Triterpene Glycosides from the Cultures of Phytolacca americana.

Abstract

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.

Tandem mass spectrometric analysis of a complex triterpene saponin mixture of Chenopodium quinoa

“…4 displayed an aglycone-specific product ion at m/z 533. Elimination of three water molecules, formic acid, and formaldehyde point to an aglycone similar to PA but bearing an additional hydroxyl group, e.g., at the C-2 [37] or the C-16 [38]. Sugar loss of Compound 9 results in a signal detected at m/z 515.…”

Impact of Phytolacca americana Extracts on Gene Expression of Colon Cancer Cells

“…The tandem mass data showed that they have the same aglycone. However, this aglycone is 2 mass units higher than that reported from earlier studies (Takahashi et al ., ). Further studies are needed to purify both PRE and PREW using column chromatography and identify their structures and concentrations using 1D and 2D NMR analysis.…”

Rabbit conjunctivae edema and release of NO, TNF-α, and IL-1β from macrophages induced by fractions and esculentosides isolated fromPhytolacca americana

“…They were identified as esculentoside B (1), esculentoside A (2), esculentoside C (3), and esculentoside F (4), respectively, by comparison of their spectral (UV, IR, NMR, and MS, Supplementary Material Tables 1-5) and/or mp data with those of corresponding authentic samples or data from the literature (Liu, 2006;Takahashi et al, 2001;Wang & Yi, 1984).…”