394 



DESCRIPTION.S OF ANTIBIOTICS 



tions; decomposes in alkaline solutions (1). Very 

 thermostable (18). Desulfurization of thiolutin 

 yields white crystalline desthiolutin, CeHuNoOo , 

 which has no ultraviolet maximum above 220 ni/x 

 and is antibiotically inactive. Acid hydrolysis 

 yields acetic acid and pyrrothine, C6H6N2OS2 , a 

 weak amine (also a hydrolysis product of aureo- 

 thricin), which gives a characteristic red color 

 with glutaconic aldehyde (2, 15, 18). Complete 

 structure of thiolutin (3-acetamido derivative of 

 3-amino -5-methylpyrrolin - 4 - ono - (4 , 3 - d) - 1 , 2 di - 

 thiole) : 



O 



S C==C— NH— CCH3 



/ 

 S 



\ 

 CH=C C=() 



CH3 



Biological activity: Active against gram-positive 

 and gram-negative bacteria in concentrations of 

 1 to 15 Aig per ml. Pseudomonas and Brucella are 

 resistant. Pathogenic fungi inhibited in concen- 

 trations of 1 to 5 Mg per ml ; C. albicans is resistant. 

 Mild but definite microbicidal action against 

 bacteria, fungi, and protozoa (1). Active on Chlo- 

 rella pyrenoidosa at 5 /xg per ml (22). Active i>i 

 vitro on influenza A (PR 8) (23). Molluscacide 

 (17). Active on fire blight {Erwinia amylovora) 

 (3, 13), and moderately active on frog eye disease 

 (Physalospora abtusa) of' apple (13). Controls 

 late blight of potato (Phytophthora infestans) (8), 

 and has a protective effect against Fusarium wilt 

 of tomato (4). Partial control of Rhizoctonia in- 

 fection of lettuce and tomatoes, and VerticiUium 

 infection in tomatoes and potatoes (9). Control 

 of tobacco blue mold {Peronospora tabacina) (16), 

 and downy mildew of broccoli (Peronospora para- 

 sitica) (20). Moderate protection against Hehnin- 

 thosporium infection of oat seed; slight protection 

 against cotton anthracnose (Colletotrichum gos- 

 sypii) (5). Stimulates germinating seed growth 

 of Agave toumeyana (6), oat, buffet grass, and 

 Madrid sweet clover, and top growth of the latter 

 three (11). Increases number of actinomycetes 

 and bacteria in fallow soils to which it is added, 

 and nodules on sweet clover grown in such soil, 

 but decreases fungal population (11). Has a Bi- 

 sparing effect on virus-tumor tissue of Rumex 

 acetosa (7). 



Toxicity: LD50 (mice) 25 mg per kg subcutane- 

 ously, 25 mg per kg orally (1). Not toxic at 200 



ppm applied as spray to young tomato plants, or 

 at 50 ppm as root solution to corn, pea, tomato, 

 or sunflower plants, or at 120 ppm to carnation 

 cuttings (19). Not inhibitory to germination of 

 corn, pea, or radish seeds soaked in 100 ppm for 

 8 hours (5). Toxic at therapeutic levels to human 

 spermatozoa (10). 



Utilization: Plant disease. Plant growth stimu- 

 lation. 



References: 



1. Seneca, H. Antibiotics & Chemotherapy 



2: 357-360, 1952. 



2. Celmer, W. D. et al. J. Am. Chem. Soc. 



74:6304-6305, 1952. 



3. Murneek, E. Phytopathology 42:57,1952. 



4. Gopalkrishnan, K. S. and Jump, J. A. Phy- 



topathology 42: 338-339, 1952. 



5. Gopalkrishnan, K. S. and Jump, J. A. Proc. 



Indiana Acad. Sci. 61: 97-110, 1952. 



6. Nickell, L. G. Proc. Soc. Exptl. Biol. 



Med. 80:615-617,1952. 



7. Nickell, L. G. Anti})iotics & Chemother- 



apy 3: 449-459, 1953. 



8. Bonde, R. Phytopathologv 43: 463-464, 



1953. 



9. Hilborn, M. T. Phytopathology 43: 475, 



1953. 



10. Seneca, H. and Ides, D. J. Urol. 70: 947- 



958, 1953. 



11. Hervey, R. J. Southern Seedsman 16: 



13, 72, 1953. 



12. British Patent 692,066, May 27, 1953. 



13. Heuberger, J. W. and Poulos, P. L. Plant 



Disease Reptr. 37 : 81-83, 1953. 



14. Nishimura, H. and Kimura, T. Japanese 



Patent 5400, 1954. 



15. Celmer, W. D. and Solomons, I. A. Anti- 



biotics Ann. 622-625, 1953-1954. 



16. Grosso, J. J. Plant Disease Reptr. 38: 



333, 1954. 



17. Seneca, H. and Bergendahl, E. Antibiotics 



& Chemotherapy 5: 737-741, 1955. 



18. Celmer, W. D. and Solomons, I. A. J. Am. 



Chem. Soc. 77: 2861-2865, 1955. 



19. Gasiorkiewdcz, E. C. Plant Disease Reptr. 



40: 421-423, 1956. 



20. Natti, J. J. Plant Disease Reptr. 41: 780- 



788, 1957. 



21. Nakamura, M. et al. Ann. Rept. Takamine 



Lab. 9:35-43,1957. 



22. Tomisek, A. e/ fl/. Plant Physiol. 32:7-10, 



1957. 



23. Miyakawa, T. et al. Japan. J. Microbiol. 



2: 53-62. 1958. 



