805 INTRODUCTION Cirriformia spirabrancha (Moore, 1904) is a small polychaete worm found in large numbers along the California coast (Ricketts and Calvin, 1952). The worm, which bears a number of tentacles on the anterior end of the body, lives buried in the sand or mud with its tentacles usually out of the substrate and waving in the water. The worm is found both intertidally and subtidally. Being basically a sedentary animal and living in large clumps, it, or its tentacles, should offer a food source to a number of predators. This, however. has not been observed and no previously published literature men- tions any predation on C. spirabrancha. This paper is an attempt to determine whether, in fact, there is significant predation on adult C. spirabrancha and to report an amine present in the animal that may lessen predation. MATERIALS & METHODS Predation observations Observations were carried out in the field in Pacific Grove and Montery, California. These were made at all times of the day and night and throughout the tidal cycle. Observations were made both by wading in hip boots and also by scuba diving up to a depth of 15 feet. All types of predation were looked for including pred- ation by other invertebrates, by fish and also by shore birds. After several weeks of field work, suspected predators were taken into the laboratory for closer scrutiny. The animals were maintained in 5 gallon aquaria filled with running sea water. Two aquaria were set up for each species of predator. One contained 4 inches of sand and mud and the other had no substrate. Suspected predators were left in a tank for + days with 10 specimens of C. spirabrancha and then specimens of Notomastus tenuis Moore, 1909 and Lumbrineris erecta (Moore, 1904), two other marine polychaetes, were placed in the tank and left for another 24 hours. Predators observed in the laboratory were: the polychaetes Nereis grubei (Kinberg, 1866) and Glycera convoluta Keferstein, 1862; the crab Cancer gracilis Dana, 1852; the nudibranch Hermissenda crassicornis (Eschscholtz, 1831); two types of small intertidal fish, Oligocottus snyderi Greeley and Clinocottus analis (Girard) (As determined by keys in Light, et. al., 1954). Attempts were also made to directly feed the fish different sections of C. spirabrancha, tentacles, pieces of body wall only, and also pieces of gut alone. Extraction and isolation 1. Assay. The assay used to detect the presence or absence of the noxious substance in C. spirabrancha was soaking N. tenuis or L. erecta in C. spirabrancha extract for 5 minutes and then offering these to the fish. The same thing was also tried with the steam distillate of extract of C. spirabrancha. If the fish rejected the food it was assumed the noxious substance was present; if the fish ate the food immediately it was considered absent. 2. Extraction. Extract was made of the entire body, of tentacles alone, of body wall alone and also of the anterior and posterior parts of the body alone. Extract was made by grinding C 07 the tissue with mortar and pestle and then homongenizing it with a teflon homongenizer. The extract was centrifuged for 10 minutes at 2000 rpm and the sediment disgarded. 3. Alkaline steam distillation. Extract (not centrifuged) was raised to a pH 9.5 by the addition of 1ON NaoH and placed in a 25 ml test tube connected by plastic tubing to a second test tube placed in an ice bath. The tube in the ice bath was connected by a second piece of tubing to an asperator. The tube containing the extract was heated in a water bath and the distillate collected under vacume. 4. Purification. Extract was mixed with an equal volume (50 ml) of IN HCl. This was centrifuged for 10 minutes at 2000 rpm and the supernate saved. The pellet was resuspended in 30 ml of IN HCl and again centrifuged as before. The two supernates were pooled and then made strongly basic by the addition of lON NaoH. This solution was extracted twice with 150 ml of anhydrous ether. The aqueous phase was disgarded and the ether washed twice with 50 ml. of water. The ether was extracted five times with 10 ml of 1N HCl which was pooled, washed once with ether (25 ml), and kept for analysis. 