A short review concerning new polar steroids isolated from starfish with 75 citations is given. This review covers the literature published from 2001 through 2007. The emphasis is on new structures, together with their relevant biological activities, source organisms, and localities of collections.
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.
IorizziM, De MarinoS, ZolloF. (2001) Steroidal oligoglycosides from the Asteroidea. Current Organic Chemistry, 5, 951–973.
4.
WangW, LiF, ParkY, HongJ, LeeCh-O, KongJY, SninS, ImKS, JungJH. (2003) Bioactive sterols from the starfish Certonardoa semiregularis. Journal of Natural Products, 66, 384–391.
5.
WangW, HongJ, LeeCh-O, ImKS, ChoiJS, JungJH. (2004) Cytotoxic sterols and saponins from the starfish Certonardoa semiregularis. Journal of Natural Products, 67, 584–591.
6.
WangW, JangH, HongJ, LeeCh-O, ImKS, BaeS-J, JungJH. (2004) Additional cytotoxic sterols and saponins from the starfish Certonardoa semiregularis. Journal of Natural Products, 67, 1654–1660.
7.
LevinaEV, KalinovskyAI, DmitrenokPS, Prokof'evaNG, AndriyaschenkoPV, StonikVA. (2004) Triseramide is a new steroid conjugate from the starfish Astropecten triseriatus. Doklady Biochemistry and Biophysics, 396, 171–173.
8.
FinamoreE, MinaleL, RiccioR, RinaldoG, ZolloF. (1991) Novel marine polyhydroxylated steroids from the starfish Myxoderma platyacanthum. Journal of Organic Chemistry, 56, 1146–1153.
9.
LevinaEV, KalinovskyAI, AndriyaschenkoPV, StonikVA, DmitrenokPS. (2002) Steroid polyols from the Far-Eastern starfish Henricia sanguinolenta. Russian Chemical Bulletin, 51, 2295–2298.
10.
LevinaEV, KalinovskyAI, StonikVA, DmitrenokPS. (2003) Steroidal polyols from Far-Eastern starfishes Henricia sanguinolenta and H. leviuscula leviuscula. Russian Chemical Bulletin, 52, 1623–1628.
11.
LevinaEV, KalinovskyAI, StonikVA, DmitrenokPS, AndriyaschenkoPV. (2005) Steroid compounds from Far Eastern starfishes Henricia aspera and H. tumida. Russian Journal of Bioorganic Chemistry, 31, 467–474.
12.
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.
13.
IvanchinaNV, KichaAA, KalinovskyAI, DmitrenokPS, DmitrenokAS, ChaikinaEL, StonikVA, GavagninM, CiminoG. (2006) Polar steroidal compounds from the Far Eastern starfish Henricia leviuscula. Journal of Natural Products, 69, 224–228.
14.
MatsumoriN, KanenoD, MurataM, NakamuraH, TachibanaK. (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.
15.
FreireF, SecoJM, QuinoaE, RigueraR. (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.
16.
SecoJM, QuinoaE, RigueraR. (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.
KichaAA, IvanchinaNV, KalinovskyAI, DmitrenokPS, AgafonovaIG, StonikVA. (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.
ZhangL-X, FanX, ShiJ-G. (2005) A novel polyhydroxyl sterol from Asterina pectinifera. Journal of Asian Natural Products Research, 7, 25–29.
19.
KalinovskiiAI, StonikVA. (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.
KapustinaII, PonomarenkoLP, MoiseenkoOP, StonikVA. (2001) Free and sulfated sterols of two Far-East Leptasterias starfish. Chemistry of Natural Compounds, 37, 515–519.
21.
KichaAA, IvanchinaNV, KalinovskyAI, DmitrenokPS, StonikVA. (2003) Alkaloidosteroids from the starfish Lethasterias nanimensis chelifera. Tetrahedron Letters, 44, 1935–1937.
22.
KichaAA, IvanchinaNV, KalinovskiiAL, DmitrenokPS, KainaraSO, AmininDL, AgafonovaIG, StonikVA. (2004) Polar steroidal compounds from the Far-Eastern starfish Lethasterias nanimensis chelifera. Russian Chemical Bulletin, 53, 447–454.
23.
KichaAA, IvanchinaNV, KalinovskyAI, DmitrenokPS, StonikVA. (2001) Sulfated steroid compounds from the starfish Aphelasterias japonica of the Kuril population. Russian Chemical Bulletin, 50, 724–727.
24.
LiuH-W, LiJ-K, WangN-L, YaoX-H, CaiG-P. (2006) Sulfated sterols isolated from starfish Asterias amurensis. Journal of Chinese Pharmaceutical Science, 15, 1–5.
25.
LevinaEV, KalinovskiiAI, AndriyashchenkoPV, DmitrenokPS, EvtushenkoEV, StonikVA. (2004) A new steroidal glycoside phrygioside A and its aglycone from the starfish Hippasteria phrygiana. Russian Chemical Bulletin, 53, 2634–2638.
26.
LevinaEV, KalinovskyAI, AndriyashchenkoPV, MenzorovaNI, DmitrenokPS. (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.
