Production and Synthetic Modifications of Shikimic Acid

Candeias, Nuno R.; Assoah, Benedicta; Simeonov, Svilen P.

doi:10.1021/acs.chemrev.8b00350

Cited by 59 publications

(24 citation statements)

References 405 publications

(771 reference statements)

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“…It was extracted with n-hexane, then quantified by HPTLC and applied directly to flash chromatography using hexane:acetone (40:60) in order to isolate methyl linoleate as pale-yellow viscous oil (Jubie, Dhanabal, & Chaitanya, 2015). Tamiflu (Candeias, Assoah, & Simeonov, 2018). This drug is an efficient inhibitor of the surface protein neuraminidase (NA) enzyme of the seasonal influenza virus types A and B, avian influenza virus H5N1, and human influenza virus H1N1 (Bradley, 2005).…”

Section: Isolation Of Methyl Linoleatementioning

confidence: 99%

Star anise (Illicium verum): Chemical compounds, antiviral properties, and clinical relevance

Patra

Das

Bose³

et al. 2020

Phytotherapy Research

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Medicinal herbs are one of the imperative sources of drugs all over the world. Star anise (Illicium verum), an evergreen, medium-sized tree with star-shaped fruit, is an important herb with wide distribution throughout southwestern parts of the Asian continent. Besides its use as spice in culinary, star anise is one of the vital ingredients of the Chinese medicinal herbs and is widely known for its antiviral effects. It is also the source of the precursor molecule, shikimic acid, which is used in the manufacture of oseltamivir (Tamiflu ® ), an antiviral medication for influenza A and influenza B. Besides, several other molecules with numerous biological benefits including the antiviral effects have been reported from the same plant. Except the antiviral potential, star anise possesses a number of other potentials such as antioxidant, antimicrobial, antifungal, anthelmintic, insecticidal, secretolytic, antinociceptive, antiinflammatory, gastroprotective, sedative properties, expectorant and spasmolytic, and estrogenic effects. This review aimed to integrate the information on the customary attributes of the plant star anise with a specific prominence on its antiviral properties and the phytochemical constituents along with its clinical aptness. K E Y W O R D S antiviral, Illicium verum, oseltamivir, shikimic acid, star anise, Tamiflu

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Section: Isolation Of Methyl Linoleatementioning

confidence: 99%

Star anise (Illicium verum): Chemical compounds, antiviral properties, and clinical relevance

Patra

Das

Bose³

et al. 2020

Phytotherapy Research

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“…Shikimic acid from Illicium verum is used as a precursor for the synthesis of oseltamivir [37] , [38]. The pKa of shikimic acid is 4.1; thus, shikimic acid was analyzed as a negatively-charged analyte by CZE using ammonium bicarbonate buffer at pH 9.5.…”

Section: Resultsmentioning

confidence: 99%

Pressurized Hot Water Extraction and Capillary Electrophoresis for Green and Fast Analysis of Useful Metabolites in Plants

2019

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The search for useful compounds from plants is an important research area. Traditional screening that involves isolation and identification/quantitation is tedious, time consuming, and generates a significant amount of chemical waste. Here, we present a simple, fast, and green strategy to assess ≥0.1% wt/wt quantities of useful compounds in plants/spices using pressurized hot water extraction using a household espresso machine followed by chemical analysis using capillary electrophoresis. Three demonstrations with polygodial, cinnamaldehyde, coumarin, and shikimic acid as target metabolites are shown. Direct analysis of extracts was by the developed micellar electrokinetic chromatography and capillary zone electrophoresis methods. The approach, which can be implemented in less developed countries, can process many samples within a day, much faster than traditional techniques that would normally take at least a day. Finally, 0.8–1.1% wt/wt levels of shikimic acid were found in Tasmanian-pepperberry and Tasmanian-fuschia leaves via the approach.

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“…Many active secondary metabolites belonging to the polyphenolic, flavonoid, tannin, alkaloid, triterpenoid, saponin, and anthraquinone classes of phytochemicals were found to be present in star anise (SA) and many of these are potent antiviral agents. A popular and widely studied metabolite that is abundant in SA, shikimic acid (3,4,5-trihydroxy-1-cyclohexene-1-carboxylic acid), is a key intermediate of the shikimic acid pathway and is used in the industrial synthesis of the antiviral drug oseltamivir phosphate (OSP) (Candeias et al 2018). This drug effectively inhibits surface protein neuraminidase (NA) enzyme of the seasonal influenza virus types A and B, avian influenza virus H5N1, and human influenza virus H1N1 (Bradley 2005).…”

Section: Illicium Verum Hook Fmentioning

confidence: 99%

Coronavirus Disease 2019 and Herbal Therapy: Pertinent Issues Relating to Toxicity and Standardization of Phytopharmaceuticals

Komolafe

Fatoki

et al. 2021

Rev. Bras. Farmacogn.

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Coronavirus disease 2019 (COVID-19) is a virulent viral disease that has now become a public health emergency of global significance and still without an approved treatment regimen or cure. In the absence of curative drugs and with vaccines development still in progress, alternative approaches to stem the tide of the pandemic are being considered. The potential of a phytotherapeutic approach in the management of the dreaded disease has gained attention, especially in developing countries, with several claims of the development of anti-COVID-19 herbal formulations. This is a plausible approach especially with the increasing acceptance of herbal medicine in both alternative and orthodox medical practices worldwide. Also, the established efficacy of herbal remedies in the treatment of numerous viral diseases including those caused by coronaviruses, as well as diseases with symptoms associated with COVID-19, presents a valid case for serious consideration of herbal medicine in the treatment of COVID-19. However, there are legitimate concerns and daunting challenges with the use of herbs and herbal products. These include issues of quality control, unethical production practice, inadequate information on the composition, use and mechanisms, weak regulatory policies, herb-drug interactions and adverse reactions, and the tendency for abuse. This review discusses the feasibility of intervention with herbal medicine in the COVID-19 pandemic and the need to take proactive measures to protect public health by improving the quality and safety of herbal medicine deployed to combat the disease.

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Production and Synthetic Modifications of Shikimic Acid

Cited by 59 publications

References 405 publications

Star anise (Illicium verum): Chemical compounds, antiviral properties, and clinical relevance

Star anise (Illicium verum): Chemical compounds, antiviral properties, and clinical relevance

Pressurized Hot Water Extraction and Capillary Electrophoresis for Green and Fast Analysis of Useful Metabolites in Plants

Coronavirus Disease 2019 and Herbal Therapy: Pertinent Issues Relating to Toxicity and Standardization of Phytopharmaceuticals

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