7′,8′-Dihydroobolactone, a typanocidal α-pyrone from the rainforest tree Cryptocarya obovata

Davis, Rohan A.; Demirkiran, Özlem; Sykes, Melissa; Avery, Vicky M.; Suraweera, Lekha; Fechner, Gregory Allen; Quinn, Ronald J.

doi:10.1016/j.bmcl.2010.05.091

Cited by 34 publications

(35 citation statements)

References 13 publications

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“…Several Cryptocarya -derived compounds have been found to have diverse biological functions, i.e., anti-dengue virus by alkylated flavanones [ 10 ], anti-HIV by phenanthroindolizidine alkaloids [ 11 ], anti-tuberculosis by pinocembrin [ 12 ], anti-plasmodial by (+)-N-methylisococlaurine, atherosperminine, and 2-hydroxy-atherosperminine [ 13 ], anti-trypanosomal by 7′,8′-dihydroobolactone [ 14 ], and anti-inflammatory by (2S)-5,7-dihydroxyflavanone and cryptocaryanone B [ 15 ].…”

Section: Introductionmentioning

confidence: 99%

Antiproliferation of Cryptocarya concinna-derived cryptocaryone against oral cancer cells involving apoptosis, oxidative stress, and DNA damage

Chang

Tang

Yen

et al. 2016

BMC Complement Altern Med

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BackgroundCryptocarya-derived crude extracts and their compounds have been reported to have an antiproliferation effect on several types of cancers but their impact on oral cancer is less well understood.MethodsWe examined the cell proliferation effect and mechanism of C. concinna-derived cryptocaryone (CPC) on oral cancer cells in terms of cell viability, apoptosis, reactive oxygen species (ROS), mitochondrial depolarization, and DNA damage.ResultsWe found that CPC dose-responsively reduced cell viability of two types of oral cancer cells (Ca9-22 and CAL 27) in MTS assay. The CPC-induced dose-responsive apoptosis effects on Ca9-22 cells were confirmed by flow cytometry-based sub-G1 accumulation, annexin V staining, and pancaspase analyses. For oral cancer Ca9-22 cells, CPC also induced oxidative stress responses in terms of ROS generation and mitochondrial depolarization. Moreover, γH2AX flow cytometry showed DNA damage in CPC-treated Ca9-22 cells. CPC-induced cell responses in terms of cell viability, apoptosis, oxidative stress, and DNA damage were rescued by N-acetylcysteine pretreatment, suggesting that oxidative stress plays an important role in CPC-induced death of oral cancer cells.ConclusionsCPC is a potential ROS-mediated natural product for anti-oral cancer therapy.Electronic supplementary materialThe online version of this article (doi:10.1186/s12906-016-1073-5) contains supplementary material, which is available to authorized users.

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Section: Introductionmentioning

confidence: 99%

Antiproliferation of Cryptocarya concinna-derived cryptocaryone against oral cancer cells involving apoptosis, oxidative stress, and DNA damage

Chang

Tang

Yen

et al. 2016

BMC Complement Altern Med

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“…33 The bromotyrosine 19 is an example of a novel molecule with a previously unreported carbon skeleton that was isolated as part of the HAT campaign. 34 The known compounds 4, 28 5 and 6, 35 9, 30 11 and 12, 31 and 15 and 16 36 have newly described biological function ( Figure 6 and Table 2). Though limited to two compounds in each series, the demonstration of SAR across four series is noteworthy.…”

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confidence: 99%

Drug-like Properties: Guiding Principles for the Design of Natural Product Libraries

et al. 2011

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While natural products or their derivatives and mimics have contributed around 50% of current drugs, there has been no approach allowing front-loading of chemical space compliant with lead- and drug-like properties. The importance of physicochemical properties of molecules in the development of orally bioavailable drugs has been recognized. Classical natural product drug discovery has only been able to undertake this analysis retrospectively after compounds are isolated and structures elucidated. The present approach addresses front-loading of both extracts and subsequent fractions with desired physicochemical properties prior to screening for drug discovery. The physicochemical profiles of natural products active against two neglected disease targets, malaria and African trypanosomiasis, are presented based on this strategy. This approach can ensure timely development of natural product leads at a hitherto unachievable rate.

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“…The plant genus Cryptocarya (Lauraceae) includes over 200 species which are commonly distributed all over the tropical and subtropical regions of the world . Phytochemical studies on this species have led to the discovery of a variety of secondary metabolites, which include lignans, benzylisoquinolines,– proaporphine alkaloids,– flavonoids, cryptochinones, pavines,– and a variety of α ‐pyrone derivatives –. Many of these compounds display numerous biological activities, such as antioxidant, cytotoxic,, antimycobacterial, and antiparacytic activities.…”

Section: Introductionmentioning

confidence: 99%

Total Synthesis of Cryptorigidifoliol K: Confirmation of Structure and Absolute Configuration

et al. 2018

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Total synthesis of the revised cryptorigidifoliol K and 2'-epi-cryptorigidifoliol K was accomplished. Salient features of the synthesis involve tandem isomerization followed by CÀ O and CÀ C bond forming reaction, iodolactonization and Nozaki-Hiyama-Kishi reaction. The synthesis allowed for confirmation of the structure as well as the elucidation of the unassigned stereocenter present in the side chain of the revised structure by correlating the spectral and analytical data of the synthetic cryptorigidifoliol K and 2'epi-cryptorigidifoliol K with the natural product data, which was found to be 1S,5R,7S,2'R,3'E.[a] G.

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7′,8′-Dihydroobolactone, a typanocidal α-pyrone from the rainforest tree Cryptocarya obovata

Cited by 34 publications

References 13 publications

Antiproliferation of Cryptocarya concinna-derived cryptocaryone against oral cancer cells involving apoptosis, oxidative stress, and DNA damage

Antiproliferation of Cryptocarya concinna-derived cryptocaryone against oral cancer cells involving apoptosis, oxidative stress, and DNA damage

Drug-like Properties: Guiding Principles for the Design of Natural Product Libraries

Total Synthesis of Cryptorigidifoliol K: Confirmation of Structure and Absolute Configuration

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