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Two New Steroid Glycosides from the Far East Starfish Hippasteria Kurilensis

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Two New Steroid Glycosides from the Far East Starfish Hippasteria Kurilensis ISSN 1068-1620, Russian Journal of Bioorganic Chemistry, 2009, Vol. 35, No. 4, pp. 504–509. © Pleiades Publishing, Ltd., 2009. Original Russian Text © A.A. Kicha, N.V. Ivanchina, A.I. Kalinovsky, P.S. Dmitrenok, A.V. Smirnov, 2009, published in Bioorganicheskaya Khimiya, 2009, Vol. 35, No. 4, pp. 5577–562. Two New Steroid Glycosides from the Far East Starfish Hippasteria kurilensis A. A. Kichaa,1, N. V. Ivanchinaa, A. I. Kalinovskya, P. S. Dmitrenoka, and A. V. Smirnovb a Pacific Institute of Bioorganic Chemistry, Far East Division, Russian Academy of Sciences, pr. 100-letiya Vladivostoka, Vladivostok, 690022 Russia b Zoological Institute, Russian Academy of Sciences, St. Petersburg, Russia Received January 26, 2009; in final form, February 13, 2009 Abstract—Two new steroid glycosides were isolated from the Far East starfish Hippasteria kurilensis collected in the Sea of Okhotsk. They were characterized as (22E,24R)-3-O-(2-O-methyl-β-D-xylopyranosyl)-24-O-[2- O-methyl-β-D-xylopyranosyl-(1 5)-α-L-arabinofuranosyl]-5α-cholest-22-ene-3β,4β,6α,7α,8,15β,24-heptaol (kurilensoside I) and (24S)-3-O-(2-O-methyl-β-D-xylopyranosyl)-24-O-(α-L-arabinofuranosyl)-5α-choles- tane-3β,4β,6β,15α,24-pentaol (kurilensoside J). In addition, the earlier known glycosides linkosides F and L1, leviusculoside G, forbeside L, desulfated echinasteroside, and granulatoside A were isolated and identified. The structures of the new compounds were established with the help of two-dimentional NMR spectroscopy and mass- spectrometry. Key words: starfish, Hippasteria kurilensis, glycosides, polyhydroxysteroids, and NMR spectra DOI: 10.1134/S106816200904013X INTRODUCTION known and two new polyhydrohysteroids [3] as a result Highly oxidized steroids and related glycosides are of study of Far East starfish Hippasteria kurilensis the most widespread secondary metabolites of starfish. Fisher, 1911 (family Goniasteridae, order Valvatida), Usually, they are present in animal extracts as complex collected in the Sea of Okhotsk (Kuriles). Later, five mixtures of structurally close substances, which are dif- new monosides (kurilensosides E, F, G, H, and 15-O- ficultly separated into individual components. As a rule, sulfate of echinasteroside C) and known echinastero- for the isolation of these substances in each concrete side C were found in the same starfish [4]. Continuing case, careful selection of the optimum conditions of the study of the steroid composition of sea starfish division with the help of column chromatography on various sorbents and HPLC is required. The oxidation H. kurilensis, we isolated eight additional steroid com- degree of steroid compounds from starfish frequently pounds, including two new steroid glycosides, kurilen- exceeds those of such highly oxidized natural steroids sosides I (I) and J (II), and six earlier known glycosides as fito- and zooecdysones and some steroid polyols of (III)–(VIII). The structures of the new compounds sea sponges and soft corals [1]. The highly oxidized were established mainly with the help of 1H-1H-COSY, steroid compounds of starfish are of scientific interest HSQC, HMBC and DEPT NMR experiments. The new not only due to their unusual chemical structure, but compounds (I) and (II) have a 2-O-methyl-β-D-xylopy- also due to various biological properties, including embriotoxic, antifungal, antiviral, antibacterial, neuri- ranose residue at C3 of polyhydroxylated steroid agly- togenic, and other kinds of activity [2]. cone. Kurilensoside I (I) is a trioside and contains an additional disaccharide fragment in the side chain of Earlier, we isolated four new glycosides: triosides kurilensosides A, B, and C and bioside D, as well as one aglycone at C24. Kurilensoside J (II) belongs to bio- sides and additionally contains an α-L-arabinofuranose 1 Corresponding author; fax: (423) 231-40-50; phone: (423) 31-11- 68; e-mail: [email protected]. moiety in the side chain of aglycone at C24. 