A New 1,4-Diazepine from South China Sea Marine Sponge Callyspongia Species

被引：25

作者：

Huang, Ri-Ming ^{[1
,3
]}

Ma, Wei ^{[2
]}

Dong, Jun-De ^{[1
,4
]}

Zhou, Xue-Feng ^{[1
]}

Xu, Tunhai ^{[5
]}

Lee, Kyung Jin ^{[6
]}

Yang, Xianwen ^{[1
]}

Xu, Shi-Hai

Liu, Yonghong ^{[1
]}

机构：

[1] Jinan Univ, Dept Chem, Guangzhou 510632, Peoples R China

[2] Guangzhou First Municipal Peoples Hosp, Guangzhou 510180, Peoples R China

[3] Chinese Acad Sci, Grad Univ, Beijing 100049, Peoples R China

[4] Natl Expt Stn Trop Marine Biol, Sanya 572000, Peoples R China

[5] Beijing Univ Chinese Med, Sch Chinese Mat Med, Beijing 100102, Peoples R China

[6] Natl Inst Biol Resources, Invertebrate Res Div, Inchon 404170, South Korea

来源：

MOLECULES | 2010年 / 15卷 / 02期

基金：

中国国家自然科学基金;

关键词：

marine sponge; Callyspongia sp; diazepine; callysponine; CARIBBEAN SPONGE; DIKETOPIPERAZINES; METABOLITES; CALLYSTATIN; POLYKETIDE; ACIDS;

D O I：

10.3390/molecules15020871

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

A new 1,4-diazepine, callysponine (1), was isolated from a South China Sea Callyspongia sp. marine sponge, together with four known proline-based diketopiperazines: cyclo-(S-Pro-R-Leu) (2), cyclo-(S-Pro-R-Val) (3), cyclo-(S-Pro-R-Ala) (4), and cyclo-(S-Pro-R-Tyr) (5). The new structure was determined on the basis of NMR and MS analysis, and the absolute stereochemistry was defined by NOESY spectroscopy and optical rotation. The structures of the known compounds were identified by comparison of their spectroscopic data with those reported in the literature. Callysponine (1) did not inhibit the growth of HepG2 (hepatoma carcinoma cell), A549 (lung carcinoma cell), and HeLa (cervical cancer cell) cell lines.

引用

页码：871 / 877

页数：7

共 18 条

[1] NEW AND KNOWN DIKETOPIPERAZINES FROM THE CARIBBEAN SPONGE, CALYX CF PODATYPA [J].

ADAMCZESKI, M ;

REED, AR ;

CREWS, P .

JOURNAL OF NATURAL PRODUCTS-LLOYDIA, 1995, 58 (02) :201-208

[2] Callynormine A, a new marine cyclic peptide of a novel class [J].

Berer, N ;

Rudi, A ;

Goldberg, I ;

Benayahu, Y ;

Kashman, Y .

ORGANIC LETTERS, 2004, 6 (15) :2543-2545

[3] New methoxylated fatty acids from the Caribbean sponge Callyspongia fallax [J].

Carballeira, NM ;

Pagán, M .

JOURNAL OF NATURAL PRODUCTS, 2001, 64 (05) :620-623

[4] A NEW EGF-ACTIVE POLYMERIC PYRIDINIUM ALKALOID FROM THE SPONGE CALLYSPONGIA-FIBROSA [J].

DAVIESCOLEMAN, MT ;

FAULKNER, DJ ;

DUBOWCHIK, GM ;

ROTH, GP ;

POLSON, C ;

FAIRCHILD, C .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (22) :5925-5930

[5]

DIAA TAY, 2000, J NAT PRODUCTS, V63, P1406

[6] Chemical characterization of diketopiperazines in beer [J].

Gautschi, M ;

Schmid, JP ;

Peppard, TL ;

Ryan, TP ;

Tuorto, RM ;

Yang, XG .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1997, 45 (08) :3183-3189

[7] Sulfated meroterpenoids from the Brazilian sponge Callyspongia sp. are inhibitors of the antileishmaniasis target adenosine phosphoribosyl transferase [J].

Gray, Christopher A. ;

de Lira, Simone P. ;

Silva, Marcio ;

Pimenta, Eli F. ;

Thiemann, Otavio H. ;

Oliva, Glaucius ;

Hajdu, Eduardo ;

Andersen, Raymond J. ;

Berlinck, Roberto G. S. .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (23) :8685-8690

[8]

HECHER SJ, 1993, J ORG CHEM, V58, P1762

[9] Metabolites from an Antarctic sponge-associated bacterium, Pseudomonas aeruginosa [J].

Jayatilake, GS ;

Thornton, MP ;

Leonard, AC ;

Grimwade, JE ;

Baker, BJ .

JOURNAL OF NATURAL PRODUCTS, 1996, 59 (03) :293-296

[10] Callystatin A, a potent cytotoxic polyketide from the marine sponge, Callyspongia truncata [J].

Kobayashi, M ;

Higuchi, K ;

Murakami, N ;

Tajima, H ;

Aoki, S .

TETRAHEDRON LETTERS, 1997, 38 (16) :2859-2862

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