Functional characterisation of a tropine-forming reductase gene from Brugmansia arborea, a woody plant species producing tropane alkaloids

Wei, Qiang; Xia, Ke; Zhang, Qiaozhuo; Zeng, Junlan; Huang, Yue; Yang, Chunxian; Chen, Min; Liu, Xiaoqiang; Lan, Xiaozhong

doi:10.1016/j.phytochem.2016.03.008

Cited by 23 publications

(18 citation statements)

References 39 publications

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“…The signature motif of SDRs was found at the 105–108 position in SlTRI. SlTRI contained the catalytic tetrad motif characterized by N-S-Y-K, in which the tyrosine (Y) residue is considered essential for the catalytic activity of TRs ( Nakajima et al, 1999 ; Qiang et al, 2016 ). The bioinformatics analysis suggested that SlTRI might be one of the TRs, and the follow-up phylogenetic analysis gave clear clues to SlTRI’s classification.…”

Section: Resultsmentioning

confidence: 99%

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Enhancing Tropane Alkaloid Production Based on the Functional Identification of Tropine-Forming Reductase in Scopolia lurida, a Tibetan Medicinal Plant

et al. 2017

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Scopolia lurida, a native herbal plant species in Tibet, is one of the most effective producers of tropane alkaloids. However, the tropane alkaloid biosynthesis in this plant species of interest has yet to be studied at the molecular, biochemical, and biotechnological level. Here, we report on the isolation and characterization of a putative short chain dehydrogenase (SDR) gene. Sequence analysis showed that SlTRI belonged to the SDR family. Phylogenetic analysis revealed that SlTRI was clustered with the tropine-forming reductases. SlTRI and the other TA-biosynthesis genes, including putrescine N-methyltransferase (SlPMT) and hyoscyamine 6β-hydroxylase (SlH6H), were preferably or exclusively expressed in the S. lurida roots. The tissue profile of SlTRI suggested that this gene might be involved in tropane alkaloid biosynthesis. By using GC-MS, SlTRI was shown to catalyze the tropinone reduction to yield tropine, the key intermediate of tropane alkaloids. With the purified recombinant SlTRI from Escherichia coli, an enzymatic assay was carried out; its result indicated that SlTRI was a tropine-forming reductase. Finally, the role of SlTRI in promoting the tropane alkaloid biosynthesis was confirmed through metabolic engineering in S. lurida. Specifically, hairy root cultures of S. lurida were established to investigate the effects of SlTRI overexpression on tropane alkaloid accumulation. In the SlTRI-overexpressing root cultures, the hyoscyamine contents were 1.7- to 2.9-fold higher than those in control while their corresponding scopolamine contents were likewise elevated. In summary, this functional identification of SlTRI has provided for a better understanding of tropane alkaloid biosynthesis. It also provides a candidate gene for enhancing tropane alkaloid biosynthesis in S. lurida via metabolic engineering.

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Section: Resultsmentioning

confidence: 99%

“…The Escherichia coli strain Rosetta was used as the host cells for expressing the recombinant protein. The methods of producing and purifying the recombinant proteins followed those of Qiang et al (2016) . The tropinone feeding assay was used to identify the function of SlTRI.…”

Section: Methodsmentioning

confidence: 99%

Enhancing Tropane Alkaloid Production Based on the Functional Identification of Tropine-Forming Reductase in Scopolia lurida, a Tibetan Medicinal Plant

et al. 2017

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“…TAs have been observed to attach to and inhibit muscarinic acetylcholine receptors [9]. TAs found in the Solanaceae are well known for both their anticholinergic and antispasmodic properties that affect the parasympathetic nervous system [10][11][12]. These plants have been used for pain relief, anesthesia, and as a treatment for drug addiction [10].…”

