Isolation and structures of erylosides from the carribean sponge Erylus goffrilleri

被引:24
作者
Afiyatullov, Shamil Sh. [1 ]
Kalinovsky, Anatoly I. [1 ]
Antonov, Alexandr S. [1 ]
Ponomarenko, Ludmila P. [1 ]
Dmitrenok, Pavel S. [1 ]
Aminin, Dmitry L. [1 ]
Krasokhin, Vladimir B. [1 ]
Nosova, Valentina M. [2 ]
Kisin, Alexandr V. [2 ]
机构
[1] Russian Acad Sci, Pacific Inst Bioorgan Chem, Far E Branch, Vladivostok 690022, Russia
[2] State Res Inst Chem & Technol Organelement Cpds, Moscow, Russia
来源
JOURNAL OF NATURAL PRODUCTS | 2007年 / 70卷 / 12期
关键词
D O I
10.1021/np070319y
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
Eight new triterpene glycosides, erylosides R (1), S (2), T (3), U (4), F-5-F-7 (5-7), and V (8), were isolated from the sponge Erylus goffrilleri collected near Arresife-Seko Reef (Cuba). Structures of 1 and 2 were determined as the corresponding monosides having aglycons related to penasterol with additional oxidation and methylation patterns in their side chains. Eryloside T (3) was structurally identified as the Delta(7)-isomer of 1, containing an unusual (14 -> 9)-lactone ring in the tetracyclic aglycon moiety, and eryloside U (4) was shown to be the 7,8-epoxide of 3. Erylosides F-5-F-7 (5-7) and V (8) contain new variants of carbohydrate chains with two (5-7) and three (8) sugar units, respectively.
引用
收藏
页码:1871 / 1877
页数:7
相关论文
共 23 条
[1]   Isolation and structures of erylosides from the carribean sponge Erylus formosus [J].
Antonov, Alexandr S. ;
Kalinovsky, Anatoly I. ;
Stonik, Valentin A. ;
Afiyatullov, Shamil S. ;
Aminin, Dmitry L. ;
Dmitrenok, Pavel S. ;
Mollo, Ernesto ;
Cimino, Guido .
JOURNAL OF NATURAL PRODUCTS, 2007, 70 (02) :169-178
[2]   Mycalosides B-I, eight new spermostatic steroid oligoglycosides from the sponge Mycale laxissima [J].
Antonov, AS ;
Afiyatullov, SS ;
Kalinovsky, AI ;
Ponomarenko, LP ;
Dmitrenok, PS ;
Aminin, DL ;
Agafonova, IG ;
Stonik, VA .
JOURNAL OF NATURAL PRODUCTS, 2003, 66 (08) :1082-1088
[3]   SEMIEMPIRICAL DERIVATION OF C-13 NUCLEAR MAGNETIC-RESONANCE CHEMICAL-SHIFTS - HYDROCARBONS, ALCOHOLS, AMINES, KETONES, AND OLEFINS [J].
BEIERBECK, H ;
SAUNDERS, JK ;
APSIMON, JW .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1977, 55 (15) :2813-2828
[4]   THE STRUCTURE OF ERYLOSIDE A, A NEW ANTITUMOR AND ANTIFUNGAL 4-METHYLATED STEROIDAL GLYCOSIDE FROM THE SPONGE ERYLUS-LENDENFELDI [J].
CARMELY, S ;
ROLL, M ;
LOYA, Y ;
KASHMAN, Y .
JOURNAL OF NATURAL PRODUCTS, 1989, 52 (01) :167-170
[5]  
CHAIRUL CSM, 1994, PHYTOCHEMISTRY, V35, P1305
[6]   STRUCTURE CHARACTERIZATION BY 2-DIMENSIONAL NMR-SPECTROSCOPY, OF 2 MARINE TRITERPENE OLIGOGLYCOSIDES FROM A PACIFIC SPONGE OF THE GENUS ERYLUS [J].
DAURIA, MV ;
PALOMA, LG ;
MINALE, L ;
RICCIO, R .
TETRAHEDRON, 1992, 48 (03) :491-498
[7]   H-1 AND C-13 NMR ASSIGNMENTS FOR LANOSTAN-3 BETA-OL DERIVATIVES - REVISED ASSIGNMENTS FOR LANOSTEROL [J].
EMMONS, GT ;
WILSON, WK ;
SCHROEPFER, GJ .
MAGNETIC RESONANCE IN CHEMISTRY, 1989, 27 (11) :1012-1024
[8]   New steroidal saponins from the sponge Erylus lendenfeldi [J].
Fouad, M ;
Al-Trabeen, K ;
Badran, M ;
Wray, V ;
Edrada, R ;
Proksch, P ;
Ebel, R .
ARKIVOC, 2004, :17-27
[9]  
GEORGE R, 1975, CAN J CHEM, V53, P1424
[10]   CONSTITUENTS OF THE LATEX OF EUPHORBIA-ANTIQUORUM [J].
GEWALI, MB ;
HATTORI, M ;
TEZUKA, Y ;
KIKUCHI, T ;
NAMBA, T .
PHYTOCHEMISTRY, 1990, 29 (05) :1625-1628