A convergent stereocontrolled synthesis of [3‐<sup>14</sup>C]solanesol

Roe, Stephen J.; Oldfield, Mark F.; Geach, N. J.; Baxter, Andrew

doi:10.1002/jlcr.3083

Cited by 14 publications

(15 citation statements)

References 12 publications

(34 reference statements)

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“…After chemical synthesis, solanesol contains cis and trans structures; in contrast, solanesol derived from natural sources in plants contains only the trans Phytochem Rev structure with a and b forms (Roe et al 2013). X-ray diffraction study showed, a form was in one plane, and b form was folded (Stedman 1968).…”

Section: Existing Forms In Plantsmentioning

confidence: 97%

“…While artificially synthesised solanesol contains both cis and trans structures, solanesol formed in plants contains only the trans structure (Roe et al 2013), and this should be considered when developing novel solanesol-based drugs. Solanesol has strong free radical absorption properties because of its nonconjugated double bonds; as a natural extract, solanesol is expected to have applications in the inhibition of skin aging and senile plaque formation (Bai et al 2014).…”

Section: Production Of New Drugsmentioning

confidence: 99%

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Solanesol: a review of its resources, derivatives, bioactivities, medicinal applications, and biosynthesis

et al. 2015

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Solanesol, which mainly accumulates in solanaceous crops, including tobacco, tomato, potato, eggplant, and pepper plants, is a long-chain polyisoprenoid alcohol compound with nine isoprene units. Chemical synthesis of solanesol is difficult; therefore, solanesol is primarily extracted from solanaceous crops, particularly tobacco leaves. In plants, solanesol exists in both free and esterified forms, and its accumulation is influenced by genetic and environmental factors. Solanesol is widely used in the pharmaceutical industry as an intermediate for the synthesis of ubiquinone drugs, such as coenzyme Q10 and vitamin K2. Solanesol possesses antibacterial, antifungal, antiviral, anticancer, anti-inflammatory, and anti-ulcer activities, and solanesol derivatives also have anti-oxidant and antitumour activities, in addition to other bioactivities. Solanesol derivatives can also be used for the treatment of cardiovascular disease, osteoporosis, acquired immune deficiency syndrome, and wound healing. Solanesol biosynthesis occurs in plastids of higher plants via the 2-C-methyl-D-erythritol-4-phosphate (MEP) pathway. The key enzymes in solanesol biosynthesis, including 1-deoxy-D-xylulose-5-phosphate synthase, 1-deoxy-D-xylulose-5-phosphate-reductoisomerase, isopentenyl pyrophosphate isomerase, and solanesyl diphosphate synthase, are also important regulators of the MEP pathway, and their overexpression is favourable for downstream metabolic flow, further promoting the synthesis of downstream metabolites, such as solanesol. Future studies should determine the pharmacokinetic properties of solanesol and its derivatives and investigate the metabolic pathways and regulatory mechanisms mediating solanesol biosynthesis, metabolic and genetic engineering of solanesol, the synthetic biology of solanesol, and the physiological role of solanesol. In the present review, we systematically summarise current knowledge on solanesol resources, derivatives, bioactivities and medicinal applications, metabolic pathways, and key biosynthetic enzymes.

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Section: Existing Forms In Plantsmentioning

confidence: 97%

Section: Production Of New Drugsmentioning

confidence: 99%

Solanesol: a review of its resources, derivatives, bioactivities, medicinal applications, and biosynthesis

et al. 2015

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“…Because the chemical synthesis of solanesol is difficult [11], we assessed some aspects of its biosynthesis in tobacco plants and observed differential accumulation of solanesol in the leaves, stems, and roots of tobacco plants, with the content in leaves being the highest (Figure 2A). Thus, tobacco leaves could be the ideal material for extracting solanesol [3,12].…”

