By Gordon W. Gribble
Despite the lengthy organization of organohalogen compounds with human actions, nature is the manufacturer of approximately 5,000 halogen-containing chemical substances. as soon as brushed off as injuries of nature or isolation artifacts, organohalogen compounds symbolize an immense and ever becoming category of usual items, in lots of circumstances showing extraordinary organic job. because the final entire assessment in 1996 (Vol. sixty eight, this series), there were came upon an extra 2,500 organochlorine, organobromine, and different organohalogen compounds. those ordinary organohalogens are biosynthesized via micro organism, fungi, lichen, vegetation, marine organisms of every kind, bugs, and better animals together with people. those compounds also are shaped abiogenically, as in volcanoes, wooded area fires, and different geothermal events.In a few circumstances, usual organohalogens are exactly the similar chemical substances that guy synthesizes for business use, and a few of the amounts of those usual chemical compounds some distance exceed the amounts emitted via man.
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Extra info for Naturally Occurring Organohalogen Compounds - A Comprehensive Update
Unnatural brominated azaphilones (“forced metabolites”) are produced when bromide is added to the cultures (451). The novel GABA-containing isochromophilone IX (160) is found in cultures of Penicillium sp. (452). 30 3 Occurrence Cl Cl O O O HO O HO H OR OH 153 R = H (isochromophilone III) 154 R = Ac (isochromophilone IV) 155 (isochromophilone V) Cl Cl O O O N AcO AcO OH OH O O 157 (isochromophilone VII) 156 (isochromophilone VI) Cl Cl O O O HO AcO O O H O O 158 (isochromophilone VIII) 159 (5-chloroisorotiorin) Cl O AcO N CO2H O 160 (isochromophilone IX) A new family of azaphilones, the RP-1551s (161–168), is produced by Penicillium sp.
A new sesquiterpene dichloroimine, stylotellane A (312), was isolated from the sponge Stylotella aurantium (Fig. 3) (542). Feeding experiments with carbon-14 reagents revealed the incorporation of both cyanide and thiocyanate into 312. , axinyssimides A–C (313–315), and possess strong larval settlement inhibitory activity against the infamous barnacle Balanus amphitrite (543). The Australian sponge Ulosa spongia has furnished the new carbonimide dichlorides ulosins A (316) and B (317) (544), and 316 was isolated independently from the sponge Stylotella aurantium along with the new 318 (545).
3 Simple Functionalized Cyclic Organohalogens 29 Cl Cl O O (E ) O O (E ) O HO OH HO O 144 (luteusin A) 145 (luteusin B) (Z ) 146 (luteusin C) 147 (luteusin D) (Z ) O Cl Cl O O O O O O O O O O OH (E ) CO2H 148 (luteusin E) 149 (helicusin A) 150 (helicusin B) (Z ) Cl O O O O O (E ) 151 (helicusin C) 152 (helicusin D) (Z ) CO2H A full account and structures are reported for isochromophilones I (E) and II (F) from Penicillium multicolor FO-2338 (445, 446). The latter study also confirms the structure of sclerotiorin.
Naturally Occurring Organohalogen Compounds - A Comprehensive Update by Gordon W. Gribble