504 TWO NEW STEROID GLYCOSIDES FROM THE FAR EAST STARFISH 505 (2) O OH OH 1'' (3) OH O O O 1''' O OH HO 21 O 20 27 24 HO HO 18 22 25 OMe 23 26 12 17 19 11 13 16 OH 14 15 1 9 OH 2 10 8 H 3 5 7 OH (1) 4 6 H O OH 1' O O H O HO OH H HO HO HO OH OMe HO HO OMe (I) (II) OH OH OH (III) OH H O O OH OH (IV) HO HO OMe OH OR1 OH O OH (V) HO A OH OH H O O (VI) R = R1 = H H 1 HO OH (VII) R = H R = A RO 1 HO OMe (VIII) R = Me R = A RESULTS AND DISCUSSION The mass spectrum HR-ESI (registration of cations) of kurilensoside I (I) contained the peak of a pseudo- The fractions of highly oxidized steroid compounds molecular ion with m/z 929.4711 [M + Na]+ correspond- were isolated from an ethanolic extract of the starfish ing to the molecular formula C44H74O19. It followed H. kurilensis with the help of column chromatography from the spectra 1ç-, 13C-, and DEPT NMR that glyco- on an Amberlite XAD-2, silica gel, and Florisil. The side (I) contains 44 carbon atoms, including carbons of use of HPLC on the semipreparative and analytical col- five methyl, eight methylene, and 24 methine groups; umns of Diasphere-110-C18 allowed us to isolate two and three quaternary carbon atoms, including one oxy- new glycosides, (I) and (II), and six known compounds genated, two protonated olefin carbon atoms, and two (III)–(VIII) from these fractions. The results of the methoxyl groups (Table 2). Three anomeric protons (at chromatographic separation of the steroid fractions are δ 4.45, 4.91, and 4.33 ppm) are exhibited in the given in Table 1. The known glycosides were identified 1H-NMR spectrum of (I); they were bound in a HSQC by a comparison of their spectra, 1ç- and 13ë-NMR, spectrum with three signals of carbon atoms at δ 102.3, and mass spectra with the corresponding data for these 109.0, and 105.3 ppm, respectively. In the mass spec- substances found in published works. trum, there were peaks of fragment ions at m/z 783 RUSSIAN JOURNAL OF BIOORGANIC CHEMISTRY Vol. 35 No. 4 2009 506 KICHA et al. Table 1. Steroid glycosides isolated from the starfish H. kurilensis (+)-MALDI–TOF Starfish from which the compound Compound Quantity, mg R* mass spectrum f was first isolated [reference] [M + Na]+ Kurilensoside I (I) 1.5 0.17 929** Kurilensoside J (II) 3.2 0.39 753 Lincoside F (III) 1.0 0.52 647 Linckia laevigata [5] Echinasteroside A desulfated (IV) 1.5 0.54 647 Henricia downeyae [6] Forbeside L (V) 0.5 0.50 663** Asterias forbesi [7] Linckoside LI (VI) 1.0 0.54 637 Linckia laevigata [8] Granuloside A (VII) 17.4 0.33 769 Choriaster granulatus [9] Leviusculoside G 1.0 0.46 783** Henricia leviuscula [10], (=Forbeside J) (VIII) Asterias forbesi [7] Notes: * It is determined in a toluene–ethanol system (9 : 5); ** (+)-ESI mass spectrum [(M + Na) – 146]+, corresponding to a loss of the termi- protons and carbon atoms—H1'(2-O-Me-Xyl)/C3, nal residue of O-methylpentose, and at m/z 651 [(M + H1'''(2-O-Me-Xyl)/C5''(Ara), H1'(Ara)/C24—and Na) – 146–132]+, corresponding to a loss of the O-meth- also by the presence of the cross-peak ç24/C1''(Ara). ylpentose and pentose residues. The data indicate the By analogy with kurilensoside C, the R-configuration presence in the glycoside molecule (I) of three pentosyl was suggested for chiral center C24. The monosaccharide residues and a heptasubstituted L-configuration was ascribed to the arabinose residue, cholestane aglycone. and the D-configuration to the 2-O-methylxylose, A comparison of the chemical shifts of carbon atoms since only such forms of monosaccharide units have and protons and the corresponding coupling constants in been found earlier in steroid glycosides of starfish [1, the 1H- and 13C-NMR spectra of glycoside (I) and kurilen- 2]. On the basis of available data, the structure of kurilensoside I was determined as (22E,24R)-3-O-(2- soside C from the same starfish [3] showed that both com- β β pounds have 3β,4β,6α, 7α,8,15β,24-heptahydroxy-5α- O-methyl- -D-xylopyranosyl)-24-O-[2-O-methyl- - β D-xylopyranosyl-(1 5)-α-L-arabinopyranosyl]-5α- cholestane aglycone with 2-O-methyl -D-xylopyranose β β α α β residues at C3 and 2-O-methyl β-D-xylopyranosyl- cholest-22-ene-3 ,4 ,6 ,7 ,8,15 , 24-heptaol. Thus, it (1 5)-α-L was established that glycoside (I) represents a -arabinofuranose residue at C24. However, ∆22 unlike kurilensoside C, the NMR spectra of (I) contained -analogue of kurilensoside C [3]. signals of a double bond in the side chain of aglycone and Kurilensoside I (I) is the fourth representative of a its molecular mass was, respectively, smaller by two mass rare structural group of polyhydroxylated steroid trigly- units. According to 13C-NMR spectra, in the side chain of cosides of the starfish containing two carbohydrate glycoside (I) were three methyl groups (δ 20.8, 19.1, and fragments, one of which, a monosaccharide residue, is 18.5 ppm); three methine groups, one of which was attached to C3 of the steroid nucleus, and another, a dis- attached to oxygen atom (δ 40.9, 33.8, and 86.2 ppm); and accharide residue, is localized at C24 of the aglycone two carbon atoms of a double bond (δ 140.6 and chain. Previously, three such earlier steroid triosides 128.3 ppm). 1H-1H-COSY, HSQC, and HMBC NMR have been known: kurilensosides A, B, and C; they experiments allowed for the determination of signals of all have also been found in the starfish H.
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