13C NMR spectroscopy of eudesmane sesquiterpenes

Oliveira, Francimeire C.; Ferreira, Marcelo J. P.; Núñez, Cecília Veronica; Rodriguez, G. V.; Emerenciano, Vicente de Paulo

doi:10.1016/s0079-6565(00)00021-2

Cited by 20 publications

(8 citation statements)

References 174 publications

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“…The 1 H and 13 C-NMR spectral values of the eudesmane moiety were compared with the reported spectral data of these compounds. [ 12 13 14 ] On the basis of the foregoing discussion the structure of IR-3 has been formulated as 15-[(13z, 18’z, 20’z)-n-tricos-13, 18, 20-trienyl]-eudesmal-4 (11), 6, 12 (13)-trien-8, 14-olide-15-oate. This is a new sesquiterpenic ester.…”

Section: Discussionmentioning

confidence: 99%

Aliphatic and eudesmalolide esters extracted from the roots of Inula racemosa Hook

et al. 2014

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Background:Phytochemical investigation of hydroalcoholic extract of the root of Inula racemosa Hook.Materials and Methods:Open silica gel column chromatographic techniques with different solvent systems was used for isolation of aliphatic and eudesmalolide esters from hydroalcoholic extract of the root of Inula racemosa. The structure elucidation of the compounds was done on the basis of spectral data analysis, chemical reactions and comparision with literature data.Results:Phytochemical investigation of the hydroalcoholic extract of the root of Inula racemosa Hook. f. led to the isolation of (5z, 13z)-n-decanyl-n-docos-5, 13-dienoate, a new fatty acid ester, two new sesquiterpenic ester identified as 15-[(13z, 18′z, 20′z)-n-tricos-13, 18, 20-trienyl]-eudesmal-4 (11), 6, 12 (13)-trien-8,14-olide-15-oate and 15- [(16′z), (21′z)-n- tetracos-16′, 21′- dienyl]-eudesmal-4 (11) 6, 12 (13)-trien-8, 14-olide-15-oate, two new eudesmanolide ester i.e. 15-[(16z)-n-monadec-16′- enyl]-eudesmal-4 (11) 6, 12 (13)-trien-8,14-olide-15-oate and 15-[(16′z)-n-tetracos-16′- enyl]-endesmal-4 (11), 6, 12 (13)-trien-8,14-olide-15-oate along with the known compound n-Hexadecanyl n-docosanoate.Conclusion:Five new phytoconstituents were identified along with one known compound as aliphatic and eudesmalolide esters from the hydroalcoholic extract of the root of Inula racemosa, as mentioned above.

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Section: Discussionmentioning

confidence: 99%

Aliphatic and eudesmalolide esters extracted from the roots of Inula racemosa Hook

et al. 2014

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“…However, when the DENDRAL researchers tried to use the structure generator to identify chemical structures of natural products, whose structural diversity and complexity are higher, numerous problems were detected. [19] The SISTEMAT system has been developed with the construction of specific databases of each natural product class, such as monoterpenes, [20] sesquiterpenes, [14] diterpenes, [15] triterpenes [21] and flavonoids. The solution to this problem was the use of information restrictions in the structural determination process, so that this process was not random.…”

Section: Introductionmentioning

confidence: 99%

Application of a New Program, H1MACH, for Prediction of Iridoid Skeletons

Ferreira

Costantin

Rodrigues

et al. 2004

Spectroscopy Letters

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A procedure is presented that utilizes 1 H NMR for prediction of the skeleton of iridoids. A new program was developed, named H1MACH, that presents a database with 800 data points from the 1 H NMR spectra of iridoids. This program was widely tested for the prediction of the skeleton of 40 compounds and compared with other programs in the expert system SISTEMAT. The results obtained show that H1MACH is very useful for the prediction of the skeleton of iridoids, especially for the iridane skeleton.

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“…SISTEMAT [5,6] is an expert system developed as an auxiliary tool to help predict the chemical class, carbon skeleton type and substructures of an unknown compound using spectroscopic and botanical source data. The development and expansion of the system were carried out for each class of natural products including monoterpenes and iridoids [7][8][9][10] lactonic and non-lactonic sesquiterpenes [11], diterpenes [12], triterpenes [13], flavonoids [14] and lignans [15,16] using mainly 13 C NMR spectra and botanical source data. The aim of this paper is to show the performance of the SISTEMAT system in the skeleton prediction and structural elucidation of neolignans.…”

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confidence: 99%

“…The neolignans display 29 diverse skeletons in 1000 occurrences in 30 plant families. The MACRONO, SISCONST, C13MACH, H1MACH and SISOCBOT programs, used for the neolignan skeleton prediction, were described elsewhere [7][8][9][10][11] in detail, although their main characteristics are briefly described below.…”

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Computer-aided Structure Elucidation of Neolignans

Costantin

Ferreira

Rodrigues

et al. 2010

Natural Product Communications

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This paper describes a new module of the expert system SISTEMAT used for the prediction of the skeletons of neolignans by 13 C NMR, 1 H NMR and botanical data obtained from the literature. SISTEMAT is composed of MACRONO, SISCONST, C13MACH, H1MACH and SISOCBOT programs, each analyzing data of the neolignan in question to predict the carbon skeleton of the compound. From these results, the global probability is computed and the most probable skeleton predicted. SISTEMAT predicted the skeletons of 75% of the 20 neolignans tested, in a rapid and simple procedure demonstrating its advantage for the structural elucidation of new compounds.

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13C NMR spectroscopy of eudesmane sesquiterpenes

Cited by 20 publications

References 174 publications

Aliphatic and eudesmalolide esters extracted from the roots of Inula racemosa Hook

Aliphatic and eudesmalolide esters extracted from the roots of Inula racemosa Hook

Application of a New Program, H1MACH, for Prediction of Iridoid Skeletons

Computer-aided Structure Elucidation of Neolignans

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