Total Synthesis of a Dimeric Thymol Derivative Isolated from <i>Arnica sachalinensis</i>

Silvestro, Irene De; Drew, Samuel L; Nichol, Gary S.; Duarte, Fernanda; Lawrence, Andrew L.

doi:10.1002/anie.201701481

Cited by 18 publications

(11 citation statements)

References 51 publications

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“…Column chromatography followed by preparative HPLC could then be used to access analytically pure samples of thymarnicol (1;4 0mgp repared so far), but still as an unavoidable mixture of the two lactol epimers.Crystallization from acetonitrile resulted in crystals suitable for single-crystal X-ray diffraction studies. [10] Thec rystal structure obtained matched that reported for the natural material, [1b] which consists of just one lactol epimer (Scheme 2). Nevertheless, subsequent analysis of these crystals by solution-phase 1 HNMR spectroscopy showed the presence of both lactol epimers.Itmust be concluded that thymarnicol (1)isstereodynamic;itexists as amixture of lactol epimers in solution but can exist as asingle epimer in the solid state.T hus,asix-step total synthesis of thymarnicol (1)has been achieved, involving the formation of nine new bonds (three C À C, six C À O), three new rings,and four new stereogenic centres.…”

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confidence: 79%

“…[18] Similarly,a ttempts to cleave the MOM ethers in epoxide 18 led to the formation of bislactones 19 in high yield (Scheme 5b). [10,19] Thep redisposed nature of these rearrangements,w hich presumably occur through [1,2]-shift mechanisms (see Scheme 5), leads us to speculate that structures akin to 17 and 19 might be isolated as natural products in the future. [20] In conclusion, through our synthetic efforts,wehave been able to investigate the chemical feasibility of Passreiters suggested biosynthetic pathway for thymarnicol (1).…”

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confidence: 99%

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Total Synthesis of a Dimeric Thymol Derivative Isolated from Arnica sachalinensis

et al. 2017

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The total synthesis of a dimeric thymol derivative (thymarnicol) isolated from Arnica sachalinensis was accomplished in 6 steps. A key biomimetic Diels–Alder dimerization was found to occur at ambient temperature and the final oxidative cyclization occurs when the substrate is exposed to air and visible light. These results indicate that this natural product is likely the result of spontaneous (non‐enzyme‐mediated) reactivity.

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confidence: 99%

Total Synthesis of a Dimeric Thymol Derivative Isolated from Arnica sachalinensis

et al. 2017

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“…Eugenol, a phenylpropanoid, can be isolated from the plant like Syzygium aromaticum [ 44 ], Eugenia caryophyllata [ 45 ], and Ocimum gratissimum L. [ 46 ]. Thymol, a phenolic monoterpenoid, can be isolated from various natural sources like T. vulgaris L. [ 43 ], O. dictamnus L. [ 41 ] and Arnica sachalinensis [ 47 ]. Geraniol, acyclic alcohol monoterpene, can be isolated from various sources like Rosa damascene [ 48 ], Cymbopogon winterianus [ 49 ], etc.…”

Section: Methodsmentioning

confidence: 99%

Molecules and Metabolites from Natural Products as Inhibitors of Biofilm in Candida spp. pathogens

Singla

Dubey

2019

CTMC

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Background: Biofilm is a critical virulence factor associated with the strains of Candida spp. pathogens as it confers significant resistance to the pathogen against antifungal drugs. Methods: A systematic review of the literature was undertaken by focusing on natural products, which have been reported to inhibit biofilms produced by Candida spp. The databases explored were from PubMed and Google Scholar. The abstracts and full text of the manuscripts from the literature were analyzed and included if found significant. Results: Medicinal plants from the order Lamiales, Apiales, Asterales, Myrtales, Sapindales, Acorales, Poales and Laurales were reported to inhibit the biofilms formed by Candida spp. From the microbiological sources, lactobacilli, Streptomyces chrestomyceticus and Streptococcus thermophilus B had shown the strong biofilm inhibition potential. Further, the diverse nature of the compounds from classes like terpenoids, phenylpropanoid, alkaloids, flavonoids, polyphenol, naphthoquinone and saponin was found to be significant in inhibiting the biofilm of Candida spp. Conclusion: Natural products from both plant and microbial origins have proven themselves as a goldmine for isolating the potential biofilm inhibitors with a specific or multi-locus mechanism of action. Structural and functional characterization of the bioactive molecules from active extracts should be the next line of approach along with the thorough exploration of the mechanism of action for the already identified bioactive molecules.

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“…Titanium scaffold treatment protocol, to avoid particulates, autoclave sterilization followed by an ultrasonic bath for 5 min in deionized H 2 O, and then for 5 min in H 2 O 2 at 120 v / v , and again for 10 min in deionized H 2 O, was performed, as decribed by Di Silvestro et al [ 30 ]. Furthermore, to avoid alterations of the superficial layer of the scaffolds, an important factor in cell/surface interaction, particular care was taken in performing any and all manipulations of the titanium scaffolds using only plastic or pure titanium instruments.…”

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confidence: 99%

Rapid Rapamycin-Only Induced Osteogenic Differentiation of Blood-Derived Stem Cells and Their Adhesion to Natural and Artificial Scaffolds

Arianna

Cozzoli

Flavio³

et al. 2017

Stem Cells International

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Stem cells are a centerpiece of regenerative medicine research, and the recent development of adult stem cell-based therapy systems has vigorously expanded the scope and depth of this scientific field. The regeneration of damaged and/or degraded bone tissue in orthopedic, dental, or maxillofacial surgery is one of the main areas where stem cells and their regenerative potential could be used successfully, requiring tissue engineering solutions incorporating an ideal stem cell type paired with the correct mechanical support. Our contribution to this ongoing research provides a new model of in vitro osteogenic differentiation using blood-derived stem cells (BDSCs) and rapamycin, visibly expressing typical osteogenic markers within ten days of treatment. In depth imaging studies allowed us to observe the adhesion, proliferation, and differentiation of BDSCs to both titanium and bone scaffolds. We demonstrate that BDSCs can differentiate towards the osteogenic lineage rapidly, while readily adhering to the scaffolds we exposed them to. Our results show that our model can be a valid tool to study the molecular mechanisms of osteogenesis while tailoring tissue engineering solutions to these new insights.

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Total Synthesis of a Dimeric Thymol Derivative Isolated from Arnica sachalinensis

Cited by 18 publications

References 51 publications

Total Synthesis of a Dimeric Thymol Derivative Isolated from Arnica sachalinensis

Total Synthesis of a Dimeric Thymol Derivative Isolated from Arnica sachalinensis

Molecules and Metabolites from Natural Products as Inhibitors of Biofilm in Candida spp. pathogens

Rapid Rapamycin-Only Induced Osteogenic Differentiation of Blood-Derived Stem Cells and Their Adhesion to Natural and Artificial Scaffolds

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