Oligomeric proanthocyanidin glycosides ofRhodiola pamiroalaica. II

In a continuation of investigations of proanthocyanidins of the roots ofRhodiola pamiroalaica, we have isolated proanthocyanidins RP-3 and RP-4. Their compositions, structures, and relative configurations have been investigated: RP-3 is 7-O-(6-O-galloyl--D-Glcp)-3-O-galloyl-(-)-epigallocatechin-(4-8)-[(-)-epicatechin-(4-8)-(3-O-galloyl-(-)-epigallocatechin)]₂-(4-8)-[5-O-(-D-GlcpO--D-Glcp)-(+)-catechin], and RP-4 is 7-O-(6-O-galloyl--D-Glcp-3-O-galloyl-(-)-epigallocatechin-(4-8)-[3-O-galloyl-(-)-galloyl-5-(-D-GlcpO--D-Glcp)-(-)-epigallocatechinTranslated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 42–49, January–February, 1999.     

Oligomeric proanthocyanidin glycosides ofClementsia semenovii

Five new proanthocyanidins have been isolated from the roots ofClementsia semenovii A. Bor. The structures of two of these compounds have been established by various chemical and physical methods: 7-0-[6-0-galloyl-β-D-Glcp 0-β-D-Glcp 0-βD-Glcp 0-β-D-Glcp ]-(+)-gallocatechin-(4a-8)-(+)-gallo-catechin-(4a-8)-(-)-epigallocatechin-(4β-8)-(-)-epigallocatechin-(4β-8)-(-) -epigalloactechin-(4β-8)-(+)-catechin - CS-1 and 3-0-galloyl-7-0-(β-D-Glcp 0-B-D-Glcp)-(-)-epigallocatechin-(4β-8)-[3-0-galloyl-(-)-epigallocatechin]-(4β-8)-[3-0-galloyl-5-0-(6-0-galloyl-0-β-D-Glcp)]-(-)-epicatechin - CS-2. 1) Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic of Uzbekistan, Tashkent, fax (371) 120 64 75; 2) Osh State University, Osh, fax (33 222) 2 23 73. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 756–763, November–December, 1998.     

Oligomeric proanthocyanidin glycosides ofClementsia semenovii. II

The structures of proanthocyanidins CS-3 and CS-4, isolated from the roots ofClementsia semenovii have been established on the basis of chemical and spectral studies. CS-3 is 7-O-(6-O-galloyl--D-Glcp O--D-Glcp O--D-Glcp O--D-Glcp O--D-Glcp)-(+)-catechin-(4—8)-(–)-epigallocatechin-(4—8)-(+)-catechin-(4—8)-(–)-epigaLLocatechin-(4—8)-(–)-epigallocatechin-(4—8)-(–)-epigallocatechin, and CS-4 is 3-O-galloyl-7-O-[6-O-galloyl--D-Glcp O--D-Glcp O--D-Glcp-(+)-gallocatechin-(4—8)-[(+)-catechin-(4—8)-(3-O-galloyl-(–)-epigallocatechin]₂-(4—8)-(–)-epicatechin.Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 50–58, January–February, 1999.     

Oligomeric proanthocyanidin glycosides ofClementsia semenovii and their biological activity. III

The structures of two oligomeric proanthocyanidins isolated from roots ofClementsia semenovii have been established using chemical and spectral data. Animal studies showed that these compounds possess hypocholesterinemic, hypolipidemic, and anti-inflammatory activities.S. Yu. Yunusov Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic of Uzbeistan, Tashkent, fax (998-71) 120-64-75. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 47–53, January–February, 2000.     

Flavonoids of the epigeal part ofRhodiola rosea. II. Structures of new glycosides of herbacetin and of gossypetin

The structure of four new flavonol glycosides isolated from the epigeal part ofRhodiola rosea have been established: 7-O-α-L-rhamnopyranosylgossypetin (rhodiolgin), 8-O-β-D-glucopyranosyl-7-O-α-L-rhamnopyranosylgossypetin (rhodiolgidin), 8-O-β-D-glucopyranosol-7-O-α-L-rhamnopyranosylherbacetin (rhodionidin), and 3-O-β-D-glucopyranosyl-8-O-β-D-xylopyranosylherbacetin (rhodalidin). The properties of the previously undescribed incomplete methyl ethers of herbacetin and gossypetin obtained during the structural analysis of the glycosides have been studied. It has been found that diazomethane methylates the 5-OH groups in the diglycosides investigated.     

Terpenoids of the rhizomes ofRhodiola rosea

The structures of two new monoterpene compounds isolated from the rhizomes ofRhodiola rosea L. (Crassulaceae) have been established: 3,7-dimethylocta-2,6-diene-1,4-diol (rosiridol) and 3,7-dimethylocta-2,6-diene-1,4-diol 1-O-β-D-glucopyranoside (rosiridin). Daucosterol has been isolated from the rhizomes of this plant for the first time.     

Oligomeric silazanes

High conversions of oligomeric silazanes that are not volatile at 200°C/0.1 mm are obtained when hexamethylcyclotrisilazane or octamethylcyclotetrasilazane is heated with a molar deficiency of dichlorodimethylsilane at 175°C. The oligomers, which show moderate solvolytic stability, contain disilazane, trisilylamine, and cyclodisilazane units. They are structurally similar to materials that have been prepared by others from hexamethylcyclotrisilazane and ammonium bromide. When the oligomers are treated with ammonia and heated to 325°C, evidence can be found in their spectra for the presence of oligocyclodisilazane structures.     

Glycosides of cinnamyl alcohol from the rhizomes ofRhodiola rosea

Three new cinnamyl alcohol glycosides have been isolated for the first time from the rhizomes of roseroot stonecropRhodiola rosea L. (Sedum rosea). On the basis of chemical transformations and the results of UV, IR, PMR, and mass spectroscopy the following structures are proposed for the compounds isolated: rozin — trans-cinnamyl O-β-D-glucopyranoside; rozavin — transcinnamyl O-(6′-O-α-L-arabinopyranosyl-β-D-glucopyranoside); and rozarin — trans-cinnamyl O-(6′-O-α-L-arabinofuranosyl-β-glucopyranoside).     

New oligomeric proanthocyanidin glycosides platanoside-A and platanoside-B from <Emphasis Type=Italic>Platanus orientalis</Emphasis> trunk bark

Two new oligomeric proanthocyanidin glycosides were isolated from trunk bark of Platanus orientalis. Their structures and relative configurations were found to be 7-O-β-D-Glcp-(–)-epicatechin-(4β-8)-(–)-epicatechin(4β-8)-(–)-epicatechin-3-O-gallate (platanoside-A) and 7-O-β-D-Glc textpxrightarrow6 {text{p}}xrightarrow{6} galloyl-(+)-catechin-3-O-gallate(4α-8)-(–)-epicatechin-3-O-gallate-(4β-8)-(–)-epicatechin-3-O-gallate-(4β-8)-5-O-β-D-Glcp-(–)epicatechin-3-O-gallate (platanoside-B).