On the Biosynthesis of Cantharidin

Guenther, H.; Ramstad, Egil; Floss, Heinz G.

doi:10.1002/jps.2600581027

Cited by 17 publications

(9 citation statements)

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“…However, Guenther et al [71] verified that cantharidin could not be synthesized by acetate through degradation experiment. McCormick, et al [72] have demonstrated that cantharidin is produced by degradation of the farnesol carbon skeleton and suggested the possibility of cantharidin as a juvenile hormone metabolite by tracing the source of oxygen atoms in cantharidin using the isotope-labeling method.…”

Section: Discussionmentioning

confidence: 99%

Comparative Proteomics and Expression Analysis of Five Genes in Epicauta chinensis Larvae from the First to Fifth Instar

Wang²,

ShuMin

et al. 2014

PLoS ONE

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Blister beetle is an important insect model for both medicinal and pure research. Previous research has mainly focused on its biology and biochemistry, but very little data is yet available in the molecular biology. This study uses differential proteomics technology to analyze the soluble proteins extracted from each of the 5 instars larvae of Epicauta chinensis. 42 of the differentially-expressed proteins were identified successfully by MALDI-TOF/TOF-MS. Some of these proteins’ function and their expression profiles are analyzed. Our analysis revealed dynamics regulation of the following proteins: Axin-like protein pry-1 (APR-1), dihydrolipoyl dehydrogenase (DLD), vitellogenin (Vg) and lysozyme C (Lmz-S). APR-1 negatively regulates the Wnt signaling pathway. Its overexpression could result in embryo, leg, eye and ovary ectopica or malformation. DLD catalyzes the pyruvate into acetyl-CoA, the latter is the starting material of juvenile hormone (JH) and ipsdienol biosynthesis through the MVA pathway in insects. While Vg synthesis can be regulated by JH and stimulated by food factors. So DLD may affect the synthesis of JH, ipsdienol and Vg indirectly. The activity of lysozyme is an indicator of the immunity. Nutrition/food should be taken into account for its potential role during the development of larva in the future. Among the five genes and their corresponding proteins’ expression, only hsc70 gene showed a good correspondence with the protein level. This reflects the fluctuating relationship between mRNA and protein levels.

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Section: Discussionmentioning

confidence: 99%

Comparative Proteomics and Expression Analysis of Five Genes in Epicauta chinensis Larvae from the First to Fifth Instar

Wang²,

ShuMin

et al. 2014

PLoS ONE

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“…As has been described earlier, CTD is exclusively biosynthesized by male beetles of the family Meloidae. Although detailed mechanism of biosynthesis of CTD is unknown at present, the above facts can conclude that the production of CTD may be a more complicated process and seem to even cast some doubts on the mevalonoid origin of this compound; however, specialized researches on this have suggested that instead of the two obvious possible routes – the tail‐to‐tail condensation of two isoprene units and the head‐to‐tail condensation of two isoprene units followed by a methyl shift – several unknown oxidation processes from farnesol 4 would be involved in CTD biosynthesis (Figure ).…”

