New triterpenoid glycosides fromThalictrum minus L.

Трофимова, Н. Н.; Gromova, A. S.; Lutsky, V. I.; Semenov, A. A.; Avilov, Sergey A.; Li, D.; Owen, Noel L.

doi:10.1007/bf02496188

Cited by 4 publications

(7 citation statements)

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“…Thalicosides H1 (57) [51] and H3 (58) [27] differ from glycosides 55 and 56 by the presence of an additional hydroxyl on C-24. The S-configuration of chiral center C-22 in both genins (53 and 54, respectively) was determined using the literature method [28].…”

Section: Cycloartane Compoundsmentioning

confidence: 99%

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

et al. 2005

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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.

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Section: Cycloartane Compoundsmentioning

confidence: 99%

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

et al. 2005

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“…The 21-O-CH 3 -glycosides (22)(23)(24)(25) proved to be native, i.e. Thalicosides H1 (41) 59 and H3 (42) 37 differ from thalicosides A1 and A3 by an additional hydroxyl group on C-24. The absence of methanol during the isolation procedure provided Table 2 The structures of triterpenoid compounds with a THF ring on C-17 atom Those saponins which have been isolated from T. Herba (Takatogusa) are diastereomeric with reference to C-21, (thalictosides I (33) and II (34) 56 and thalictosides III (35) and IV (36) 57 ), but unlike those isolated from T. squarrosum they have an a-configured 22-hydroxyl group.…”

Section: Triterpenoid Glycosides and Their Geninsmentioning

confidence: 99%

“…From the roots of T. dioicum, used medicinally in Mexico as a diuretic, m-meconina (5,6-dimetoxiftalid) (98) has been isolated. 112…”

Section: Phenolic Compoundsmentioning

confidence: 99%

“…Thalicosides A1 (39) and A3 (40) 34 are based on a new genin-thalicogenin A1 (43). Thalicosides H1 (41) 59 and H3 (42) 37 differ from thalicosides A1 and A3 by an additional hydroxyl group on C-24. Glycosides 39-42 have the 22S-configuration.…”

Section: Cycloartanes With An Acyclic Side Chain (On Atom C-17)mentioning

confidence: 99%

“…In the Thalictrum genus these constituents have only been discovered in two species: T. aquilegifolium 110 and T. simplex. 98 The identification and relative quantities of the hydrocarbons were determined by gas liquid chromatography-mass spectroscopy (GC-MS), (the alcohols were preliminary acetylated). In the dried whole plant (including the roots) of T. aquilegifolium 13 n-alkanes and 9 alcohols were found.…”

Section: Hydrocarbons and High Molecular Weight Alcoholsmentioning

confidence: 99%

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

et al. 2006

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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.

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ChemInform Abstract: New Triterpenoid Glycosides from Thalictrum minus L. Part 11. Structure of Thalicoside H₁.

et al. 1999

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New triterpenoid glycosides fromThalictrum minus L.

Cited by 4 publications

References 3 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

ChemInform Abstract: New Triterpenoid Glycosides from Thalictrum minus L. Part 11. Structure of Thalicoside H₁.

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New triterpenoid glycosides fromThalictrum minus L.

Cited by 4 publications

References 3 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

ChemInform Abstract: New Triterpenoid Glycosides from Thalictrum minus L. Part 11. Structure of Thalicoside H1.

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ChemInform Abstract: New Triterpenoid Glycosides from Thalictrum minus L. Part 11. Structure of Thalicoside H₁.