Caylobolide B, a macrolactone from symplostatin 1-producing marine cyanobacteria Phormidium spp. from Florida.
A Phormidium spp. collection from Key West, Florida, afforded caylobolide B (1), an analogue of the known macrolactone caylobolide A, previously isolated from a Lyngbya majuscula collection from the Bahamas. The planar structure of 1 was determined using NMR and MS experiments. The relative configuration for subunits C7-C9 and C25-C29 was assigned using Kishi's Universal NMR Database. Caylobolide B (1) displayed cytotoxic activity against HT29 colorectal adenocarcinoma and HeLa cervical carcinoma cells with IC(50) values of 4.5 and 12.2 μM, respectively.
Salvador
Lilibeth A
LA
Department of Medicinal Chemistry, University of Florida, Gainesville, Florida 32610, USA.
Paul
Valerie J
VJ
Luesch
Hendrik
H
D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001444:Bahamas; D000458:Cyanobacteria / Q000737:chemistry*; D047630:Depsipeptides / Q000737:chemistry / Q000302:isolation & purification; D004354:Drug Screening Assays, Antitumor; D005260:Female; D005431:Florida; D019073:HT29 Cells; D006367:HeLa Cells; D006801:Humans; D020128:Inhibitory Concentration 50; D007783:Lactones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D008386:Marine Biology; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular
D000970:Antineoplastic Agents; D047630:Depsipeptides; D007783:Lactones; C456999:caylobolide A; C552994:caylobolide B; C115534:symplostatin 1
J Nat Prod. 1990 Nov-Dec;53(6):1533-42
2128517
J Org Chem. 2002 Nov 15;67(23):7927-36
12423120
J Am Chem Soc. 2004 Aug 18;126(32):9944-5
15303868
Angew Chem Int Ed Engl. 2000 Dec 1;39(23):4279-4281
29711895
J Nat Prod. 2010 Mar 26;73(3):409-15
20108948
J Am Chem Soc. 2001 Mar 7;123(9):2076-8
11456839
J Nat Prod. 2007 Mar;70(3):451-60
17335244
J Nat Prod. 2001 Jul;64(7):907-10
11473421
J Nat Prod. 1998 Sep;61(9):1075-7
9748368
Phytochemistry. 2007 Apr;68(7):954-79
17336349
Int J Cancer. 2003 Apr 20;104(4):512-21
12584751
Org Lett. 2002 May 2;4(9):1535-8
11975622
Mar Drugs. 2010 Jun 09;8(6):1817-37
20631872