Global InformationHectochlorin information
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3D model (JSmol)
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PubChem CID
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CompTox Dashboard (EPA)
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InChI
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SMILES
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| Properties | |
Chemical formula
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C27H34Cl2N2O9S2 |
| Molar mass | 665.59 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
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Hectochlorin is a lipopeptide that exhibits potent antifungal activity against C. albicans and a number of plants pathogens, as well as inhibiting growth of human cell lines by hyperpolymerization of actin.[1] It was originally isolated from the filamentous cyanobacterium Moorea producens JHB, collected from Hector Bay, Jamaica, 1996,[2] which is a strain also known for being the producer of other two potent biomolecules named Jamaicamide A[3] and Cryptomaldamide.[4] Due to its activity against plants pathogens, synthetic efforts elucidated the compound’s total synthesis in 2002.[5] Moorea species are normally the main component of the dietary of some sea hares, which concentrate the cyanobacterial metabolites as a mechanism of defense from predators. Therefore, in 2005, hectochlorin was re-isolated from the Thai sea hare Bursatella leachii, along with a new analogue, deacetylhectochlorin.[6] Another reisolation of hectochlorin was reported in 2013, from another Moorea producens strain (RS05), isolated from the Red Sea, surprising in a non-tropical environment, as opposed to the other Moorea strains isolated before. The predicted biosynthesis of hectochlorin was published in 2007 and consists in a hybrid NRPS-PKS, with a hexanoic acid as start unit that becomes halogenated twice in the position 5, producing fairly rare gem-dichloro group, that along with two 2,3-dihydroxyisovaleric acid (DHIV) units compose a very interesting bioactive molecule.
- ^ Ramaswamy, A. V., Sorrels, C. M. & Gerwick, W. H. Cloning and biochemical characterization of the hectochlorin biosynthetic gene cluster from the marine cyanobacterium Lyngbya majuscula. J. Nat. Prod. 70, 1977–1986 (2007).
- ^ Marquez, B. L. et al. Structure and absolute stereochemistry of hectochlorin, a potent stimulator of actin assembly. J. Nat. Prod. 65, 866–871 (2002).
- ^ Marquez, B. L. et al. Structure and absolute stereochemistry of hectochlorin, a potent stimulator of actin assembly. J. Nat. Prod. 65, 866–871 (2002).
- ^ Kinnel RB et al; A Maldiisotopic Approach to Discover Natural Products: Cryptomaldamide, a Hybrid Tripeptide from the Marine Cyanobacterium Moorea producens. J Nat Prod. 2017 May 26;80(5):1514-1521. doi: 10.1021/acs.jnatprod.7b00019.
- ^ Cetusic, J. R. P., Green, F. R., Graupner, P. R. & Oliver, M. P. Total Synthesis of Hectochlorin. Org. Lett. 4, 1307–1310 (2002).
- ^ Suntornchashwej, S., Chaichit, N., Isobe, M. & Suwanborirux, K. Hectochlorin and morpholine derivatives from the Thai sea hare, Bursatella leachii. J. Nat. Prod. 68, 951–955 (2005).