Lycospidine A, a New Type of Lycopodium Alkaloid from Lycopodium complanatum

被引:26
作者
Cheng, Jin-Tang [1 ,2 ]
Liu, Fei [1 ,2 ]
Li, Xiao-Nian [1 ]
Wu, Xing-De [1 ]
Dong, Liao-Bin [1 ,2 ]
Peng, Li-Yan [1 ]
Huang, Sheng-Xiong [1 ]
He, Juan [1 ]
Zhao, Qin-Shi [1 ]
机构
[1] Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650201, Peoples R China
[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China
基金
中国国家自然科学基金;
关键词
HUPERZINE-A; BIOSYNTHESIS; SKELETON;
D O I
10.1021/ol400907v
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Lycospidine A (1), the first example of a Lycopodium alkaloid which contains an unprecedented five-membered A ring, was Isolated from Lycopodium complanatum. The unique five-membered A ring in 1 indicates that carbons 2-5 in 1 are presumably derived from proline Instead of the lysine biosynthetically, which suggests that 1 represent a new class of Lycopodium alkaloid. In addition, the unique structural feature and biosynthetic origin of 1 shed new insight into the structural diversity of Lycopodium alkaloid analogue libraries potentially accessible by engineered biosynthesis.
引用
收藏
页码:2438 / 2441
页数:4
相关论文
共 49 条
[1]  
ALLEY MC, 1988, CANCER RES, V48, P589
[2]   THE LYCOPODIUM ALKALOIDS [J].
AYER, WA .
NATURAL PRODUCT REPORTS, 1991, 8 (05) :455-463
[3]   ALKALOIDS OF LYCOPODIUM-SELAGO - ON THE IDENTITY OF SELAGINE WITH HUPERZINE-A AND THE STRUCTURE OF A RELATED ALKALOID [J].
AYER, WA ;
BROWNE, LM ;
ORSZANSKA, H ;
VALENTA, Z ;
LIU, JS .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1989, 67 (10) :1538-1540
[4]   cis-Decahydroquinolines via Asymmetric Organocatalysis: Application to the Total Synthesis of Lycoposerramine Z [J].
Bradshaw, Ben ;
Luque-Corredera, Carlos ;
Bonjoch, Josep .
ORGANIC LETTERS, 2013, 15 (02) :326-329
[5]   BIOSYNTHESIS OF LYCOPODINE - PELLETIERINE AS AN OBLIGATORY INTERMEDIATE [J].
BRAEKMAN, JC ;
SPENSER, ID ;
MACLEAN, DB ;
GUPTA, RN .
CANADIAN JOURNAL OF CHEMISTRY, 1972, 50 (16) :2591-&
[6]  
BURNELL RH, 1959, J CHEM SOC, P3091
[7]   LYCOPODIUM ALKALOIDS .4. ALKALOIDS OF JAMAICAN LYCOPODIUM CLAVATUM LINN [J].
BURNELL, RH ;
MOOTOO, BS .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1961, 39 (05) :1090-&
[8]   BIOSYNTHESIS OF LYCOPODINE - INCORPORATION OF DELTA1-PIPERIDEINE AND OF PELLETIERINE [J].
CASTILLO, M ;
GUPTA, RN ;
HO, YK ;
MACLEAN, DB ;
SPENSER, ID .
CANADIAN JOURNAL OF CHEMISTRY, 1970, 48 (18) :2911-&
[9]  
Castillo M., 1970, J. Am. Chem. Soc, V92, P1074, DOI DOI 10.1021/JA00707A061
[10]   Carinatumins A-C, new alkaloids from Lycopodium carinatum inhibiting acetylcholinesterase [J].
Choo, Chee Yan ;
Hirasawa, Yusuke ;
Karimata, Chiaki ;
Koyama, Koichiro ;
Sekiguchi, Mitsuhiro ;
Kobayashi, Jun'ichi ;
Morita, Hiroshi .
BIOORGANIC & MEDICINAL CHEMISTRY, 2007, 15 (04) :1703-1707