Journal of the Society of Cosmetic Scientists of Korea (대한화장품학회지)

Society of Cosmetic Scientists of Korea (대한화장품학회)
권호 표지
DOI QR코드

DOI QR Code

Antioxidative Effects and Component Analysis of Graviola (Annona muricata) Leaf Extract/Fractions

그라비올라(Annona muricata) 잎 추출물 및 분획물의 항산화 활성과 성분 분석

  • Park, So Hyun (Department of Fine Chemistry, Cosmetic R&D Center, Cosmetic Industry Coupled Collaboration Center, Seoul National University of Science and Technology) ;
  • Kim, Ji Min (Hansung Science High School) ;
  • Kim, Jin Hwan (Hansung Science High School) ;
  • Oh, Yoon Soo (Hansung Science High School) ;
  • Joo, Dong Hee (Hansung Science High School) ;
  • Lee, Eun Young (Hansung Science High School) ;
  • Shin, Hyuk Soo (Department of Fine Chemistry, Cosmetic R&D Center, Cosmetic Industry Coupled Collaboration Center, Seoul National University of Science and Technology) ;
  • Kim, A Rang (Department of Fine Chemistry, Cosmetic R&D Center, Cosmetic Industry Coupled Collaboration Center, Seoul National University of Science and Technology) ;
  • Lee, Sang Lae (Department of Fine Chemistry, Cosmetic R&D Center, Cosmetic Industry Coupled Collaboration Center, Seoul National University of Science and Technology) ;
  • Park, Soo Nam (Department of Fine Chemistry, Cosmetic R&D Center, Cosmetic Industry Coupled Collaboration Center, Seoul National University of Science and Technology)
  • 박소현 (서울과학기술대학교 정밀화학과 화장품종합기술연구소, 코스메틱 융.복합산업 지원 센터) ;
  • 김지민 (한성과학고등학교) ;
  • 김진환 (한성과학고등학교) ;
  • 오윤수 (한성과학고등학교) ;
  • 주동휘 (한성과학고등학교) ;
  • 이은영 (한성과학고등학교) ;
  • 신혁수 (서울과학기술대학교 정밀화학과 화장품종합기술연구소, 코스메틱 융.복합산업 지원 센터) ;
  • 김아랑 (서울과학기술대학교 정밀화학과 화장품종합기술연구소, 코스메틱 융.복합산업 지원 센터) ;
  • 이상래 (서울과학기술대학교 정밀화학과 화장품종합기술연구소, 코스메틱 융.복합산업 지원 센터) ;
  • 박수남 (서울과학기술대학교 정밀화학과 화장품종합기술연구소, 코스메틱 융.복합산업 지원 센터)
  • Received : 2017.10.26
  • Accepted : 2017.11.26
  • Published : 2017.12.30
Download PDF
⟨ Previous Next ⟩

Abstract

In this study, the antioxidative effects and component analysis of 50% ethanol extract, ethyl acetate fraction and aglycone fraction obtained from Annona muricata leaf were investigated. Free radical scavenging activities were performed by 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay, total antioxidant capacities were estimated using luminol-dependent chemiluminescence assay and $^1O_2$ quenching effects were estimated. Free radical scavenging activities ($FSC_{50}$) of 50% ethanol extract, ethyl acetate fraction and aglycone fraction were 45.6, 29.8 and $18.0{\mu}g/mL$, and total antioxidant capacities ($OSC_{50}$) were 4.4, 1.1 and $2.8{\mu}g/mL$, respectively. As a result of $^1O_2$ quenching experiment, ethyl acetate and aglycone fraction showed similar activities to L-ascorbic acid used as a comparative control. The cellular protective effects of 50% ethanol extract on the $^1O_2-induced$ cellular damage of human erythrocytes were exhibited at concentration-dependent ($5-50{\mu}g/mL$). TLC and HPLC were used to analyse components in the ethyl acetate fraction and aglycone fraction of Annona muricata leaf. In ethyl acetate fraction, rutin (quercetin-3-O-rutinoside), kaempferol-3-O-neohesperidoside, nicotiflorin (kaempferol-3-O-rutinoside), p-coumaric acid were identified. In aglycone fraction, kaempferol was identified. These results suggest that the extracts of Annona muricata leaf have the applicability as antioxidant cosmeceutical ingredients.