Section: Solanesol Is Abundant In Tobacco Leavesmentioning

confidence: 99%

RNA-seq Analysis of Solanesol Biosynthesis Genes in <em>Nicotiana tabacum</em>

Ning

Zhang

et al. 2016

Preprint

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Solanesol is a noncyclic terpene alcohol composed of nine isoprene units and it mainly accumulates in solanaceous plants, especially tobacco (Nicotiana tabacum L.). Here, RNA-seq analyses of tobacco leaves, stems, and roots were used to identify solanesol biosynthesis genes. Six 1-deoxy-D-xylulose 5-phosphate synthase, two 1-deoxy-D-xylulose 5-phosphate reductoisomerase, two 2-C-methyl-D-erythritol 4-phosphate cytidylyltransferase, four 4-diphosphocytidyl-2-Cmethyl-D-erythritol kinase, two 2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase, four 1-hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate synthase, two 1-hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate reductase, six isopentenyl diphosphate isomerase, and two solanesyl diphosphate synthase (SPS) genes were identified to be involved in solanesol biosynthesis. Furthermore, the two N. tabacum SPS (NtSPS1 and NtSPS2), which had two conserved aspartate-rich DDxxD domains, were highly homologous with SPS enzymes from other solanaceous plant species. In addition, the solanesol contents of three organs, and leaves from four growing stages, corresponded with the distribution of chlorophyll. Our findings provide a comprehensive evaluation of the correlation between the expression of different biosynthetic genes and the accumulation of solanesol in tobacco.

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“…Solanesol exist in both cis and trans states, for this experiment we considered only trans as it is 122 only found in natural sources (Roe, Oldfield, Geach, & Baxter, 2013). The structure of Solanesol 123 was obtained from PubChem compound (CID 5477212) (Kim et al, 2015;NCBI 2016).…”

Section: Ligand Preparation 121mentioning

confidence: 99%

Establishing wonder oil, Solanesol, as a novel inhibitor for Focal Adhesive Kinase by in silico strategies

Daneial

Das²,

et al. 2016

Preprint

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Kinase by in silico strategies32 Focal adhesion kinase (FAK) plays a primary role in regulating the activity of many 33 signaling molecules. Increased FAK expression has been implicated in a series of cellular 34 processes, including cell migration and survival. Inhibiting the activity of FAK for cancer 35 therapy is currently under investigation. Hence, FAK and its inhibitors has been the subject 36 of intensive research. To understand the structural factors affecting inhibitory potency, 37 kinetic analysis, molecular docking and molecular dynamics simulation were studied in 38 this project. Though, Solanesol was found have inhibitory activities towards FAK, no in 39 silico tests were ever done on the same. 40 Due to high flexibility of Solanesol (Rotatable bonds = 25), it is difficult to analyze using 41 normal docking protocols. This paper introduces a novel method to dock and analyze 42 molecules with high flexibility based on weighed contact based scoring method. This 43 method uses blind docking technique, which was developed for protein peptide docking 44 method, to generate conformations which were used to calculate contact based weights of 45 residues. This method reveals the possible binding site for the small molecule. An 46 exhaustive docking search on the acquired area reveals the docked confirmation of the 47 compound. The final docked conformation was subjected to molecular dynamics to 48 understand of binding stability. This study is in a good agreement with experimental results 49 which shows Solanesol binds at ATP binding site and inhibit the phosphorylation of Focal 50 Adhesion Kinase.51

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A convergent stereocontrolled synthesis of [3‐¹⁴C]solanesol

Cited by 14 publications

References 12 publications

Solanesol: a review of its resources, derivatives, bioactivities, medicinal applications, and biosynthesis

Solanesol: a review of its resources, derivatives, bioactivities, medicinal applications, and biosynthesis

RNA-seq Analysis of Solanesol Biosynthesis Genes in <em>Nicotiana tabacum</em>

Establishing wonder oil, Solanesol, as a novel inhibitor for Focal Adhesive Kinase by in silico strategies

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A convergent stereocontrolled synthesis of [3‐14C]solanesol

Cited by 14 publications

References 12 publications

Solanesol: a review of its resources, derivatives, bioactivities, medicinal applications, and biosynthesis

Solanesol: a review of its resources, derivatives, bioactivities, medicinal applications, and biosynthesis

RNA-seq Analysis of Solanesol Biosynthesis Genes in <em>Nicotiana tabacum</em>

Establishing wonder oil, Solanesol, as a novel inhibitor for Focal Adhesive Kinase by in silico strategies

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A convergent stereocontrolled synthesis of [3‐¹⁴C]solanesol