Korean Journal of Food Science and Technology (한국식품과학회지)

Korean Society of Food Science and Technology (한국식품과학회)
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Antioxidant and cytotoxic activities of curcumin and its analogs: An exploration of structure-activity relationships

Curcumin과 관련 성분들의 산화방지활성과 세포독성 분석 및 구조와 활성 연관성 조사

  • Lee, Bo-Hyun (Division of Applied Food System, College of Natural Science, Seoul Women's University) ;
  • Kim, Hee Jeong (Division of Applied Food System, College of Natural Science, Seoul Women's University) ;
  • Hong, Jungil (Division of Applied Food System, College of Natural Science, Seoul Women's University)
  • 이보현 (서울여자대학교 자연과학대학 식품응용시스템학부) ;
  • 김희정 (서울여자대학교 자연과학대학 식품응용시스템학부) ;
  • 홍정일 (서울여자대학교 자연과학대학 식품응용시스템학부)
  • Received : 2021.06.01
  • Accepted : 2021.07.15
  • Published : 2021.08.31
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Abstract

Bioactivities of curcumin, a major pigment of Curcuma longa L., have been widely investigated. In this study, the antioxidant and cytotoxic properties of curcumin and its analogs including ferulic acid, dibenzoylmethane (DBM), and tetrahydrocurcumin (THC), and their structure-activity relationships were assessed. Ferulic acid, THC, and curcumin showed strong scavenging activities against several radicals and exhibited considerable lipid peroxidation inhibitory activity. Curcumin showed the strongest cytotoxic activities against HeLa, HCT-116, IEC-6 and INT 407 cells, whereas ferulic acid did not show any cytotoxic effect up to 100 µM against these cell lines. Cytotoxicity of curcumin and THC was significantly enhanced by superoxide dismutase and diminished by N-acetylcysteine. The combination treatment of curcumin and ferulic acid enhanced the cytotoxicity, whereas the combination of curcumin and DBM offset their toxicity. These results suggest that methoxy phenolic and β-diketon moieties are crucial for the antioxidant- and cytototoxic activities of curcumin, respectively.

본 연구에서는 curcumin과 관련 구조물질인 ferulic acid, DBM, THC을 사용하여 이들의 산화방지활성과 세포독성을 나타내는 활성과 구조 간의 연관성을 분석하였다. 각종 라디칼 소거활성과 지질산화 억제 반응에서 DBM은 거의 활성을 나타내지 못해, methoxy phenolic기가 중요한 기능 구조로 나타났으며 α, β-unsaturated carbonyl기도 이들의 산화방지 활성에 일부 관여하는 것으로 보인다. Curcumin 유도체들의 세포독성과 이들의 산화방지활성 간에는 연관성이 거의 없었으며, ROS의 생성에는 α, β-unsaturated carbonyl기가 중요한 역할을 담당하나 세포독성의 직접적인 원인이 아닌 것으로 판단된다. 세포독성 유발에는 β-diketone 구조가 중요한 역할을 하였으며, SOD/catalase 등에 의한 구조의 안정화가 세포독성을 더욱 강화시키는 것으로 판단된다. Curcumin과 ferulic acid의 조합처리에 의해 독성이 증가한 반면, DBM과 curcumin을 같이 처리 시 독성이 상쇄되었으며 THC과 curcumin은 서로 부가적인 세포독성을 나타냈다.

Keywords

Acknowledgement

본 연구는 과학기술정보통신부의 재원의 한국연구재단 중견연구자 지원사업(NRF-2019R1A2C1089617)과 2021년 서울여자대학교 교내학술 연구비(연구년) 지원에 의해 수행되었음(2021-0151).

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