Citrinin Derivatives from Marine-derived Fungus Penicillim Grisefulvum and Antibacterial Activity†

doi:10.7503/cjcu20160315

Abstract

Abstract:

The marine fungus Penicillim grisefulvum was cultivated with 43 d at 28 ℃, bioassay-guide fractionation of the marine fungus Penicillim grisefulvum led to the isolation of three citrinin derivatives(1—3), which were separated by silica gel column chromatography, C₁₈ column chromatography, Sephadex LH-20, and semi-preparative HPLC. Based on the HR-ESI-MS, 1D and 2D NMR, compounds 1—3 were assigned as 7-methyl-penicitrinone A(1), citrinin(2) and penicitrinone A(3), respectively. The absolute configuration of compound 1 was determined by comparision of experimental and calculated electronic cicular dichroism(ECD) data. Compound 1 displayed strong antibacterial activity against Vibrio parahemolyticus(MIC=0.8 μmol/L), which was stronger than the positive control of ciprofloxacin(MIC=1.3 μmol/L).

Key words: Marine fungus, Penicillim grisefulvum, Citrinin derivative, Antibacterial activity

CLC Number:

O629.9

TrendMD:

GAO Tong, CAI Siyuan, XU Lanlan, CAO Fei, ZHU Huajie. Citrinin Derivatives from Marine-derived Fungus Penicillim Grisefulvum and Antibacterial Activity^†[J]. Chem. J. Chinese Universities, 2016, 37(7): 1282.

Figures/Tables 4

References 21

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C atom	¹³C NMR(150 MHz, DMSO-d₆), δ	¹H NMR(600 MHz, DMSO-d₆), δ	HMBC
C1	153.0(C)
C3	80.8(CH)	5.03(brq, J=6.6 Hz, 1H)	3-Me, C4
3-Me	18.0(CH₃)	1.29(d, J=6.6 Hz, 3H)	C3, C4
C4	33.7(CH)	3.17(brq, J=7.1 Hz, 1H)	4-Me, C8a, C5
4-Me	18.6(CH₃)	1.20(d, J=7.1 Hz, 3H)	C3, C4, C5
C4a	130.8(C)
C5	131.5(C)
5-Me	10.7(CH₃)	1.98(s, 3H)	C5, C6
C6	182.6(C)
C7	108.2(C)
7-Me	8.0(CH₃)	1.96(s, 3H)	C6, C7, C8
C8	155.0(C)
C8a	98.6(C)
C2'	87.1(CH)	4.61(qd, J=3.6, 6.6 Hz, 1H)	2'-Me, C3a'
2'-Me	20.7(CH₃)	1.32(d, J=6.6 Hz, 3H)	C2', C3'
C3'	43.7(CH)	3.23(dq, J=3.6, 6.9 Hz, 1H)	3'-Me
3'-Me	18.9(CH₃)	1.25(d, J=6.9 Hz, 3H)	C3', C2', C3a'
C3a'	138.8(C)
C4'	116.4(C)
4'-Me	11.6(CH₃)	2.15(s, 3H)	C4', C5'
C5'	139.1(C)
C6'	102.3(C)
C7'	135.2(C)
C7a'	137.1(C)

C atom	¹³C NMR(150 MHz, DMSO-d₆), δ	¹H NMR(600 MHz, DMSO-d₆), δ	HMBC
C1	153.0(C)
C3	80.8(CH)	5.03(brq, J=6.6 Hz, 1H)	3-Me, C4
3-Me	18.0(CH₃)	1.29(d, J=6.6 Hz, 3H)	C3, C4
C4	33.7(CH)	3.17(brq, J=7.1 Hz, 1H)	4-Me, C8a, C5
4-Me	18.6(CH₃)	1.20(d, J=7.1 Hz, 3H)	C3, C4, C5
C4a	130.8(C)
C5	131.5(C)
5-Me	10.7(CH₃)	1.98(s, 3H)	C5, C6
C6	182.6(C)
C7	108.2(C)
7-Me	8.0(CH₃)	1.96(s, 3H)	C6, C7, C8
C8	155.0(C)
C8a	98.6(C)
C2'	87.1(CH)	4.61(qd, J=3.6, 6.6 Hz, 1H)	2'-Me, C3a'
2'-Me	20.7(CH₃)	1.32(d, J=6.6 Hz, 3H)	C2', C3'
C3'	43.7(CH)	3.23(dq, J=3.6, 6.9 Hz, 1H)	3'-Me
3'-Me	18.9(CH₃)	1.25(d, J=6.9 Hz, 3H)	C3', C2', C3a'
C3a'	138.8(C)
C4'	116.4(C)
4'-Me	11.6(CH₃)	2.15(s, 3H)	C4', C5'
C5'	139.1(C)
C6'	102.3(C)
C7'	135.2(C)
C7a'	137.1(C)

Compd.	Strains
Compd.	S. typhi	V. anguillarum	V. parahemolyticus
1	>25.0	>25.0	0.8
2	0.4	12.5	>25.0
3	0.4	6.3	>25.0
Ciprofloxacin	0.6	0.6	1.3

Compd.	Strains
Compd.	S. typhi	V. anguillarum	V. parahemolyticus
1	>25.0	>25.0	0.8
2	0.4	12.5	>25.0
3	0.4	6.3	>25.0
Ciprofloxacin	0.6	0.6	1.3