X-ray Diffraction, Electronic Circular Dichroism, and Quantum Mechanics (TD-DFT) Investigations on 4-Dehydroxyaltersolanol A, a Secondary Metabolite from Endophytic Fungus Nigrospora oryzae
Background and objectives: A tetrahydro anthraquinone derivative, 4-dehydroxyaltersolanol A, has been obtained from Nigrospora oryzae, which was isolated from Uncaria borneensis Havil as an endophytic fungus. This is a recently described compound whose stereochemistry was assumed from biogenetic con...
Published in: | RESEARCH JOURNAL OF PHARMACOGNOSY |
---|---|
Main Authors: | , , , , , , , , , |
Format: | Article |
Language: | English |
Published: |
IRANIAN SOC PHARMACOGNOSY
2024
|
Subjects: | |
Online Access: | https://www-webofscience-com.uitm.idm.oclc.org/wos/woscc/full-record/WOS:001133708000010 |
author |
Hussain Fatimah Bebe Mohamed; Sultan Sadia; Bayach Imene; Naz Humera; Singh Gurmeet Kaur Surindar; Shah Syed Adnan Ali; Ashraf Kamran; Salim Fatimah; Weber Jean-Frederic Faizal |
---|---|
spellingShingle |
Hussain Fatimah Bebe Mohamed; Sultan Sadia; Bayach Imene; Naz Humera; Singh Gurmeet Kaur Surindar; Shah Syed Adnan Ali; Ashraf Kamran; Salim Fatimah; Weber Jean-Frederic Faizal X-ray Diffraction, Electronic Circular Dichroism, and Quantum Mechanics (TD-DFT) Investigations on 4-Dehydroxyaltersolanol A, a Secondary Metabolite from Endophytic Fungus Nigrospora oryzae Pharmacology & Pharmacy |
author_facet |
Hussain Fatimah Bebe Mohamed; Sultan Sadia; Bayach Imene; Naz Humera; Singh Gurmeet Kaur Surindar; Shah Syed Adnan Ali; Ashraf Kamran; Salim Fatimah; Weber Jean-Frederic Faizal |
author_sort |
Hussain |
spelling |
Hussain, Fatimah Bebe Mohamed; Sultan, Sadia; Bayach, Imene; Naz, Humera; Singh, Gurmeet Kaur Surindar; Shah, Syed Adnan Ali; Ashraf, Kamran; Salim, Fatimah; Weber, Jean-Frederic Faizal X-ray Diffraction, Electronic Circular Dichroism, and Quantum Mechanics (TD-DFT) Investigations on 4-Dehydroxyaltersolanol A, a Secondary Metabolite from Endophytic Fungus Nigrospora oryzae RESEARCH JOURNAL OF PHARMACOGNOSY English Article Background and objectives: A tetrahydro anthraquinone derivative, 4-dehydroxyaltersolanol A, has been obtained from Nigrospora oryzae, which was isolated from Uncaria borneensis Havil as an endophytic fungus. This is a recently described compound whose stereochemistry was assumed from biogenetic considerations. However, using ECD spectral analysis in combination with TD-DFT calculations, its stereochemistry could be determined unambiguously. Method: In the current research, the selected TH1P45 culture was analysed using semi-preparative HPLC, which led to the isolation of six secondary metabolites, including 4-dehydroxyaltersolanol A (1). We have further presented full evidence of the stereochemistry of compound 1. With the help of quantum calculations, we also determined the mechanism by which this compound degrades in solution. Results: The analysis of TH1P45 culture led to the isolation of six secondary metabolites, including 4-dehydroxyaltersolanol A, three anthraquinone derivatives (macrosporin, bostrycin and altersolanol B), and two pyrones (pestalopyrone and hydroxypestalopyrone). Conclusion: A full evidence of the stereochemistry of compound 1 with the help of the combination of X-ray crystallography, ECD, and TD-DFT quantum calculations, allowed unambiguously assigning the absolute stereochemistry of 4 dehydroxyaltersolanol A as 1S,2R,3S as correctly assumed by Proksh and collaborators from biogenetic considerations. IRANIAN SOC PHARMACOGNOSY 2345-4458 2345-5977 2024 11 1 10.22127/RJP.2023.402252.2136 Pharmacology & Pharmacy WOS:001133708000010 https://www-webofscience-com.uitm.idm.oclc.org/wos/woscc/full-record/WOS:001133708000010 |
