ChemInform Abstract: Unexpected Biosynthetic Precursors of Amarogentin — A Retrobiosynthetic <sup>13</sup>C NMR Study.

Wang, Chang‐Zeng; Maier, Ulrich; Eisenreich, Wolfgang; Adam, Petra; Obersteiner, Ingrid; Keil, Michael; Bacher, Adelbert; Zenk, Meinhart H.

doi:10.1002/chin.200209235

Cited by 8 publications

(10 citation statements)

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“…The pharmacological efficacy of S. chirayita has been partly attributed to the biological activity of major phytoconstituents including amarogentin, swertiamarin, mangiferin, swerchirin, sweroside, amaroswerin, and gentiopicrin (Figure 3 ). Amarogentin is reported to be anti-diabetic (Phoboo et al, 2013 ), anticancerous (Saha et al, 2006 ; Pal et al, 2012 ), and antileishmanial (Ray et al, 1996 ; Medda et al, 1999 ), whereas swertiamarin has been tested for its anti-hepatitis (Wang et al, 2001 ), anticancer (Kavimani and Manisenthlkumar, 2000 ), anti-arthritic activities (Saravanan et al, 2014 ). It has been shown to exhibit anti-diabetic (Vaidya et al, 2013 ) properties.…”

Section: Phytochemistrymentioning

confidence: 99%

A Review of Swertia chirayita (Gentianaceae) as a Traditional Medicinal Plant

2016

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Swertia chirayita (Gentianaceae), a popular medicinal herb indigenous to the temperate Himalayas is used in traditional medicine to treat numerous ailments such as liver disorders, malaria, and diabetes and are reported to have a wide spectrum of pharmacological properties. Its medicinal usage is well-documented in Indian pharmaceutical codex, the British, and the American pharmacopeias and in different traditional medicine such as the Ayurveda, Unani, Siddha, and other conventional medical systems. This ethnomedicinal herb is known mostly for its bitter taste caused by the presence of different bioactive compounds that are directly associated with human health welfare. The increasing high usage of Swertia chirayita, mostly the underground tissues, as well as the illegal overharvesting combined with habitat destruction resulted in a drastic reduction of its populations and has brought this plant to the verge of extinction. The increasing national and international demand for Swertia chirayita has led to unscrupulous collection from the wild and adulteration of supplies. The aim of this review is to provide a synthesis of the current state of scientific knowledge on the medicinal uses, phytochemistry, pharmacological activities, safety evaluation as well as the potential role of plant biotechnology in the conservation of Swertia chirayita and to highlight its future prospects. Pharmacological data reported in literature suggest that Swertia chirayita shows a beneficial effect in the treatment of several ailments. However, there is lack of adequate information on the safety evaluation of the plant. The pharmacological usefulness of Swertia chirayita requires the need for conservation-friendly approaches in its utilization. Providing high-quality genetically uniform clones for sustainable use and thereby saving the genetic diversity of this species in nature is important. In this regard, plant biotechnological applications such as micropropagation, synthetic seed production, and hairy root technology can play a significant role in a holistic conservation strategy. In addition to micropropagation, storage of these valuable genetic resources is equally important for germplasm preservation. However, more advanced research is warranted to determine the activities of bioactive compounds in vitro and in vivo, establish their underlying mechanisms of action and commence the process of clinical research.

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Section: Phytochemistrymentioning

confidence: 99%

A Review of Swertia chirayita (Gentianaceae) as a Traditional Medicinal Plant

2016

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“…Amarogentin (AG, Figure 1 ), a secoiridoid glycoside that is mainly extracted from Swertia and Gentiana roots [ 13 , 14 ], exhibits many biological effects, including anti-oxidative, anti-tumour, and anti-diabetic activities. As a folk medicine, Swertia mileensis T. N. Ho and W. L. Shih ( Gentianaceae ) has been used to treat viral hepatitis in China for centuries [ 15 ], and Swertia chirayita (Roxb.…”

Section: Introductionmentioning

confidence: 99%

Protective Effects of Amarogentin against Carbon Tetrachloride-Induced Liver Fibrosis in Mice

