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A high-performance molluscicidal activeingredient from strain SL-30 studied by Dr. Danzhao Guo

In China, Schistosomiasis caused by Schistosoma japonicum is epidemic in the Southeast, especially in the areas of Yangtze River valley. Snail (Oncomelania hupensis) is the only intermediate host of Schistosoma japonicum, therefore in schistosomiasis control programs, snail control is an important and effective preventive strategy. The present study focuses on identifying the molluscicidal ingredient (named as MI) obtained from molluscicidal strain SL-30’s exocellular broth.

NMR analysis

1H NMR(CD3OD) chemical shifts of the MI were given as follows: 6.06 (1H, s, H-7), 6.02-5.99 (1H, d, H-8), 5.72-5.70 (1H, d, H-9), 4.86 (1H, s, H-6), 4.73-4.69 (1H, d, H-5a), 4.48-4.45 (1H, d, H-3a), 4.35-4.31 (1H, d, H-3a), 3.79-3.74 (1H, d, H-10), 3.22 (3H, s, 2-CH3), and 3.08-3.03 (1H, d, H-10). As for13CNMR(CD3OD) chemical shift values, 6 carbon signals (110-170) appeared in the downfield region, which included two acidamide-carbonyl (166.50, C-1 and 164.84, C-4), one quaternary carbon atom (132.13, C-9a), and three methenyl (128.76, C-9, 123.54, C-8 and 119.21, C-7). At the same time, seven carbon signals (20-80) appeared in the upfield region, which included two quaternary carbon atom (78.08, C-3 and 75.97, C-10a), two methenyl (73.20, C-5aand 69.24, C-6), two methene (59.06, C-3aand 35.87, C-10), and one methyl (26.78, C-2-Me). The two acidamide-carbonyl (166.50, C-1 and 164.84, C-4) mentioned above suggested that a diketopiperazine-framework existed in the structure of the active ingredient.

DQF 1H-1H COSY and 1H-13CHSQC spectra analysis were applied to clarify proton–proton couplings and proton–carbon correlations. In 1H-1H COSY spectrum, H-8 (6.02-5.99) was coupled with H-7 (6.06) and H-9 (5.72-5.70), and the information that H-7 (6.06) was coupled with H-8 (6.02-5.99), and H-9 (5.72-5.70) was coupled with H-8 (6.02-5.99), suggested a diene framework existed in the structure of the active ingredient. In addition, H-6 (4.86) was coupled with H-7 (6.06), H-6 (4.86) was coupled with H-5a(4.73-4.69), H-3a(4.48-4.45) was coupled with H-3a(4.35-4.31), and H-10 (3.79-3.74) was coupled with H-10 (3.08-3.03). From 1H-13CHSQC spectrum the result showed as follows, δH 6.06 was correlated with δC 119.21, δH 6.02-5.99 was correlated with δC 123.54, δH 5.72-5.70 was correlated with δC 128.76, δH 4.86 was correlated with δC 69.24, δH 4.73-4.69 was correlated with δC 73.20, δH 4.48-4.45 and δH 4.35-4.31 were correlated with δC 59.06, δH 3.79-3.74 and δH 3.08-3.03 were correlated with δC 35.87, δH 3.22 was correlated with δC 26.78; furthermore, no hydrogen signal was correlated with δC 166.50, δC 164.84, δC 132.13, δC 78.08, and δC 75.97. All the information obtained from 1H-13CHSQC spectrum mentioned above confirmed the assignment of H and C, and agreed with the molecular structure of Gliotoxin.

MS2 analysis

MS2 analysis was further performed to obtain the information of molecular structure and to confirm the molecular structure of the MI. The information of MS2 spectra agreed with the data previously reported, therefore the MI from strain SL-30’s exocellular broth was further confirmed as gliotoxin.

(School of Food and Biological Engineering)

Returns〗 Hits: Date:2015-06-19
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