title |
X-ray Diffraction, Electronic Circular Dichroism, and Quantum Mechanics (TD-DFT) Investigations on 4-Dehydroxyaltersolanol A, a Secondary Metabolite from Endophytic Fungus Nigrospora oryzae |
title_short |
X-ray Diffraction, Electronic Circular Dichroism, and Quantum Mechanics (TD-DFT) Investigations on 4-Dehydroxyaltersolanol A, a Secondary Metabolite from Endophytic Fungus Nigrospora oryzae |
title_full |
X-ray Diffraction, Electronic Circular Dichroism, and Quantum Mechanics (TD-DFT) Investigations on 4-Dehydroxyaltersolanol A, a Secondary Metabolite from Endophytic Fungus Nigrospora oryzae |
title_fullStr |
X-ray Diffraction, Electronic Circular Dichroism, and Quantum Mechanics (TD-DFT) Investigations on 4-Dehydroxyaltersolanol A, a Secondary Metabolite from Endophytic Fungus Nigrospora oryzae |
title_full_unstemmed |
X-ray Diffraction, Electronic Circular Dichroism, and Quantum Mechanics (TD-DFT) Investigations on 4-Dehydroxyaltersolanol A, a Secondary Metabolite from Endophytic Fungus Nigrospora oryzae |
title_sort |
X-ray Diffraction, Electronic Circular Dichroism, and Quantum Mechanics (TD-DFT) Investigations on 4-Dehydroxyaltersolanol A, a Secondary Metabolite from Endophytic Fungus Nigrospora oryzae |
container_title |
RESEARCH JOURNAL OF PHARMACOGNOSY |
language |
English |
format |
Article |
description |
Background and objectives: A tetrahydro anthraquinone derivative, 4-dehydroxyaltersolanol A, has been obtained from Nigrospora oryzae, which was isolated from Uncaria borneensis Havil as an endophytic fungus. This is a recently described compound whose stereochemistry was assumed from biogenetic considerations. However, using ECD spectral analysis in combination with TD-DFT calculations, its stereochemistry could be determined unambiguously. Method: In the current research, the selected TH1P45 culture was analysed using semi-preparative HPLC, which led to the isolation of six secondary metabolites, including 4-dehydroxyaltersolanol A (1). We have further presented full evidence of the stereochemistry of compound 1. With the help of quantum calculations, we also determined the mechanism by which this compound degrades in solution. Results: The analysis of TH1P45 culture led to the isolation of six secondary metabolites, including 4-dehydroxyaltersolanol A, three anthraquinone derivatives (macrosporin, bostrycin and altersolanol B), and two pyrones (pestalopyrone and hydroxypestalopyrone). Conclusion: A full evidence of the stereochemistry of compound 1 with the help of the combination of X-ray crystallography, ECD, and TD-DFT quantum calculations, allowed unambiguously assigning the absolute stereochemistry of 4 dehydroxyaltersolanol A as 1S,2R,3S as correctly assumed by Proksh and collaborators from biogenetic considerations. |
publisher |
IRANIAN SOC PHARMACOGNOSY |
issn |
2345-4458 2345-5977 |
publishDate |
2024 |
container_volume |
11 |
container_issue |
1 |
doi_str_mv |
10.22127/RJP.2023.402252.2136 |
topic |
Pharmacology & Pharmacy |
topic_facet |
Pharmacology & Pharmacy |
accesstype |
|
id |
WOS:001133708000010 |
url |
https://www-webofscience-com.uitm.idm.oclc.org/wos/woscc/full-record/WOS:001133708000010 |
record_format |
wos |
collection |
Web of Science (WoS) |
_version_ |
1809678577565696000 |