NMR Studies on Natural Product—Stereochemical Determination and Conformational Analysis in Solution and in Membrane

Matsumori, Nobuaki; Murata, Michio

doi:10.1007/978-981-10-5966-7_14

Cited by 3 publications

(2 citation statements)

References 54 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…For geometrically flexible molecules such as multiple stereocenters of acyclic chains or macrocycles, it cannot be concluded with NOEs. To handle such molecules, NMR-based approaches including J -based configuration analysis (JBCA), universal NMR database (UDB), theoretical calculation of NMR parameters and residual dipolar couplings (RDCs) [32] were applied as tools to determine the relative configuration of natural products. Of 732 molecules, relative stereochemistry of at least four molecules 541 , 552 , 702 , and 708 were elucidated with the aid of JBCA method, while the relative configuration of one molecule as in 595 was elucidated by JBCA-QCC tactics.…”

Section: Introductionmentioning

confidence: 99%

Marine Natural Products from Indonesian Waters

et al. 2019

View full text Add to dashboard Cite

Natural products are primal and have been a driver in the evolution of organic chemistry and ultimately in science. The chemical structures obtained from marine organisms are diverse, reflecting biodiversity of genes, species and ecosystems. Biodiversity is an extraordinary feature of life and provides benefits to humanity while promoting the importance of environment conservation. This review covers the literature on marine natural products (MNPs) discovered in Indonesian waters published from January 1970 to December 2017, and includes 732 original MNPs, 4 structures isolated for the first time but known to be synthetic entities, 34 structural revisions, 9 artifacts, and 4 proposed MNPs. Indonesian MNPs were found in 270 papers from 94 species, 106 genera, 64 families, 32 orders, 14 classes, 10 phyla, and 5 kingdoms. The emphasis is placed on the structures of organic molecules (original and revised), relevant biological activities, structure elucidation, chemical ecology aspects, biosynthesis, and bioorganic studies. Through the synthesis of past and future data, huge and partly undescribed biodiversity of marine tropical invertebrates and their importance for crucial societal benefits should greatly be appreciated.

show abstract

Section: Introductionmentioning

confidence: 99%

Marine Natural Products from Indonesian Waters

et al. 2019

View full text Add to dashboard Cite

show abstract

“…An anti configuration between H-9 and -10 was determined by a proton coupling constant ( 3 J H‑9,H‑10 = 9.3 Hz) in the DQCOSY spectrum and large heteronuclear coupling constants ( 2 J H‑9, C‑10 = 2 J H‑10, C‑9 = −4.9 Hz) in the HECADE spectrum. This indicates that H-9 and the oxygen atom on C-10, and also H-10 and the hydroxy group on C-9, have gauche relationships . Subsequently the relative orientation between the spiroketal and dihydroindolizinium moieties is established based on the ROESY correlations of H-7/H-10 and H 3 -20/H 2 -22 (Figure ).…”

Section: Resultsmentioning

confidence: 95%

Voratins A–C: Pyridinium Alkaloids from the Marine Dinoflagellate Effrenium voratum with Inhibitory Effects on Biomarkers for Benign Prostatic Hyperplasia

et al. 2022

View full text Add to dashboard Cite

Three voratin compounds (1−3) were isolated from the symbiotic marine dinoflagellate Ef f renium voratum. The planar structures of 1−3 were determined by 1D and 2D NMR spectroscopy and HRESIMS, and the relative and absolute configurations were established using ROESY correlations, Mosher's method, and quantum calculations. All of the compounds are zwitterionic and contain a dihydroindolizinium ring and a spiroketal moiety. Compounds 1−3 were found to exhibit therapeutic effects against benign prostatic hyperplasia (BPH), as evaluated using testosterone propionate-treated LNCap and RWPE-1 human prostate cells. This excellent activity suggests that 1−3 are promising for the development of BPH treatments.

show abstract

Summary of DFT calculations coupled with current statistical and/or artificial neural network (ANN) methods to assist experimental NMR data in identifying diastereomeric structures

Nazarski

2021

Tetrahedron Letters

View full text Add to dashboard Cite

NMR Studies on Natural Product—Stereochemical Determination and Conformational Analysis in Solution and in Membrane

Cited by 3 publications

References 54 publications

Marine Natural Products from Indonesian Waters

Marine Natural Products from Indonesian Waters

Voratins A–C: Pyridinium Alkaloids from the Marine Dinoflagellate Effrenium voratum with Inhibitory Effects on Biomarkers for Benign Prostatic Hyperplasia

Summary of DFT calculations coupled with current statistical and/or artificial neural network (ANN) methods to assist experimental NMR data in identifying diastereomeric structures

Contact Info

Product

Resources

About