Lysaketotriol (1) and lysaketodiol (2), along with two previously known polyhydroxylated steroidal sulfates (3, 4), were isolated from the ethanolic extract of ambulakrums separated from the arms of the starfish Lysastrosoma anthosticta (Sea of Japan). The chemical structures have been elucidated using 1D and 2D NMR spectroscopy (1H, 13C, DEPT, COSY-45, HSQC and HMBC) and mass spectrometry. Compound 1 produced moderate stimulation of lysosomal activity in mouse splenocytes and compounds 1-2 showed immunomodulatory activity.
StonikVA. (2001) Marine polar steroids. Russian Chemical Reviews, 70, 673–715.
2.
MinaleL, RiccioR, ZolloF. (1993) Steroidal oligoglycosides and polyhydroxysteroids from Echinoderms. In Progress in the Chemistry of Organic Natural Products. Vol. 62, HerzW, KirbyGW, MooreRE, SteglichW, TammCh., (Eds). Springer-Verlag, Wien New York. 75–308.
3.
KichaAA, IvanchinaNV, GorshkovaIA, PonomarenkoLP, LikhatskayaGN, StonikVA. (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.
4.
KichaAA, IvanchinaNV, StonikVA. (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.
5.
EyakovGB. LevinaEV, LevinVS, KapustinaII. (1976) Glycosides of marine invertebrates –V. A comparative study of glycoside fractions from starfish. Comparative Biochemistry and Physiology B, 55, 57–60.
6.
LevinaEV, KalinovskyAI, AndriyashenkoPV, DmitrenokPS, AmininDL, StonikVA. (2005) Phrygiasterol, a cytotoxic cyclopropane-containing polyhydroxysteroid, and related compounds from the pacific starfish Hippasteria phrygiana. Journal of Natural Products, 68, 1541–1544.
7.
LevinaEV, AndriyashchenkoPV, KalinovskyAI, StonikVA. (2001) Steroid compounds from the Pacific starfish Lysastrosoma anthosticta. Russian Chemical Bulletin, 50, 313–315.
8.
De SimoneF, DiniA, FinamoreE, MinaleL, PizzaC, RiccioR. (1979) Starfish saponins-IV. Sapogenins from the starfish Asropecten aurantiacus and Marthasterias glacialis. Comparative Biochemistry Physiology B, 64, 25–32.
9.
SmithDSH, TurnerAB, MackieAM. (1973) Marine steroids. Part I. Structures of the principal aglycones from the saponins of the starfish, Marthasterias glacialis. Journal of the Chemical Society. Perkin Transactions1, 1745–1754.
10.
IvanchinaNV, KichaAA, KalinovskyAI, DmitrenokPS, StonikVA, RigueraR, JimenezC. (2000) Hemolytic polar steroidal constituents of the starfish Aphelasterias japonica. Journal of Natural Products, 63, 1178–1181.
