New polar steroids from starfish

Natural Product Communications

Volumn 3, Issue 10, 2008, Pages 1587-1610

  Stonik, Valentin A ^a   Ivanchina, Natalia V ^a   Kicha, Alla A ^a  

^a PACIFIC INSTITUTE OF BIOORGANIC CHEMISTRY   (Russian Federation)

Author keywords

Biological activities; Polyhydroxysteroids; Starfish; Steroid glycosides; Steroidal sulfates

Indexed keywords

ANTIINFECTIVE AGENT; CERTONARDOSTEROL A; CERTONARDOSTEROL B; CERTONARDOSTEROL C; CERTONARDOSTEROL D; CERTONARDOSTEROL E; CERTONARDOSTEROL F; CERTONARDOSTEROL G; CERTONARDOSTEROL H; CERTONARDOSTEROL I; CERTONARDOSTEROL J; CERTONARDOSTEROL K; CERTONARDOSTEROL L; CERTONARDOSTEROL M; GLYCOSIDE; HEPTAOL; HEXAOL; PHRYGIASTEROL; STEROID; TETRAOL; TRISERAMIDE; UNCLASSIFIED DRUG;

ANIMAL CELL; BIOLOGICAL ACTIVITY; CONTROLLED STUDY; DRUG ISOLATION; FEMALE; HUMAN; HUMAN CELL; MEDICAL LITERATURE; MOUSE; NONHUMAN; ORGANISM; RAT; REVIEW; STARFISH;

ASTEROIDEA;

EID: 58549103559     PISSN: 1934578X     EISSN: 15559475     Source Type: Journal    
DOI: 10.1177/1934578x0800301005     Document Type: Review

References (75)

