Triterpene glycosides and their genins fromThalictrum foetidum. V. Structure of cyclofoetoside B

Ганенко, Т. В.; Исаев, М. И.; Gromova, A. S.; Абдуллаев, Н. Д.; Semenov, A. A.; Gorovits, M. B.; Abubakirov, N. K.

doi:10.1007/bf00598304

Cited by 7 publications

(16 citation statements)

References 2 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Whereas acid hydrolysis of cyclofoetoside A (21) gave in low yield native genin 9 [29,30], cyclofoetoside B (22) was not hydrolyzed by enzymes (gastric juice of the grape snail) or under usual acid-hydrolysis conditions [31,32]. Stronger acid-hydrolysis conditions produced an artifact (10a).…”

Section: Cycloartane Compoundsmentioning

confidence: 89%

“…Enzymatic hydrolysis (gastric juice of Helix pomatia) of the total saponins produced two cycloartane genins, squarrogenins 1 (31) and 2 (32), which are the OCH 3 -21R-and 21S-isomers, respectively [42]. The relative configuration of the THF substituents was determined using the NOE.…”

Section: Cycloartane Compoundsmentioning

confidence: 99%

“…Glycosylation of the carboxyl (12 and its glycoside 28) causes a strong-field shift of the carbonyl C atom by 6.4 ppm. [20] 15 [23] 16 [24] 17 [25] 18 [26] 19 [26] 20 [ (21)(22)(23)(24)(25)(26)(27) C atom 21 [29] 22 [32] 23 [33] b 24 [35] 25 [36] 26 [36] 27 [39] Assignment of signals is equally probable within columns. f Signal overlaps with solvent.…”

Section: Structural Studies Of Cycloartane Triterpenoids Using 13 C Nmentioning

confidence: 99%

See 2 more Smart Citations

Structural Studies and Biological Activity of Plant Triterpenoids from the Thalictrum Genus

et al. 2005

Self Cite

View full text Add to dashboard Cite

Structures and chemical and spectral properties of triterpenoids isolated from plants of the Thalictrum genus were systematized for the first time. Features of 13 C NMR spectra of cycloartane triterpenoids were discussed. Data for the biological activities of certain cycloartane and oleanane triterpenoids were given.Triterpenoids are natural isoprenoids, the skeleton of which is constructed of 30 C atoms. They are widely distributed in both terrestrial plants and marine flora and fauna. They occur in the free state and as esters and glycosides called saponins. Triterpenoids are usually classified by the number of rings in the C skeleton. Tetra-and pentacyclic compounds are most widely distributed in nature. This review covers representatives of them.Plants of the Thalictrum (Ranunculaceae) genus produce a large quantity of triterpenoids and other secondary metabolites. The former are interesting because of their chemical structures and practical uses. It should be noted that investigations of secondary metabolites from these plants focused rather successfully and until recently on the alkaloids [1-5]. The first publications devoted to the study of triterpene saponins from plants of the Thalictrum genus appeared at the start of the 1981s [6].There is a reason for the interest in representatives of the broad Thalictrum genus. Plants of this genus have been used since long ago by peoples of many nations for medicinal purposes to treat gastrointestinal and gynecological illnesses, various neoplasms, and tuberculosis [7-10]. This, in turn, stimulated studies of the chemical composition of the plants, the isolation of biologically active compounds, and investigations of their pharmacologic activity.We have for the first time systematized and generalized information on triterpenoids from plants of the Thalictrum genus (from 1981 to 2003), features of their spectral and chemical properties, and their biological activity. Individual representatives of these compounds were included in reviews on triterpenoids [11,12] and cycloartanes [13,14]. However, the complete picture will be given for the first time. TRITERPENOID GENINS AND THEIR GLYCOSIDESTriterpenoid saponins from plants of the Thalictrum genus were first isolated and characterized in 1981-1983 from T. minus and T. foetidum collected in eastern Siberia [6,15,16]. Compounds of this type were not observed in the same species from Middle Asia and Europe. Based on this, which indicates that the chemical composition of a species is dependent on the ecological and geographical habitat, it was proposed [17,18] to separate the species growing in eastern Siberia into a Siberian chemorace. Then, the triterpenoid compounds were isolated only from species growing in the east (Japan, China, Korea). Now it is probably possible to generalize and view the Siberian chemorace as the "eastern Asian" one.

show abstract

Section: Cycloartane Compoundsmentioning

confidence: 89%

Section: Cycloartane Compoundsmentioning

confidence: 99%

Section: Structural Studies Of Cycloartane Triterpenoids Using 13 C Nmentioning

confidence: 99%

See 1 more Smart Citation

Structural Studies and Biological Activity of Plant Triterpenoids from the Thalictrum Genus

et al. 2005

Self Cite

View full text Add to dashboard Cite

show abstract

“…42 The C-24 configuration of 12 was established as S. The isolation of the aglycone was important for their structural elucidation.…”

Section: Triterpenoid Glycosides and Their Geninsmentioning

confidence: 99%

“…A b-isomer of the trioside has not been found. Thalicosides A1 (39) and A3 (40) 34 are based on a new genin-thalicogenin A1 (43). not modified during the isolation procedure.…”

Section: Triterpenoid Glycosides and Their Geninsmentioning

confidence: 99%

Natural products from medicinal plants: non-alkaloidal natural constituents of the Thalictrum species

et al. 2006

View full text Add to dashboard Cite

Thalictrum is an important plant genus that is widely used in traditional medicine. In this review considerable attention has been given to triterpenoid saponins in connection with their specific distribution in the Thalictrum genus and with their biological activity. All other non-alkaloid compounds isolated from the Thalictrum genus are also reviewed; these metabolites are discussed in relation to their structural features and to their role in the plants.

show abstract

α-Glucosidase inhibitory and anti-inflammatory activities of dammarane triterpenoids from the leaves of Cyclocarya paliurus

Deng

Liu

et al. 2021

Bioorganic Chemistry

View full text Add to dashboard Cite

Triterpene glycosides and their genins fromThalictrum foetidum. V. Structure of cyclofoetoside B

Cited by 7 publications

References 2 publications

Structural Studies and Biological Activity of Plant Triterpenoids from the Thalictrum Genus

Structural Studies and Biological Activity of Plant Triterpenoids from the Thalictrum Genus

Natural products from medicinal plants: non-alkaloidal natural constituents of the Thalictrum species

α-Glucosidase inhibitory and anti-inflammatory activities of dammarane triterpenoids from the leaves of Cyclocarya paliurus

Contact Info

Product

Resources

About