RSS-Feed abonnieren
DOI: 10.1055/s-0029-1240811
© Georg Thieme Verlag KG Stuttgart · New York
Piperidine Alkaloids from Chinese Mangrove Sonneratia hainanensis
Publikationsverlauf
received September 7, 2009
revised December 2, 2009
accepted December 31, 2009
Publikationsdatum:
27. Januar 2010 (online)

Abstract
A new diphenacyl-piperidine alkaloid, sonneratine A (2), identified as a piperidine ring bearing two phenacyl substitutes at C-2 and C-6, and a known related derivative, (±)1-(2-piperidyl)-4-(p-methoxyphenyl)-butanone-2 (3), were isolated from the leaves and stems of the Hainan mangrove Sonneratia hainanensis. The structure of the new compound was determined by extensive analysis of its spectroscopic data and by comparison of its NMR data with those reported in the literature.
Key words
Sonneratiaceae - Sonneratia hainanensis - diphenacyl‐piperidine alkaloid - sonneratine A
- Supporting Information for this article is available online at
- Supporting Information .
References
- 1 Felpin F X, Lebreton J. History, chemistry and biology of alkaloids from Lobelia inflata. Tetrahedron. 2004; 60 10127-10153
- 2 Watson P S, Jiang B, Scott B. A diastereoselective synthesis of 2,4-disubstituted piperidines: scaffolds for drug discovery. Org Lett. 2000; 2 3679-3681
-
3 Hegnauer R.
Eine Übersicht über die Verbreitung und die systematische Bedeutung der Pflanzenstoffe. Harborne JB Chemotaxonomie der Pflanzen, Vol. 8. Basel, Boston, Berlin; Birkhäuser Verlag 1989: 407-408 - 4 Wieland H, Koschara E D, Renz J, Schwarze W, Linde W. Lobelia alkaloids. VII. Accessory alkaloids of Lobelia inflate. Liebigs Ann Chem. 1939; 540 103-156
-
5 Qin H N, Graham S, Gilbert M G.
Sonneratia linnaeus f., Suppl. Pl. 38, 252. 1782, nom. cons. Wu ZY Flora of China, Vol. 13. Beijing; Science Publishers 2007: 286-288 - 6 Bandaranayake W M. Traditional and medicinal uses of mangroves. Mangroves and Salt Marshes. 1998; 2 133-148
- 7 Gong J X, Shen X, Yao L G, Jiang H L, Krohn K, Guo Y W. Total synthesis of gymnorrhizol, an unprecedented 15-membered macrocyclic polydisulfide from the Chinese mangrove Bruguiera gymnorrhiza. Org Lett. 2007; 9 1715-1716
- 8 Sun Y Q, Guo Y W. Gymnorrhizol, an unusual macrocyclic polydisulfide from the Chinese mangrove Bruguiera gymnorrhiza. Tetrahedron Lett. 2004; 45 5533-5535
- 9 Wang J D, Zhang W, Li Z Y, Xiang W S, Guo Y W. Elucidation of excogallochaols A–D, four unusual diterpenoids from the Chinese mangrove Excoecaria agallocha. Phytochemistry. 2007; 68 2426-2431
- 10 Wang J D, Li Z Y, Xiang W S, Guo Y W. Further new secoatisane diterpenoids from Chinese mangrove Excoecaria agallocha L. Helv Chim Acta. 2006; 89 1367-1372
- 11 Czaroncki Z, Wrobel J T. N-bromoamides as reagents for novel synthesis of indolizidine derivatives. Bull Pol Acad Sci Chem. 1983; 31 225-231
- 12 Kursinszki L, Ludányi K, Szőke E. LC-DAD and LC-MS-MS analysis of piperidine alkaloids of Lobelia inflata L. (in vitro and in vivo). Chromatographia. 2008; 68 S27-S33
- 13 Mill S, Hootelé C. A revised structure for the piperidine alkaloid andrachamine. Can J Chem. 1996; 74 2434-2443
- 14 Ali Z, Khan I A. Alkaloids and saponins from blue cohosh. Phytochemistry. 2008; 69 1037-1042
- 15 Robinson R. LXXV – A theory of the mechanism of the phytochemical synthesis of certain alkaloids. J Chem Soc. 1917; 111 876-899
- 16 Sriphong L, Sotanaphun U, Limsirichaikul S, Wetwitayaklung P, Chaichantipyuth C, Pummangura S. Cytotoxic alkaloids from the flowers of Senna spectabilis. Planta Med. 2003; 69 1054-1056
- 17 Viegas C J, Alexandre-Moreira M S, Fraga C A M, Barreiro E J, Bolzani V D S, de Miranda A L P. Antinociceptive profile of 2,3,6-trisubstituted piperidine alkaloids: 3-O-acetyl-spectaline and semi-synthetic derivatives of (−)-spectaline. Chem Pharm Bull. 2008; 56 407-412
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
201203 Shanghai
People's Republic of China
Telefon: + 86 21 50 80 58 13
Fax: + 86 21 50 80 58 13
eMail: ywguo@mail.shcnc.ac.cn
- www.thieme-connect.de/ejournals/toc/plantamedica