Isolation and Identification of Macamides from the Lipidic Extract of Maca [Lepidium meyenii] using Supercritical Carbon Dioxide

초임계 이산화탄소를 이용한 maca [Lepidium meyenii]의 지질 추출물로부터 macamides 분리 및 동정

  • 이승호 ((주)내추럴하우스 기술연구소) ;
  • 강정일 ((주)내추럴하우스 기술연구소) ;
  • 이상윤 ((주)내추럴하우스 기술연구소) ;
  • 하효철 (풀무원 식문화연구원 기능성연구소) ;
  • 송영근 (아주대학교 분자과학기술학과) ;
  • 변상요 (아주대학교 분자과학기술학과)
  • Published : 2008.04.29

Abstract

Maca (Lepidium meyenii) has been used as a food and medicine in Peru for thousands of years. More recently a wide array of commercial maca products have gained popularity as dietary supplements with claims of anabolic and aphrodisiac effects. Even though the biologically active principles of maca are not fully known, the lipidic extract of maca tubers containing macamides showed promising physiological activities. In this study, the lipidic extract were collected from maca tubers by using supercritical carbon dioxide ($SCO_2$). Substance estimated as macamide in the extract was isolated and purified by preparative HPLC with recycling system. Two of the purified substance was identified as N-benzyl-5-oxo-6E,8E-octadecadienamide and N-benzylhexadecan amide by LC/MS, $^1H$-NMR and $^{13}C$-NMR analyses.

생리활성이 뛰어난 마카의 지질 분획으로부터 macamides를 분리 동정하기 위해 본 연구에서는 초임계 이산화탄소 추출을 통해 마카 지질 추출물을 제조하여 재순환 분취용 HPLC로부터 2종의 macamides 물질을 분리 정제하였다. 분리된 2종의 macamides 물질의 구조 해석을 위해 LC/MS와 $^1H$-NMR과 $^{13}C$-NMR 분석을 실시한 결과 분자량이 384인 N-benzyl-5-oxo-6E,8E-octadecadienamide와 분자량이 346인 N-benzylhexadecanamide로 동정되었다. 본 연구를 통해 분리된 2종의 macamides는 향후 마카분말 및 마카제품의 macamides의 지표물질로 활용이 가능할 것으로 사료된다.

Keywords

References

  1. Balick, M. J. and Lee,R. (2002), Maca : from traditional food crop to energy and libido stimulant, Alternative Ther. Health Med. 8, 96-98
  2. Dini, A., Migliuolo, G., Rastrelli, L., Saturnino, P., and Schettino, O. (1994), Chemical composition of Lepidium meyenii, Food chemistry. 49(4), 347-349 https://doi.org/10.1016/0308-8146(94)90003-5
  3. Valentova, K. and Ulrichova, J. (2003) Smallanthus sonchifolius and Lepidium meyenii-prospective Andean crops for the prevention of chronic diseases, Biomed. Papers. 147(2), 119-130 https://doi.org/10.5507/bp.2003.017
  4. Valerio, L. G. and Gnzales, G. F. (2005), Toxicological aspects of the south American herbs Cat's Claw (Uncaria tomentosa) and Maca (Lepidium meyenii), Toxicological reviews. 24(1), 11-35 https://doi.org/10.2165/00139709-200524010-00002
  5. Yata, M. J. V. (2007) Fertility property of maca and its effect on hormone levels, FOOD STYLE 21. 11(4), 60-63
  6. Jin, W.-w., Zhang, Y.-z., and Ao, M.-z. (2007), Improvement of mice immune function with compounds of powdered Maca (Lepidium meyenii)and ginsenosides, Chinese journal of new drugs. 16(1), 45-48
  7. Rubio, J., Dang, H., Gong, M., Liu, X., Chen, S. l., and Gonzales, G. F. (2007), Aqueous and hydroalcoholic extracts of Black Maca (Lepidium meyenii) improve scopolamine-induced memory impairment in mice, Food and chemical toxicology. 45(10), 1882-1890 https://doi.org/10.1016/j.fct.2007.04.002
  8. Gonzales, G. F. and Valerio, L. G. (2006), Medicinal plants from Peru: A review of plants as potential agents against cancer, Anti-cancer agents in medicinal chemistry. 6, 429-444 https://doi.org/10.2174/187152006778226486
  9. Zhang, Y.-z., Yu, L.-j., and Wan, J.-m. (2007), Effect of ethanol extract of Lepidium meyenii Walp. (Maca) on immunological function of mice. Natural product R & D, 19(2), 274-276
  10. Cicero, A. F. G., Piacente, S., Plaza, A., Sala, E., Arletti, R., and Pizza, C. (2002), Hexanic Maca extract improves rat sexual performance more effectively than methanolic and chloroformic Maca extracts, Andrologia. 34(3), 177-179 https://doi.org/10.1046/j.1439-0272.2002.00490.x
  11. Zheng, B. L., He, K., Kim, C. H., Rogers, L., Shao, Y., Huang, Z. Y., Lu, Y., Yan, S. J., Qien, L. C., and Zheng, Q. Y. (2000), Effect of a lipidic extract from Lepidium meyenii on sexual behavior in mice and rats, Urology. 55(4), 598-602 https://doi.org/10.1016/S0090-4295(99)00549-X
  12. Muhammad, I., Zhao, J., Dunbar, D. C., and Khan, I. A. (2002), Constituents of Lepidium meyenii 'maca', Phytochemistry. 59(1), 105-110 https://doi.org/10.1016/S0031-9422(01)00395-8
  13. Zhao, J., Muhammad, I., Dunbar, D. C., Mustafa, J., and Khan, I. A. (2005), New alkamides from Maca (Lepidium meyenii), J. Agric. Food Chem. 53, 690-693 https://doi.org/10.1021/jf048529t
  14. Ganzera, M., Zhao, J., Muhammad, I., and Khan, I. A. (2002), Chemical profiling and standardization of Lepidium meyenii (Maca) by reversed phase high performance liquid chromatography, Chem. Pharm. Bull. 50(7), 988-991 https://doi.org/10.1248/cpb.50.988
  15. Korea Food and Drug Administration. (2008), Food Code, Korean Foods Industry Association, Seoul
  16. Row, K. H. and Hong S. P. (2002), Separation of Acanthoside-D in acanthopanax senticosus by preparative recycle chromatograpy, HWAHAK KONGHAK. 40(4), 488-491
  17. C. Turner, J. W. King, and L. Mathiasson (2001), Supercritical fluid extraction and chromatography for fat-soluble vitamin analysis, J. Chromatography A. 936, 215-237 https://doi.org/10.1016/S0021-9673(01)01082-2
  18. Lee, S. J. and B. S. Chun (2002), Extraction of volatile essential oil from citrus junos peel by supercritical carbon dioxide, Korean J. Biotechnol. Bioeng. 17(2), 148-152