Three acetylated polyacetylenes from the roots of Panax ginseng

doi:10.1016/0031-9422(91)83465-W

Phytochemistry

Volume 30, Issue 12, 1991, Pages 4053-4055

https://doi.org/10.1016/0031-9422(91)83465-W Get rights and content

Abstract

Three new acetylated polyacetylenes named ginsenoynes F, G and H were isolated from the hexane extract of the roots of Panax ginseng. The structures were determinated by spectral and chemical methods.

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Cited by (19)

Isolation and characterization of bioactive polyacetylenes Panax ginseng Meyer roots
2017, Journal of Pharmaceutical and Biomedical Analysis
Citation Excerpt :
Major polyacetylenes fingerprints such as panaxynol and panaxydol were speculated to differ between the solvents used for extraction. For instance, hexane was found to have resulted in the extraction of rare polyacetylenes such as ginsenoyne A–K [14–16], while petroleum ether resulted in the extraction of carbonyl- group polyacetylenes [6,17]. On the other hand, alcohol is commonly preferred due to its medium-high polarity and wide range solubility.
Panax ginseng has been studied for its chemo-preventive properties and pharmaceutical potential. Polyacetylenic compounds isolated from Panax ginseng root typically comprised of non-polar C₁₇ compound have been reported to exhibit bioactive properties. The objective of this project is to extract, isolate, and characterize bioactive polyacetylenes from Panax ginseng root using various extraction and separation methods Ginseng was extracted by reflux using methanol, ethanol, hexane, ethyl acetate, methanolic ultrasonication. The extracts were partitioned with hexane to obtain water-soluble portion and hexane-soluble portion. Hexane was subsequently removed under vacuum, and formed a crude polyacetylenes extract (crude PA). Silica gel chromatography and semi-preparative HPLC were utilized to prepare 5 fractions and the polyacetylenes were measure by HPLC and molecular weights confirm my APCI–MS and MNR. The bioactive effect was measured by MTT viability assay using murine 3T3-L1 cells. Extraction with methanol under reflux produced significantly larger amount of polyacetylenes (p < 0.05). Liquid-liquid extraction and column chromatography were used to separate polyacetylenic compounds into five different fractions. Major polyacetylenes, panaxynol and panaxydol were found in fraction 1 and 2 respectively. Dose-response relationships were observed in 3T3-L1 cells and LC50 were 13.52 ± 3.05 μg/mL (fraction 1), 3.69 ± 1.09 μg/mL (fraction 2), 52.88 ± 11.16 μg/mL (fraction 3), 85.91 ± 27.37 μg/mL (fraction 4) and 135.52 ± 32.91 μg/mL (fraction 5). Fraction 2 containing panaxydol was found to have exhibited the greatest anti-proliferative effects on 3T3-L1 preadipocytes. Extraction with methanol under reflux produced significantly more polyacetylenes. Fractions that contain panaxydol was the most cytotoxic.
A convenience UPLC/PDA method for the quantitative analysis of panaxfuraynes A and B from Panax ginseng
2010, Food Chemistry
Panaxfurayne A and B, biologically novel tetrahydrofuranic polyacetylene glycosides, were founded from roots of Panax ginseng C. A. Meyer (Araliaceae). To study the contents of panaxfurynes A and B, a quantitative analysis method was developed using ultra performance liquid chromatography (UPLC) coupled with photo diode array detector. The dried (65 °C, 72 h) and powdered sample (5 g) was extracted with ethanol (15%, 100 ml) for 30 min at 50 °C and concentrate. The constituents were separated using an isocratic mobile phase consisting acetonitrile (16%) in water for 10 min on a ODS column. The contents of panaxfuraynes A and B in the roots of Panax quinquefolium, Panax japonicum, Panax notoginseng and P. ginseng were found to less than 3 and 2 ng/g approximately, respectively. The constituents were not detected from P. japonicum.
Panaxfuraynes A and B, two new tetrahydrofuranic polyacetylene glycosides from Panax ginseng C. A. Meyer
2009, Tetrahedron Letters
Panaxfurayne A (1), a tetrahydrofuranic polyacetylene glycoside, was isolated from the roots of Panax ginseng C. A. Meyer (Araliaceae) together with panaxfurayne B (2) as a geometric isomer of 1. The chemical structures of these two compounds were ascertained by UV, Mass, 1D, and 2D NMR experiments. During these experiments, these tetrahydrofuranic polyacetylene compounds proved to be of biogenetically novel type.
Syntheses of two diastereoisomers of panaxytriol, a potent antitumor agent isolated from Panax ginseng
1999, Tetrahedron
Polyacetylenes fromPanax quinquefolium
1994, Phytochemistry
Cytotoxic Properties of C<inf>17</inf> Polyacetylenes from the Fresh Roots of Panax ginseng on Human Epithelial Ovarian Cancer Cells
2022, Molecules

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^☆: Part 2 in the series ‘The Constituents of Panax ginseng’. For Part 1 see ref. [1].

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Three acetylated polyacetylenes from the roots of Panax ginseng☆

Abstract

Phytochemistry

Arch. Pharm.