Regioselective route for arylnaphthalene lactones: convenient synthesis of taiwanin C, justicidin E, and daurinol

Park, Ju-Eun; Lee, Juyeun; Seo, Seung‐Yong; Shin, Dongyun

doi:10.1016/j.tetlet.2013.12.014

Cited by 31 publications

(21 citation statements)

References 20 publications

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“…Daurinol used in this study was chemically synthesized according to recently reported methods (9). Natural daurinol was isolated from Haplophyllum dauricum as previously described (6).…”

Section: Methodsmentioning

confidence: 99%

“…Thus, we prepared synthetic daurinol using recently described regioselective chemical synthesis methods (9) and tested its anticancer activity in various cancer cells, including HCT116 cells. The anti-proliferative activity (IC 50 value) of synthetic daurinol was equivalent to that of natural daurinol in HCT116 cells.…”

Section: Synthetic Daurinol and Natural Daurinol Have Equivalent Antimentioning

confidence: 99%

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Daurinol, a catalytic inhibitor of topoisomerase IIα, suppresses SNU-840 ovarian cancer cell proliferation through cell cycle arrest in S phase

Kang

Nho

Kim

et al. 2014

International Journal of Oncology

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Abstract. Daurinol, a lignan from the ethnopharmacological plant Haplophyllum dauricum, was recently reported to be a novel topoisomerase II inhibitor and an alternative to the clinical anticancer agent etoposide based on a colorectal cancer model. In the present study, we elucidated the detailed biochemical mechanism underlying the inhibition of human topoisomerase IIα by daurinol based on a molecular docking study and in vitro biochemical experiments. The computational simulation predicted that daurinol binds to the ATP-binding pocket of topoisomerase IIα. In a biochemical assay, daurinol (10-100 µM) inhibited the catalytic activity of topo isomerase IIα in an ATP concentration-dependent manner and suppressed the ATP hydrolysis activity of the enzyme. However, daurinol did not inhibit topoisomerase I activity, most likely because topoisomerase I does not contain an ATP-binding domain. We also evaluated the anti-proliferative activity of daurinol in ovarian, small cell lung and testicular cancer cells, common target cancers treated with etoposide. Daurinol potently inhibited SNU-840 human ovarian cancer cell proliferation through cell cycle arrest in S phase, while etoposide induced G2/M phase arrest. Daurinol induced the increased expression of cyclin E, cyclin A and E2F-1, which are important proteins regulating S phase initiation and progression. Daurinol did not induce abnormal cell and nuclear enlargement in SNU-840 cells, in contrast to etoposide. Based on these data, we suggest that daurinol is a potential anticancer drug candidate for the treatment of human ovarian cancer with few side effects. IntroductionTopoisomerases are essential enzymes in all organisms that are involved in the topological homeostasis of DNA molecules during DNA replication, transcription and chromosomal segregation. Topoisomerases are classified into two classes, topoisomerase I and II, which create single and double-strand breaks, respectively. Because topoisomerases are crucial enzymes in DNA replication, they have served as primary targets for the development of anticancer agents (1,2). Topoisomerase II inhibitors such as etoposide, teniposide and doxorubicin have been extensively used in clinical cancer treatment. However, these agents also have undesirable side effects, including immunosuppression, myelosuppression, gastrointestinal toxicity and the development of secondary leukemia (3). Thus, the discovery of new topoisomerase inhibitors with fewer side effects from natural products has received a great deal of attention (4,5).Daurinol is a natural arylnaphthalene lignan isolated from the traditional medicinal plant Haplophyllum dauricum (6). According to an ethnopharmacological study, this plant has been used to treat tumors in Russia (7). The chemical structure of daurinol is similar to that of the clinical anticancer agent VP-16 (also known as etoposide phosphate). Recently, we suggested that daurinol could be a promising antitumor agent with minimal side effects, compared to etoposide, based on in vitro and in vivo resu...

