Literature DB >> 17067159

Dehydrozingerone, chalcone, and isoeugenol analogues as in vitro anticancer agents.

Jin Tatsuzaki1, Kenneth F Bastow, Kyoko Nakagawa-Goto, Seiko Nakamura, Hideji Itokawa, Kuo-Hsiung Lee.   

Abstract

Twenty-eight compounds related to dehydrozingerone (1), isoeugenol (3), and 2-hydroxychalcone (4) were synthesized and evaluated in vitro against human tumor cell replication. Except for isoeugenol analogues 27-35, most compounds exhibited moderate or strong cytotoxic activity against KB, KB-VCR (a multidrug-resistant derivative), and A549 cell lines. In particular, chalcone 15 showed significant cytotoxic activity against the A549 cell line with an IC50 value of 0.6 microg/mL. Furthermore, dehydrozingerone analogue 11 and chalcones 16 and 17 showed significant and similar cytotoxic activity against both KB (IC50 values of 2.0, 1.0, and 2.0 microg/mL, respectively) and KB-VCR (IC50 values of 1.9, 1.0, and 2.0 microg/mL, respectively) cells, suggesting that they are not substrates for the P-glycoprotein drug efflux pump.

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Year:  2006        PMID： 17067159      PMCID： PMC2532514          DOI： 10.1021/np060252z

Source DB:  PubMed          Journal:  J Nat Prod        ISSN： 0163-3864            Impact factor:   4.050


  22 in total

1.  Mappain, a new cytotoxic prenylated stilbene from Macaranga mappa.

Authors:  J E van Der Kaaden; T K Hemscheidt; S L Mooberry
Journal:  J Nat Prod       Date:  2001-01       Impact factor: 4.050

2.  Cytotoxic isoflavones from Erythrina indica.

Authors:  A E Nkengfack; A G Azebaze; A K Waffo; Z T Fomum; M Meyer; F R van Heerden
Journal:  Phytochemistry       Date:  2001-12       Impact factor: 4.072

3.  Antitumor agents. Part 214: synthesis and evaluation of curcumin analogues as cytotoxic agents.

Authors:  Junko Ishida; Hironori Ohtsu; Yoko Tachibana; Yuka Nakanishi; Kenneth F Bastow; Masahiro Nagai; Hui-Kang Wang; Hideji Itokawa; Kuo-Hsiung Lee
Journal:  Bioorg Med Chem       Date:  2002-11       Impact factor: 3.641

4.  Prenylated benzophenones and xanthones from Hypericum scabrum.

Authors:  Naonobu Tanaka; Yoshihisa Takaishi; Yasuhiro Shikishima; Yuka Nakanishi; Kenneth Bastow; Kuo-Hsiung Lee; Gisho Honda; Michiho Ito; Yoshio Takeda; Olimjon K Kodzhimatov; Ozodbek Ashurmetov
Journal:  J Nat Prod       Date:  2004-11       Impact factor: 4.050

5.  Antitumor agents. 217. Curcumin analogues as novel androgen receptor antagonists with potential as anti-prostate cancer agents.

Authors:  Hironori Ohtsu; Zhiyan Xiao; Junko Ishida; Masahiro Nagai; Hui-Kang Wang; Hideji Itokawa; Ching-Yuan Su; Charles Shih; Tzuying Chiang; Eugene Chang; YiFen Lee; Meng-Yin Tsai; Chawnshang Chang; Kuo-Hsiung Lee
Journal:  J Med Chem       Date:  2002-11-07       Impact factor: 7.446

6.  Antimutagenic effects of dehydrozingerone and its analogs on UV-induced mutagenesis in Escherichia coli.

Authors:  N Motohashi; Y Ashihara; C Yamagami; Y Saito
Journal:  Mutat Res       Date:  1997-06-09       Impact factor: 2.433

7.  A facile synthetic approach to prenylated flavanones: first total syntheses of (+/-)-bonannione A and (+/-)-sophoraflavanone A.