KichaAA, IvanchinaNV, KalinovskyAI, DmitrenokPS, StonikVA. (2005) Structures of new polar steroids from the Far-Eastern starfish Ctenodiscus crispatus. Russian Chemical Bulletin, 54, 1266–1271.
28.
KornprobstJM, SallenaveC, BarnathanG. (1998) Sulfated compounds from marine organisms. Comparative Biochemistry and Physiology B, 119, 1–51.
29.
LevinaEV, AndriyaschenkoPV, StonikVA, KalinovskyAI. (1996) Ophiuroid-type steroids in starfish of the genus Pteraster. Comparative Biochemistry and Physiology B, 114, 49–52.
30.
LevinaEV, AndriyaschenkoPV, KalinovskyAI, StonikVA. (1998) New ophiuroid-type steroids from the starfish Pteraster tesselatus. Journal of Natural Products, 61, 1423–1426.
31.
IvanchinaNV, KichaAA, KalinovskyAI, DmitrenokPS, StonikVA. (2003) Hemolytic steroid disulfates from the Far Eastern starfish Pteraster pulvillus. Journal of Natural Products, 66, 298–301.
32.
LevinaEV, AndriyashchenkoPV, KalinovskyAI, DmitrenokPS, StonikVA. (2002) Steroid compounds from the Far Eastern starfish Diplopteraster multiples. Russian Journal of Bioorganic Chemistry, 28, 189–193.
33.
LevinaEV, KalinovskyAI, DmitrenokPS. (2007) Steroid compounds from the Far East starfish Pteraster obscurus and the ophiura Asteronyx loveni. Russian Journal of Bioorganic Chemistry, 33, 341–346.
34.
TakahashiN, OjikaM, EjimaD (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.
WangW, LiF, AlamN, LiuY, HongJ, LeeCK, ImKS, JungJH. (2002) New saponins from the starfish Certonardoa semiregularis. Journal of Natural Products, 65, 1649–1656.
36.
WangWH, LiFM, HongJK, LeeCO, ChoHY, ImKS, JungJH. (2003) Four new saponins from the starfish Certonardoa semiregularis. Chemical & Pharmaceutical Bulletin, 51, 435–439.
37.
RiccioR, FinamoreE, SantanielloM, ZolloF. (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.
WangW, JangH, HongJ, LeeCO, BaeSJ, ShinmS, JungJH. (2005) New cytotoxic sulfates saponins from the starfish Certonardoa semiregularis. Archives of Pharmacal Research, 28, 285–289.
39.
GilJH, JungJH, KimKJ, KimMS, HongJ. (2006) Structural determination of saponins extracted from starfish by fast atom bombardment collision-induced dissociation mass spectrometry. Analytical Science, 22, 641–644.
40.
QiJH, OjikaM, SakagamiY. (2002) Linckosides A and B, two new neuritogenic steroid glycosides from the Okinawan starfish Linckia laevigata. Bioorganic & Medicinal Chemistry, 10, 1961–1966.
41.
QiJH, OjikaM, SakagamiY. (2004) Linckosides C-E, three new neuritogenic steroid glycosides from the Okinawan starfish Linckia laevigata. Bioorganic & Medicinal Chemistry, 12, 4259–4265.
42.
HanCG, QiJH, OjikaM. (2006) Structure-activity relationships of novel neuritogenic steroid glycosides from the Okinawan starfish Linckia laevigata. Bioorganic & Medicinal Chemistry, 14, 4458–4465.
43.
HanC, QiJ, OjikaM. (2007) Linckosides M-Q: neuritogenic steroid glycosides from the Okinawan starfish Linckia laevigata. Journal of Natural Medicines, 61, 138–145.
44.
QiJ, HanC, SasayamaY, NakaharaH, ShibataT, UchidaK, OjikaM. (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.
KichaAA, IvanchinaNV, KalinovskyAI, DmitrenokPS, PalyanovaNV, PankovaTM, StarostinaMV, GavagninM, StonikVA. (2007) New neuritogenic steroid glycosides from the Vietnamese starfish Linckia laevigata. Natural Product Communications, 2, 41–46.
46.
KichaAA, IvanchinaNV, KalinovskyAI, DmitrenokPS, SokolovaEV, AgafonovaIG, MorreJ, StonikVA. (2007) Four new steroid glycosides from the Vietnamese starfish Linckia laevigata. Russian Chemical Bulletin, 56, 823–830.
47.
KichaAA, IvanchinaNV, KalinovskiiAI, DmitrenokPS, SokolovaEV, AgafonovaIG (2007) Sulfated steroid glycosides from the Vietnamese starfish Linckia laevigata. Chemistry of Natural Compounds, 43, 76–80.
48.
ChludilHD, MaierMS. (2005) Minutosides A and B, antifungal sulfated steroid xylosides from the Patagonian starfish Anasterias minuta. Journal of Natural Products, 68, 1279–1283.
49.
LevinaEV, AndriyashchenkoPV, KalinovskyAI, DmitrenokPS, StonikVA, Prokof'evaNG. (2002) Steroid compounds from the starfish Lysastrosoma anthosticta collected in the Sea of Japan. Russian Chemical Bulletin, 51, 535–539.