본 연구에서는 그라비올라(Annona muricata) 잎으로부터 50% 에탄올 추출물, 에틸아세테이트 분획 및 아글리콘 분획을 제조하였고 이들 추출물/분획에 대하여 항산화 활성을 평가하였다. 1,1-Phenyl-2-picrylhydrazyl (DPPH) 라디칼 시험법을 이용한 자유라디칼 소거 활성, 루미놀 발광법을 이용한 총 항산화능 및 $^1O_2$ 소광 효과를 평가하였다. 50% 에탄올 추출물, 에틸아세테이트 분획 및 아글리콘 분획의 라디칼 소거 활성($FSC_{50}$)은 각각 45.6, 29.8 및 $18.0{\mu}g/mL$이었고, 총 항산화능($OSC_{50}$)은 4.4, 1.1 및 $2.8{\mu}g/mL$이었다. 에틸아세테이트 분획의 총 항산화능은 수용성 항산화제로 잘 알려진 L-ascorbic acid ($1.5{\mu}g/mL$)보다 높은 항산화능을 나타내었다. $^1O_2$ 소광 상수 실험 결과, 에틸아세테이트 및 아글리콘 분획은 비교물질로 사용된 L-ascorbic acid와 유사한 활성을 보여주었다. $^1O_2$으로 유도된 적혈구 세포 손상에 있어서, 그라비올라 잎 50% 에탄올 추출물은 농도 의존적($5-50{\mu}g/mL$)으로 세포보호 활성을 나타내었다. 실험에 사용된 그라비올라 잎 추출물의 에틸아세테이트 분획과 아글리콘 분획에 대하여 TLC 및 HPLC를 이용한 성분 분석을 수행하였다. 에틸아세테이트 분획에서는 rutin (quercetin-3-O-rutinoside), kaempferol-3-O-neohesperidoside, nicotiflorin (kaempferol-3-O-rutinoside), p-coumaric acid을 확인하였다. 아글리콘 분획에서는 kaempferol이 존재함을 확인하였다. 이상의 결과들은 그라비올라 잎 추출물이 항산화 화장품 원료로서 응용 가능성이 있음을 시사한다.