5. Identification. The first attempt at identification was the Hinsberg procedure for distinguishing between primary, secondary, and tertiary amines. Further attemps at identification were those given for amines by McElvain (1946). RESULTS 1. Predation observations. Table 1 summerizes the reactions 208 of the suspected predators to C. spirabrancha. All of the predators would eat N. tenuis or L. erecta before C. spirabrancha. The immediate reaction by the fish tested was to spit out all parts of C. spirabrancha taken into the mouth. All parts of the worm were repulsive to the fish. This reaction still continued after 14 days of starvation. The only change was an increase in the number of attempts to eat the worm. One piece was taken in the mouth 33 times between 7 different fish before being abandoned as unpalatable. 2. Presence of noxious substance. N. tenuis and L. erecta, which normally are immediately devoured by the fish, were like- wise spit out after being soaked in C. spirabrancha extract. This reaction lasted, on the average, about 1 minute--the time it would take for the water to wash the extract from the soaked worms. After this, the fish would eat the worm. Extracts of various parts of the body worked equally well with no localization of the adverse compound apparent. N. tenuis and L. erecta soaked in distillate of C. spirabrancha extract were again unpalatable to the fish until the distillate washed off. Worms soaked in the residue left after steam distillation and then introduced to the fish were immediately eaten by the fish. Injecting 1 cc of extract down the throats of several fish produced no ill effects although the fish tried to cough it up after it was placed in their throats. The steam distillate had the extremely pungent odor of C. spirabrancha extract and the ether extraction product in alkali solution had the same characteristic odor. 209 3. Identification of noxious substance. Upon addition of the benzenesulfonyl chloride in basic solution a white precipitate appeared. This, however, disappeared upon dilution with water. When made acidic a second white precipitate appeared. Although a primary amine by the reaction in acid, the appearent positive reaction in alkali suggests that there is a second functional group on the molecule. DISCUSSION The obvious lack of predation on C. spirabrancha points to some means of protection for the worm. On the basis of the results it is evident that this protection is two-fold. The first means of protection is the substrate itself. C. spirabrancha lives in the black sand and mud found in the inter- tidal region. This mud would probably discourage predation by those animals which normally don't burrow as deeply as C. spira¬ brancha (i.e. H. crassicornis). Secondly, and more important, is the bad taste of the worm itself. Although not poisonous, the worm is noxious enough that predators choose other prey before C. spirabrancha. The bad taste seems to be from a compound found throughout the body tissue. This compound can be seperated from the body extract and the remainder of the extract is completely palatable. The compound appears to be a primary amine-its further structure being unknown at present. SUMMARY The lack of predation on C. spirabrancha seems to be due mainly R TABLE 1 Predation on C. spirabrancha REACTION IN REACTION TO PREFER OTHER ANIMAL SUBSTRAT WORMS * EXPOSED WORM Pos.* Neg.* Pos. Neg. Neries grubei 2. Glycera convoluta X 3. Cancer gracilis X 4. Hermissenda X X crassicornis Oligocottus snyderi X X 6. Clinocottus analis X X * Positive reaction means at least 1 worm eaten in 4 day period Negative reaction means all 10 worms present after 4 days ** N. tenuis and L. erecta eaten before C. spirabrancha C to a compound, found within the body tissue, which has thus far been identified only as a primary amine. This compound seems to make C. spirabrancha unpalatable to other animals. ACKNOWLEDGEMENTS I'd like to thank, among others, my advisor, Dr. Pearse, for his help and also Dr. Phillips without whose help I couldn't have completed the chemical end of this paper. This work supported in part by the Undergraduate Research Participation Program of the National Science Foundation Grant GY-4369. BIBLIOGRAPHY Light, S.F., Smith R.I., Pitelka F.A., Abbott D.P. & Weesner F.M. (1954) Intertidal Invertebrates of the Central California Coast, University of California Press, Berkeley, California. McElvain, Samuel M. (1946) The Characterization of Organic Compounds, The MacMillian Company, New York. Ricketts and Calvin (1952) Between Pacific Tides, Stanford University Press, Stanford, California 80 C