spectral data involving comparison with the literature.

scholarly journals Unusual Polyhydroxylated Steroids from the Starfish Anthenoides laevigatus, Collected off the Coastal Waters of Vietnam

Molecules ◽  
2020 ◽  
Vol 25 (6) ◽  
pp. 1440
Author(s):  
Alla A. Kicha ◽  
Dinh T. Ha ◽  
Timofey V. Malyarenko ◽  
Anatoly I. Kalinovsky ◽  
Roman S. Popov ◽  
...  
Keyword(s):  
Coastal Waters ◽  
2D Nmr ◽  
2D Nmr Spectroscopy ◽  
Cytotoxic Effects ◽  
One Dimensional ◽  
The Common ◽  
Polyhydroxylated Steroids ◽  
New Compounds ◽  
Ht 29 ◽  
Inhibit Cell Proliferation

Four new polyhydroxylated steroids 1–4 were isolated along with two previously known related steroids 5 and 6 from the methanolic extract of the starfish Anthenoides laevigatus collected off the coastal waters of Vietnam. Structures of new compounds were substantially elucidated by one-dimensional (1D) and two-dimensional (2D) NMR spectroscopy and HRESIMS techniques. Heptaol 1 and hexaol 2 contain the common 5α-cholestane skeleton, while hexaol 3 and heptaol 4 have the rare among starfish steroid compounds 5β-cholestane skeleton. Compounds 1, 5, and 6 do not show cytotoxic effects against normal JB6 Cl41 and cancer HT-29 and MDA-MB-231 cells, however they inhibit cell proliferation and colony formation of cancer HT-29 and MDA-MB-231 cells.

scholarly journals Flavonoids from Curcuma longa Leaves and their NMR Assignments

2015 ◽  
Vol 10 (1) ◽  
pp. 1934578X1501000 ◽  
Author(s):  
Chia-Ling Jiang ◽  
Sheng-Fa Tsai ◽  
Shoei-Sheng Lee
Keyword(s):  
Nmr Assignments ◽  
Soluble Fraction ◽  
Curcuma Longa ◽  
2D Nmr ◽  
Etoh Extract ◽  
Spectroscopic Analyses ◽  
Nmr Data ◽  
The Common ◽  
Reported Data ◽  
C Nmr

Chemical investigation of the n-BuOH-soluble fraction of the EtOH extract of the aerial part of Curcuma longa led to the isolation of 11 flavonol glycosides and one dihydroflavonol glucoside (1) via chromatography over Sephadex LH-20 and Lobar RP-18 columns. Although they are known, the 1H and 13C NMR data recorded in CD3OD rather than the common DMSO- d6 are doubly checked via extensive 2D NMR spectroscopic analyses, leading to some revisions of the reported data, especially for the glycon part.

Anwendungen der 2 D-NMR-Spektroskopie in der Organophosphorchemie Beispiel: L-Menthyldichlorphosphan / Applications of the 2D NMR Spectroscopy in the Organophosphorus Chemistry Example: L-Menthyldichlorophosphine

1982 ◽  
Vol 37 (12) ◽  
pp. 1661-1664 ◽  
Author(s):  
Martin Feigel ◽  
Gerhard Hägele ◽  
Axel Hinke ◽  
Gudrun Tossing
Keyword(s):  
Nmr Spectroscopy ◽  
2D Nmr ◽  
2D Nmr Spectroscopy ◽  
H Nmr ◽  
Nmr Parameters ◽  
Nmr Data ◽  
Organophosphorus Chemistry ◽  
C Nmr

2D NMR ist used to determine the 1H NMR parameters of L-Menthyldichlorophosphine. 13C NMR data are given

3-Oxo-12α-hydroxyfriedelane from Maytenus gonoclada : structure elucidation by 1 H and 13 C chemical shift assignments and 2D-NMR spectroscopy

2007 ◽  
Vol 45 (10) ◽  
pp. 895-898 ◽  
Author(s):  
Mauro Lúcio G. Oliveira ◽  
Lucienir Pains Duarte ◽  
Grácia Divina F. Silva ◽  
Sidney Augusto Vieira Filho ◽  
Vagner Fernandes Knupp ◽  
...  
Keyword(s):  
Nmr Spectroscopy ◽  
Chemical Shift ◽  
Structure Elucidation ◽  
2D Nmr ◽  
Chemical Shift Assignments ◽  
2D Nmr Spectroscopy

scholarly journals Alkaloids From the Marine Fungus Lecanicillium fusisporum Using an Amino Acid-Directed Strategy

2021 ◽  
Vol 16 (10) ◽  
pp. 1934578X2110460
Author(s):  
Qin Huang ◽  
Hou-Jin Li ◽  
Chang-Bai Huang ◽  
Zi-Han Wang ◽  
Wen-Jian Lan ◽  
...  
Keyword(s):  
Amino Acid ◽  
Spectroscopic Data ◽  
Marine Fungi ◽  
Optical Rotation ◽  
Indole Alkaloid ◽  
2D Nmr ◽  
Marine Fungus ◽  
Culture Broth ◽  
Synthetic Approach ◽  
C Nmr