1. Stonik VA. (2001) Marine polar steroids. Uspekhi Khimii (Russian Chemical Reviews), 70, 673-715.
2. Minale L, Riccio R, Zollo F. (1993) Steroidal oligoglycosides and polyhydroxysteroids from Echinoderms. In Progress in the Chemistry of Organic Natural Products. Vol. 62, Herz W, Kirby GW, Moore RE, Steglich W, Tamm Ch. (Eds). Springer-Verlag, Wien New York. 75-308.
3. Iorizzi M, De Marino S, Zollo F. (2001) Steroidal oligoglycosides from the Asteroidea. Current Organic Chemistry, 5, 951-973.
4. Wang W, Li F, Park Y, Hong J, Lee Ch-O, Kong JY, Snin S, Im KS, Jung JH. (2003) Bioactive sterols from the starfish Certonardoa semiregularis. Journal of Natural Products, 66, 384-391. (Pubitemid 36384016)
5. Wang W, Hong J, Lee Ch-O, Im KS, Choi JS, Jung JH. (2004) Cytotoxic sterols and saponins from the starfish Certonardoa semiregularis. Journal of Natural Products, 67, 584-591. (Pubitemid 38533929)
6. Wang W, Jang H, Hong J, Lee Ch-O, Im KS, Bae S-J, Jung JH. (2004) Additional cytotoxic sterols and saponins from the starfish Certonardoa semiregularis. Journal of Natural Products, 67, 1654-1660. (Pubitemid 39426117)
7. Levina EV, Kalinovsky AI, Dmitrenok PS, Prokof'eva NG, Andriyaschenko PV, Stonik VA. (2004) Triseramide is a new steroid conjugate from the starfish Astropecten triseriatus. Doklady Biochemistry and Biophysics, 396, 171-173.
8. Finamore E, Minale L, Riccio R, Rinaldo G, Zollo F. (1991) Novel marine polyhydroxylated steroids from the starfish Myxoderma platyacanthum. Journal of Organic Chemistry, 56, 1146-1153.
9. Levina EV, Kalinovsky AI, Andriyaschenko PV, Stonik VA, Dmitrenok PS. (2002) Steroid polyols from the Far-Eastern starfish Henricia sanguinolenta. Russian Chemical Bulletin, 51, 2295-2298. (Pubitemid 36218799)
10. Levina EV, Kalinovsky AI, Stonik VA, Dmitrenok PS. (2003) Steroidal polyols from Far-Eastern starfishes Henricia sanguinolenta and H. leviuscula leviuscula. Russian Chemical Bulletin, 52, 1623-1628.
11. Levina EV, Kalinovsky AI, Stonik VA, Dmitrenok PS, Andriyaschenko PV. (2005) Steroid compounds from Far Eastern starfishes Henricia aspera and H. tumida. Russian Journal of Bioorganic Chemistry, 31, 467-474. (Pubitemid 41502310)
12. Levina EV, Kalinovsky AI, Andriyashenko PV, Dmitrenok PS, Aminin DL, Stonik VA. (2005) Phrygiasterol, a cytotoxic cyclopropane-containing polyhydroxysteroid, and related compounds from the pacific starfish Hippasteria phrygiana. Journal of Natural Products, 68, 1541-1544.
13. Ivanchina NV, Kicha AA, Kalinovsky AI, Dmitrenok PS, Dmitrenok AS, Chaikina EL, Stonik VA, Gavagnin M, Cimino G. (2006) Polar steroidal compounds from the Far Eastern starfish Henricia leviuscula. Journal of Natural Products, 69, 224-228.
14. Matsumori N, Kaneno D, Murata M, Nakamura H, Tachibana K. (1999) Stereochemical determination of acyclic structures based on carbon-proton spin-coupling constants. A method of configuration analysis for natural products. Journal of Organic Chemistry, 64, 866-876. (Pubitemid 29098013)
15. Freire F, Seco JM, Quinoa E, Riguera R. (2005) The assignment of the absolute configuration of 1,2-diols by low-temperature NMR of a single MPA derivative. Organic Letters, 7, 4855-4858. (Pubitemid 41579879)
16. Seco JM, Quinoa E, Riguera R. (2001) A practical guide for the assignment of the absolute configuration of alcohols, amines and carboxylic acids by NMR. Tetrahedron: Asymmetry, 12, 2915-2925.
17. Kicha AA, Ivanchina NV, Kalinovsky AI, Dmitrenok PS, Agafonova IG, Stonik VA. (2008) Steroidal triglycosides, kurilensosides A, B and C, and other polar steroids from the Far Eastern starfish. Hippasteria kurilensis. Journal of Natural Products, 71, 793-798.
18. Zhang L-X, Fan X, Shi J-G. (2005) A novel polyhydroxyl sterol from Asterina pectinifera. Journal of Asian Natural Products Research, 7, 25-29. (Pubitemid 40096641)
19. Kalinovskii AI, Stonik VA. (2004) A new approach to the study of the conformation of ring D in some polysubstituted steroids by H-1 NMR spectroscopy. Doklady Chemistry, 395, 50-53.
