Total Synthesis of (−)‐Dendrobine

Kreis, Lukas M.; Carreira, Erick M.

doi:10.1002/anie.201108564

Cited by 44 publications

(22 citation statements)

References 43 publications

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“…The Kreis-Carreira synthesis of dendrobine. 12 been published over the last forty years, not necessarily in chronological order and which represent a personal choice.…”

Section: Synthesis Of Dendrobine Sesquiterpene Alkaloidsmentioning

confidence: 99%

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The Chemistry of the Sesquiterpene Alkaloids

Brocksom¹,

Oliveira²,

Desiderá³

2017

J. Braz. Chem. Soc.

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“…The Kreis-Carreira synthesis of dendrobine. 12 been published over the last forty years, not necessarily in chronological order and which represent a personal choice.…”

Section: Synthesis Of Dendrobine Sesquiterpene Alkaloidsmentioning

confidence: 99%

“…This discussion starts with the most recent synthesis, performed by Kreis and Carreira, 12 published in 2012,…”

Section: Synthesis Of Dendrobine Sesquiterpene Alkaloidsmentioning

confidence: 99%

The Chemistry of the Sesquiterpene Alkaloids

Brocksom¹,

Oliveira²,

Desiderá³

2017

J. Braz. Chem. Soc.

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“…Moreover, dendrobine also exhibits antipyretic, hypertensive, and antiviral effects [8]. Although several groups have reported racemic and enantioselective syntheses for this compound during the past five decades [9][10][11][12], study on its biosynthetic pathway remains limited [13,14].…”

Section: Digital Signaturementioning

confidence: 99%

Transcriptomic landscape of Dendrobium huoshanense and its genes related to polysaccharide biosynthesis

et al. 2018

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Dendrobium huoshanense has long been used to treat various diseases in oriental medicine. In order to study its gene expression profile, transcripts involved in the biosynthesis of precursors of polysaccharides, as well as mechanisms underlining morphological differences between wild and cultivated plants, three organs of both wild type and cultivated D. huoshanense were collected and sequenced by Illumina HiSeq4000 platform, yielding 919,409,540 raw reads in FASTQ format. After Trinity de novo assembly and quality control, 241,242 nonredundant contigs with the average length of 967.5 bp were generated. qRT-PCR experiment on the selected transcripts showed the transcriptomic data were reliable. BLASTx was conducted against NR, SwissProt, String, Pfam, and KEGG. Gene ontology annotation revealed more than 40,000 contigs assigned to catalytic activity and metabolic process, suggesting its dynamic physiological activities. By searching KEGG pathway, six genes potentially involved in mannose biosynthetic pathway were retrieved. Gene expression analysis for stems between wild and cultivated D. huoshanense resulted in 956 genes differentially expressed. Simple sequence repeats (SSRs) analysis revealed 143 SSRs with the unit size of 4 and 3,437 SSRs the size of 3. The obtained SSRs are the potential molecular markers for discriminating distinct cultivars of D. huoshanense.

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“…The active medicinal ingredients in D. officinale include: polysaccharides, alkaloids, phenols, terpenes, flavonoids and bibenzyl [9][10]. In Dendrobium plants, the content of sesquiterpene alkaloid is the main measure of its quality and medicinal efficacy [11][12]. Notably, previous studies have found that bibenzyl compounds (belonging to sesquiterpene alkaloids) might be the only bioactive ingredients in D. officinale [13][14].…”

Section: Introductionmentioning

confidence: 99%

Transcriptomic analyses reveal putative genes associated with bibenzyl biosynthesis in the traditional Chinese herb Dendrobium officinale

Oi¹,

Guan²,

Yang³

et al. 2019

Preprint

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Background: Dendrobium plants are well known for their uses in traditional Chinese herbal medicine. Bibenzyl compounds are the main active compounds in Dendrobium officinale. However, the physiological and molecular basis for the biosynthesis of bibenzyl compounds in Dendrobium plants remains underexplored. Results: In this study, the accumulation of erianin and gigantol were studied as representative compounds of bibenzyl. Their presence in plant tissues were investigated. Our results show that root tissues contained the highest content of bibenzyl (erianin and gigantol). Based on the pre-experimental result that exogenous application of Methyl-Jasmonate promotes the biosynthesis of bibenzyl compounds in D. officinale root tissues, comparative transcriptomic analyses were conducted between the bibenzyl-accumulated root tissues and a control. In total, we identified 1,342 differentially expressed genes (DEGs) with 912 up-regulated and 430 down-regulated genes. Most of the identified DEGs are functionally involved in the JA signaling pathway and the biosynthesis of secondary metabolites. In particular, we identified 11 enzymatic genes functionally involved in bibenzyl biosynthesis.Conclusions: Our study provide insights on the identification of putative genes associated with bibenzyl biosynthesis and accumulation in Dendrobium plants, and also paves the way for future research on dissecting the physiological and molecular mechanisms of bibenzyl synthesis in plants as well as on how to best utilize genetic engineering and molecular modification techniques to genetically improve Dendrobium varieties by increasing the content of bibenzyl for drug production and industrialization. Keywords: Bibenzyl, D. officinale , Differentially expressed genes, Secondary metabolites, Transcriptome analysis.

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Total Synthesis of (−)‐Dendrobine

Cited by 44 publications

References 43 publications

The Chemistry of the Sesquiterpene Alkaloids

The Chemistry of the Sesquiterpene Alkaloids

Transcriptomic landscape of Dendrobium huoshanense and its genes related to polysaccharide biosynthesis

Transcriptomic analyses reveal putative genes associated with bibenzyl biosynthesis in the traditional Chinese herb Dendrobium officinale

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