Title: Latrunculins
Literature References: Highly potent toxins which disrupt microfilament organization by binding the actin monomer. Isolated from the Red Sea sponge Latrunculia magnifica Keller; also found in the Pacific nudibranch Chromodoris elisabethina and the Fijian sponge Spongia mycofijiensis. Isoln and biological activities: I. Néeman et al., Mar. Biol. 30, 293 (1975). First family of natural products possessing the 2-thiazolidinone moiety; latrunculins A-D are 14- or 16- membered macrolides, infrastructures previously unknown in marine isolates. Structure elucidation of A and B: A. Groweiss et al., J. Org. Chem. 48, 3512 (1983); of A through D: Y. Kashman et al., Tetrahedron 41, 1905 (1985). Chemistry of A and B: D. Blasberger et al., Ann. 1989, 1171. Total synthesis of B: R. Zibuck et al., J. Am. Chem. Soc. 108, 2451 (1986); of A: J. D. White, M. Kawasaki, J. Am. Chem. Soc. 112, 4991 (1990); of A, B, C and M: A. B. Smith, III et al., ibid. 114, 2995 (1992). Comparative study with cytochalasin D, q.v., on the effects actin organization and cell processes: I. Spector et al., Cell Motil. Cytoskel. 13, 127 (1989). Inhibition of the actin monomer: W. M. Morton et al., Nat. Cell. Biol. 2, 376 (2000). Review of use as research tool: K. Ayscough, Methods Enzymol. 298, 18-25 (1998).
Derivative Type: Latrunculin A
CAS Registry Number: 76343-93-6
CAS Name: (4R)-4-[(1R,4Z,8E,10Z,12S,15R,17R)-17-Hydroxy-5,12-dimethyl-3-oxo-2,16-dioxabicyclo[13.3.1]nonadeca-4,8,10-trien-17-yl]-2-thiazolidinone
Additional Names: LAT-A
Molecular Formula: C22H31NO5S
Molecular Weight: 421.55
Percent Composition: C 62.68%, H 7.41%, N 3.32%, O 18.98%, S 7.61%
Properties: Foam. [a]D24 +152° (c = 1.2 in chloroform). uv max (methanol): 218 nm (e 23500).
Optical Rotation: [a]D24 +152° (c = 1.2 in chloroform)
Absorption maximum: uv max (methanol): 218 nm (e 23500)
Derivative Type: Latrunculin B
CAS Registry Number: 76343-94-7
CAS Name: (4R)-4-[(1R,4Z,8Z,10S,13R,15R)-15-Hydroxy-5,10-dimethyl-3-oxo-2,14-dioxabicyclo[11.3.1]heptadeca-4,8-dien-15-yl]-2-thiazolidinone
Additional Names: LAT-B
Molecular Formula: C20H29NO5S
Molecular Weight: 395.51
Percent Composition: C 60.74%, H 7.39%, N 3.54%, O 20.23%, S 8.11%
Literature References: Major toxin. Localization within the Red Sea sponge: O. Gillor et al., Mar. Biotechnol. 2. 213 (2000).
Properties: Crystals. [a]D24 +112° (c = 0.48 in chloroform). uv max (methanol): 212 nm (e 17200).
Optical Rotation: [a]D24 +112° (c = 0.48 in chloroform)
Absorption maximum: uv max (methanol): 212 nm (e 17200)
Use: In elucidation of molecular mechanisms of motile processes.

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