|
|
|
| Two new diterpene alkaloids from the South China Sea Sponge Agelas aff. Nemoechinata |
| Tao Lia, Bin Wangb, Nicole J. de Voogdc, Xu-Li Tangd, Qi Wangd, Mei-Jun Chud, Ping-Lin Lid, Guo-Qiang Lid |
a Marine Science and Technology College, Zhejiang Ocean University, Zhoushan 316022, China;
b School of Food and Pharmacy, Zhejiang Ocean University, Zhoushan 316022, China;
c National Museum of Natural History, 2300 RA Leiden, Netherlands;
d College of Chemistry and Chemical Engineering, Ocean University of China, Qingdao 266100, China;
e School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China |
|
|
|
|
Abstract Two new N-methyladenine-containing diterpenes, nemoechines F (1) and G (2), were isolated from the South China Sea sponge Agelas aff. nemoechinata. The structures were assigned on the basis of spectroscopic date. Compound 2 showed weak activity against Jurkat cell lines with IC50 of 17.1 μmol/L.
|
|
Received: 28 March 2016
Published: 26 May 2016
|
| Fund:This work was supported by the National Natural Science Foundation of China (Nos. 41376142 and 41476107), NSFCShandong Joint Fund for Marine Science Research Centers (No. U1406402). Special thanks are given to engineer L. Liu (Ocean University of China, Qingdao, China) for the cytotoxicity tests. |
|
Corresponding Authors:
Ping-Lin Li, Guo-Qiang Li
E-mail: lipinglin@ouc.edu.cn;liguoqiang@ouc.edu.cn
|
|
|
|
| [1] |
J.W. Blunt, B.R. Copp, R.A. Keyzers, et al., Marine natural products, Nat. Prod. Rep. 32 (2015) 116-211.
|
| [2] |
M. Gordaliza, Terpenyl-purines from the sea, Mar. Drugs 7 (2009) 833-849.
|
| [3] |
H. Wu, H. Nakamura, J. Kobayashi, M. Kobayashi, Y. Ohizumi, Y. Hirata, Strctures of agelasines, diterpenes having a 9-methyladeninium chromophore isolated from the Okinawan marine sponge Agelas nakamurai Hoshino, Bull. Chem. Soc. Jpn. 59 (1986) 2495-2504.
|
| [4] |
T. Hertiani, R. Edrada-Ebel, S. Ortlepp, et al., From anti-fouling to biofilm inhibition: new cytotoxic secondary metabolites from two Indonesian Agelas sponges, Bioorg. Med. Chem. 18 (2010) 1297-1311.
|
| [5] |
D.B. Abdjul, H. Yamazaki, S.I. Kanno, et al., Structures and biological evaluations of agelasines isolated from the Okinawan marine sponge Agelas nakamurai, J. Nat. Prod. 78 (2015) 1428-1433.
|
| [6] |
K. Ishida, M. Ishibashi, H. Shigemori, et al., Agelasine G, a new antileukemic alkaloid from the Okinawan marine sponge Agelas sp, Chem. Pharm. Bull. (Tokyo) 40 (1992) 766-767.
|
| [7] |
A. Vik, E. Hedner, C. Charnock, et al., (+)-agelasine D: improved synthesis and evaluation of antibacterial and cytotoxic activities, J. Nat. Prod. 69 (2006) 381-386.
|
| [8] |
R.J. Capon, D.J. Faulkner, Antimicrobial metabolites from a Pacific sponge, Agelas sp, J. Am. Chem. Soc. 106 (1984) 1819-1822.
|
| [9] |
F. Yang, M.T. Hamann, Y.K. Zou, et al., Antimicrobial metabolites from the Paracel Islands sponge Agelas mauritiana, J. Nat. Prod. 75 (2012) 774-778.
|
| [10] |
J. Appenzeller, G. Mihci, M.T. Martin, et al., Agelasines J, K, and L from the Solomon Islands marine sponge Agelas cf. mauritiana, J. Nat. Prod. 71 (2008) 1451-1454.
|
| [11] |
H.M. Wu, H. Nakamura, J. Kobayashi, Y. Ohizumi, Y. Hirata, Agelasine-E and-F, novel monocyclic diterpenoids with 9-methyladeninium unit possessing inhibitory effects on Na, K-ATPase isolated from the Okinawan sea sponge Agelas nakamurai Hoshino, Tetrahedron Lett. 25 (1984) 3719-3722.
|
| [12] |
Gaussian Inc., Gaussian 09, Revision A.1, Gaussian Inc, Wallingford CT, 2009.
|
| [13] |
D.M. McCann, P.J. Stephens, Determination of absolute configuration using density functional theory calculations of optical rotation and electronic circular dichroism: chiral alkenes, J. Org. Chem. 71 (2006) 6074-6098.
|
| [14] |
L. Calcul, K. Tenney, J. Ratnam, J.H. McKerrow, P. Crews, Structural variations to the 9-N-methyladeninium diterpenoid hybrid commonly isolated from Agelas sponges, Aust. J. Chem. 63 (2010) 915-921.
|
| [15] |
T. Kubota, T. Iwai, A. Takahashi-Nakaguchi, et al., Agelasines O-U, new diterpene alkaloids with a 9-N-methyladenine unit from a marine sponge Agelas sp, Tetrahedron 68 (2012) 9738-9744.
|
| [16] |
P. Basabe, A. Diego, S. Delgado, et al., Short and efficient synthesis of (+)-subersic acids, Tetrahedron 59 (2003) 9173-9177.
|
|
|
|
