Biscembranoids and their probable biogenetic precursor from the hainan soft coral Sarcophyton tortuosum

被引：49

作者：

Jia, Rui

Guo, Yue-Wei

Chen, Ping

Yang, Yi-Ming

Mollo, Ernesto

Gavagnin, Margherita

Cimino, Guido

机构：

[1] Chinese Acad Sci, Shanghai Inst Biol Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China

[2] CNR, Ist Chim Biomol, I-80078 Naples, Italy

来源：

JOURNAL OF NATURAL PRODUCTS | 2007年 / 70卷 / 07期

关键词：

D O I：

10.1021/np060220b

中图分类号：

Q94 [植物学];

学科分类号：

071001 [植物学];

摘要：

Five novel biscembranoids, ximaolides A-E (2-6), and their proposed biogenetic precursor, methyl tortuosoate (1), were isolated from the Hainan soft coral Sarcophyton tortuosum. The structures of compounds 1-6 were elucidated by spectroscopic methods, mainly NMR techniques. The relative stereochemistry of biscembranoids 2 and 6 was secured by X-ray diffraction analysis, whereas the relative configurations of chiral centers in compounds 1, 3, 4, and 5 have been suggested by both biogenetic considerations and NOESY experiments.

引用

页码：1158 / 1166

页数：9

共 17 条

[1]

CHEN ZC, 2000, CHINESE J CHEM, V18, P777

[2]

THE CHEMISTRY AND CHEMICAL ECOLOGY OF OCTOCORALS (COELENTERATA, ANTHOZOA, OCTOCORALLIA) [J].

COLL, JC .

CHEMICAL REVIEWS, 1992, 92 (04) :613-631

[3]

Isoprenoids of the soft coral Sarcophyton glaucum:: Nyalolide, a new biscembranoid, and other terpenoids [J].

Feller, M ;

Rudi, A ;

Berer, N ;

Goldberg, I ;

Stein, Z ;

Benayahu, Y ;

Schleyer, M ;

Kashman, Y .

JOURNAL OF NATURAL PRODUCTS, 2004, 67 (08) :1303-1308

[4]

Studies on the total synthesis of methyl sartortuoate construction of the 2,3,3,6-tetrasubstituted D-ring segment [J].

Gao, Y ;

Nan, F ;

Xu, XX .

TETRAHEDRON LETTERS, 2000, 41 (24) :4811-4813

[5]

ISOLATION OF A MONOMERIC COUNTERPART OF THE MARINE BISCEMBRANOIDS, A BIOGENETIC DIELS-ALDER PRECURSOR [J].

ISHITSUKA, MO ;

KUSUMI, T ;

KAKISAWA, H .

TETRAHEDRON LETTERS, 1991, 32 (25) :2917-2918

[6]

Biscembranes from the soft coral Sarcophyton glaucum [J].

Iwagawa, Tetsuo ;

Hashimoto, Kanta ;

Okamura, Hiroaki ;

Kurawaki, Jun-ichi ;

Nakatani, Munehiro ;

Hou, De-Xing ;

Fujii, Makoto ;

Doe, Matsumi ;

Morimoto, Yoshiki ;

Takemura, Kaoru .

JOURNAL OF NATURAL PRODUCTS, 2006, 69 (08) :1130-1133

[7]

Sarcophytonolides A-D, four new cembranolides from the Hainan soft coral Sarcophyton sp. [J].

Jia, R ;

Guo, YW ;

Mollo, E ;

Cimino, G .

HELVETICA CHIMICA ACTA, 2005, 88 (05) :1028-1033

[8]

A NOVEL CHLORINATED BISCEMBRANOID FROM THE MARINE SOFT CORAL SARCOPHYTON-GLAUCUM [J].

KUSUMI, T ;

IGARI, M ;

ISHITSUKA, MO ;

ICHIKAWA, A ;

ITEZONO, Y ;

NAKAYAMA, N ;

KAKISAWA, H .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (26) :6286-6289

[9]

ANOMALY IN THE MODIFIED MOSHER METHOD - ABSOLUTE-CONFIGURATIONS OF SOME MARINE CEMBRANOLIDES [J].

KUSUMI, T ;

FUJITA, Y ;

OHTANI, I ;

KAKISAWA, H .

TETRAHEDRON LETTERS, 1991, 32 (25) :2923-2926

[10]

STUDIES OF AUSTRALIAN SOFT CORALS .49. A NEW BISCEMBRANOID AND ITS PROBABLE BIOSYNTHETIC PRECURSORS FROM THE SOFT CORAL SARCOPHYTON-TORTUOSUM [J].

LEONE, PA ;

BOWDEN, BF ;

CARROLL, AR ;

COLL, JC ;

MEEHAN, GV .

JOURNAL OF NATURAL PRODUCTS, 1993, 56 (04) :521-526

← 1 2 →