Section: Similarities and Differences In Medicinal Propertiesmentioning

confidence: 99%

Tropane and Granatane Alkaloid Biosynthesis: A Systematic Analysis

et al. 2016

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Abstract:The tropane and granatane alkaloids belong to the larger pyrroline and piperidine classes of plant alkaloids, respectively. Their core structures share common moieties and their scattered distribution among angiosperms suggest that their biosynthesis may share common ancestry in some orders, while they may be independently derived in others. Tropane and granatane alkaloid diversity arises from the myriad modifications occurring to their core ring structures. Throughout much of human history, humans have cultivated tropane-and granatane-producing plants for their medicinal properties. This manuscript will discuss the diversity of their biological and ecological roles as well as what is known about the structural genes and enzymes responsible for their biosynthesis. In addition, modern approaches to producing some pharmaceutically important tropanes via metabolic engineering endeavors are discussed.

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“…sedatives as well as to treat asthma, sialorrhea, Parkinson's disease, and motion sickness (Jakabová et al, 2012). Scopolamine has a higher market demand and price than other tropane alkaloids due to its higher pharmacological activity and lower side effects (Qiang et al, 2016).…”

Section: Introductionmentioning

confidence: 99%

“…The global scopolamine market was valued at US$ 370.4 million in 2017 (Coherent Market Insights Analysis, 2018). As these tropane alkaloids are difficulty and high costly to synthase, these alkaloids continue to be extracted from several species of Solanaceae, including Hyoscyamuns niger L., Anisodus tanguticus, Scopolia tangutica Maxim, Atropa belladonna, and several Datura species (Cardillo et al, 2010;Qiang et al, 2016). The aerial parts of Datura spp., obtained principally from India, is the main source, containing not less than 0.25% of alkaloids calculated as hyoscyamine (Evans, 2009).…”

Section: Introductionmentioning

confidence: 99%

Brugmansia suaveolens Leaf Productivity and Alkaloid Contents Under Different Doses of Organic Fertilizer

Reis¹,

Bragagnolo²,

Gianeti³

et al. 2019

JAS

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According to the World Health Organization, the use of mineral fertilizers and pesticides should be avoided in the cultivation of medicinal plants due to their potential antagonistic actions. Brugmansia spp. is a perennial bush native to South America, but it is also cultivated in Europe, Central America, and Asia due to its ornamental characteristics. Aerial parts of this plant are used in ethnomedicine to alleviate ulcers and pain, as well as to treat abscesses, fungal infection of the skin, and dermatitis. Tropane alkaloids scopolamine and atropine are recognized as active principles of this plant. This study evaluated the applicability of organic agricultural techniques in the cultivation of Brugmansia suaveolens. The influence of different dosages (0-60 tons/ha) of organic fertilizer on the mass productivity of plant shoot as well as their atropine and scopolamine contents were investigated. The average dry matter of leaves (26.54±5.12-55.41±12.85 g) and stems (26.73±8.51-58.60±17.62 g) per plant increased with increasingly availability of organic fertilizer (0-60 ton/ha). The same behavior was observed when the contents of the active tropane alkaloids scopolamine (0.72±0.03-0.86±0.13 mg/g) and atropine (0.79±0.03-0.96±0.11 mg/g) were monitored by gas chromatography coupled with mass spectrometer. Overall, the treatment at the maximum level tested in this work (60 ton/ha) should be preferred over the other treatments. B. suaveolens could be a potential source of tropane alkaloids for the community of Botucatu city, which is a leading city in Brazil for the cultivation of food products under organic, biodynamic, and agroecology premises.

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Functional characterisation of a tropine-forming reductase gene from Brugmansia arborea, a woody plant species producing tropane alkaloids

Cited by 23 publications

References 39 publications

Enhancing Tropane Alkaloid Production Based on the Functional Identification of Tropine-Forming Reductase in Scopolia lurida, a Tibetan Medicinal Plant

Enhancing Tropane Alkaloid Production Based on the Functional Identification of Tropine-Forming Reductase in Scopolia lurida, a Tibetan Medicinal Plant

Tropane and Granatane Alkaloid Biosynthesis: A Systematic Analysis

Brugmansia suaveolens Leaf Productivity and Alkaloid Contents Under Different Doses of Organic Fertilizer

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