Authors:  Y Wang; W Tan; W Z Li; Y Li
Journal:  J Nat Prod       Date:  2001-02       Impact factor: 4.050

8.  Constituents of Boronia pinnata.

Authors:  C Ito; M Itoigawa; T Otsuka; H Tokuda; H Nishino; H Furukawa
Journal:  J Nat Prod       Date:  2000-10       Impact factor: 4.050

9.  Total synthesis of (R,S)-sophoraflavanone C

Authors: 
Journal:  J Nat Prod       Date:  1998-10       Impact factor: 4.050

10.  Synthesis and biological evaluation of novel curcumin analogs as anti-cancer and anti-angiogenesis agents.

Authors:  Brian K Adams; Eva M Ferstl; Matthew C Davis; Marike Herold; Serdar Kurtkaya; Richard F Camalier; Melinda G Hollingshead; Gurmeet Kaur; Edward A Sausville; Frederick R Rickles; James P Snyder; Dennis C Liotta; Mamoru Shoji
Journal:  Bioorg Med Chem       Date:  2004-07-15       Impact factor: 3.641
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  13 in total

1.  Cancer preventive agents 10. Prenylated dehydrozingerone analogs as potent chemopreventive agents.

Authors:  Jin Tatsuzaki; Kyoko Nakagawa-Goto; Harukuni Tokuda; Kuo-Hsiung Lee
Journal:  J Asian Nat Prod Res       Date:  2010-03       Impact factor: 1.569

2.  Cytotoxic chalcones and antioxidants from the fruits of a Syzygium samarangense (Wax Jambu).

Authors:  Mario J Simirgiotis; Seiji Adachi; Satoshi To; Hui Yang; Kurt A Reynertson; Margaret J Basile; Roberto R Gil; I Bernard Weinstein; Edward J Kennelly
Journal:  Food Chem       Date:  2008-03-15       Impact factor: 7.514

3.  Structure-function activity of dehydrozingerone and its derivatives as antioxidant and antimicrobial compounds.

Authors:  Ismail Rahath Kubra; Bheemanakere Kempaiah Bettadaiah; Pushpa Srinivas Murthy; Lingamallu Jagan Mohan Rao
Journal:  J Food Sci Technol       Date:  2011-08-17       Impact factor: 2.701

4.  Alkyne-azide cycloaddition analogues of dehydrozingerone as potential anti-prostate cancer inhibitors via the PI3K/Akt/NF-kB pathway.

Authors:  Chetan Kumar; Reyaz Ur Rasool; Zainab Iqra; Yedukondalu Nalli; Prabhu Dutt; Naresh K Satti; Neha Sharma; Sumit G Gandhi; Anindya Goswami; Asif Ali
Journal:  Medchemcomm       Date:  2017-11-02       Impact factor: 3.597

5.  Crystal structure of 5-(4-methyl-phen-yl)-3-[(E)-2-(4-methyl-phen-yl)ethen-yl]cyclo-hex-2-en-1-one.

Authors:  Joel T Mague; Shaaban K Mohamed; Mehmet Akkurt; Antar A Abdelhamid; Mustafa R Albayati
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2015-05-07

6.  4-Eth-oxy-3-meth-oxy-benzaldehyde.

Authors:  Zorica Leka; Sladjana B Novaković; Goran A Bogdanović; Jovana Muškinja; Rastko D Vukićević
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2013-11-06

7.  The antityrosinase and antioxidant activities of flavonoids dominated by the number and location of phenolic hydroxyl groups.

Authors:  Ai-Ren Zuo; Huan-Huan Dong; Yan-Ying Yu; Qing-Long Shu; Li-Xiang Zheng; Xiong-Ying Yu; Shu-Wen Cao
Journal:  Chin Med       Date:  2018-10-19       Impact factor: 5.455

8.  Curcumin half analog modulates interleukin-6 and tumor necrosis factor-alpha in inflammatory bowel disease.

Authors:  Phani Krishna Kondamudi; Hemalatha Kovelamudi; Pawan G Nayak; Mallikarjuna Chamallamudi Rao; Rekha Raghuveer Shenoy
Journal:  Pharmacogn Mag       Date:  2015-10       Impact factor: 1.085

9.  Dehydrozingerone, a Curcumin Analog, as a Potential Anti-Prostate Cancer Inhibitor In Vitro and In Vivo.

Authors:  Sariya Mapoung; Shugo Suzuki; Satoshi Fuji; Aya Naiki-Ito; Hiroyuki Kato; Supachai Yodkeeree; Natee Sakorn; Chitchamai Ovatlarnporn; Satoru Takahashi; Pornngarm Limtrakul Dejkriengkraikul
Journal:  Molecules       Date:  2020-06-12       Impact factor: 4.411

10.  Privileged Scaffold Chalcone: Synthesis, Characterization and Its Mechanistic Interaction Studies with BSA Employing Spectroscopic and Chemoinformatics Approaches.

Authors:  Nidhi Singh; Neeraj Kumar; Garima Rathee; Damini Sood; Aarushi Singh; Vartika Tomar; Sujata K Dass; Ramesh Chandra
Journal:  ACS Omega       Date:  2020-01-27
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