20. Kapustina II, Ponomarenko LP, Moiseenko OP, Stonik VA. (2001) Free and sulfated sterols of two Far-East Leptasterias starfish. Chemistry of Natural Compounds, 37, 515-519. (Pubitemid 33384478)
21. Kicha AA, Ivanchina NV, Kalinovsky AI, Dmitrenok PS, Stonik VA. (2003) Alkaloidosteroids from the starfish Lethasterias nanimensis chelifera. Tetrahedron Letters, 44, 1935-1937.
22. Kicha AA, Ivanchina NV, Kalinovskii AL, Dmitrenok PS, Kainara SO, Aminin DL, Agafonova IG, Stonik VA. (2004) Polar steroidal compounds from the Far-Eastern starfish Lethasterias nanimensis chelifera. Russian Chemical Bulletin, 53, 447-454.
23. Kicha AA, Ivanchina NV, Kalinovsky AI, Dmitrenok PS, Stonik VA. (2001) Sulfated steroid compounds from the starfish Aphelasterias japonica of the Kuril population. Russian Chemical Bulletin, 50, 724-727. (Pubitemid 33328819)
24. Liu H-W, Li J-K, Wang N-L, Yao X-H, Cai G-P. (2006) Sulfated sterols isolated from starfish Asterias amurensis. Journal of Chinese Pharmaceutical Science, 15, 1-5.
25. Levina EV, Kalinovskii AI, Andriyashchenko PV, Dmitrenok PS, Evtushenko EV, Stonik VA. (2004) A new steroidal glycoside phrygioside A and its aglycone from the starfish Hippasteria phrygiana. Russian Chemical Bulletin, 53, 2634-2638.
26. Levina EV, Kalinovsky AI, Andriyashchenko PV, Menzorova NI, Dmitrenok PS. (2007) Trofosides A and B and other cytostatic steroid-derived compounds from the Far East starfish Trofodiscus uber. Russian Journal of Bioorganic Chemistry, 33, 334-340.
27. Kicha AA, Ivanchina NV, Kalinovsky AI, Dmitrenok PS, Stonik VA. (2005) Structures of new polar steroids from the Far-Eastern starfish Ctenodiscus crispatus. Russian Chemical Bulletin, 54, 1266-1271.
28. Kornprobst JM, Sallenave C, Barnathan G. (1998) Sulfated compounds from marine organisms. Comparative Biochemistry and Physiology B, 119, 1-51.
29. Levina EV, Andriyaschenko PV, Stonik VA, Kalinovsky AI. (1996) Ophiuroid-type steroids in starfish of the genus Pteraster. Comparative Biochemistry and Physiology B, 114, 49-52.
30. Levina EV, Andriyaschenko PV, Kalinovsky AI, Stonik VA. (1998) New ophiuroid-type steroids from the starfish Pteraster tesselatus. Journal of Natural Products, 61, 1423-1426.
31. Ivanchina NV, Kicha AA, Kalinovsky AI, Dmitrenok PS, Stonik VA. (2003) Hemolytic steroid disulfates from the Far Eastern starfish Pteraster pulvillus. Journal of Natural Products, 66, 298-301.
32. Levina EV, Andriyashchenko PV, Kalinovsky AI, Dmitrenok PS, Stonik VA. (2002) Steroid compounds from the Far Eastern starfish Diplopteraster multiples. Russian Journal of Bioorganic Chemistry, 28, 189-193. (Pubitemid 37116168)
33. Levina EV, Kalinovsky AI, Dmitrenok PS. (2007) Steroid compounds from the Far East starfish Pteraster obscurus and the ophiura Asteronyx loveni. Russian Journal of Bioorganic Chemistry, 33, 341-346.
34. Takahashi N, Ojika M, Ejima D (2000) Isolation and identification of a trihydroxysteroid disulfate from the starfish Plazaster borealis which induces avoidance reaction-inducing substance in the sea urchin Strongylocentrotus nudus. Fisheries Science, 66, 412-413.
35. Wang W, Li F, Alam N, Liu Y, Hong J, Lee CK, Im KS, Jung JH. (2002) New saponins from the starfish Certonardoa semiregularis. Journal of Natural Products, 65, 1649-1656. (Pubitemid 35386796)
36. Wang WH, Li FM, Hong JK, Lee CO, Cho HY, Im KS, Jung JH. (2003) Four new saponins from the starfish Certonardoa semiregularis. Chemical & Pharmaceutical Bulletin, 51, 435-439. (Pubitemid 41694823)
37. Riccio R, Finamore E, Santaniello M, Zollo F. (1990) Stereoselective synthesis of (24S) and (24R)-24-(hydroxymethyl)-cholesta-5,22(E)-dien-3β-ol - model compounds for stereochemical assignment of polyhydroxylated marine steroids. Journal of Organic Chemistry, 55, 2548-2552.
38. Wang W, Jang H, Hong J, Lee CO, Bae SJ, Shinm S, Jung JH. (2005) New cytotoxic sulfates saponins from the starfish Certonardoa semiregularis. Archives of Pharmacal Research, 28, 285-289. (Pubitemid 44698745)
39. Gil JH, Jung JH, Kim KJ, Kim MS, Hong J. (2006) Structural determination of saponins extracted from starfish by fast atom bombardment collision-induced dissociation mass spectrometry. Analytical Science, 22, 641-644.
