Thalicosides A1−A3, Minor Cycloartane Bisdesmosides from <i>Thalictrum minus</i>

Gromova, A. S.; Lutsky, V. I.; Li, Du; Wood, Steve; Owen, Noel L.; Semenov, A. A.; Grant, David M.

doi:10.1021/np000017v

Cited by 13 publications

(16 citation statements)

References 6 publications

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“…Later new trioside and tetraoside saponins, thalictosides A (25) and C (26) with the same genin thalictogenin a (11), were observed in the aerial part of T. thunbergii [36]. The PMR and 13 C NMR spectra indicate that thalictogenin a has the same structure as the genin thalifoenoside A (24). The difference in melting points [202-204°C and 190-192°C (Table 1)] is probably explained by the different crystallization conditions and the different purities of the isolated compounds.…”

Section: Cycloartane Compoundsmentioning

confidence: 97%

“…Later another two saponins containing genin 4 were isolated from T. minus: thalicoside C (15) [23] and thalicoside A2 (16) [24]. The first of these was a trisdesmoside; the second, a bisdesmoside.…”

Section: Cycloartane Compoundsmentioning

confidence: 99%

“…Thalicosides A1 (55) and A3 (56) [24] contain the same new genin thalicogenin A1 (52). The structure and stereochemistry of the asymmetric center in the sidechain (22S) of this group of compounds were determined by spectral methods using the NMR spectrum of artifact 4a [23] and squarrofuric acid (59) [49] and their XSA [21,50].…”

Section: Cycloartane Compoundsmentioning

confidence: 99%

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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: 97%

Section: Cycloartane Compoundsmentioning

confidence: 99%

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

et al. 2005

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“…HMBC correlations of Me(26) with C(7), C(8), C(9), and C (14), and of Me(27) with C(8), C(13), C (14), and C(15) required the connection of fragments a and b through two quaternary C-atoms (C(8) and C (14)). HMBC Cross-peaks CH 2 The data of the sugar moiety were consistent with the presence of a b-d-glucopyranose unit in 1 [5]; according to the HMBC cross peaks HÀC(3)/C(1') and HÀC(1')/C(3), it was located at C(3).…”

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confidence: 53%

Two New E-Secoursane Glycosides: Bodiniosides A and B, Isolated fromElsholtzia bodinieri

Li²,

Wang³

et al. 2005

HCA

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Two unusual 18,19-secoursane glycosides, bodiniosides A (1) and B (2), and two known triterpenoids, hypadienic acid (3) and 2,3,19-trihydroxyurs-12-en-28-oic acid (4), were isolated from the whole plants of Elsholtzia bodinieri. The structures of 1 and 2 were determined by intensive interpretation of spectral data. This is the first report of E-secoursane glycosides. In addition, the biogenetic relationships among these four triterpenoids are discussed.

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“…Thus, in the HMBC spectrum of 4 ( Cycloartane glycosides had been found to widely distribute in the plants of the genus Cimicifuga. 2,3) Based on the literature information [7][8][9][10] and the results of this paper, these cycloartane glycosides have also been isolated from plants of the genus Thalictrum of the same family (Ranunculaceae). This could imply a close relationship between the two genera.…”

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confidence: 93%

Four New Cycloartane Glycosides from Thalictrum fortunei

Zhang

et al. 2006

CHEMICAL & PHARMACEUTICAL BULLETIN

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Thalictrum fortunei S. MOORE is a perennial plant distributed in the southeastern part of China. The aerial part of this plant is used as an anticancer, antibacterial and anti-inflammatory agent in traditional Chinese medicines.1) We previously reported on new cycloartane glycosides from several Cimicifuga species.2,3) As part of the continuing investigation on the triterpene glycosides of Ranunculaceous plants, [4][5][6] this paper deals with the isolation and structural elucidation of four new cycloartane glycosides (1-4).The dried aerial parts of T. fortunei were extracted with 95% ethanol. The n-BuOH-soluble fraction was subjected to repeated silica gel column chromatography followed by reversed-phase column chromatography to afford four cycloartane glycosides 1-4.Compound 1 was obtained as a white powder. The molecular formula of 1 was determined to be C 48 C-NMR spectrum of 1 (Table 1) showed the corresponding signals due to cyclopropane methylene at d 29.7, methylene carbon bearing oxygen at d 67.4 (C-26), methine carbons bearing oxygen at d 73.0 (C-22) and d 88.7 (C-3), and three anomeric carbons at d 103.0, 106.9 and 107.0. Further comparison of the 13 C-NMR data of 1 with those of thelictogenin A (5) indicated that the triterpene was glycosylated at C-3 and C-26. The interglycosidic linkages of the sugar chains could be deduced from an HMBC experiment. Thus, in the HMBC spectrum of 1 (Fig. 1) (Table 1), the signals due to the aglycone moiety were in good agreement with those of 1. Furthermore, a comparative assignment of the 13 C-NMR spectrum of 2 with that of 1 also indicated presence of an additional quinovopyranosyl unit in 2. The interglycosidic linkages of the sugar chains could be deduced from an HMBC experiment. Thus, in the HMBC spectrum of 2 (Fig. 1), correlation signals were observed be- Compound 3 was obtained as a white powder. The molecular formula of 3 was determined to be C 53 H 88 O 21 by HR-

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Thalicosides A1−A3, Minor Cycloartane Bisdesmosides from Thalictrum minus

Cited by 13 publications

References 6 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

Two New E-Secoursane Glycosides: Bodiniosides A and B, Isolated fromElsholtzia bodinieri

Four New Cycloartane Glycosides from Thalictrum fortunei

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