Ocean and Polar Research

  • 제38권4호
  • /
  • Pages.287-294
  • /
  • 2016
  • /
  • 1598-141X(pISSN)
  • /
  • 2234-7313(eISSN)
한국해양과학기술원 (Korea Institute of Ocean Science & Technology)
권호 표지
DOI QR코드

DOI QR Code

열대 해면동물 Lipastrotethya sp.에서 분리된 사포닌 화합물

A New Triterpenoid Saponin from the Tropical Marine Sponge Lipastrotethya sp.

  • 엄태양 (한국해양과학기술원 해양생명공학연구센터) ;
  • 이연주 (한국해양과학기술원 해양생명공학연구센터) ;
  • 이희승 (한국해양과학기술원 해양생명공학연구센터)
  • 투고 : 2016.10.07
  • 심사 : 2016.10.29
  • 발행 : 2016.12.30
PDF 다운로드
⟨ 이전 논문 다음 논문 ⟩

초록

Marine sponges have been a remarkably rich source of pharmacologically active and structurally diverse natural products. As a part of our continuing search for novel secondary metabolites of biomedical importance from marine invertebrate, we encountered the sponge Lipastrotethya sp. from Chuuk, Micronesia. The crude organic extract of this animal exhibited considerable cytotoxicity against the K562 cell line. Guided by the $^1H$ NMR analysis, flash chromatography of the crude extract followed by HPLC yielded a new triterpene glycoside, along with ten known saponins of the sarasinoside class. The structure of this new compound was determined by combined spectroscopic methods such as COSY, HSQC and HMBC experiment. Among these metabolites, six compounds exhibited moderate cytotoxicity against ACHN, MDA-MB-231, NCI-H23 and NUGC-3 cell lines.

키워드

참고문헌

  1. Andersson L, Bohlin L, Iorizzi M, Riccio R, Minale L, Moreno-Lopez W (1989) Biological activity of saponins and saponin-like compounds from starfish and brittle stars. Toxicon 27(2):179-188 https://doi.org/10.1016/0041-0101(89)90131-1
  2. Dai HF, Edrada RA, Ebel R, Nimtz M, Wray V, Proksch P (2005) Norlanostane triterpenoidal saponins from the marine sponge Melophlus sarassinorum. J Nat Prod 68:1231-1237 https://doi.org/10.1021/np050152d
  3. D'Auria M, Paloma LG, Minale L, Riccio R (1992) Structure characterization by two-dimensional NMR spectroscopy of two marine triterpene oligoglycosides from a pacific sponge of the genus Erylus. Tetrahedron 48(3):491-498 https://doi.org/10.1016/S0040-4020(01)89011-6
  4. Dyck SV, Gerbaux P, Flammang P (2010) Qualitative and quantitative saponin contents in five sea cucumbers from the Indian ocean. Mar Drugs 8:173-189 https://doi.org/10.3390/md8010173
  5. Ebada SS, Lin WH, Proksch P (2010) Bioactive sesterterpenes and triterpenes from marine sponges: occurrence and pharmacological significance. Mar Drugs 8:313-346 https://doi.org/10.3390/md8020313
  6. Espada A, Jimenez C, Rodriguez J, Phillip C, Riguera R (1992) Sarasinosides D-G: four new triterpenoid saponins from the sponge Asteropus sarasinosum. Tetrahedron 48(40):8685-8696 https://doi.org/10.1016/S0040-4020(01)89444-8
  7. Hostettmann K, Marston A (1995) Saponins. Cambridge University Press, Cambridge, 232 p
  8. James DB (1986) Holothurian toxin as a poison to eradicate undesirable organisms from fish farm. Proc Symp Coast Aquacult 4:1339-1341
  9. Kang SS (1996) Saponin: triterpenoid. Seoul National University Press, Seoul, 67 p
  10. Kobayashi M, Okamoto Y, Kitagawa I (1991) Marine natural products XXVIII. the structures of sarasinosides $A_1$, $A_2$, $A_3$, $B_1$, $B_2$, $B_3$, $C_1$, $C_2$, $C_3$, nine new norlanostanetriterpenoidal oligoglycosides from the palauan marine sponge Asteropus sarasinosum. Chem Pharm Bull 39(11):2867-2877 https://doi.org/10.1248/cpb.39.2867
  11. Kuo SC, Lee HZ, Juang JP, Lin YT, We TS, Chang JJ, Lednicer D, Paull KD, Lin CM, Hamel E, Lee KH (1993) Synthesis and cytotoxicity of 1,6,7,8-substituted 2-(4'-substituted phenyl)-4-quinolones and related compounds: Identification as antimitotic agents interacting with tubulin. J Med Chem 36:1146-1156 https://doi.org/10.1021/jm00061a005
  12. Lee HS, Seo Y, Cho KW, Rho JR, Shin J, Paul VJ (2000) New triterpenoid saponins from the sponge melophlus isis. J Nat Prod 63:915-919 https://doi.org/10.1021/np990589j
  13. Lee JH, Jang KH, Lee YJ, Lee HS, Sim CJ, Oh KB, Shin J (2011) Triterpene galacotsides of the pouoside class and corresponding aglycones from the sponge Lipastrotethya sp. J Nat Prod 74:2563-2570 https://doi.org/10.1021/np200748g
  14. Lee JH, Jeon JE, Lee YJ, Lee HS, Sim CJ, Oh KB, Shin JH (2012) Nortriterpene glycosides of the sarasinoside class from the sponge Lipastrotethya sp. J Nat Prod 75:1365-1372 https://doi.org/10.1021/np300297d
  15. Li M, Miao ZH, Chen Z, Chen Q, Gui M, Lin LP, Sun P, Yi YH, Ding J (2010) Echinoside A, a new marinederived anticancer saponin, targets topoisomerase $2{\alpha}$ by unique interference with its DNA binding and catalytic cycle. Annals of Oncology 21:597-607 https://doi.org/10.1093/annonc/mdp335
  16. Mao SC, Manzo E, Guo YW, Gavagnin M, Mollo E, Ciavatta ML, Soest RV, Cimino G (2007) New diastereomeric bis-sesquiterpenes from Hainan marine sponge Axinyssa variabilis and Lipastrotethya ana. Tetrahedron 63:11108-11113 https://doi.org/10.1016/j.tet.2007.08.028
  17. Park HJ, Kim MM, Lee DH (2011) Effect of saponin with antioxidant activity on matrix metalloproteinase in human dermal fibroblasts. J Life Sci 21:1266-1273 https://doi.org/10.5352/JLS.2011.21.9.1266
  18. Santalova EA, Denisenko VA, Dmitrenok PS, Berdyshev DV, Stonik VA (2006) Two new sarasinosides from the sponge Melophlus sarasinorum. Nat Prod Commun 1:265-271
  19. Schmitz FJ, Ksebati MB, Gunasekera SP, Agarwal S (1988) Sarasinoside A1: A saponin containing amino sugars isolated from a sponge. J Org Chem 53:5941-5947 https://doi.org/10.1021/jo00260a025
  20. Tong Y, Zhang X, Tian F, Yi Y, Xu Q, Li L, Tong L, Lin L, Ding J (2005) Philinopside A, a novel marine-derived compound possessing dual anti-angiogenic and antitumor effects. Int J Cancer 114:843-853 https://doi.org/10.1002/ijc.20804

피인용 문헌

  1. Marine natural products vol.35, pp.1, 2018, https://doi.org/10.1039/C7NP00052A