40. Qi JH, Ojika M, Sakagami Y. (2002) Linckosides A and B, two new neuritogenic steroid glycosides from the Okinawan starfish Linckia laevigata. Bioorganic & Medicinal Chemistry, 10, 1961-1966. (Pubitemid 34286389)
41. Qi JH, Ojika M, Sakagami Y. (2004) Linckosides C-E, three new neuritogenic steroid glycosides from the Okinawan starfish Linckia laevigata. Bioorganic & Medicinal Chemistry, 12, 4259-4265.
42. Han CG, Qi JH, Ojika M. (2006) Structure-activity relationships of novel neuritogenic steroid glycosides from the Okinawan starfish Linckia laevigata. Bioorganic & Medicinal Chemistry, 14, 4458-4465.
43. Han C, Qi J, Ojika M. (2007) Linckosides M-Q: neuritogenic steroid glycosides from the Okinawan starfish Linckia laevigata. Journal of Natural Medicines, 61, 138-145.
44. Qi J, Han C, Sasayama Y, Nakahara H, Shibata T, Uchida K, Ojika M. (2006) Granulatoside A, a starfish steroid glycoside, enhances PC12 cell neuritogenesis induced by nerve growth factor through an activation of MAP kinase. ChemMedChem, 1, 1351-1354.
45. Kicha AA, Ivanchina NV, Kalinovsky AI, Dmitrenok PS, Palyanova NV, Pankova TM, Starostina MV, Gavagnin M, Stonik VA. (2007) New neuritogenic steroid glycosides from the Vietnamese starfish Linckia laevigata. Natural Product Communications, 2, 41-46.
46. Kicha AA, Ivanchina NV, Kalinovsky AI, Dmitrenok PS, Sokolova EV, Agafonova IG, Morre J, Stonik VA. (2007) Four new steroid glycosides from the Vietnamese starfish Linckia laevigata. Russian Chemical Bulletin, 56, 823-830.
47. Kicha AA, Ivanchina NV, Kalinovskii AI, Dmitrenok PS, Sokolova EV, Agafonova IG (2007) Sulfated steroid glycosides from the Vietnamese starfish Linckia laevigata. Chemistry of Natural Compounds, 43, 76-80.
48. Chludil HD, Maier MS. (2005) Minutosides A and B, antifungal sulfated steroid xylosides from the Patagonian starfish Anasterias minuta. Journal of Natural Products, 68, 1279-1283.
49. Levina EV, Andriyashchenko PV, Kalinovsky AI, Dmitrenok PS, Stonik VA, Prokof'eva NG. (2002) Steroid compounds from the starfish Lysastrosoma anthosticta collected in the Sea of Japan. Russian Chemical Bulletin, 51, 535-539.
50. Kalinovskii AI, Levina EV, Stonik VA, Dmitrenok PS, Andriyashchenko PV. (2004) Steroid polyols from the Far Eastern starfish Henricia sanguinolenta and H. leviuscula leviuscula. Russian Journal of Bioorganic Chemistry, 30, 191-195.
51. Kicha AA, Ivanchina NV, Kalinovsky AI, Dmitrenok PS, Stonik VA. (2000) Asterosaponin P-2 from the Far-Eastern starfish Patiria (Asterina) pectinifera. Russian Chemical Bulletin, 49, 1794-1795.
52. Ivanchina NV, Kicha AA, Kalinovsky AI, Dmitrenok PS, Prokofeva NG, Stonik VA. (2001) New steroid glycosides from the starfish Asterias rathbuni. Journal of Natural Products, 64, 945-947.
53. Levina EV, Kalinovsky AI, Levin VS. (2006) New steroid glycosides from the starfish Fromia milleporella. Russian Journal of Bioorganic Chemistry, 32, 84-88.
54. Ivanchina NV, Malyarenko TV, Kicha AA, Kalinovsky AI, Dmitrenok PS. (2008) Polar steroidal compounds from the Far Eastern starfish Lethasterias fusca. Izvestiya Academii Nauk, seriya khimicheskaya, 57, 196-200 (in Russian).
55. Kicha AA, Kapustina II, Ivanchina NV, Kalinovsky AI, Dmitrenok PS, Stonik VA, Pal'yanova NV, Pankova TM, Starostina MV. (2008) Polyhydroxylated steroid compounds from the Far Eastern starfish Distolasterias nipon. Russian Journal of Bioorganic Chemistry, 34, 118-124.
56. Levina EV, Kalinovsky AI, Andriyaschenko PV, Dmitrenok PS. (2008) Evasteriosides A and B and other sulfated steroids from Pacific starfish Evasterias retifera. Russian Chemical Bulletin, in press.
57. Ivanchina NV, Malyarenko TV, Kicha AA, Kalinovskii AI, Dmitrenok PS, Mollo E. (2006) Polar steroidal compounds from the Antarctic starfish Diplasterias brucei. Chemistry of Natural Compounds, 42, 621-622.
58. Ivanchina NV, Kicha AA, Kalinovsky AI, Stonik VA. (2004) Absolute configuration of side chains of polyhydroxylated steroidal compounds from the starfish Henricia derjugini. Russian Chemical Bulletin, 53, 2639-2642.
