Cardiac glycosides of Cheiranthus allioni. V

Chemistry of Natural Compounds - Two additional cardiac glycosides, glucoerysimoside and glucoerysimosol, have been isolated from the seeds ofCheiranthus allioni Hort. Glucoerysimoside is...     

Cardiac glycosides of Cheiranthus allioni. VI

Summary Another two cardiac glycosides have been isolated from the seeds ofCheiranthus allioni Hort. It has also been established that in cheiroside A the D-glucose is attached at C₄ of the D-fucose. The second glycoside, which we have called glucoalliside, is new, and has the structure of bipindogenin 3-O-[O--D-glucopyranosyl-(1 » 4)--L-glucomethylopyranoside].For Communication V, see [2].Khar'kov Chemical and Pharmaceutical Scientific-Research Institute. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 40–45, January, 1971.     

Cardiac glycosides of Cheiranthus allioni. XI

Summary Another three cardiac glycosides have been isolated from the seeds ofCheiranthus allioni hort. One of them has been identified as digifucocellobioside (digitoxigenin 3 -O-[O--D-glycopyranosyl(1 4)-O--D-glucopyranosyl(1 4)-O--D-fucopyranoside]). The two other glycosides, called digitoxigenin gulomethyloside and glucodigigulomethyloside are, respectively, digitoxigenin 3 -O--D-gulomethyloside and digitoxigenin 3 -O-(4-O--D-glucosyl--D-gulomethyloside).For Communication X, see [1].Khar'kov Scientific-Research Institute of Pharmaceutical Chemistry. All-Union Scientific-Research Institute of Medicinal Plants. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 754–758, November–December, 1975.     

Cardiac glycosides of Cheiranthus allioni. X

Summary Another two cardiac glycosides have been isolated from the seeds ofCheiranthus allioni hort. One of them has been identified as bipinogulomethyloside. The second, which we have called glucobipindogulomethyloside is new and is bipindogenin 3-O-[O--D-glucopyranosyl-(14)--D-gulomethylopyranoside].The glycoside M-64 isolated previously from this plant, which is uzarigenen 3-O-[O--D-glucopyranosyl-(14)--D-glucopyranoside] is also new and has been called neouzarin.Khar'kov Scientific-Research Institute of Pharmaceutical Chemistry. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 738–741, November–December, 1974.     

Cardiac glycosides of Cheiranthus allioni. IX

Summary From the seends ofCheiranthus allioni hort. another three cardiac glycosides have been isolated. One of them has been identified as cheirotoxin. It has been established that in cheirotoxin the D-glucose is attached to C₄ of the D-gulomethylose and this glycoside therefore has the structure of strophanthidin 3-O-[4-O--D-glucopyranosyl--D-gulomethylopyranoside]. The two other glycosides, which have been named sarmentogulomethyloside and gulosarmentoglucoside are new and are, respectively, sarmentogenin-3-O--D-gulomethylopyranoside and sarmentogenin 3-O-[4-O--D-glucopyranosyl--D-gulomethylopyranoside].For Communication VIII see [1].Khar'kov Scientific-Research Institute of Pharmaceutical Chemistry. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 607–611, September–October, 1974.     

Cardiac glycosides of Cheiranthus allioni. XIII. Glucoerycordin

From plains erysimum (Cheiranthus allioni) Hort., (Erysimum asperum) a new cardiac glycoside has been isolated which has been called glucoerycordin. Its chemical structure has been established mainly by stepwise hydrolysis and the identification of the hydrolysis products. Glucoerycordin C₄₁H₆₄ O₁₉, mp 131–135°C, [] _D ²⁰ –22.2 ± 3° (c 0.65; methanol) is 3-[O--D-glucopyranosyl-(1 4)-O--D-glycopyranosyl-(1 4)-gulomethylopyranosyloxy]-14,19-dihydroxy-5, 14-card-20(22)-enolide.All-Union Scientific-Research Institute of Drug Chemistry and Technology, Khar'kov. Khar'kov State Pharmaceutical Institute. Translated from Khimiya Prirodnykh, No. 1, pp. 73–75, January–February, 1989.     

Cardiac glycosides of theCheiranthus allioni. XII

The seeds ofCheiranthus allioni hort. have yielded three new cardenolides the structures of which have been established and which have been named as 4-dehydrosarmentogenin (II), 4-dehydrosarmentogenin rhamnoside (I), and 4-dehydrosarmentogenin rhamnoglucoside (IV). (II) — C₂₃H₃₂O₅. m.p. 296–302°, [] _D ²⁰ +26.2±3° (in pyridine) is 3,11,14-trihydroxy-14-card-4,20(22)-dienolide. (I) C₂₉-H₄₂O₉, m.p. 268–275°, [] _D ²⁰ –38.2±3° (chloroform-ethanol) is 11,14-dihydroxy-3--L-rhamnopyranosyloxy-14-card-4,20(22)-dienolide.(IV) C₃₅H₅₂O₁₄, [] _D ^20D –44.1±3° (methanol), is 3-(4-O--D-glucopyranosyl--L-rhamnopyranosyloxy)-14-card-4, 20(22)-dienolide. An independent synthesis of 4-dehydrosarmentogenin (II) has been carried out, starting from 3,5,11,14-tetrahydroxy-5,14-card-20(22)-enolide, which has confirmed its structure.For Communication XI, see [1].All-Union Scientific-Research Drug Institute, Kharkov. Kharkov State Pharmaceutical Institute. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 119–125, January–February, 1987.     

Cardenolide glycosides ofCheiranthus allioni. XV. Glucocheiranthoside

Another new cardenolide glycoside has been isolated from the plantCheiranthus allioni Hort., and has been named glucocheiranthoside. Its chemical structure has been established as 3β-(4′-O-β-D-glucopyranosyl-β-D-gulmoethylpyranosyloxy)-14-hydroxy-19-oxo-5β,14β-card-20(22)-enolide. State Scientific Center for Drugs, Ukraine, 310085, Kharkov, USSR. ul. Astronomicheskaya, 33. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 269–271, March–April, 1994.     

Cardenolide glycosides ofCheiranthus allioni. XVI. Neoevonoside and cellobiosyl-digigulomethyloside

Another three isomeric glycosides have been isolated from the seeds ofCheiranthus allioni Hort., two of which are new: after their chemical structures were determined they were named neoevonoside and cellobiosyl-digigulomethyloside.State Scientific Center for Drugs of the Academy of Sciences and the Ministry of Health of the Ukraine, 310085, Kharkov, ul. Astronomicheskaya, 33. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 66–69, January–February, 1996. Original article submitted May 22, 1995.     

Cardiac glycosides of Erysimum contractum. II

The structure of a new cardiac glycoside isolated from the seeds ofErysimum contractum has been established. The glycoside, which has been called nigrescigenin digilanidobioside is 3β,5,11α,14-tetrahydroxy-19-oxo-5β,14β-card-20(22)-enolide 3-O-(4-O-β-D-glucopyranosyl-β-D-digitoxopyranoside).     

Cardiac glycosides of Erysimum contractum. II

The structure of a new cardiac glycoside isolated from the seeds ofErysimum contractum has been established. The glycoside, which has been called nigrescigenin digilanidobioside is 3,5,11,14-tetrahydroxy-19-oxo-5,14-card-20(22)-enolide 3-O-(4-O--D-glucopyranosyl--D-digitoxopyranoside).All-Union Scientific-Research Institute of Drug Chemistry and Technology, Kharkov. G. S. Skovorod Kharkov State Pedagogic Institute. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 693–695, September–October, 1991.