Triterpene saponins fromThalictrum minus. VIII. Structure of thalicoside D

Thalicoside D — a new triterpene glycoside isolated fromThalictrum minus L. (Ranunculaceae) — has the structure of oleanolic acid 3-O-[O-α-L-rhamnopyranosyl-(1→2)-O-β-D-glucopyranosyl-(1→4)-α-L-arabinopyranoside 28-O-[O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranoside]. This structure was established by the use of the results of acid and alkaline hydrolyses, SIMS spectra, and one- and two-dimensional NMR spectroscopy. Deceased.     

Triterpene saponins fromThalictrum minus. VII. Structure of thalicoside E

A new minor cycloartane glycoside — thalicoside E, 9,19-cyclo-20(S)-lanost-23-ene-3β,16β,22ζ,25,29-pentaol 3-O-β-D-galactoside 29-O-β-D-glucopyranoside — has been isolated from the epigeal part ofThalictrum minus L. (Ranunculaceae).     

Triterpene saponins fromThalictrum minus. IV. The structure of thalicoside A

The predominating saponin, which has been called thalicoside A, has been isolated from low meadow rue (Thalictrum minus). It has been established by chemical and spectral methods that thalicoside A is 3,16,22(S),29-tetrahydroxy-9,19-cyclo-20(S)-lanost-24-ene 3-O--D-galactopyranoside 29-O--D-glucopyranoside.Irkutsk Institute of Organic Chemistry, Siberian Branch, Academy of Sciences of the USSR. Pacific Ocean Institute of Bioorganic Chemistry, Far Eastern Scientific Center, Academy of Sciences of the USSR, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 213–219, March–April, 1984.     

Triterpene saponins fromThalictrum minus. II. Structure of an artefact

The acid hydrolysis of the predominating saponins isolated fromThalictrum minu? L. has led to the formation of a triterpenoid (I), which is an artefact of the native genin. The structure of (I) has been established as 22,25-epoxylanost-9(11)-ene-3β,16β,29-triol.     

Triterpene saponins from Thalictrum minus. VI. Structure of thalicoside C

From the epigeal part ofThalictrum minus L. (Ranuncluaceae) we have isolated a minor cycloartane trisdesmoside — thalicoside C — 3,16,22(S),29-tetrahydroxy-9,19-cyclo-20(S)-lanost-24-ene 3-O--galactopyranoside 22,29-di-O--D-glucopyranoside. Its structure was established from the results of chemical transformations and of FAB-mass and NMR spectroscopies (¹H₁,¹³C,¹H-¹H₁, and¹³C-¹H).Irkutsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences. Translated from Khimiya Prirodnykh Soedeninii, No. 1, pp. 103–109, January–February, 1993.     

Triterpene saponins fromThalictrum minus. V. Structure of thalicoside B

The epigeal part ofThalictrum minus L. has yielded a new bidesmoside — thalicoside B — which has the structure of oleanolic acid 28-O--D-glucopyranoside 3-O-[O--L-rhamnopyranosyl-(1 2)-O--D-glucopyranosyl-(1 3)--L-arabinopyranoside].Irkutsk Institute of Organic Chemistry, Siberian Branch, Academy of Sciences of the USSR; A. A. Zhdanov Irkutsk State University; and Pacific Ocean Institute of Bioorganic Chemistry, Far Eastern Scientific Center, Academy of Sciences of the USSR, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 670–676, September–October, 1985.     

Triterpene saponins fromThalictrum minus. III. The structure of thalicogenin

The periodate oxidation with subsequent alkaline degradation of the products of the oxidation of the predominant saponin isolated fromThalictrum minus has yielded the native genin, which has been called thalicogenin. The structure of thalicogenin as 3,16,22(S),29-tetrahydroxy-9,19-cyclo-20(S)-lanost-24-ene has been established on the basis of chemical transformations and by spectral methods.Irkutsk Institute of Organic Chemistry, Siberian Branch, Academy of Sciences of the USSR. Pacific Ocean Institute of Bioorganic Chemistry, Far Eastern Scientific Center, Academy of Sciences of the USSR, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 207–213, March–April, 1984.     

Triterpene saponins fromThalictrum minus. VIII. Structure of thalicoside D

Thalicoside D — a new triterpene glycoside isolated fromThalictrum minus L. (Ranunculaceae) — has the structure of oleanolic acid 3-O-[O--L-rhamnopyranosyl-(12)-O--D-glucopyranosyl-(14)--L-arabinopyranoside 28-O-[O--D-glucopyranosyl-(16)--D-glucopyranoside]. This structure was established by the use of the results of acid and alkaline hydrolyses, SIMS spectra, and one- and two-dimensional NMR spectroscopy.Deceased.Irkutsk Institute of Organic Chemistry, Siberian Division, Russian Academy of Sciences. Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic of Uzbekistan [IKhRV AN RUz], Tashkent, FAX (3712) 62 73 48. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 398–403, May–June, 1994.     

Triterpene saponins fromThalictrum minus. VII. Structure of thalicoside E

A new minor cycloartane glycoside — thalicoside E, 9,19-cyclo-20(S)-lanost-23-ene-3,16,22,25,29-pentaol 3-O--D-galactoside 29-O--D-glucopyranoside — has been isolated from the epigeal part ofThalictrum minus L. (Ranunculaceae).Irkutsk Institute of Organic Chemistry (IrIOKh). Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 567–571, July–August, 1993.     