Keywords

References

  1. A. Kammeyer and R. M. Luiten, Oxidation events and skin aging, Ageing Res. Rev., 21, 16 (2015). https://doi.org/10.1016/j.arr.2015.01.001
  2. M. Yaar and B. A. Gilchrest, Photoageing: mechanism, prevention and therapy, Br. J. Dermatol., 157(5), 874 (2007). https://doi.org/10.1111/j.1365-2133.2007.08108.x
  3. H. J. Yang, E. H. Kim, and S. N. Park, Antioxidative activity and component analysis of Psidium guajava leaf extracts, J. Soc. Cosmet. Scientists Korea, 34(3), 233 (2008).
  4. H. U. Simon, A. Haj-Yehia, and F. Levi-Schaffer, Role of reactive oxygen species (ROS) in apoptosis induction, Apoptosis, 5(5), 415 (2000). https://doi.org/10.1023/A:1009616228304
  5. S. N. Park, Skin aging, and antioxidant, J. Soc. Cosmet. Scientists Korea, 23(1), 75 (1997).
  6. Y. Al-Nuaimi, M. J. Sherratt, and C. E. M. Griffiths, Skin health in older age, Maturitas, 79(3), 256 (2014). https://doi.org/10.1016/j.maturitas.2014.08.005
  7. J. Wohlrab, K. Hilpert, and L. Wolff, Epidermal aging and anti-aging strategies, Hautarzt, 67(2), 107 (2016). https://doi.org/10.1007/s00105-015-3734-6
  8. S. A. Kyrtopoulos, N-nitroso compoud formation in human gastric juice, Cancer Surv., 8(2), 423 (1989).
  9. R. S. Sohala and W. C. Orr, The redox stress hypothesis of aging, Free Radic. Biol. Med., 52(3), 539 (2012). https://doi.org/10.1016/j.freeradbiomed.2011.10.445
  10. S. N. Park, Protective effect of isoflavone, genistein from soybean on singlet oxygen induced photohemolysis of human erythrocytes, Korean J. Food Sci. Technol., 35(3), 510 (2003).
  11. J. Yamakoshi, F. Otsuka, A. Sano, S. Tokutake, M. Saito, M. Kikuchi, and Y. Kubota, Lightening effect on ultraviolet-induced pigmentation of guinea pig skin by oral administration of a proanthocyanidin-rich extract from grape seeds, Pig. Cell Res., 16(6), 629 (2003). https://doi.org/10.1046/j.1600-0749.2003.00093.x
  12. M. L. Circu and T. Y. Aw, Reactive oxygen species, cellular redox system, and apoptosis, Free Radic. Biol. Med., 48(6), 749 (2010). https://doi.org/10.1016/j.freeradbiomed.2009.12.022
  13. Y. Gavamukulya, F. Abou-Elella, F. Wamunyokoli, and H. AEl-Shemy, Phytochemical screening, anti-oxidant activity and in vitro anticancer potential of ethanolic and water leaves extracts of Annona muricata (Graviola), Asian Pac. J. Trop. Med., 7S1, S355 (2014).
  14. J. Paul, R. Gnanam, R. M. Jayadeepa, and L. Arul, Anti cancer activity on Graviola, an exciting medicinal plant extract vs various cancer cell lines and a detailed computational study on its potent anti-cancerous leads, Curr. Top. Med. Chem., 13(14), 1666 (2013). https://doi.org/10.2174/15680266113139990117
  15. S. Sun, J. Liu, H. Kadouh, X. Sun, and K. Zhou, Three new anti-proliferative Annonaceous acetogenins with mono-tetrahydrofuran ring from graviola fruit (Annona muricata), Bioorg. Med. Chem. Lett., 24(12), 2773 (2014). https://doi.org/10.1016/j.bmcl.2014.03.099
  16. T. D. Thang, D. N. Dai, T. M. Hoi, and I. A. Ogunwande, Study on the volatile oil contents of Annona glabra L., Annona squamosa L., Annona muricata L. and Annona reticulata L., from Vietnam, Nat. Prod. Res., 27(13), 1232 (2013). https://doi.org/10.1080/14786419.2012.724413
  17. M. Nawwar, N. Ayoub, S. Hussein, A. Hashim, R. El-Sharawy, K. Wende, M. Harms, and U. Lindequist, A flavonol triglycoside and investigation of the antioxidant and cell stimulating activities of Annona muricata Linn., Arch. Pharm. Res., 35(5), 761 (2012). https://doi.org/10.1007/s12272-012-0501-4
  18. A. Matsushige, Y. Kotake, K. Matsunami, H. Otsuka, S. Ohta, and Y. Takeda, Annonamine, a new aporphine alkaloid from the leaves of Annona muricata, Chem. Pharm. Bull. (Tokyo), 60(2), 257 (2012). https://doi.org/10.1248/cpb.60.257
