Synthesis and evaluation of (−)-Massoialactone and analogues as potential anticancer and anti-inflammatory agents

Barros, Maria E.S.B.; Freitas, Juliano Carlo Rufino; Oliveira, José Nuno; Cruz, Carlos; Silva, Paulo B.N. da; Araújo, Larissa Cardoso Corrêa de; Militão, Gardênia Carmen Gadelha; Silva, Teresinha G. da; Oliveira, Roberta A.; Menezes, Paulo H.

doi:10.1016/j.ejmech.2014.02.013

Cited by 34 publications

(24 citation statements)

References 62 publications

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“…The procedures used for synthesis of the lactones 6-(but-3-enyl)-5,6-dihydro-2H-pyran-2-one (5a), 6-(allyloxymethyl)-5,6-dihydro-2H-pyran-2-one (5b), 6-ethyl-5,6-dihydro-2H-pyran-2-one (5c), 6-(phenoxymethyl)-5,6-dihydro-2H-pyran-2-one (5d), 6-phenyl-5,6-dihydro-2H-pyran-2-one (5e), and 5-phenyl-5,6-dihydro-2H-pyran-2-one (5f) are described by Barros et al (2014) and by Oliveira et al (2011). The physical and spectroscopic data are in agreement with those reported in the literature, the purity of all compounds was ≥95%, and the yields obtained were 68%, 77%, 73%, 62%, 53% and 67%, respectively.…”

Section: Synthesis Of the αβ-Unsaturated Lactonesmentioning

confidence: 99%

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Effects of α,β-unsaturated lactones on larval survival and gut trypsin as well as oviposition response of Aedes aegypti

Barros

Freitas

Santos

et al. 2015

Experimental Parasitology

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Lactones are organic cyclic esters that have been described as larvicides against Aedes aegypti and as components of oviposition pheromone of Culex quinquefasciatus. This work describes the effect of six α,β-unsaturated lactones (5a-5f) on survival of A. aegypti fourth instar larvae (L4). It is also reported the effects of the lactones on L4 gut trypsin activity and oviposition behavior of A. aegypti females. Five lactones were able to kill L4 being the lactones 5a (LC50 of 39.05 ppm), 5e (LC50 of 36.30 ppm) and 5f (LC50 of 40.46 ppm) the most promising larvicides. Only the lactone 5a inhibited L4 gut trypsin activity, with an IC50 of 115.15 µg/mL. Lactones 5a, 5c, 5d and 5e did not exert deterrent or stimulatory effects on oviposition, whereas lactone 5b exhibited a strong deterrent oviposition activity. In conclusion, this work introduces new α,β-unsaturated lactones as promising alternatives to control A. aegypti dissemination. The larvicidal mechanism of the lactone 5a can involve the disruption of proteolysis at larval gut.

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Section: Synthesis Of the αβ-Unsaturated Lactonesmentioning

confidence: 99%

“…1) were synthesized and investigated for the in vitro antitumor and antiinflammatory activities with moderate toxicity (Barros et al, 2014;Freitas et al, 2012).…”

Section: Introductionmentioning

confidence: 99%

Effects of α,β-unsaturated lactones on larval survival and gut trypsin as well as oviposition response of Aedes aegypti

Barros

Freitas

Santos

et al. 2015

Experimental Parasitology

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“…The 3,5-dihydroxydecanoic acids released from liamocins can be spontaneously transformed into 5-hydroxy-2-decenoic acid lactone which is a massoia lactone, a natural coconut flavor. The formed massoia lactone also has many functions and applications [9]. It has been reported that massoia lactone produced by A. pullulans YTP6-14 indeed showed significant surface tension reduction capacity of 43.3 mN/ml at 1.0 mg/ml [6].…”

Section: Introductionmentioning

confidence: 97%

Genetic evidences for the core biosynthesis pathway, regulation, transport and secretion of liamocins in yeast-like fungal cells

