Acorn worm

Dure and Cormier (1961) demonstrated a luciferin-luciferase reaction for the first time in the extracts of the acorn worm Balanoglossus biminiensis, and also discovered that the luminescence reaction is stimulated by H2O2, of which the details are described below. Recently, Kanakubo and Isobe (2005) reported the chemical structure of a probable luciferin of another acorn worm Ptychodera flava. 

Fig. 10.4.1 Light emission profile of the luminescence reaction of the acorn worm Balanoglossus biminiensi, when H2O2 is injected into a mixture of the luciferin and luciferase. From Dure and Cormier, 1961, with permission from the American Society for Biochemistry and Molecular Biology.

Fig. 10.4.3 Left panel Bioluminescence spectrum of the acorn worm Ptychodera flava stimulated with H2O2. Right panel (a) The spectrum of the chemiluminescence emitted when 70% dioxane containing 1.7% H2C>2 (5 ml) was added to a mixture of a solution of 2,3,5,6-tetrabromohydroquinone (TBHQ) in ethyl acetate (2.5 ml), 50 mM glycine buffer (pH 12.0 2.5 ml), and riboflavin (b) when riboflavin was omitted and (c) when TBHQ was omitted. Dioxane was included to solubilize the ethyl acetate solution containing TBHQ. From Kanakubo et al., 2005, with permission from Elsevier.

Kanakubo, A., and Isobe, M. (2005). Isolation of brominated quinones showing chemiluminescence activity from luminous acorn worm, Ptychodera flava. Bioorg. Med. Chem. 13 2741-2747. 

Kanakubo, A., Koga, K., Isobe, M., and Yoza, K. (2005). Tetrabromohy-droquinone and riboflavin are possibly responsible for green luminescence in the luminous acorn worm, Ptycbodera flava. Luminescence 20 397-400. 

Acantbephyra, 162, 336 Acantboscina, 336 Acholoe, 335 Achromobacter, 35, 36 Acorn worms (enteropneusts), 315 Acylhomoserine lactone, 43 Advice to students, 375 Aequorea, 159, 161, 162, 334, 375 Aequorea aequorea, 92-94, 346 collection, 93, 94 distribution, 92 squeezate, 94 synonyms, 92 Aequorea GFP, 150-154 chromophore, 153 cloning, 154 crystallization, 130 fluorescence quantum yield, 152 isolation, 129 molecular weight, 152 spectral properties, 130, 152 Aequorea victoria, 92 Aequorin, 92-129, 159, 160,172,173, 175, 346, 349, 350, 364, 375 assay, 98... 

Some animals, such as the marine acorn worms (Balanoglossus), produce light via a peroxidation reaction and appear not to require molecular oxygen for luminescence. The luciferase in this case is a peroxidase of the classical type and catalyzes the reaction Luciferin +... 

A study of the natural radiocarbon (14C) in the acorn worm Saccoglossus bromophenolosus, which was collected off the Maine coast, revealed that the 2,4-dibromophenol produced by these worms is of recent origin, in contrast to that from petroleum-derived anthropogenic 2,4-dibromophenol (1746). Thus, this result combined with the earlier study (1223) supports a natural source of 2,4-dibromophenol in these animals. It should be noted that the more recent radiocarbon work utilizes improved methodology (1746). 

Bromophenols represent an enormous class of marine natural products, particularly from acorn worms of families Polychaete and Hemichordata. These sediment dwelling animals can live anywhere from the intertidal zone to a depth of 1,400 m (2542, 2543). Thus, one function of 2,4,6-tribromophenol produced by the deep-sea... 

Kanakubo A, Isobe M (2005) Isolation of Brominated Quinones Showing Chemiluminescence Activity from Luminous Acorn Worm, Ptychoderaflava. Bioorg Med Chem 13 2741... 

Higa, T., Fujiyama, T., and Scheuer, P. J., Halogenated phenol and indole constituents of acorn worms, Comp. Biochem. Physiol., 65B, 525, 1980. 

Higa, T., Ichiba, T., and Okuda, R. K., Marine indoles of novel substitution pattern from the acorn worm Glossobalanus sp. Experientia, 41, 1487, 1985. 

The marine bacterium Chromobacterium sp. produces 2,3,4,5-tetrabromopyrrole (1) <74MB281>, and the marine acorn worm Polyphysia crassa has yielded the antibacterial metabolite 2,3,4-tribromopyrrole (2), an extremely labile compound <90JNP703>. The Red Sea sponge Acanthella carteri contains bromopyrrole amide (3) <97JNP180>, and the isomeric... 

Some naturally occurring organohalogen compounds are produced in massive quantities. Forest fires, volcanoes, and marine kelp release up tx>SmiUimi tons oTCHj,Cl pt r yejir. for example, while annual industrial emissions total only about 26,000 tons. A detailed examination of one species of Okinawan acorn worm in a 1 km study urea showed that tl>ey released nearly IQO pounds per day of halogenated phenols, compounds previously thought to be nonnatural pollutants. 

Acorn worm Acoustics Actinides Action potential Activated complex Active galactic nuclei Acupressure Acupuncture... 

Triple bromination of A -TIPS-pyri ole (6) with NBS affords tribromopyrrole 12 (97%) [22], which can either be deprotected to afford the marine acorn worm metabolite 2,3,4-tribromoindole 13 [22,23] or lithiated selectively at C-2 to give, after quenching with carbon dioxide, pyrrole carboxylic acid 14 [24],... 

CHEMICAL STUDIES ON BIOLUMINESCENCE OF ACORN WORM, PTYCHODERA FLAVA ISOLATION AND CHARACTERIZATION OF LUMINOUS SUBSTANCES... 

Higa T, Fujiyama T, Scheuer PJ. Halogenated phenol and indole constitute of acorn worm. Comp Biochem Physiol 1980 65B 525-30. 

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