Revising the Absolute Configurations of Coatlines via Density Functional Theory Calculations of Electronic Circular Dichroism Spectra

Genta‐Jouve, Grégory; Weinberg, Lionel; Cocandeau, Vincent; Maestro, Yannick; Thomas, Olivier P.; Holderith, Serge

doi:10.1002/chir.22129

Cited by 17 publications

(12 citation statements)

References 27 publications

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“…This method has demonstrated to be very efficient for the determination of the absolute configuration of many natural compounds in the last few years. 24,25 The calculations were performed on the most stable conformer, after geometry optimization and as depicted on figure 3, a good agreement was observed between the experimental and the theoretical spectra. The absolute configuration of 1 was then attributed as follow: 2S, 3S, 7R, 15S, 16S, 17R, 20R, 21S.…”

Section: Kg Of Dried and Crushed Leaves Collected In The Frenchmentioning

confidence: 67%

Cymoside, a monoterpene indole alkaloid with a hexacyclic fused skeleton from Chimarrhis cymosa

Lémus

Kritsanida

Canet

et al. 2015

Tetrahedron Letters

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Section: Kg Of Dried and Crushed Leaves Collected In The Frenchmentioning

confidence: 67%

Cymoside, a monoterpene indole alkaloid with a hexacyclic fused skeleton from Chimarrhis cymosa

Lémus

Kritsanida

Canet

et al. 2015

Tetrahedron Letters

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“…4 ). In order to determine the absolute configuration of the compounds 1 – 3 , ECD spectra prediction was used [ 36 – 37 ]. The absolute configuration of 1 was assigned as 2 R , 6 S , 7 R , 10 R , and 11 S by ECD analysis supported by the theoretical calculation using time-dependent density functional theory.…”

Section: Resultsmentioning

confidence: 99%

Three new trixane glycosides obtained from the leaves of Jungia sellowii Less. using centrifugal partition chromatography

Azevedo

Faqueti

Kritsanida

et al. 2016

Beilstein J. Org. Chem.

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Summary Jungia sellowii (Asteraceae) is a shrub that grows in Southern Brazil and polar extract of its leaves presents anti-inflammatory properties. Cyperane, guaiane, nortrixane, and trixane sesquiterpene types were reported as the main metabolites in Jungia species. This work aims to describe the isolation and identification of sesquiterpenes in the leaves of J. sellowii using liquid–liquid partition and centrifugal partition chromatography. Thus, the crude extract of fresh leaves of J. sellowii was partitioned with hexane, dichloromethane, ethyl acetate and butanol, respectively. The butanol fraction was then subjected to a selected ternary system optimized for the CPC (centrifugal partition chromatography): ethyl acetate–ethanol–water (9:2:10, v/v/v). The separation was carried out isocratically at a flow rate of 25 mL/min at 1200 rpm, affording seven fractions A to G. TLC of fractions B, C and F displayed a single spot corresponding to three new glycosylated sesquiterpenoids. Their structures were established by using spectroscopic data in comparison to those reported in the literature. Furthermore, the isolates were evaluated for their leishmanicidal and cytotoxic effects. No cytotoxic effect was observed against the three cancer cell lines (HL60, JURKAT and REH), but compound 1 showed a weak antiprotozoal activity. Liquid–liquid partition and CPC turned to be a versatile technique of glycoside purification which is environmentally friendly and requires a limited amount of organic solvents.

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“…In the previous study, the acquisition of the ECD spectra was performed on the pure compounds but in the present case, we decided to turn to on-line detection in order to monitor the sign of the Cotton effect (CE) at 280 nm due to the minor amount of compounds present. This method has already been used for several natural products in the past, and proved highly efficient and sensitive [15,16,17]. …”

Section: Resultsmentioning

confidence: 99%

Metabolome Consistency: Additional Parazoanthines from the Mediterranean Zoanthid Parazoanthus Axinellae

Audoin¹,

Cocandeau²,

Thomas

et al. 2014

Metabolites

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Ultra-high pressure liquid chromatography coupled to high resolution mass spectrometry (UHPLC-MS/MS) analysis of the organic extract obtained from the Mediterranean zoanthid Parazoanthus axinellae yielded to the identification of five new parazoanthines F-J. The structures were fully determined by comparison of fragmentation patterns with those of previously isolated parazoathines and MS/MS spectra simulation of in silico predicted compounds according to the metabolome consistency. The absolute configuration of the new compounds has been assigned using on-line electronic circular dichroism (UHPLC-ECD). We thus demonstrated the potential of highly sensitive hyphenated techniques to characterize the structures of a whole family of natural products within the metabolome of a marine species. Minor compounds can be characterized using these techniques thus avoiding long isolation processes that may alter the structure of the natural products. These results are also of interest to identify putative bioactive compounds present at low concentration in a complex mixture.

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Revising the Absolute Configurations of Coatlines via Density Functional Theory Calculations of Electronic Circular Dichroism Spectra

Cited by 17 publications

References 27 publications

Cymoside, a monoterpene indole alkaloid with a hexacyclic fused skeleton from Chimarrhis cymosa

Cymoside, a monoterpene indole alkaloid with a hexacyclic fused skeleton from Chimarrhis cymosa

Three new trixane glycosides obtained from the leaves of Jungia sellowii Less. using centrifugal partition chromatography

Metabolome Consistency: Additional Parazoanthines from the Mediterranean Zoanthid Parazoanthus Axinellae

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