Absolute Configuration Determination of One New Compound Trichoderol A from Trichoderma sp. Fungus†

doi:10.7503/cjcu20160499

Abstract

Abstract:

One new compound, trichoderol A(1), was isolated from cultures of the fungus Trichoderma sp. The structure of compound 1 was established by means of NMR and mass spectrometry. The absolute configuration(AC) was determined by means of comparing experimental electronic circular dichroism(ECD) and optical rotation(OR) of compound 1 with the calculated ECD and OR data of compound 1 using quantum methods, also using matrix model. Compound 1 was evaluated for antibacterial activities against three species of pathogenic bacteria, and the results showed that compound 1 had weak antibacterial activities(MIC=25 μmol/L).

Key words: Trichoderma sp., Electronic circular dichroism, Optical rotation, Matrix, Antibacterial activity

CLC Number:

O629.9

TrendMD:

XU Lanlan, ZHAO Qiqi, YU He, WANG Jingchen, WANG Huijun, YANG Qin, ZHU Huajie, LI Yan. Absolute Configuration Determination of One New Compound Trichoderol A from Trichoderma sp. Fungus^†[J]. Chem. J. Chinese Universities, 2016, 37(11): 1972.

Figures/Tables 5

References 21

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C atom	¹³C NMR(150 MHz, CDCl₃), δ	¹H NMR(600 MHz,CDCl₃), δ	HMBC
1	27.3, CH₃	2.30(s, 3H)	C2, C3
2	199.0, C
3	131.0, CH	6.18(d, J=15.6 Hz, 1H)	C1, C2, C4, C5
4	142.7, CH	7.15(dd, J=15.6, 11.4 Hz, 1H)	C2, C5
5	129.7, CH	6.61(dd, J=15.6, 11.4 Hz, 1H)	C3, C4, C6, C7
6	142.5, CH	6.22(d, J=15.6 Hz, 1H)	C4, C5, C7, C8
7	77.1, C
8	77.0, CH	4.12(d, J=7.8 Hz, 1H)	C6, C7, C9, C10, C12
9	128.2, CH	5.52(dd, J=15.0, 7.8 Hz, 1H)	C8,C11
10	131.4, CH	5.83(dq, J=15.0, 6.6 Hz)	C9, C11
11	18.0, CH₃	1.76(d, J=6.6 Hz, 3H)	C9, C10
12	66.0, CH₂	3.56(d, J=11.4 Hz, 1H)	C6, C7, C8
		3.88(d, J=11.4 Hz, 1H)	C6,C7, C8

C atom	¹³C NMR(150 MHz, CDCl₃), δ	¹H NMR(600 MHz,CDCl₃), δ	HMBC
1	27.3, CH₃	2.30(s, 3H)	C2, C3
2	199.0, C
3	131.0, CH	6.18(d, J=15.6 Hz, 1H)	C1, C2, C4, C5
4	142.7, CH	7.15(dd, J=15.6, 11.4 Hz, 1H)	C2, C5
5	129.7, CH	6.61(dd, J=15.6, 11.4 Hz, 1H)	C3, C4, C6, C7
6	142.5, CH	6.22(d, J=15.6 Hz, 1H)	C4, C5, C7, C8
7	77.1, C
8	77.0, CH	4.12(d, J=7.8 Hz, 1H)	C6, C7, C9, C10, C12
9	128.2, CH	5.52(dd, J=15.0, 7.8 Hz, 1H)	C8,C11
10	131.4, CH	5.83(dq, J=15.0, 6.6 Hz)	C9, C11
11	18.0, CH₃	1.76(d, J=6.6 Hz, 3H)	C9, C10
12	66.0, CH₂	3.56(d, J=11.4 Hz, 1H)	C6, C7, C8
		3.88(d, J=11.4 Hz, 1H)	C6,C7, C8

C atom	Measured 1, δ	Calcd.(7R,8S), δ	Corr.(7R,8S), δ	Error	Calcd.(7S,8S), δ	Corr.(7S,8S), δ	Error
1	27.3	153.183686	25.88644033	-1.41356	152.739175	24.93860729	-2.36139
2	199.0	-18.861112	194.3190418	-4.68096	-18.688808	194.2648832	-4.73512
3	131.0	48.474701	128.3969896	-2.60301	49.350635	127.0596038	-3.9404
4	142.7	34.695964	141.8864327	-0.81357	34.30144	141.9242957	-0.7757
5	129.7	43.990052	132.7874804	3.08748	45.749192	130.6168931	0.916893
6	142.5	28.348542	148.1005863	5.600586	31.037306	145.1484114	2.648411
7	77.1	98.122963	79.79112634	2.691126	100.769681	76.27095529	-0.82904
8	77.0	99.963119	77.98960566	0.989606	95.51673	81.45950511	4.459505
9	128.2	49.256528	127.6315776	-0.56842	45.596091	130.7681171	2.568117
10	131.4	44.9979	131.8007928	0.400793	42.5425	133.7842711	2.384271
11	18.0	162.476119	16.78910823	-1.21089	162.673094	15.12647813	-2.87352
12	66.0	113.720758	64.52081756	-1.47918	108.601879	68.53478004	2.53478
Correl(%)			0.998629			0.998386

C atom	Measured 1, δ	Calcd.(7R,8S), δ	Corr.(7R,8S), δ	Error	Calcd.(7S,8S), δ	Corr.(7S,8S), δ	Error
1	27.3	153.183686	25.88644033	-1.41356	152.739175	24.93860729	-2.36139
2	199.0	-18.861112	194.3190418	-4.68096	-18.688808	194.2648832	-4.73512
3	131.0	48.474701	128.3969896	-2.60301	49.350635	127.0596038	-3.9404
4	142.7	34.695964	141.8864327	-0.81357	34.30144	141.9242957	-0.7757
5	129.7	43.990052	132.7874804	3.08748	45.749192	130.6168931	0.916893
6	142.5	28.348542	148.1005863	5.600586	31.037306	145.1484114	2.648411
7	77.1	98.122963	79.79112634	2.691126	100.769681	76.27095529	-0.82904
8	77.0	99.963119	77.98960566	0.989606	95.51673	81.45950511	4.459505
9	128.2	49.256528	127.6315776	-0.56842	45.596091	130.7681171	2.568117
10	131.4	44.9979	131.8007928	0.400793	42.5425	133.7842711	2.384271
11	18.0	162.476119	16.78910823	-1.21089	162.673094	15.12647813	-2.87352
12	66.0	113.720758	64.52081756	-1.47918	108.601879	68.53478004	2.53478
Correl(%)			0.998629			0.998386

Compound	IC₅₀/(μmol·L^-1)
Compound	HL-60	SMMC-7721	A-549	MCF-7	SW480
1	>40	>40	>40	>40	>40
MW300	2.22	10.21	7.25	12.16	10.07
Taxol	<0.008	<0.008	<0.008	<0.008	<0.008