Polyacetylenes from the roots of Panax ginseng

doi:10.1016/0031-9422(91)83203-W

Phytochemistry

Volume 30, Issue 10, 1991, Pages 3327-3333

https://doi.org/10.1016/0031-9422(91)83203-W Get rights and content

Abstract

Five new polyacetylenes named ginsenoynes A, B, C, D and E were isolated from the hexane extract of the root of Panax ginseng. These structures were determined by spectral and chemical methods.

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Traditional uses, chemical diversity and biological activities of Panax L. (Araliaceae): A review
2020, Journal of Ethnopharmacology
Panax L. (Araliaceae) is globally-recognized plant resource suitable for the globalization of traditional Chinese medicines. It has traditionally been used as tonic agents in various ethnomedicinal systems of East Asia, especially in China. It is often used to regulate bodily functions and considered as adjuvant therapy for tumor, resuscitation of traumatic hemorrhagic shock, etc.
This review systematically summarized the information on distributions, botanical characteristics, traditional uses, chemical components and biological activities of the genus Panax, in order to explore and exploit the therapeutic potential of this plant.
The available information about genus Panax was collected via the online search on Web of Science, Google Scholar, PubMed, Baidu Scholar, Science Direct, China National Knowledge Infrastructure and Springer search. The keywords used include Panax, saponin, secondary metabolites, chemical components, biological activity, pharmacology, traditional medicinal uses, safety and other related words. The Plant List (www.theplantlist.org) and Catalogue of Life: 2019 Annual Checklist (www.catalogueoflife.org/col/) databases were used to provide the scientific names, subspecies classification and distribution information of Panax.
Panax is widely assessed concerning its phytochemistry and biological activities. To date, at least 748 chemical compounds from genus Panax were isolated, including saponins, flavonoids, polysaccharides, steroids and phenols. Among them, triterpenoid saponins and polysaccharides were the representative active ingredients of Panax plants, which have been widely investigated. Modern pharmacological studies showed that these compounds exhibited a wide range of biological activities in vitro and in vivo including antineoplastic, anti-inflammatory, hepatorenal protective, neuroprotective, immunoregulatory, cardioprotective and antidiabetic activities. Many studies also confirmed that the mechanisms of organ-protective were closely related to molecular signaling pathways, the expression of related proteins and antioxidant reactions. To sum up, genus Panax has high medicinal and social value, deserving further investigation.
The genus Panax is very promising to be fully utilized in the development of nutraceutical and pharmaceutical products. However, there is a lack of in-depth studies on ethnomedicinal uses of Panax plants. In addition, further studies of single chemical component should be performed based on the diversity of chemical structure, significant biological activities and clinical application. If the bioactive molecules and multicomponent interactions are discovered, it will be of great significance to the clinical application of Panax plants. It is an urgent requirement to carry out detailed phytochemical, pharmacology and clinical research on Panax classical prescriptions for the establishment of modern medication guidelines. Exploring the molecular basis of herbal synergistic actions may provide a new understanding of the complex disease mechanisms and accelerate the process of pharmaceutical development.
Synchronous characterization of carbohydrates and ginsenosides yields deeper insights into the processing chemistry of ginseng
2017, Journal of Pharmaceutical and Biomedical Analysis
Citation Excerpt :
By the 1st-h steaming, panaxydol steeply increased from 0.34 mg/g to 1.67 mg/g, but during the ensuing 11-h steaming, it slowly decreased to 0.60 mg/g (RG7) (Fig. 4A5). Panaxydol is volatile under high temperature [5], and could be reversibly transformed with panaxytriol, another polyacetylene, by oxidation and reduction when heated (Fig. 5) [28]. These physical and chemical reactions could occur to varying degrees, thereby explaining the quantitative variation of panaxydol during the processing.
