Studies on the Saponin in Fatsia japonica DECNE et PLANCH

Tanemura, Mitsuru; Takamura, Keiichi

doi:10.1248/yakushi1947.95.1_1

Cited by 10 publications

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“…One of the methyl signals shifts downfield to 1.81 owing to 1,3-diaxial interaction to the hydroxyl group at C-l6a, and this has been assigned to CH3-27. The 13Cnmr signals of the aglycone are very close to those of the aglycone (quillaic acid) in dubioside A (15,16) [3] and kalopanax-saponin La (3-0-ot-L-arabinopyranosyl-22a-hydroxyhederagenin) [4] (7) except for the following signals. The 13C-nmr signals of the aglycone of dubioside A show upfield shifts for C-14 (55.1 ppm) and C-6 (20.7 ppm) as against 43.5 ppm and 18.2 ppm in 2 and 42.6 ppm and 18.2 ppm in 4, respectively, due to the aldehyde group at C-4 in 3 aglycone.…”

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confidence: 66%

“…In 2 and 3 aglycone, C-16 appears at 74.8 ppm and 73.9 ppm, respectively, due to a hydroxyl group at this position. Similarly in kalopanax La (4], the signal for C-22 appears at 71.5 ppm due to the hydroxyl group at C-22, whereas this methylene appears at 32.9 ppm and 32.1 ppm, respectively, in 2 and 3 aglycone. In 3 aglycone, the signal for C-23 at 209.3 ppm is due to the aldehyde function (Table 1).…”

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confidence: 96%

“…(Araliaceae). The different names reported for this saponin are: akeboside Stb (3,7,8), ß2^$ (4), PA (seed saponin A) (5,6), and leontoside A (9).…”

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confidence: 99%

“…C-23 was assigned to 67.0 (as against 64.8) (8) as this was close to the assignment in hederagenin ( 67.9), 23-hydroxyursolic acid ( 68.1) (10), and collinsogenin ( 68.1) (vide supra). The 1H-1H [2], Aglycone of Dubioside A (3 aglycone), Kalopanax-Saponin La [4], and Collinsogenin [5] (in pyridineV5). COSY and the hetero COSY (HETCOR) spectra allowed correlation of the 13C and chemical shifts as listed in Table 2.…”

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confidence: 99%

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Saponins from Collinsonia canadensis

Joshi¹,

Moore²,

Pelletier³

et al. 1992

J. Nat. Prod.

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and two new saponins named collinsonin and collinsonidin were isolated from the roots of Collinsonia canadensis. On the basis of chemical and spectral studies, the structure of collinsonin [2] has been established as 3-0-ot-L-arabinopyranosylcollinsogenin. 16-a-Hydroxyhederageni , obtained by the hydrolysis of 2, is a new sapogenin named collinsogenin [5]. Collinsonidin [6] has been identified as 3-0-3-D-glucopyranosyl-(l"|->3')--L-arabinopyranosy lhederagenin.Collinsonia canadensis L. (Labiatae) (common names: horse balm, rich weed, stone root, etc.) is native to North America and grows wild from Massachusetts and Vermont to Florida and Arkansas. A tincture of the roots is reported to be used as a tonic, diuretic, and household remedy for headaches and indigestion (1,2). No chemical work has been carried out earlier on the roots of C. canadensis. An EtOH extract of the powdered roots showed in vitro antifungal activity. Bioassay-directed fractionation led to the isolation of three pure compounds which were responsible for the in vitro antifungal activity of the crude EtOH extract. These compounds were found to be saponins, of which two are new. We report here the structure determination of these saponins based mainly on the *Hand 13C-nmr and ms data. RESULTS AND DISCUSSIONOn the basis of the ms, 3Hand 13C-nmr spectral data, and elemental analysis (C35H5608), the first saponin was assigned the structure hederagenin-3-0-a-L-arabinopyranoside [!}. A literature search showed that saponin 1 has been isolated from several plant species, e.g., Akebia quínala Decne. (Lardizabalaceae), Falsía japónica Decne et OH 4 R=a-L-arabinopyranosyl, 22-OH 7 R=ß-D-glucopyranosyl-f l"i->4')-a-L-arabinopyranosyl 8 R= P-D-glucopyranosyl-( l"1->2')-a-L-arabinopyranosyl

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confidence: 66%

mentioning

confidence: 96%

“…(Araliaceae). The different names reported for this saponin are: akeboside Stb (3,7,8), ß2^$ (4), PA (seed saponin A) (5,6), and leontoside A (9).…”

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confidence: 99%

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confidence: 99%

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Saponins from Collinsonia canadensis

Joshi¹,

Moore²,

Pelletier³

et al. 1992

J. Nat. Prod.

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“…(Araliaceae) (Japanese name: "Yatsude"), which contains hemolytic and toxic constituents, is used in various folk remedies (9,10). A number of triterpenoid saponins have been isolated from the flowers, mature fruits, and leaves of this species (11,12).In the present investigation, F. japónica was identified using our pre-screen as a potential source of novel DNA topoisomerase inhibitors. Activityguided fractionation resulted in the isolation of three triterpene glycosides of known structure, FJ-1-3 [1-31• The structures of FJ-1-3 were identified as 3-0-a-Larabinopyranosyl-oleanolic acid [1], 3-0-a-L-arabinopyranosyl-hederagenin [2], and 3--ß-D-glucopyranosyl (1 ->4)-ct-L-arabinopyranosyl]-hederagenin [31, respectively. The activities of these three compounds as DNA topoisomerase II inhibitors have been evaluated.…”

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confidence: 95%

Antitumor Agents, 162. Cell-Based Assays for Identifying Novel DNA Topoisomerase Inhibitors: Studies on the Constituents of Fatsia japonica

Kitanaka¹,

Yasuda²,

Kashiwada³

et al. 1995

J. Nat. Prod.

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Two pleiotropic multi-drug resistant (PDR) KB cell lines were hypersusceptible to a cytotoxic extract from Fatsia japonica. Fractionation of an active extract using a cell-based assay for DNA topoisomerase inhibitors led to the isolation of three known triterpene glycosides, FJ-1-3 [1-3]. The structures of 1-3 were identified as 3-O-alpha-L-arabinopyranosyl-oleanolic acid [1], 3-O-alpha-L-arabinopyranosyl-hederagenin [2], and 3-O-[beta-D-glucopyranosyl(1-->4)-alpha-L-arabinopyranosyl]-hed eragenin [3], respectively. However, these isolates were not DNA topoisomerase II inhibitors in vitro and nor were they active when re-tested for differential cytotoxicity. Compounds 1-3 appear to function by interfering selectively with cellular drug accumulation. Other fractions probably contained compounds active against DNA topoisomerase I; however, the enriched preparations were not cytotoxic. The present findings indicate a simple modification to improve the cell-based bioassay procedure employed to guide fractionation.

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Araliaceae

Hegnauer

1989

Chemotaxonomie Der Pflanzen

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Studies on the Saponin in Fatsia japonica DECNE et PLANCH

Cited by 10 publications

References 0 publications

Saponins from Collinsonia canadensis

Saponins from Collinsonia canadensis

Antitumor Agents, 162. Cell-Based Assays for Identifying Novel DNA Topoisomerase Inhibitors: Studies on the Constituents of Fatsia japonica

Araliaceae

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