Journal of Applied Biological Chemistry

The Korean Society for Applied Biological Chemistry (한국응용생명화학회)
권호 표지
DOI QR코드

DOI QR Code

Phenolic compounds from the flowers of Cosmos bipinnatus and their anti-atopic activity

코스모스(Cosmos bipinnatus) 꽃으로부터 phenolic 화합물의 분리 동정과 항아토피 효과

  • Jeon, Hyeong-Ju (Department of Food & Nutrition, Jangan University) ;
  • Kim, Hyoung-Geun (Graduate School of Biotechnology and Department of Oriental Medicinal Biotechnology, Kyung Hee University)
  • Received : 2022.08.19
  • Accepted : 2022.09.02
  • Published : 2022.09.30
Download PDF
⟨ Previous Next ⟩

Abstract

The flowers of Cosmos bipinnatus were extracted with solvent made with methanol:water (4:1) and the concentrates were partitioned into ethyl acetate (EtOAc), n-butanol (n-BuOH), and water (H2O) fractions. The octadecyl silica gel (ODS) and silica gel (SiO2) column chromatographies were repeated for the EtOAc fraction to isolated of two phenolic compounds. The chemical structure of the isolated compounds were identified as benzyl O-β-ᴅ-glucopyranoside (1), and 2-phenylethyl O-β-ᴅ-glucopyranoside (2) through spectroscopic datas such as nuclear magnetic resornance, infrarad spectroscopy, and mass spectroscopy. These two compounds were first isolated from C. bipinnatus flowers through this study. To evaluate the anti-atopic activity of the two isolated compounds using a HaCaT cell line induced by ultraviolet light, several experiments were conducted and neither both compounds showed toxicity in the concentration range of 1 to 1,000 ㎍/mL. In the results of anti-atopic activity through Thymus and activation regualted chemokine (TARC) assay, both compounds showed dose-dependent TARC inhibitory activity. In particular, compound 1 showed significant activity even in a low concentration range of 10 ㎍/mL, and in different concentration ranges. Also compound 1 showed higher inhibitory activity than other compound, confirming that the anti-atopic activity was the most excellent. Based on these results, it is considered that it can be used as a functional cosmetic material.

코스모스 꽃을 MeOH : H2O = 4 : 1 용매로 추출하여, 얻어진 추출물을 EtOAc n-BuOH 및 water로 용매 분획 하였다. 이 중 n-BuOH 분획으로부터 silica gel (SiO2)과 octadecyl silica gel(ODS) column chromatography로 정제하여 2종의 화합물을 분리하였다. NMR, MS 및 IR 등의 스텍트럼 데이터를 통해 화합물의 화학구조를 benzyl O-β-ᴅ-glucopyranoside (1)와 and 2-phenylethyl O-β-ᴅ-glucopyranoside (2)로 동정하였다. 분리한 두 화합물의 자외선(UVB)으로 광노화가 유도된 HaCaT 세포주를 이용한 항아토피 효능을 평가하기 위해 실험을 진행하였으며, 1-1,000 ㎍/mL의 농도범위에서 2종의 화합물에서 모두 독성을 나타내지 않았다. TARC생성억제활성을 통한 항아토피 활성결과에서는 2종의 화합물에서 모두 농도의존적인 TARC 억제활성이 나타났지만, 특히 화합물 1에서 낮은 농도범위인 10 ㎍/mL에서도 유의적인 활성이 나타났으며, 다른 농도범위에서도 타 화합물에 비해 억제활성이 높은 것으로 나타나, 항아토피 활성이 가장 우수한 것으로 확인되었다. 이 결과를 통해 기능성 화장품 원료로 활용이 가능할 것으로 사료된다.

Keywords

References

  1. Dubey S, Singh VK (2011) Population dynamics of Aphis spiracecola Patch (Homoptera: Aphididae) on medicinal plant Cosmos bipinnatus in eastern Uttar Pradesh, India. Adv Life Sci 1: 54-58 https://doi.org/10.5923/j.als.20110102.10
  2. Alexandros SB (2007) Plants used traditionally to treat malaria in Brazil. J Ethnobiol Ethnomed 3: 18. doi: 10.1186/1746-4269-3-18
  3. Molder M, Owens JN (1985) Cosmos. CRC handbook of flowering. CRC, Boca Raton
  4. Jang IC, Park JH, Park EJ, Park HR, Lee SC (2008) Antioxidative and Antigenotoxic Activity of Extracts from Cosmos (Cosmos bipinnatus) Flowers. Plant Foods Hum Nutr 63: 205-210. doi: 10.1007/s11130-008-0086-8
  5. Kim M, Ahn S, Park S (2020) Identifying antibacterial activity components of cosmos flower extracts. J Appl Biol Chem 63: 249-257. doi: 10.3839/jabc.2020.034
  6. Mohammad S, Hafiz AA, Muhammad FA, Uzma S, Iram I (2017) Chemical characterisation and hepatoprotective potential of Cosmos sulphureus Cav. and Cosmos bipinnatus Cav. Nat Prod Res 33: 897-900. doi: 10.1080/14786419.2017.1413557
  7. Park HS, Woo SJ, Jung GS, Kim MO (2018) Composition for improving skin wrinkle comprising Cosmos bipinnatus extract. Skincure Co. Ltd., S. Korea
  8. Jang (2013) Radical Scavenging and Tyrosinase Inhibitory Effects of the Extracts and Fractions of Asteraceae Medicinal Plants. Dissertation, University of Sunchon
  9. Saito K (1976) Flavone glycosides in the ray flowers of Cosmos bipinnatus. Planta Med 30(4): 349-355. doi: 10.1055/s-0028-1097742
  10. Nakaoki T (1935) Glucoside of the flavone of the white flower. IV. Constituents of Cosmos bipinnatus, Cav. Yakugaku Zasshi 55: 967-968 https://doi.org/10.1248/yakushi1881.55.9_967
  11. Lee YG, Lee J, Lee NY, Kim NK, Jung DW, Wang W, Kim Y, Kim HG, Nguyen TN, Park H, Baek NI (2017) Evaluation for the flowers of compositae plants as whitening cosmetics functionality. J Appl Biol Chem 60: 5-11. doi: 10.3839/jabc.2017.002
  12. Ko JH, Nam YH, Joo SW, Kim HG, Lee YG, Kang TH, Baek NI (2018) Flavonoid 8-O-Glucuronides from the Aerial Parts of Malva verticillata and Their Recovery Effects on Alloxan-Induced Pancreatic Islets in Zebrafish. Molecules 23: 833-847. doi: 10.3390/molecules23040833
  13. Maleki SJ, Crespo JF, Cabanillas B (2019) Anti-inflammatory effects of flavonoids. Food Chem 299: 125124. doi: 10.1016/j.foodchem.2019.125124
  14. Kim HG, Jung YS, Oh SM, Oh HJ, Ko JH, Kim DO, Kang SC, Lee YG, Lee DY, Baek NI (2020) Coreolanceolins A-E, New Flavanones from the Flowers of Coreopsis lanceolata and Their Antioxidative and Anti-inflammatory Effects. Antioxidants 9: 539-555 doi: 10.3390/antiox9060539
  15. Zhang C, Ma Y, Gao H, Liu X, Chen L, Zhang Q, Wang Z, Li A (2013) Non-alkaloid components from Sophora flavescens. Zhongguo Zhongyao Zazhi 38: 3520-352