An amino acid-directed strategy has been developed to explore the potential of marine fungi to produce alkaloids. The marine fungus Lecanicillium fusisporum was cultured in glucose-peptone-yeast (GPY) medium to which were added L-tryptophan, L-phenylalanine, L-threonine, D, L-methionine, L-serine, L-lysine and L-valine. A new indole alkaloid, lecasporinoid (1), along with five known alkaloids (2−6) were discovered from the culture broth. The planar structure of lecasporinoid (1) was determined by HR-ESIMS, and 1D and 2D NMR spectroscopic data. The absolute configuration was established by optical rotation and 13C NMR calculations combining with a chemical synthetic approach.

The 1H and 13C NMR Chemical Shift Assignments for Thirteen Bufadienolides Isolated from the Traditional Chinese Drug Ch'an Su

2001 ◽  
Vol 66 (12) ◽  
pp. 1841-1848 ◽  
Author(s):  
Yoshiaki Kamano ◽  
Toshihiko Nogawa ◽  
Ayano Yamashita ◽  
George R. Pettit
Keyword(s):  
Chemical Shift ◽  
13C Nmr ◽  
Nmr Spectra ◽  
2D Nmr ◽  
Chinese Drug ◽  
Chemical Shift Assignments ◽  
1H And 13C Nmr ◽  
Nmr Chemical Shift Assignments ◽  
2D Nmr Spectra ◽  
C Nmr

The 1H and 13C NMR spectra of thirteen natural bufadienolides, which were isolated from the Chinese drug Ch'an Su, were assigned using a combination of 2D NMR spectra that included 1H-1H COSY, NOESY, HMQC, and HMBC techniques.

scholarly journals Amycolatomycins A and B, Cyclic Hexapeptides Isolated from an Amycolatopsis sp. 195334CR

Antibiotics ◽  
2021 ◽  
Vol 10 (3) ◽  
pp. 261
Author(s):  
Gian Primahana ◽  
Chandra Risdian ◽  
Tjandrawati Mozef ◽  
Joachim Wink ◽  
Frank Surup ◽  
...  
Keyword(s):  
Inhibitory Concentration ◽  
High Resolution Mass Spectrometry ◽  
2D Nmr ◽  
2D Nmr Spectroscopy ◽  
Planar Structures ◽  
Cyclic Hexapeptides ◽  
Weak Activity ◽  
Absolute Stereochemistry ◽  
Resolution Mass ◽  
Acid Unit

The rare actinobacterium Amycolatopsis sp. strain 195334CR was found to produce previously undescribed cyclic hexapeptides, which we named amycolatomycin A and B (1 and 2). Their planar structures were determined by high-resolution mass spectrometry as well as extensive 1D and 2D NMR spectroscopy, while the absolute stereochemistry of its amino acids were determined by Marfey’s method. Moreover, 1 and 2 differ by the incorporation of l-Ile and l-allo-Ile, respectively, whose FDVA (Nα-(2,4-Dinitro-5-fluorphenyl)-L-valinamide) derivatives were separated on a C4 column. Their hallmark in common is a unique 2,6-dichloro-tryptophan amino acid unit. Amycolatomycin A (1) exhibited weak activity against Bacillus subtilis DSM 10 (minimum inhibitory concentration (MIC) = 33.4 µg/mL).

Dendrophen, a Novel Glycyrrhetyl Amino Acid from Dendronephthya hemprichi

2011 ◽  
Vol 66 (4) ◽  
pp. 425-432 ◽  
Author(s):  
Mohamed Shaaban ◽  
Khaled A. Shaaban ◽  
Howaida I. Abd-Alla ◽  
Atef G. Hanna ◽  
Hartmut Laatsch
Keyword(s):  
Mass Spectrometry ◽  
Amino Acid ◽  
Acrylic Acid ◽  
Red Sea ◽  
Chromatographic Separation ◽  
2D Nmr ◽  
Pentanoic Acid ◽  
Nmr Studies ◽  
Amino Acid Conjugate ◽  
Acid Conjugate

Chemical investigation of the extract of Dendronephthya hemprichi, collected from the Red Sea, Egypt, delivered dendrophen (1), the first 3β -acetoxy-glycyrrhetyl amino acid conjugate obtained from nature. Additionally, a new polyhydroxy sterol, dendrotriol (2), together with cholesterol and hexitol were isolated. Chromatographic separation of the low-polarity components of the D. hemprichi extract afforded 4-oxo-pentanoic acid, 2-methyl-acrylic acid 2-diethylaminoethyl ester (3), juniper camphor (4), and 2-octadecanone. The structures of 1 and 2 were confirmed by 1D and 2D NMR studies and mass spectrometry.

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