  19. A. Matsushige, K. Matsunami, Y. Kotake, H. Otsuka, and S. Ohta, Three new megastigmanes from the leaves of Annona muricata, J. Nat. Med., 66(2), 284 (2012). https://doi.org/10.1007/s11418-011-0583-1
  20. S. Adewole and J. Ojewole, Protective effects of Annona muricata Linn. (Annonaceae) leaf aqueous extract on serum lipid profiles and oxidative stress in hepatocytes of streptozotocin-treated diabetic rats, Afr. J. Tradit. Complement. Altern. Med., 6(1), 30 (2009).
  21. G. A. Asare, D. Afriyie, R. A. Ngala, H. Abutiate, D. Doku, S. A. Mahmood, and H. Rahman, Antiproliferative activity of aqueous leaf extract of Annona muricata L. on the prostate, BPH-1 cells, and some target genes, Integr. Cancer Ther., 14(1), 65 (2015). https://doi.org/10.1177/1534735414550198
  22. I. O. Ishola, O. Awodele, A. M. Olusayero, and C. O. Ochieng, Mechanisms of analgesic and anti-inflammatory properties of Annona muricata Linn. (Annonaceae) fruit extract in rodents, J. Med. Food, 17(12), 1375 (2014). https://doi.org/10.1089/jmf.2013.0088
  23. S. Z. Moghadamtousi, H. Karimian, E. Rouhollahi, M. Paydar, M. Fadaeinasab, and H. A. Kadir, Annona muricata leaves induce G1 cell cycle arrest and apoptosis through mitochondria-mediated pathway in human HCT-116 and HT-29 colon cancer cells, J. Ethnopharmacol., 156, 277 (2014). https://doi.org/10.1016/j.jep.2014.08.011
  24. M. P. Torres, S. Rachagani, V. Purohit, P. Pandey, S. Joshi, E. D. Moore, S. L. Johansson, P. K. Singh, A. K. Ganti, and S. K. Batra, Graviola: a novel promising natural-derived drug that inhibits tumorigenicity and metastasis of pancreatic cancer cells in vitro and in vivo through altering cell metabolism, Cancer Lett., 323(1), 29 (2012). https://doi.org/10.1016/j.canlet.2012.03.031
  25. S. N. Park, Quenching effect of carotenoids on singlet oxygen, J. Soc. Cosmet. Scientists Korea, 10(1), 75-89 (1984).
  26. K. M. Kim, A. R. Kim, A. Y. Kim, J. H. Ha, S. H. Xuan, Y. J. Jeong, Y. M. Park, H. J. Jeong, I. G. Hong, and S. N. Park, Antioxidative and cellular protective effects of Dolwoe (Gynostemma pentaphyllum Makino) extracts against oxidative stress, Kor. J. Pharmacogn., 48(2), 125 (2017).
  27. A. Y. Kim, J. H. Ha, A. R. Kim, H. J. Jeong, K. M. Kim, and S. N. Park, Cellular protective effect and active component analysis of Lavender (Lavandula angustifolia) extract/fraction, Appl. Chem. Eng., 28(4), 479 (2017). https://doi.org/10.14478/ACE.2017.1051
  28. S. H. Xuan, G. Y. Kim, J. Y. Yu, J. W. Kim, Y. R. Yang, Y. H. Jeon, Y. J. Jeong, A. R. Kim, and S. N. Park, Antioxidant and cellular protective effects against oxidative stress of Calendula officinalis flowers extracts in human skin cells, Appl. Chem. Eng., 27(6), 620 (2016). https://doi.org/10.14478/ace.2016.1093
  29. R. J. Grayer, G. C. Kite, M. Abou-Zaid, and L. J. Archer, The application of atmospheric pressure chemical ionisation liquid chromatography-mass spectrometry in the chemotaxonomic study of flavonoids: characterisation of flavonoids from Ocimum gratissimum var. gratissimum, Phytochem. Anal., 11, 257 (2000). https://doi.org/10.1002/1099-1565(200007/08)11:4<257::AID-PCA521>3.0.CO;2-A
  30. A. Plazonic, F. Bucar, Z. Males, A. Mornar, B. Nigovic, and N. Kujundzic, Identification and quantification of flavonoids and phenolic acids in Burr Parsley (Caucalis platycarpos L.), using high-performance liquid chromatography with diode array detection and electrospray ionization mass spectrometry, Molecules, 14(7), 2466 (2009). https://doi.org/10.3390/molecules14072466
  31. T. Iwashina and G. Kokubugata, Flavone and flavonol glycosides from the leaves of Triumfetta procumbens in Ryukyu islands, Bull. Natl. Mus. Nat. Sci., 38(2), 63 (2012).