Saponins from root cultures of phytolacca acinosa

Strauss, André; Spengel, Sigrid; Schaffner, W.

doi:10.1016/0031-9422(94)00749-j

Cited by 28 publications

(24 citation statements)

References 13 publications

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“…3,13,14) The spectral data of 2-6 were in full agreement with those described in the literature. 13 C-NMR spectrum, the aglycone part of 1 was similar to phytolaccinic acid (7) 13) except for C-3 which was shifted down-field by 8.1 ppm in comparison with that of 7, thus indicating that the sugar part was attached at the C-3 position. In order to confirm the linkages of the two sugar parts and the structure of the aglycone, heteronuclear multi-bond correlation (HMBC) experiments ( Fig.…”

supporting

confidence: 84%

“…16) In this study, we obtained six triterpene glycosides, among which three compounds 2, 3 and 6 were isolated from the same plant roots, 3,4) and 4 and 5 were reported from the roots of P. acinosa 13) and P. dodecandra. 15) Although, the production of betacyanin from the cell cultures of P. americana 11) has been reported, this is the first report on the production of the triterpene glycosides from the cultures of P. americana.…”

mentioning

confidence: 97%

“…The methanol extract was subjected to silica gel, Sephadex LH-20 and HPLC (octadecyl silica gel (ODS) column) to afford a new triterpene glycoside 1 and the five known triterpene glycosides, esculentoside B (2), 4,13,14) phytolaccoside E (3), 3,4,13) esculentoside S (4), 13,15) esculentoside L1 (5), 13,15) and esculentoside G (6). 3,13,14) The spectral data of 2-6 were in full agreement with those described in the literature. 13 C-NMR spectrum, the aglycone part of 1 was similar to phytolaccinic acid (7) 13) except for C-3 which was shifted down-field by 8.1 ppm in comparison with that of 7, thus indicating that the sugar part was attached at the C-3 position.…”

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confidence: 99%

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Triterpene Glycosides from the Cultures of Phytolacca americana.

Takahashi

Namikawa

Tanaka

2001

CHEMICAL & PHARMACEUTICAL BULLETIN

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Phytolacca americana L. (Phytolaccaceae) is a perennial plant originating from North America. Its rhizome has been used as a traditional crude diuretic drug in spite of having strong toxicity. A number of triterpenes, their glycosides, and neolignanes have been isolated from the roots of P. americana and identified.1-7) As a part of our search for neurotrophic substances in natural products, we reported the isolation and structure of americanol A (8) and isoamericanol A (9) from the seeds of P. americana.8,9) Moreover, we accomplished the convenient syntheses of americanol A (8) and isoamericanol A (9) by horseradish peroxidase (HRP) catalyzed oxidative coupling of caffeic acid. 10) In this paper, we describe our next attempt aiming at production of neurotrophic substances 8 and 9 from the cultures of P. americana. First of all, we tried to establish the cell cultures of P. americana independently of the previously known procedure. 11)A cell culture of P. americana was cultured in the Murashige & Skoog (MS) liquid medium 12) (pH 5.6) containing 10 mM 1-naphthaleneacetic acid (1-NAA) and 3% of glucose, on a rotary shaker (90 rpm) at 25°C. The cell cultures were subcultured at intervals of 4 weeks. The filtered cells were freeze-dried and extracted with methanol. The methanol extract was subjected to silica gel, Sephadex LH-20 and HPLC (octadecyl silica gel (ODS) column) to afford a new triterpene glycoside 1 and the five known triterpene glycosides, esculentoside B (2), 4,13,14) phytolaccoside E (3), 3,4,13) esculentoside S (4), 13,15) esculentoside L1 (5), 13,15) and esculentoside G (6). 3,13,14) The spectral data of 2-6 were in full agreement with those described in the literature.Compound 1 for the anomeric protons of xylose and glucose in 1 indicated that the anomeric configurations of D-xylose and D-glucose are b. These results indicated that 1 was the triterpene glycoside linked with D-xylose and D-glucose. In the 13 C-NMR spectrum, the aglycone part of 1 was similar to phytolaccinic acid (7) 13) except for C-3 which was shifted down-field by 8.1 ppm in comparison with that of 7, thus indicating that the sugar part was attached at the C-3 position. In order to confirm the linkages of the two sugar parts and the structure of the aglycone, heteronuclear multi-bond correlation (HMBC) experiments (Fig. 1) A new triterpene glycoside 1 was isolated together with the five known triterpene glycosides 2-6 from the cultures of Phytolacca americana. The structure of 1 was elucidated by analysis of spectroscopic data and comparison of its NMR data with those of 2-7 and chemical degradation.

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mentioning

confidence: 97%

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Triterpene Glycosides from the Cultures of Phytolacca americana.

Takahashi

Namikawa

Tanaka

2001

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Compounds 2 (esculentoside S) 9 -12 and 3 (esculentoside L 1 ) 12 have been isolated before from another Phytolacca species. The earlier reports presented 13 C chemical shifts of 2 and 3 whereas the 1 H data were incomplete, only the chemical shifts of methyl protons, H-12 and the anomeric protons being given.…”

Section: Signal and Structural Assignmentsmentioning

confidence: 99%

Identification and structure determination of four triterpene saponins from some Middle‐East plants

Soliman

Simon

Tóth

et al. 2001

Magnetic Reson in Chemistry

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“…(Table 2), which are characteristic of b-D-glucose. 19 The anomeric proton H-1 0 of the glucose moiety in 7 resonated as a doublet at d 6.32 ppm. A coupling constant of 8.5 Hz for H-1 0 indicated that the stereochemistry of the glycosidic linkage at C-1 0 of D-glucose is b.…”

Section: Resultsmentioning

confidence: 99%