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“…Daurinol used in this study was chemically synthesized according to recently reported methods (9). Natural daurinol was isolated from Haplophyllum dauricum as previously described (6).…”

Section: Methodsmentioning

confidence: 99%

Section: Synthetic Daurinol and Natural Daurinol Have Equivalent Antimentioning

confidence: 99%

Daurinol, a catalytic inhibitor of topoisomerase IIα, suppresses SNU-840 ovarian cancer cell proliferation through cell cycle arrest in S phase

Kang

Nho

Kim

et al. 2014

International Journal of Oncology

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“…Since the report of early efforts on the synthesis of arylnaphthalene lignan lactone in 1895 by Michael and Bucher ( 1895 ) and in 1910 by Bucher ( 1910 ) using the thermal cyclative condensation reaction of arylpropiolic acids, many synthetic methodologies for arylnaphthalene lignan lactones and their applications for natural arylnaphthalene lignan lactones have been investigated. Representative synthetic methodologies include intramolecular Diels–Alder type ring formation of arylpropiolic anhydride by Stevenson's group (Brown and Stevenson, 1964 , 1965 ; Maclean and Stevenson, 1966 ; Holmes and Stevenson, 1970 , 1971 ; Block and Stevenson, 1971 , 1973 ; Stevenson and Block, 1971 ; Stevenson and Holmes, 1971 ; Stevenson and Weber, 1989 , 1991 ; Anastas and Stevenson, 1991 ; Park et al, 2014 ), intermolecular Diels–Alder reaction of isobenzofurans and dimethyl acetylenedicarboxylate (De Silva et al, 1980 ; Plaumann et al, 1980 ), sequential Blaise reaction-intramolecular [4 + 2] reaction of 2-alkynylbenzonitriles (He et al, 2014 ), and Garratt–Braverman cyclization of substituted bis-propargyl ethers (Mondal et al, 2011 , 2012 ). Photo-assisted cyclization methods provide arylnaphthalene lignan lactones efficiently (Block and Stevenson, 1971 , 1973 ; Arnold et al, 1973 ; Yamamoto et al, 2015 ).…”

Section: Introductionmentioning

confidence: 99%

Transition Metal-Mediated Annulation Approaches for Synthesis of Arylnaphthalene Lignan Lactones

Park

Kim

et al. 2020

Front. Chem.

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Arylnaphthalene lignan lactones belong to a class of natural lignans, and more than 60 analogs have been isolated. Their pharmacological activities as well as unique structural features have attracted considerable attention from medicinal and synthetic chemists. Since the first synthesis in 1895, many synthetic methodologies with ionic or pericyclic reaction mechanisms have been reported. Transition metal catalysts sometimes provide exceptional synthetic versatility for the syntheses of natural compounds. Recently, transition metal-mediated methodologies were investigated for the construction of basic scaffolds of arylnaphthalene lignan lactones. Five kinds of transition metal catalysts containing gold, manganese, nickel, palladium, and silver have been explored. Most of the metal catalysts successfully created arylnaphthalene lactones by intermolecular or intramolecular annulative cyclization. In this review, all reports of transition metal-mediated annulative construction of arylnaphthalene lignan lactones were compiled, and synthetic approaches, mechanistic aspects, and successful applications were discussed.

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“…3 Naturally occurring arylnaphthalene lactones are a subclass of lignans present in many dietary or medicinal plants. 4 As a representative example, 1arylnaphthalene lactone lignans (Fig. 1, 1-9) 5 are reported to exhibit a lot of biological activities 6 such as antibacterial, 7 antiviral, [8][9][10][11] antitumor, [12][13][14] antiplatelet, 15,16 phosphodiesterase inhibition, 17,18 5-lipoxygenase inhibition, [19][20][21] HIV reverse transcriptase inhibition [22][23][24] and cytotoxic activities.…”

Section: Introductionmentioning

confidence: 99%

Arylnaphthalene lactone analogues: synthesis and development as excellent biological candidates for future drug discovery

et al. 2018

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Regioselective route for arylnaphthalene lactones: convenient synthesis of taiwanin C, justicidin E, and daurinol

Cited by 31 publications

References 20 publications

Daurinol, a catalytic inhibitor of topoisomerase IIα, suppresses SNU-840 ovarian cancer cell proliferation through cell cycle arrest in S phase

Daurinol, a catalytic inhibitor of topoisomerase IIα, suppresses SNU-840 ovarian cancer cell proliferation through cell cycle arrest in S phase

Transition Metal-Mediated Annulation Approaches for Synthesis of Arylnaphthalene Lignan Lactones

Arylnaphthalene lactone analogues: synthesis and development as excellent biological candidates for future drug discovery

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