Cyclobutane-containing alkaloids: origin, synthesis, and biological activities.
Present review describes research on novel natural cyclobutane-containing alkaloids isolated from terrestrial and marine species. More than 60 biological active compounds have been confirmed to have antimicrobial, antibacterial, antitumor, and other activities. The structures, synthesis, origins, and biological activities of a selection of cyclobutane-containing alkaloids are reviewed. With the computer program PASS some additional biological activities are also predicted, which point toward new possible applications of these compounds. This review emphasizes the role of cyclobutane-containing alkaloids as an important source of leads for drug discovery.
Sergeiko
Anastasia
A
Institute of Biomedical Chemistry, Russian Academy of the Medical Sciences, Moscow 119121, Russia.
Poroikov
Vladimir V
VV
Hanus
Lumir O
LO
Dembitsky
Valery M
VM
J Org Chem. 2005 Feb 18;70(4):1164-76
15704948
Org Lett. 1999 Oct 21;1(8):1263-6
10825977
Nature. 1999 Nov 25;402(6760):402-4
10586878
J Nat Prod. 1999 Sep;62(9):1295-7
10514317
J Am Chem Soc. 2001 Aug 1;123(30):7429-30
11472177
J Nat Prod. 1990 Nov-Dec;53(6):1575-7
2089124
J Environ Sci Health B. 1976;11(2):139-64
1270755
Brain Res. 1972 May 26;40(2):540-4
4337445
Vet Pathol. 1998 Jan;35(1):53-63
9545135
Planta Med. 2005 Jun;71(6):535-42
15971125
Int J Food Microbiol. 2004 Jan 15;90(2):181-8
14698099
Mycopathologia. 2004 Apr;157(3):349-57
15180164
Bioorg Med Chem Lett. 1998 Nov 3;8(21):3101-6
9873684
Fortschr Chem Org Naturst. 1985;48:1-80
3912307
J Org Chem. 2001 Mar 9;66(5):1811-7
11262132
Experientia. 1991 Mar 15;47(3):301-4
1826270
J Am Chem Soc. 2004 Dec 22;126(50):16553-8
15600360
J Photochem Photobiol B. 2001 Dec 31;65(2-3):101-4
11809365
Toxicol Appl Pharmacol. 1976 Feb;35(2):311-20
1265748
Pharm Acta Helv. 1951 Jan 31;26(1):25-31
14875466
Planta Med. 1996 Feb;62(1):28-30
8720384
Mar Biotechnol (NY). 2003 Mar-Apr;5(2):194-200
12876656
Toxicon. 1978;16(1):92-6
414379
Am J Vet Res. 1975 Jan;36(1):53-8
1115418
Experientia. 1992 Sep 15;48(9):885-7
1397186
Nat Prod Commun. 2015 Jan;10(1):57-62
25920220
J Nat Med. 2008 Jan;62(1):1-33
18404338
J Nat Prod. 2004 Aug;67(8):1262-7
15332839
Mini Rev Med Chem. 2005 Mar;5(3):319-36
15777266
Z Naturforsch C J Biosci. 2002 Jan-Feb;57(1-2):157-60
11926528
Vet Clin North Am Small Anim Pract. 2002 Mar;32(2):409-19
12012744
Phytochemistry. 2002 Dec;61(8):979-85
12453530
Prikl Biokhim Mikrobiol. 1992 Nov-Dec;28(6):858-69
1494572
FEMS Microbiol Ecol. 2005 Jun 1;53(1):51-60
16329929
Chem Biol Interact. 1989;71(2-3):105-46
2688934
Planta Med. 2001 Mar;67(2):114-7
11301854
Phytochemistry. 2002 Jan;59(2):163-8
11809451
J Agric Food Chem. 2005 Mar 23;53(6):1945-8
15769118
Am J Bot. 2001 Apr;88(4):706-16
11302858
J Antimicrob Chemother. 1993 Oct;32(4):539-50
8288495
Prikl Biokhim Mikrobiol. 1993 Jan-Feb;29(1):44-50
8475020
J Org Chem. 2002 Sep 6;67(18):6509-13
12201774
Planta Med. 2006 May;72(6):527-32
16808005
J Agric Food Chem. 2003 Apr 9;51(8):2156-60
12670149
Toxicon. 1977;15(4):293-300
882992
J Org Chem. 2001 Mar 9;66(5):1805-10
11262131
J Nat Prod. 1998 Oct;61(10):1302-3
9784176
Pharm Acta Helv. 1970 Jan;45(1):42-51
5436733
J Am Chem Soc. 2007 Apr 18;129(15):4762-75
17375928
Mini Rev Med Chem. 2007 Jun;7(6):571-89
17584156