The first example of a tweezer-like structure in diterpene derivatives of the kaurane series

Al’fonsov, V. A.; Bakaleynik, Galina A.; Губайдуллин, А. Т.; Катаев, В. Е.; Kovyljaeva, Galina I.; Коновалов, А. И.; Литвинов, И. А.; Strobykina, I. Yu.; Andreeva, O. V.; Korochkina, M. G.

doi:10.1070/mc2000v010n05abeh001314

Cited by 7 publications

(3 citation statements)

References 8 publications

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“…Compadre et al [3] reported that the mass spectra analysis of this diterpenoid and its analogs revealed differences in stereochemistry, and Hussain et al [4] used chemical ionization mass spectra to examine steviol and its aglycone. There were many reports to mention the toxicities [5], metabolism [6], bioactivities [7], microbial transformations [8], anti-HIV effects [9], genotoxicity [10], anti-inflammatory effects [11], and synthesis [12][13][14] of steviol, stevioside, isosteviol, and their derivatives dimers [15]. In this paper, we report our works on steviol derivatives, steviolbioside, and their synthetic compounds which were examined by a number of mass spectrometric techniques including electron impact (EI), fast atom bombardment (FAB), and electrospray with tandem mass spectrometry LC/MS/MS ESI.…”

Section: Fragmentation Pattern Of Steviolbioside Amide Derivativesmentioning

confidence: 99%

Mass Spectra Analyses of Amides and Amide Dimers of Steviol, Isosteviol, and Steviolbioside

Lee

Lin

et al. 2012

International Journal of Spectroscopy

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The mass spectra of a series of stevioside analogues including the amide and dimer compounds of steviol, isosteviol, and steviolbioside were examined. Positive ion mass spectral fragmentation of new steviol, isosteviol, and steviolbioside amides and the amide dimers are reported and discussed. The techniques included their synthesis procedures, fast-atom bombardment (FAB), and LC/MS/MS mass spectra. Intense [M+H]+ and [M+Na]+ ion peaks were observed on the FAB and ESI spectra. LC/MS/MS also yielded ES+ and ES− ion peaks that fairly agreed with the results of the FAB and ESI studies. Mass spectral analysis of compounds 4p-q, 5a-g, 6, and 7 revealed the different cleavage pathway patterns that can help in identifying the structures of steviolbioside and its amide derivatives.

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Section: Fragmentation Pattern Of Steviolbioside Amide Derivativesmentioning

confidence: 99%

Mass Spectra Analyses of Amides and Amide Dimers of Steviol, Isosteviol, and Steviolbioside

Lee

Lin

et al. 2012

International Journal of Spectroscopy

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“…Among isosteviol derivatives, tweezers-like structures, where two isosteviol fragments are connected with a short bridge, were obtained [3]. In this work we studied isosteviol sulphite whose synthesis procedure was described previously [4].…”

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Molecular and crystal structure of isosteviol sulphite

2015

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The molecular and crystal structure of isosteviol sulphite (1) is studied by means of the X-ray crystallographic analysis. It is demonstrated that this compound has a "dimer" structure, i.e. two isosteviol molecules are bound with a sulphite bridge. The molecule takes a tweezers-like conformation stabilized by intramolecular hydrogen bonds of acid groups. The molecules in the crystal are bound by intermolecular С-Н…О hydrogen bonds.Diterpenoid isosteviol (16-oxo-ent-beyeran-19-oic acid) with the structure proved by the X-ray crystallographic analysis [1] is synthesized by the acid hydrolysis of glycosides isolated from the Stevia rebaudiana Bertoni plant. In order to produce its derivatives with practically useful properties, isosteviol derivatives were synthesized, these derivatives belonging to more than ten various classes, including alcohols, amides, amines, ethers, azomethines, hydrazones, halogen derivatives, macrocycles, and so on [2].Among isosteviol derivatives, tweezers-like structures, where two isosteviol fragments are connected with a short bridge, were obtained [3]. In this work we studied isosteviol sulphite whose synthesis procedure was described previously [4]. 1 Experimental. The crystals of the quality suitable for the X-ray crystallographic analysis were obtained by recrystallization from a 5:1 mixture of petroleum ether:ethyl acetate; the crystals are colorless, T melt 301-303 °C. The crystallographic data of compound 1 are as follows: (C 40 H 62 O 7 S, M = 686.97) monoclinic, at 150 K a = 12.617(1) Å, b = 11.100(1) Å, c = 13.330(1) Å, β = 101.713(1)°, V = 1828.1(3) Å 3 , Z = 2, space group P2 1 , d calc = 1.248 g/cm 3 ,

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“…Среди производных изостевиола получены пинцетоподобные структуры, в которых два изостевиольных фрагмента соединены коротким мостиком [ 3 ]. В настоящей работе был исследован сульфит изостевиола, методика синтеза которого описана ранее [ 4 ].…”

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Molecular and Crystal Structure of Isosteviol Sulphite

2015

JSC

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The first example of a tweezer-like structure in diterpene derivatives of the kaurane series

Cited by 7 publications

References 8 publications

Mass Spectra Analyses of Amides and Amide Dimers of Steviol, Isosteviol, and Steviolbioside

Mass Spectra Analyses of Amides and Amide Dimers of Steviol, Isosteviol, and Steviolbioside

Molecular and crystal structure of isosteviol sulphite

Molecular and Crystal Structure of Isosteviol Sulphite

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