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

A new glycoside (cyclofoetoside B) (I) has been isolated from the epigeal part of the plantThalictrum foetidum L. (Ranunculaceae). On the basis of chemical transformations and with the aid of physicochemical characteristics it has been established that cyclofoetoside B is 24S-cycloartane-3, 16, 24, 25, 29-pentaol 3-O--L-arabinopyranoside 16-O-[O--L-rhamnopyranoside-(1 6)--D-glucopyranoside], C₄₇-H₈₀O₁₇, mp 194–197°C (methanol); [] _D ²⁴ +15.7 ± 2° (c 0.88; pyridine). The enzymatic hydrolysis of (I) has yielded cyclofoetigenin B (III), 24S-cycloartane-3,16,24,25,29-pentaol 16-O--D-glucopyranoside, (IV), C₃₆H₆₂O₁₀, mp 223–225°C (acetone), [] _D ²⁴ +37 ± 2° (c 0.97; methanol) and 24S-cycloartane-3,16,24,25,29-pentaol 16-O-[O--L-rhamnopyranosyl-(1 6)--D-glucopyranoside, C₄₂H₇₂O₁₄, mp 229–231°C (methanol), [] _D ³⁰ +41 ± 2° (c 0.7; methanol). Details of the IR and¹H and¹³C NMR spectra of the compounds are given.Irkutsk Institute of Organic Chemistry, Academy of Sciences of the USSR. Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Trashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 341–345, May–June, 1986.     

Triterpene glycosides and their genins fromThalictrum foetidum. IV. Structure of cyclofoetigenin B

A glycoside isolated from the epigeal part ofThalictrum foetidum (Ranunculaceae) has yielded a new genin — cyclofoetigenin B — the structure of which has been established on the basis of chemical transformations and spectral characteristics as 24S-cycloartane-3,16,24,25,30-pentaol.Irkutsk Institute of Organic Chemistry of the Siberian Branch of the Academy of Sciences of the USSR. Institute of the Chemistry of Plant Substances of the Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 312–320, May–June, 1986.     

New triterpenoid glycosides fromThalictrum minus L.

Two triterpenoid diglycosides of the cycloartane series were isolated from the terrestrial part ofThalictrum minus L. (Ranunculaceae). Genins of these glycosides are side-chain structural isomers—3-O-β-d-galactopyranosyl-29-O-β-d-glucopyranosyl-9β, 19-cyclo-20(S)-lanost-24(Z)-ene-3β, 16β, 22(S), 26, 29-pentaol and 3-O-β-d-galactopyranosyl-29-O-β-d-glucopyranosyl-9β, 19-cyclo-20(S)-lanost-25-ene-3β, 16β,22(S), 24ζ, 29-pentaol. The structures of these glycosides were established using 1D and 2D NMR spectroscopy and FAB mass spectrometry. For Part 9, see Ref. 1. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1434–1437, July, 1998.     

New triterpenoid glycosides fromThalictrum minus L.

From the terrestrial part ofThalictrum minus L. (Ranunculaceae) a novel triterpenoid diglycoside was isolated. The genin of this glycoside is a new cycloartane triterpenoid. The structure of the glycoside was established on the basis of 1D and 2D NMR spectroscopy and FAB mass spectrometry as 22S,25-epoxy-3-O-β-d-galactopyranosyl-29-O-β-d-glucopyranosyl-9β, 19-cyclo-20S-lanostane-3β,16β,24S,29-tetrol. For Part 10 see Ref. 1. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 602–605, March, 1999.     

Flavonoid glycosides fromThalictrum squarrosum St. ex Willd. andThalictrum minus L.

Two flavonoid allose diglycosides were found in the terrestrial part ofThalictrum squarrosum St. ex Willd. andT. minus L. (Ranunculaceae). 7,4′-Di-O-β-allopyranosylapigenin was isolated fromT. minus. InT. squarrosum, its monoacetate was also found and characterized as 7-O-(6-O-acetyl-β-allopyranosyl)-4′-O-(β-allopyranosyl)apigenin. The sites of attachment of the carbohydrate residues were determined by HMBC; the location of the acetate group was identified by ROESY. Both substances were isolated from these plants for the first time. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 392–394, February, 1999.     

Triterpene glycosides and their genins fromThalictrum foetidum. II. The structure of cyclofoetigenin A

A glycoside isolated from the epigeal parts ofThalictrum foetidum (Ranunculaceae) has yielded a new genin — cyclofoetigenin A, the structure of which has been established on the basis of chemical transformations and spectral characteristics as 24S-cycloartane-3,16,25,25-tetraol.Irkutsk Institute of Organic Chemistry, Siberian Branch, Academy of Sciences of the USSR. Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 370–375, May–June, 1985.     

Triterpene glycosides and their genins fromThalictrum foetidum. I. The structure of foetoside C

A new glycoside — foetoside C — has been isolated from the epigeal part ofThalictrum foetidum L. and, on the basis of chemical transformations and spectral characteristics its structure has been established as oleanolic acid 28-[O-α-D-glycopyranosyl-(1 → 6)-O-β-D-glucopyranoside] 3-O-[O-β-D-xylopyranosyl-(1 → 3)-O-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranoside].     

Triterpene saponins from Craniotome furcata

Three saponins, craniosaponin A (1) and buddlejasaponins Ia (2) and I (3) were isolated from the n-butanol soluble fraction of Craniotome furcata for the first time. Among them, craniosaponin A (1) was identified to be a new compound. The structure of craniosaponin A was assigned mainly by spectral methods. A preliminary assay in vitro was applied to evaluate their cytotoxicity against several tumor cell-lines.