Chemistry and Structure of Diterpene Compounds of the Kaurane Series: VIII. Azomethines Derived from Isosteviol

Al’fonsov, V. A.; Andreeva, O. V.; Bakaleinik, G. A.; Beskrovnyi, D. V.; Gubaidullin, А. Т.; Катаев, В. Е.; Kovylyaeva, G. I.; Konovalov, A. I.; Korochkina, M. G.; Литвинов, И. А.; Militsina, O. I.; Strobykina, I. Yu.

doi:10.1023/b:rugc.0000007651.53262.a5

Cited by 11 publications

(4 citation statements)

References 3 publications

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“…Dihydroisosteviol was synthesized by reduction of isosteviol in methanol according to the method of Al'fonsov et al (2000), with some modifications. Isosteviol 16-oxime was synthesized by treating isosteviol ketone with hydroxylamine hydrochloride in pyridine (Al'fonsov et al, 2003). Spectroscopic (proton nuclear magnetic resonance and mass spectra) data of the synthesized compounds were consistent with reported values (Al'fonsov et al, 2003).…”

Section: Methodsmentioning

confidence: 58%

“…Isosteviol 16-oxime was synthesized by treating isosteviol ketone with hydroxylamine hydrochloride in pyridine (Al'fonsov et al, 2003). Spectroscopic (proton nuclear magnetic resonance and mass spectra) data of the synthesized compounds were consistent with reported values (Al'fonsov et al, 2003). CFTR inh -172 was purchased from Calbiochem (San Diego, CA).…”

Section: Methodsmentioning

confidence: 95%

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A Natural Plant-Derived Dihydroisosteviol Prevents Cholera Toxin-Induced Intestinal Fluid Secretion

Pariwat

Homvisasevongsa²,

Muanprasat³

et al. 2007

J Pharmacol Exp Ther

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Stevioside and its major metabolite, steviol, have been reported to affect ion transport in many types of tissues, such as the kidney, pancreas, and intestine. The effect of stevioside, steviol, and its analogs on intestinal Cl Ϫ secretion was investigated in a human T84 epithelial cell line. Short-circuit current measurements showed that steviol and analogs isosteviol, dihydroisosteviol, and isosteviol 16-oxime inhibited in a dosedependent manner forskolin-induced Cl Ϫ secretion with IC 50 values of 101, 100, 9.6, and 50 M, respectively, whereas the parent compound stevioside had no effect. Apical Cl Ϫ current measurement indicated that dihydroisosteviol targeted the cystic fibrosis transmembrane regulator (CFTR). The inhibitory action of dihydroisosteviol was reversible and was not associated with changes in the intracellular cAMP level. In addition, dihydroisosteviol did not affect calcium-activated chloride secretion and T84 cell viability. In vivo studies using a mouse closed-loop model of cholera toxin-induced intestinal fluid secretion showed that intraluminal injection of 50 M dihydroisosteviol reduced intestinal fluid secretion by 88.2% without altering fluid absorption. These results indicate that dihydroisosteviol and similar compounds could be a new class of CFTR inhibitors that may be useful for further development as antidiarrheal agents.

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Section: Methodsmentioning

confidence: 58%

Section: Methodsmentioning

confidence: 95%

A Natural Plant-Derived Dihydroisosteviol Prevents Cholera Toxin-Induced Intestinal Fluid Secretion

Pariwat

Homvisasevongsa²,

Muanprasat³

et al. 2007

J Pharmacol Exp Ther

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“…The known compounds steviol (13-hydroxy-ent-kaur-16-en-19-oic acid, 3) (Ruddat et al, 1965;Ogawa et al, 1980), steviol epoxide (13-hydroxy, ent-kaur-16,17-epoxi-19-oic acid, 5) (Avent et al, 1990b), 17-hydroxyisosteviol (17-hydroxy-16-ketobayeran-19-oic acid, 6), isosteviol (16-ketobayeran-19-oic acid, 9), (Avent et al, 1990a) and isosteviol oxime (16-hydroxyiminobayeran-19-oic acid, 10) (Al'fonsov et al, 2003) were prepared according to the literature methods. ent-7a,13-Dihydroxy-kaur-16-en-19-oic acid (4) was prepared by the biotransformation of steviol (3) with Penicillium citrinum or G. fujikuroi .…”

Section: Test Compoundsmentioning

confidence: 99%

Plant growth regulation activity of steviol and derivatives

et al. 2008

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“…This stevioside is a commercially available natural sweetener which is isolated from stevia rebaudiana by alcoholic extraction [29–30]. In addition to their cytotoxic activities [31–34], compounds based on (−)-isosteviol have found application in various fields of synthetic chemistry [35], including the construction of tweezer-like supramolecular transporters for amino acids [36], chiral organocatalysts in aldol reactions [37], or the complex formation with aromatic compounds [38–39], Within in a nine-step synthesis triphenylene ketals based on (−)-isosteviol were prepared [40]. Receptor structures 2 equipped with amino or sulfonylamido functionalities were obtained (Fig.…”

Section: Introductionmentioning

confidence: 99%

Novel supramolecular affinity materials based on (−)-isosteviol as molecular templates

Lohoelter¹,

Brutschy²,

Lubczyk³

et al. 2013

Beilstein J. Org. Chem.

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SummaryThe readily available ex-chiral-pool building block (−)-isosteviol was combined with the C 3-symmetric platforms hexahydroxytriphenylene and hexaaminotriptycene providing large and rigid molecular architectures. Because of the persistent cavities these scaffolds are very potent supramolecular affinity materials for head space analysis by quartz crystal microbalances. The scaffolds serve in particular as templates for tracing air-borne arenes at low concentration. The affinities of the synthesized materials towards different air-borne arenes were determined by 200 MHz quartz crystal microbalances.

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Chemistry and Structure of Diterpene Compounds of the Kaurane Series: VIII. Azomethines Derived from Isosteviol

Cited by 11 publications

References 3 publications

A Natural Plant-Derived Dihydroisosteviol Prevents Cholera Toxin-Induced Intestinal Fluid Secretion

A Natural Plant-Derived Dihydroisosteviol Prevents Cholera Toxin-Induced Intestinal Fluid Secretion

Plant growth regulation activity of steviol and derivatives

Novel supramolecular affinity materials based on (−)-isosteviol as molecular templates

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