59. Prokof'eva NG, Chaikina EL, Kicha AA, Ivanchina NV. (2003) Biological activities of steroid glycosides from starfish. Comparative Biochemistry and Physiology B, 134, 695-701.
60. Ukai K, Iwanaga A, Nagai H, Namikoshi M. (2002) Prevention by polyhydroxysteroids and saponins of Asterina pectinifera of the desquamation of stratum corneum cells. Bioscience Biotechnology and Biochemistry, 66, 913-915.
61. Pal'yanova NV, Pankova TM, Starostina MV, Shtark MB, Kicha AA, Ivanchina NV, Stonik VA. (2006) Neurotrophic effects of polyhydroxylated steroids and steroid glycosides in cultured neuroblastoma cells. Bulletin of Experimental Biology and Medicine, 141, 584-587.
62. Kicha AA, Ivanchina NV, Gorshkova IA, Ponomarenko LP, Likhatskaya GN, Stonik VA. (2001) The distribution of free sterols, polyhydroxysteroids and steroid glycosides in various body components of the starfish Patiria (=Asterina) pectinifera). Comparative Biochemistry and Physiology B, 128, 43-52.
63. Kicha AA, Ivanchina NV, Stonik VA. (2004) Seasonal variations in polyhydroxysteroids and related glycosides from digestive tissues of the starfish Patiria (=Asterina) pectinifera). Comparative Biochemistry and Physiology B, 139, 581-585.
64. Kicha AA, Ivanchina NV, Stonik VA. (2003) Seasonal variations in the levels of polyhydroxysteroids and related glycosides in the digestive tissues of the starfish Patiria (=Asterina) pectinifera). Comparative Biochemistry and Physiology B, 136, 897-903.
65. Tang HF, Yi YH, Li L, Sun P, Zhou DZ, Liu BS. (2005) A new asterosaponin from the starfish Culcita novaeguineae. Chinese Chemical Letters, 16, 619-622. (Pubitemid 43872338)
66. Tang HF, Yi YH, Li L, Sun P, Zhang SQ, Zhao YP. (2005) Bioactive asterosaponins from the starfish Culcita novaeguineae. Journal of Natural Products, 68, 337-341. (Pubitemid 40545467)
67. Tang HF, Yi YH, Li L, Sun P, Zhang SQ, Zhao YP. (2005) Three new asterosaponins from the starfish Culcita novaeguineae and their bioactivity. Planta Medica, 71, 458-463.
68. Tang HF, Yi YH, Li L, Sun P, Zhang SQ, Zhao YP. (2006) Asterosaponins from the starfish Culcita novaeguineae and their bioactivities. Fitoterapia, 77, 28-34.
69. Cheng G, Zhang X, Tang HF, Zhang Y, Zhang XH, Cao WD, Gao DK, Wang XL, Jin BQ. (2006) Asterosaponin 1, a cytostatic compound from the starfish Culcita novaeguineae, functions by inducing apoptosis in human glioblastoma U87MG cells. Journal of Neuro-Oncology, 79, 235-241. (Pubitemid 44363726)
70. Chludil HD, Seldes AM, Maier MS. (2002) Antifungal steroidal glycosides from the Patagonian starfish Anasterias minuta: Structure-activity correlations. Journal of Natural Products, 65, 153-157.
71. De Marino S, Borbone N, Iorizzi M, Esposito G, McClintock JB, Zollo F. (2003) Bioactive asterosaponins from the starfish Luidia quinaria and Psilaster cassiope. Isolation and structure characterization by two-dimensional NMR spectroscopy. Journal of Natural Products, 66, 515-519.
72. Sandvoss M, Weltring A, Preiss A, Levsen K, Wuensch G. (2001) Combination of matrix solid-phase dispersion extraction and direct on-line liquid chromatography-nuclear magnetic resonance spectroscopy-tandem mass spectrometry as a new efficient approach for the rapid screening of natural products: Application to the total asterosaponin fraction of the starfish Asterias rubens. Journal of Chromatography A, 917, 75-86.
73. Sandvoss M, Preiss A, Levsen K, Weisemann R, Spraul M. (2003) Two new asterosaponins from the starfish Asterias rubens: application of a cryogenic NMR probe head. Magnetic Resonance in Chemistry, 41, 949-954.
74. Yang SW, Chan TM, Buevich A, Priestley T, Crona J, Reed J, Wright AE, Patel M, Gullo V, Chen G, Pramanik B, Chu M. (2007) Novel steroidal saponins, Sch 725737 and Sch 725739, from a marine starfish, Novodinia antillensis. Bioorganic & Medicinal Chemistry Letters, 17, 5543-5547.
75. Maier MS, Centurion R, Muniain C, Haddad R, Eberlin MN. (2007) Identification of sulfated steroidal glycosides from the starfish Heliaster helianthus by electrospray ionization mass spectrometry. Archive for Organic Chemistry (ARKIVOC), 301-309.