Planta Med 2011; 77(2): 179-181
DOI: 10.1055/s-0030-1250164
Natural Product Chemistry
Letters
© Georg Thieme Verlag KG Stuttgart · New York

9′-Epi-3β,3′β–dimethylxestospongin C, a New Macrocyclic Diamine Alkaloid from the Hainan Sponge Neopetrosia exigua

Yan Li1 , Song Qin1 , Yue-Wei Guo1 , Yu-Cheng Gu2 , Rob W. M. van Soest3
  • 1State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai, P. R. China
  • 2Syngenta, Jealott's Hill International Research Centre, Bracknell, Berkshire, UK
  • 3Zoological Museum of the University of Amsterdam, Amsterdam, The Netherlands
Further Information

Publication History

received March 2, 2010 revised June 21, 2010

accepted June 25, 2010

Publication Date:
28 July 2010 (online)

Abstract

A new bis-1-oxaquinolizidine alkaloid, 9′-epi-3β,3′β–dimethylxestospongin C (2), and three known related analogues have been isolated from the Hainan sponge Neopetrosia exigua.

References

  • 1 Baldwin J E, Whitehead R C. On the biosynthesis of manzamines.  Tetrahedron Lett. 1992;  33 2059-2062
  • 2 Nakagawa M, Endo M, Tanaka N, Lee G-P. Structures of xestospongin A, B, C and D, novel vasodilative compounds from marine sponge, Xestospongia exigua.  Tetrahedron Lett. 1984;  25 3227-3230
  • 3 Kobayashi M, Kawazoe K, Kitagawa I. Araguspongines B, C, D, E, F, G, H, and J, new vasodilative bis-1-oxaquinolizidine alkaloids from an Okinawan marine sponge, Xestospongia sp.  Chem Pharm Bull. 1989;  37 1676-1678
  • 4 Kobayashi M, Kawazoe K, Kitagawa I. Aragupetrosine A, a new vasodilative macrocyclic quinolizidine alkaloid from an Okinawan marine sponge Xestospongia sp.  Tetrahedron Lett. 1989;  30 4149-4152
  • 5 Ramireddy M V, Faulkner D J. 3β,3′β-Dimethylxestospongin C, a new bis-1-oxaquinolizidine alkaloid from the Palauan sponge Xestospongia sp.  Nat Prod Lett. 1997;  11 53-59
  • 6 Moon S S, MacMillan J B, Olmstead M M, Ta T A, Pessah I N, Molinski T F. (+)-7S-Hydroxyxestospongin A from the marine sponge Xestospongia sp. and absolute configuration of (+)-xestospongin D.  J Nat Prod. 2002;  65 249-254
  • 7 Quirion J-C, Sevenet T, Husson H-P, Weniger B, Debitus C. Two new alkaloids from Xestospongia sp., a new Caledonian sponge.  J Nat Prod. 1992;  55 1505-1508
  • 8 Venkateswarlu Y, Reddy M V R, Rao J V. Bis-1-oxaquinolizidines from the sponge Haliclona exigua.  J Nat Prod. 1994;  57 1283-1285
  • 9 Orabi K Y, El Sayed K A, Hamann M T, Dunbar D C, Al-Said M S, Higa T, Kelly M. Araguspongines K and L, new bioactive bis-1-oxaquinolizidine N-oxide alkaloids from Red Sea specimens of Xestospongia exigua.  J Nat Prod. 2002;  65 1782-1785
  • 10 Liu H W, Mishima Y, Fujiwara T, Nagai H, Kitazawa A, Mine Y, Kobayashi H, Yao X, Yamada J, Oda T, Namikoshi M. Isolation of araguspongine M, a new stereoisomer of an araguspongine/xestospongin alkaloid, and dopamine from the marine sponge Neopetrosia exigua collected in Palau.  Mar Drugs. 2004;  2 154-163
  • 11 Pettit G, Orr B, Herald D, Doubek D, Tackett L, Schmidt J, Boyd M, Pettit R, Hooper J. Isolation and X-ray crystal structure of racemic xestospongin D from the Singapore marine sponge Niphates sp.  Bioorg Med Chem Lett. 1996;  6 1313-1318
  • 12 Leone P A, Carroll A R, Towerzey L, King G, Mcardle B M, Kem G, Fisher S, Hooper J N A, Quinn R J. Exiguaquinol: a novel pentacyclic hydroquinone from Neopetrosia exigua that inhibits Helicobacter pylori Murl.  Org Lett. 2008;  10 2585-2588
  • 13 Kobayshi M, Miyamoto Y, Aoki S, Murakami N, Kitagawa I, In Y, Ishida T. Isomerization of dimeric 2,9-disubstituted 1-oxaquinolizidine alkaloids and structural revision of araguspongines B and E, isolated from a marine sponge of Xestospongia sp.  Heterocycles. 1998;  47 195-203
  • 14 Bohlmann F. Zur Konfigurationsbestimmung von Chinolizin-Derivaten.  Angew Chem. 1957;  69 641-642
  • 15 Rosen W E. Rauwofia alkloids-XLII methyl reserpate, an isomer of methyl reserpate. Part 4. Infrared spectra and configuration at C-3.  Tetrahedron Lett. 1961;  2 481-484
  • 16 Rosen W E, Shodery J N. Rauwolfia alkaloids. XLI. Methyl neoreserpate, an isomer of methyl reserpate. Part 3. Conformations and NMR spectra.  J Am Chem Soc. 1961;  83 4816-4819
  • 17 Mosmann T. Rapid colorimetrc assay for cellular growth and survival: application to proliferation and cytotoxicity assay.  J Immunol Methods. 1983;  65 55-63
  • 18 Kim K H, Choi J W, Choi S N, Lee K R. Terpene glycosides and cytotoxic constituents from the seeds of Amomum xanthioides.  Planta Med. 2010;  76 461-464

Prof. Dr. Yue-Wei Guo

State Key Laboratory of Drug Research
Shanghai Institute of Materia Medica
Chinese Academy of Sciences

Zu Chong Zhi Rd. 555

Zhangjiang Hi-Tech Park

Shanghai 201203

P. R. China

Phone: + 86 21 50 80 58 13

Fax: + 86 21 50 80 58 13

Email: ywguo@mail.shcnc.ac.cn

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