Journal of the Korean Applied Science and Technology (한국응용과학기술학회지)

The Korean Society of Applied Science and Technology (한국응용과학기술학회)
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Antioxidant, anti-inflammatory, and antimicrobial activity of hesperetin and its cyclodextrin inclusion complexes

헤스페레틴(Hesperetin)과 사이클로덱스트린(Cyclodextrin) 포접 복합체의 항산화, 항염증, 항균 활성

  • Received : 2023.10.10
  • Accepted : 2023.10.25
  • Published : 2023.10.31
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Abstract

Hesperetin(HT) is a potent antioxidant flavonoid aglycone derived from hesperidin(HD). The antioxidant, anti-inflammatory, and antimicrobial activities of HT and its cyclodextrin(CD) inclusion complexes were compared in vitro. HT was prepared by enzymatic hydrolysis of HD, and HT/CD complexes were prepared using 𝛽-cyclodextrin(𝛽-CD) and hydroxypropyl-𝛽-cyclodextrin(HP-𝛽-CD) by solvent co-evaporation method. The solubility of the HT/HP-𝛽-CD inclusion complex increased 93.5-fold compared to HT, and the solubility of HT/𝛽-CD increased 22.5-fold. The HT/HP-𝛽-CD inclusion complex showed a similar effect as HT on radical scavenging activity in antioxidant assays, whereas the HT/𝛽-CD inclusion complex showed slightly lower activity than HT. Cytotoxicity was low in the following order; HT/HP-𝛽-CD, HT/𝛽-CD, and HT in murine macrophage RAW264.7 cells. Treatment with HT and HT/CD inclusion complexes reduced the levels of inflammatory mediators such as nitric oxide(NO), tumor necrosis factor-𝛼(TNF-𝛼) and interleukin-6(IL-6) in the cells. HT and HT/HP-𝛽-CD inclusion complex were more effective than HT/𝛽-CD inclusion complex at relatively low concentrations. Inhibitory effects were tested on skin-pathogenic bacteria, Staphylococcus aureus and Pseudomonas aeruginosa, and they showed an antimicrobial effect on S. aureus in the order of HT = HT/HP-𝛽-CD > HT/𝛽-CD, but they did not show any significant inhibitory effect on P. aeruginosa. In conclusion, HT, the aglycone form of HD, and its CD inclusion complexes showed various biological activities. HT/HP-𝛽-CD inclusion complex, which is the highly soluble form of HT, showed relatively higher activity compared to HT/𝛽-CD inclusion complex.

Hesperetin은 Hesperidin에서 유도되는 강한 항산화 기능의 플라보노이드 비당체이다. 본 연구에서는 Hesperetin과 이의 Cyclodextrin 포접 복합체에 대하여 항산화, 항염증 및 항균 활성을 비교하였다. Hesperetin은 Hesperidin에 효소처리하여 제조되었으며, Hesperetin/Cyclodextrin 포접체는 용매 증류법에 의해 𝛽-Cyclodextrin 및 Hydroxypropyl-𝛽-Cyclodextrin을 사용하여 제조되었다. Hesperetin에 비해 Hesperetin/Hydroxypropyl-𝛽-Cyclodextrin 포접체의 용해도는 93.5배 증가하였고, Hesperetin/𝛽-Cyclodextrin 포접체의 용해도는 22.5배 증가하였다. 항산화 분석에서 Hydroxypropyl-𝛽-Cyclodextrin 포접체는 Hesperetin과 유사한 라디칼 소거 활성능을 보인 반면, 𝛽-Cyclodextrin 포접체는 Hesperetin 보다 약간 낮은 활성을 나타내었다. RAW 264.7 세포에 대한 세포독성은 Hydroxypropyl-𝛽-Cyclodextrin 포접체, 𝛽-Cyclodextrin 포접체, Hesperetin의 순으로 세포독성이 낮았다. Hesperetin과 Cyclodextrin 포접체는 모두 세포내 산화질소(NO), 종양괴사인자-𝛼(TNF-𝛼) 및 인터루킨-6(IL-6)과 같은 염증 매개체를 감소시켰다. Hesperetin 및 Hydroxypropyl-𝛽-Cyclodextrin 포접체는 상대적으로 𝛽-Cyclodextrin 포접체 보다 더 효과적이었다. 피부 유해성 세균인 황색 포도상구균과 녹농균에 대해 억제 효과를 시험한 결과, 황색 포도상구균에 대해서는 Hesperetin = Hydroxypropyl-𝛽-Cyclodextrin 포접체 > 𝛽-Cyclodextrin 포접체의 순서로 항균 효과를 나타내었으나, 녹농균에 대해서는 뚜렷한 억제효과를 나타내지 않았다. 결론적으로, Hesperidin의 비당체 형태인 Hesperetin과 이의 Cyclodextrin 포접체는 다양한 생물학적 활성을 보여주었으며, 용해도가 높은 Hydroxypropyl-𝛽-Cyclodextrin 포접체가 𝛽-Cyclodextrin 포접체에 비해 상대적으로 더 높은 활성을 나타내었다.

Keywords

Acknowledgement

This research was supported by the Technology development program (S3285193) funded by the Ministry of SMEs and Startups (Korea).

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