Section: Cantharidin and Norcantharidin: Origin And Historymentioning

confidence: 99%

Cantharidin‐Based Small Molecules as Potential Therapeutic Agents

2013

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Chemical and pharmacological information on cantharidin-based small molecules was analyzed. The review summarizes new facts about blister beetles' metabolites for the period 2006-2012. General synthetic approaches to cantharidin-based small molecules as well as their chemical transformations and biological activities related to cantharidin, norcantharidin, cantharidimide, and norcantharimide analogs, especially their inhibitory activity of phosphoprotein phosphatases in cancer treatment, were discussed in this mini review, which could help to design new small molecule modulators for other biological models.Key words: anticancer activity, blister beetles, cantharidin analogs, Diels-Alder cycloaddition reactions, drug design and development, protein phosphatases inhibitory activity With the development in the natural product chemistry, giving many interesting objects to study from the structural, synthetic, and pharmacological standpoints, the organic synthesis had evolved at the same rate with the generation of molecules/molecular assemblies with welldefined biological functions, and within this challenging task in the biology-oriented synthesis field, the design and development of more efficient chemical reactions and methodologies would revolutionize the next generation of chemical and biological research. Secondary metabolites of plants and animals are the main objects to study phytochemistry and organic chemistry, as shown by their centennial history that has successfully promoted the discovery and drug development. According to a recent analysis, in the last 25 years, nearly half of the drugs currently in clinical use belong to drugs of natural origin (1,2). Therefore, the success of drug discovery based on nature's secondary metabolites depends on how these natural substances are considered, mainly by medicinal and organic chemists, as source of inspiration rather than target molecules (3-6).For centuries, it has well known that many plants (shrubs, trees and grasses) possess a wide spectrum of medicinal properties and that bacterium and fungi are also capable of generating toxic constituents that inhibit the growth of other organisms in their proximity. These kingdoms have provided us more information, regarding the biological interactions of small molecules (SMs), to understand and encourage our investigations in the discovery and development of new SMs with marked physiological activities (7,8). In addition, these SMs are also useful for investigating biological systems as effective tools to elucidate the mechanism of important cellular processes that are based purely on (i) the performance of enzymatic reactions and (ii) protein-protein interactions, where the bioactive SMs are called bioprobes, and more importantly, (iii) the fact that they allow the rapid and conditional modulation of biological functions often in a reversible, dose-dependent manner (9,10).In contrast to plants and bacteria, the invertebrate animal kingdom, to which belong different insects (about a million species) including beetles,...

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“…Cantharidin (C 10 H 12 O 4 ), a terpene including 10 carbon atoms, was first supposed to be constituted by two isoprene units (Ruzicka, ). However, isotope‐labelled experiments demonstrated that CTD was formed by neither head‐to‐tail nor tail‐to‐tail linkage of two isoprene units by feeding Lytta vesicatoria with labeled precursor (Schlatter et al ., ; Guenther et al ., ). Subsequent research has found that CTD might be derived from a C 15 ‐intermediate, farnesol, with cleaving of carbon‐carbon bond and an intramolecular conversion (Peter et al ., , ; Woggon et al ., ).…”

Section: Introductionmentioning

confidence: 97%

Characterized cantharidin distribution and related gene expression patterns in tissues of blister beetles, Epicauta chinensis

Jiang

et al. 2017

Insect Science

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Cantharidin (CTD), a terpenoid defensive toxin mainly produced by blister beetles, is widely known by its toxicity to both cancer cells and pests. However, little information is known about its biosynthesis in blister beetles. In this study, first we determined the CTD content in various tissues of adult blister beetles on different days after mating, and then detected the temporal and spatial expression patterns of genes related to CTD biosynthesis in Epicauta chinensis. Results revealed that the accessory gland is the source of the highest CTD production. The second highest level was in the fat body in male blister beetles after mating. In females, the highest CTD content was in the reproductive system except the ovary after mating. As revealed by messenger RNA expression level analysis, the highest levels of 3-hydroxy-3-methylglutary-CoA reductase (HMGR) and juvenile hormone epoxide hydrolase (JHEH) transcripts of E. chinensis were observed in the fat body in males after mating. However, the highest transcript level of EcHMGR was in the ovary and EcJHEH was maintained at a nearly similar level in females. The transcript level of methyl-farnesoate epoxide was significantly higher in the head and that of CYP4BM1 in the midgut in both male and female E. chinensis. We speculate that the fat body may play a more important role than other tissues on the CTD biosynthesis in male E. chinensis after mating. There may be multiple tissues involved in the process of CTD biosynthesis. These four genes probably play regulatory roles in different tissues in males.

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On the Biosynthesis of Cantharidin

Cited by 17 publications

References 1 publication

Comparative Proteomics and Expression Analysis of Five Genes in Epicauta chinensis Larvae from the First to Fifth Instar

Comparative Proteomics and Expression Analysis of Five Genes in Epicauta chinensis Larvae from the First to Fifth Instar

Cantharidin‐Based Small Molecules as Potential Therapeutic Agents

Characterized cantharidin distribution and related gene expression patterns in tissues of blister beetles, Epicauta chinensis

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