Carbohydrates and ginsenosides in ginseng are biologically interrelated. Their synchronous analysis is therefore essential in chemical research on ginseng to characterize its “holistic” quality. Here we investigated the processing chemistry of red ginseng (RG), a ginseng product processed by water-steaming, for which both carbohydrates and ginsenosides were qualitatively and quantitatively determined through multiple analytical techniques. Results revealed that the steam-processing not only qualitatively and quantitatively altered the ginsenosides but also affected the polymeric carbohydrates via changing their physiochemical parameters, i.e. water-solubility, molecular size, types and ratios of constituent monosaccharides. Potential mechanisms involved in the transformation of ginseng chemicals are proposed and discussed, including hydrolysis (deglycosylation, demalonylation, deacetylation), dehydration, polymerization, volatilization, reduction and the Maillard reaction. The study strengthens the research on the processing chemistry of RG, and therefore should be helpful for elucidating the scientific basis of RG preparation and application.
Isolation and characterization of bioactive polyacetylenes Panax ginseng Meyer roots
2017, Journal of Pharmaceutical and Biomedical Analysis
Citation Excerpt :
Three conventional extraction methods namely reflux, ultrasound-assisted and room temperature extraction were utilized. Reflux and ultrasound-assisted are the two most common mode of extraction of ginseng species for secondary metabolites [14]. Methanol, ethanol, ethyl acetate, hexane and petroleum ether have all being previously used for extraction of polyacetylenes from ginseng, nevertheless efficiencies have not yet been highlighted.
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.
Total synthesis of distaminolyne A
2017, Tetrahedron Letters
Citation Excerpt :
Distaminolyne A3 (1) (Fig. 1) is a first occurrence diacetylene 1-amino 2-alcohol isolated from the New Zealand ascidian Pseudodistoma opacum showed a modest anti-microbial activity toward Escherichia coli, Staphylococcus aureus and Mycobacterim tuberculosis. Determination of the absolute configuration i.e. ‘S’ at the lone stereogenic carbon atom was confirmed by negative Cotton effect on CD spectra.3 Following our interest in the total synthesis of natural products containing long chain acetylenic fatty acid molecules,4 we embarked on the synthesis of distaminolyne A (1) which possesses structurally impressive polar long chain amino alcohol carbon framework.
Synthesis of panaxytriol and its stereoisomers as potential antitumor drugs
2016, Tetrahedron Asymmetry
Citation Excerpt :
It contains several types of chiral polyacetylenic alcohols, such as panaxydol 1, panaxytriol 2a, and panaxynol 3 (Fig. 1).2 We are interested in panaxytriol because it exhibits inhibitory activity against several kinds of tumor cell lines, including human gastric adenocarcinoma types (MK-1),3 human colon adenocarcinoma (SW620),4 and human breast carcinoma (Breast M25-SF).5 In addition, one biological investigation showed that panaxytriol suppressed the proliferation of mouse lymphoma cells (P388D1).6
An efficient synthesis of panaxytriol and its seven stereoisomers was achieved, and four unnatural diastereomers of 2a were prepared. The key steps involved the opening of vicinal hydroxy epoxides, the stereospecific opening of the epoxides with perchloric acid, and the Cadiot–Chodkiewicz cross-coupling of chiral terminal alkynes with bromoalkynes. Preliminary antitumor activity investigations indicated that some synthetic panaxytriols exhibited promising cytotoxic activity against three human cancer cell lines.
Total synthesis of panaxydol and its stereoisomers as potential anticancer agents
2016, Tetrahedron Asymmetry
Citation Excerpt :
Panaxydol 1a (Fig. 1) is an important chiral polyacetylenic alcohol isolated from red ginseng,2 which has been proven to possess significant antitumor activities.3–5 For instance, panaxydol showed cytotoxicity against various cancer cells, such as human breast cancer (MCF-7)4 and human melanoma (SK-MEL-1).5 Since the isolation of panaxydol 1a from red ginseng and the confirmation of its structure and absolute configuration,6,7 its total synthesis has attracted much attention and interest from chemists.
An efficient total synthesis of natural panaxydol 1a and its seven stereoisomers 1b–h was accomplished; four diastereomers of the natural form were prepared for the first time. Our strategy involves the Cadiot-Chodkiewicz cross-coupling reaction of chiral terminal alkynes with bromoalkynes, the asymmetric alkynylation of aldehydes, and the enantioselective Sharpless epoxidation of allylic alcohols. Preliminary in vitro cytotoxicity evaluation indicated that some synthetic panaxydols possess anticancer activities, and (3S,9R,10S)-panaxydol 1e showed a particularly promising cytotoxic effect.

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Polyacetylenes from the roots of Panax ginseng

Abstract

Phytochemistry

Tetrahedron Letters

Phytochemistry

Yakugaku Zasshi

Shoyakugaku Zasshi

Phytochemistry

Yakugaku Zasshi