Xue

Liu

Chi

et al. 2020

Biochemical Journal

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So far, it has been still unknown how liamocins are biosynthesized, regulated, transported and secreted. In this study, a highly reducing polyketide synthase (HR-PKS), a mannitol- 1-phosphate dehydrogenase (MPDH), a mannitol dehydrogenase (MtDH), an arabitol dehydrogenase (ArDH) and an esterase (Est1) were found to be closely related to core biosynthesis of extracellular liamocins in Aureobasidium melanogenum 6-1-2. The HR-PKS was responsible for biosynthesis of 3,5-dihydroxydecanoic acid. The MPDH and MtDH were implicated in mannitol biosynthesis and the ArDH was involved in arabitol biosynthesis. The Est1 catalyzed ester bond formation of them. A phosphopantetheine transferase (PPTase) activated the HR-PKS and a transcriptional activator Ga11 activated expression of the PKS1 gene. Therefore, deletion of the PKS1 gene, all the three genes encoding MPDH, MtDH and ArDH, the EST1, the gene responsible for PPTase and the gene for Ga11 made all the disruptants (Dpks13, Dpta13, Dest1, Dp12 and Dg11) totally lose the ability to produce any liamocins. A GLTP gene encoding a glycolipid transporter and a MDR1 gene encoding an ABC transporter took part in transport and secretion of the produced liamocins into medium. Removal of the GLTP gene and the MDR1 gene resulted in a Dgltp1 mutant and a Dmdr16 mutant, respectively, that lost the partial ability to secrete liamocins, but which cells were swollen and intracellular lipid accumulation was greatly enhanced. Hydrolysis of liamocins released 3,5-dihydroxydecanoic acid, mannitol, arabitol and acetic acid. We proposed a core biosynthesis pathway, regulation, transport and secretion of liamocins in A. melanogenum.

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“…Massoia lactone is the dominant component in Cs‐4 mycelium volatiles (accounting for 70%–80%), and thus, could be regarded as a marker for quality control of this product. Furthermore, phytochemical investigations have demonstrated that massoia lactone exhibits potential antifungal, antiviral, anticancer, and anti‐inflammatory activities, which might contribute to the pharmacological effects of Cs‐4 mycelium (Barros et al., 2014; Kishimoto, Sugihara, Mochida, & Fujita, 2005).…”

Section: Introductionmentioning

confidence: 99%

HPLC determination of massoia lactone in fermented Cordyceps sinensis mycelium Cs‐4 and its anticancer activity in vitro

et al. 2020

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The fermentation product of Cordyceps sinensis mycelium Cs‐4 was commonly used as alternative substitutes of natural C. sinensis. Massoia lactone is the dominant component in the volatile oil of Cs‐4 mycelium. In this research, we present a high performance liquid chromatography (HPLC) method for the quantitation of massoia lactone in Cs‐4 mycelium. The high and stable contents of massoia lactone with values of 2.98–3.77 mg/g, indicated that massoia lactone could be considered as a marker for the quality assessment of this product. The results of MTT and CCK‐8 assay showed that Cs‐4 mycelium volatiles exhibited cytotoxicity against eight malignant tumor cells (IC50 = 6.0–49.8 μg/ml) in comparison to the anticancer drug 5‐fluorouracil (IC50 = 17.0–425.3 μg/ml), and massoia lactone might be the chemical basis for the anticancer effects of Cs‐4 mycelium. Compared to the commercial drugs paclitaxel and docetaxel (IC50 = 253–1973 μg/ml), the Cs‐4 mycelium volatiles and massoia lactone were discovered to possess inhibitory to taxol‐resistant cell lines (IC50 = 1.5–8.6 μg/ml). Practical applications Considering that there is still a lack of marker components distinctive to Cs‐4 mycelium, the HPLC method represents a useful tool for the quality evaluation of Cs‐4 mycelium. Moreover, the volatile oil of Cs‐4 mycelium and massoia lactone have prominent anticancer property in vitro. It gives a clue that Cs‐4 mycelium, the volatile oil and massoia lactone could be potentially employed in the food and medical industries for its anticancer applications.

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Synthesis and evaluation of (−)-Massoialactone and analogues as potential anticancer and anti-inflammatory agents

Cited by 34 publications

References 62 publications

Effects of α,β-unsaturated lactones on larval survival and gut trypsin as well as oviposition response of Aedes aegypti

Effects of α,β-unsaturated lactones on larval survival and gut trypsin as well as oviposition response of Aedes aegypti

Genetic evidences for the core biosynthesis pathway, regulation, transport and secretion of liamocins in yeast-like fungal cells

HPLC determination of massoia lactone in fermented Cordyceps sinensis mycelium Cs‐4 and its anticancer activity in vitro

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