Abstract
Phytochemical investigation on Dictamnus dasycarpus (Rutaceae) has led to the isolation of four new secondary metabolites (2, 6, 9 , and 10 ) along with twelve known phytochemicals (1, 3 –5, 7, 8, 11 –16 ). Compound 4 was isolated as a natural product for the first time. The structures of compounds 1 –16 were elucidated by extensive spectroscopic analyses and comparison with previously reported spectroscopic data. The structures of 8 and 13 were further confirmed based on X‐ray data analyses. The absolute configuration of compounds 8 –12 were studied based on the CD spectra analyses.
Key words
Dictamnus dasycarpus
- Rutaceae - limonoids - quinolines - alkaloids
References
1
Zhao P H, Sun L M, Gao M A, Yuan C S.
Two limonoids from the root of Dictamnus radicis Cortex.
Chem Lett.
2007;
36
1200-1201
2
Yoon J S, Sung S H, Kim Y C.
Neuroprotective limonoids of root bark of Dictamnus dasycarpus .
J Nat Prod.
2008;
71
208-211
3
Chen I S, Chen H F, Cheng M J, Chang Y L, Teng C M, Tsutomu I, Chen J J, Tsai I L.
Quinoline alkaloids and other constituents of Melicope semecarpifolia with antiplatelet aggregation activity.
J Nat Prod.
2001;
64
1143-1147
4
Muyard F, Bevalot F, Laude B, Vaquette J.
Alkaloids from stem bark of Dutaillyea baudouinii .
Phytochemistry.
1992;
31
1087-1089
5
Liu Z L, Xu Y J, Wu J, Goh S H, Ho S H.
Feeding deterrents from Dictamnus dasycarpus Turcz. against two stored-product insects.
J Agric Food Chem.
2002;
50
1447-1450
6
Zhou X, Ji C, Fu J, Li Y G, Chen T.
Obacunone.
Acta Crystallogr E.
2006;
62
o5544-o5546
7
Yuan T, Yang S P, Zhang C R, Zhang S, Yue J M.
Two limonoids, khayalenoids A and B with an unprecedented 8-oxa-tricyclo[4.3.2.02, 7 ]undecane motif, from Khaya senegalensis .
Org Lett.
2009;
11
617-620
8
Coggon P, McPhail A T.
Structure and absolute configuration of fraxinellone: X-ray analysis of 9β -bromofraxinellone.
J Chem Soc.
1970;
1521-1524
9
Yang R L, Jia T L, Zhang R Q.
Microbial transformation of fraxinellone by Aspergillus niger .
J Asian Nat Prod Res.
2005;
7
843-845
10
Zhao W M, Wolfender J L, Hostettmann K, Xu R S, Qin G W.
Antifungal alkaloids and limonoid derivatives from Dictamnus dasycarpus .
Phytochemistry.
1998;
47
7-11
11
Barr S A, Boyd D R, Sharma N D, Loke P L.
Synthesis and absolute configuration assignments of mono- and di-substitued chiral quinoline alkaloids obtained by asymmetric oxidation.
Heterocycles.
2009;
79
831-850
12
Blaise A J, Winternitz F.
Isofraxinellone, a limonoid lactone from the bark of Fagaropsis glabra .
Phytochemistry.
1985;
24
2379-2381
13
Boustie J, Moulis C, Gleye J, Fouraste I, Servin P, Bon M.
A degraded limonoid from Fagaropsis glabra .
Phytochemistry.
1990;
29
1699-1701
14
Rugutt J K, Fischer N H, Nauman M A, Schmidt T J, Berner D K.
13C-NMR assignments for methyls and quaternary carbons of the limonoid obacunene.
Spectrosc Lett.
1996;
29
711-726
15
Dreyer D L, Pickering M V, Cohan P.
Distribution of limonoids in the rutaceae.
Phytochemistry.
1972;
11
705-713
16
Sugimoto T, Miyase T, Kuroyanagi M, Ueno A.
Limonoids and quinoline alkaloids from Evodia rutaecarpa Bentham.
Chem Pharm Bull.
1988;
36
4453-4461
17
Yoon J S, Sung S H, Kim Y C.
Neuroprotective limonoids of root bark of Dictamnus dasycarpus .
J Nat Prod.
2008;
71
208-211
18
Zhao W M, Wolfender J L, Hostettmann K, Xu R S, Qin G W.
Antifungal alkaloids and limonoid derivatives from Dictamnus dasycarpus .
Phytochemistry.
1998;
47
7-11
Prof. Yan-Ping Shi
Lanzhou Institute of Chemical Physics Chinese Academy of Sciences
Lanzhou 730000
People's Republic of China
Telefon: + 86 93 14 96 82 08
Fax: + 86 93 18 27 70 88
eMail: shiyp@licp.cas.cn