Zhao

et al. 2017

Molecules

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Amarogentin, a secoiridoid glycoside that is mainly extracted from Swertia and Gentiana roots, has been suggested to exhibit many biological effects, including anti-oxidative, anti-tumour, and anti-diabetic activities. The present study was designed to evaluate the protective effects of amarogentin on carbon tetrachloride-induced liver fibrosis in vivo and the underlying mechanism. Fibrosis was induced by subcutaneous injections of 6 mL/kg of 20% carbon tetrachloride (dissolved in olive oil) twice per week for seven weeks. Mice were orally treated with 25, 50, and 100 mg/kg amarogentin and with colchicine as a positive control. Biochemical assays and histopathological investigations showed that amarogentin delayed the formation of liver fibrosis; decreased alanine aminotransferase, aspartate aminotransferase, malondialdehyde and hydroxyproline levels; and increased albumin, cyclic guanosine monophosphate, glutathione peroxidase, and superoxide dismutase levels. Moreover, amarogentin exhibited downregulation of α-smooth muscle actin and transforming growth factor-β1 levels in immunohistochemical and Western blot analyses. The levels of phosphorylated extracellular regulated protein kinases, c-Jun N-terminal kinase, and p38 were also significantly reduced in all amarogentin-treated groups in a dose-dependent manner. These findings demonstrated that amarogentin exerted significant hepatoprotective effects against carbon tetrachloride-induced liver fibrosis in mice and suggested that the effect of amarogentin against liver fibrosis may be by anti-oxidative properties and suppressing the mitogen-activated protein kinase signalling pathway.

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“…Benzoic acids arise either from intermediates of the shikimate pathway or from L-Phe, which is an end product of the shikimate pathway. Benzoic acids that are formed via branch points in the shikimate pathway are salicylic acid in Arabidopsis (Arabidopsis thaliana) and Nicotiana benthamiana, 3-hydroxybenzoic acid in Centaurium erythraea and Swertia chirata, 2,3-dihydroxybenzoic acid in Catharanthus roseus, and gallic acid in Rhus typhina (Moreno et al, 1994;Werner et al, 1997;Abd El-Mawla et al, 2001;Wang et al, 2001;Wildermuth et al, 2001;Catinot et al, 2008).…”

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confidence: 99%

Cinnamate:CoA Ligase Initiates the Biosynthesis of a Benzoate-Derived Xanthone Phytoalexin in Hypericum calycinum Cell Cultures

Gaid

Sircar²,

Müller³

et al. 2012

Plant Physiology

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Although a number of plant natural products are derived from benzoic acid, the biosynthesis of this structurally simple precursor is poorly understood. Hypericum calycinum cell cultures accumulate a benzoic acid-derived xanthone phytoalexin, hyperxanthone E, in response to elicitor treatment. Using a subtracted complementary DNA (cDNA) library and sequence information about conserved coenzyme A (CoA) ligase motifs, a cDNA encoding cinnamate:CoA ligase (CNL) was isolated. This enzyme channels metabolic flux from the general phenylpropanoid pathway into benzenoid metabolism. HcCNL preferred cinnamic acid as a substrate but failed to activate benzoic acid. Enzyme activity was strictly dependent on the presence of Mg2+ and K+ at optimum concentrations of 2.5 and 100 mm, respectively. Coordinated increases in the Phe ammonia-lyase and HcCNL transcript levels preceded the accumulation of hyperxanthone E in cell cultures of H. calycinum after the addition of the elicitor. HcCNL contained a carboxyl-terminal type 1 peroxisomal targeting signal made up by the tripeptide Ser-Arg-Leu, which directed an amino-terminal reporter fusion to the peroxisomes. Masking the targeting signal by carboxyl-terminal reporter fusion led to cytoplasmic localization. A phylogenetic tree consisted of two evolutionarily distinct clusters. One cluster was formed by CoA ligases related to benzenoid metabolism, including HcCNL. The other cluster comprised 4-coumarate:CoA ligases from spermatophytes, ferns, and mosses, indicating divergence of the two clades prior to the divergence of the higher plant lineages.

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ChemInform Abstract: Unexpected Biosynthetic Precursors of Amarogentin — A Retrobiosynthetic ¹³C NMR Study.

Cited by 8 publications

References 1 publication

A Review of Swertia chirayita (Gentianaceae) as a Traditional Medicinal Plant

A Review of Swertia chirayita (Gentianaceae) as a Traditional Medicinal Plant

Protective Effects of Amarogentin against Carbon Tetrachloride-Induced Liver Fibrosis in Mice

Cinnamate:CoA Ligase Initiates the Biosynthesis of a Benzoate-Derived Xanthone Phytoalexin in Hypericum calycinum Cell Cultures

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ChemInform Abstract: Unexpected Biosynthetic Precursors of Amarogentin — A Retrobiosynthetic 13C NMR Study.

Cited by 8 publications

References 1 publication

A Review of Swertia chirayita (Gentianaceae) as a Traditional Medicinal Plant

A Review of Swertia chirayita (Gentianaceae) as a Traditional Medicinal Plant

Protective Effects of Amarogentin against Carbon Tetrachloride-Induced Liver Fibrosis in Mice

Cinnamate:CoA Ligase Initiates the Biosynthesis of a Benzoate-Derived Xanthone Phytoalexin in Hypericum calycinum Cell Cultures

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ChemInform Abstract: Unexpected Biosynthetic Precursors of Amarogentin — A Retrobiosynthetic ¹³C NMR Study.