50.
KalinovskiiAI, LevinaEV, StonikVA, DmitrenokPS, AndriyashchenkoPV. (2004) Steroid polyols from the Far Eastern starfish Henricia sanguinolenta and H. leviuscula leviuscula. Russian Journal of Bioorganic Chemistry, 30, 191–195.
51.
KichaAA, IvanchinaNV, KalinovskyAI, DmitrenokPS, StonikVA. (2000) Asterosaponin P-2 from the Far-Eastern starfish Patiria (Asterina) pectinifera. Russian Chemical Bulletin, 49, 1794–1795.
52.
IvanchinaNV, KichaAA, KalinovskyAI, DmitrenokPS, ProkofevaNG, StonikVA. (2001) New steroid glycosides from the starfish Asterias rathbuni. Journal of Natural Products, 64, 945–947.
53.
LevinaEV, KalinovskyAI, LevinVS. (2006) New steroid glycosides from the starfish Fromia milleporella. Russian Journal of Bioorganic Chemistry, 32, 84–88.
54.
IvanchinaNV, MalyarenkoTV, KichaAA, KalinovskyAI, DmitrenokPS. (2008) Polar steroidal compounds from the Far Eastern starfish Lethasterias fusca. Izvestiya Academii Nauk, seriya khimicheskaya, 57, 196–200 (in Russian).
55.
KichaAA, KapustinaII, IvanchinaNV, KalinovskyAI, DmitrenokPS, StonikVA, Pal'yanovaNV, PankovaTM, StarostinaMV. (2008) Polyhydroxylated steroid compounds from the Far Eastern starfish Distolasterias nipon. Russian Journal of Bioorganic Chemistry, 34, 118–124.
56.
LevinaEV, KalinovskyAI, AndriyaschenkoPV, DmitrenokPS. (2008) Evasteriosides A and B and other sulfated steroids from Pacific starfish Evasterias retifera. Russian Chemical Bulletin, in press.
57.
IvanchinaNV, MalyarenkoTV, KichaAA, KalinovskiiAI, DmitrenokPS, MolloE. (2006) Polar steroidal compounds from the Antarctic starfish Diplasterias brucei. Chemistry of Natural Compounds, 42, 621–622.
58.
IvanchinaNV, KichaAA, KalinovskyAI, StonikVA. (2004) Absolute configuration of side chains of polyhydroxylated steroidal compounds from the starfish Henricia derjugini. Russian Chemical Bulletin, 53, 2639–2642.
59.
Prokof'evaNG, ChaikinaEL, KichaAA, IvanchinaNV. (2003) Biological activities of steroid glycosides from starfish. Comparative Biochemistry and Physiology B, 134, 695–701.
60.
UkaiK, IwanagaA, NagaiH, NamikoshiM. (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'yanovaNV, PankovaTM, StarostinaMV, ShtarkMB, KichaAA, IvanchinaNV, StonikVA. (2006) Neurotrophic effects of polyhydroxylated steroids and steroid glycosides in cultured neuroblastoma cells. Bulletin of Experimental Biology and Medicine, 141, 584–587.
62.
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.
63.
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.
64.
KichaAA, IvanchinaNV, StonikVA. (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.
TangHF, YiYH, LiL, SunP, ZhouDZ, LiuBS. (2005) A new asterosaponin from the starfish Culcita novaeguineae. Chinese Chemical Letters, 16, 619–622.
66.
TangHF, YiYH, LiL, SunP, ZhangSQ, ZhaoYP. (2005) Bioactive asterosaponins from the starfish Culcita novaeguineae. Journal of Natural Products, 68, 337–341.
67.
TangHF, YiYH, LiL, SunP, ZhangSQ, ZhaoYP. (2005) Three new asterosaponins from the starfish Culcita novaeguineae and their bioactivity. Planta Medica, 71, 458–463.
68.
TangHF, YiYH, LiL, SunP, ZhangSQ, ZhaoYP. (2006) Asterosaponins from the starfish Culcita novaeguineae and their bioactivities. Fitoterapia, 77, 28–34.
69.
ChengG, ZhangX, TangHF, ZhangY, ZhangXH, CaoWD, GaoDK, WangXL, JinBQ. (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.
70.
ChludilHD, SeldesAM, MaierMS. (2002) Antifungal steroidal glycosides from the Patagonian starfish Anasterias minuta: Structure-activity correlations. Journal of Natural Products, 65, 153–157.
71.
De MarinoS, BorboneN, IorizziM, EspositoG, McClintockJB, ZolloF. (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.
SandvossM, WeltringA, PreissA, LevsenK, WuenschG. (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.
SandvossM, PreissA, LevsenK, WeisemannR, SpraulM. (2003) Two new asterosaponins from the starfish Asterias rubens: application of a cryogenic NMR probe head. Magnetic Resonance in Chemistry, 41, 949–954.
MaierMS, CenturionR, MuniainC, HaddadR, EberlinMN. (2007) Identification of sulfated steroidal glycosides from the starfish Heliaster helianthus by electrospray ionization mass spectrometry. Archive for Organic Chemistry (ARKIVOC), 301–309.
