Isolation and Identification of Two New Compounds from Aspergillus Aculeatus†

doi:10.7503/cjcu20141146

Abstract

Abstract:

In order to investigate new bioactive compounds, a piece of fungi Aspergillus aculeatus was obtained from the Jinyun mountain soil in Chongqing, China. By fermentation using Potato Dextrose(PD) within 14 d at 28 ℃, the extraction of ethyl acetate(103 g) was obtained. The extraction was then used for isolation of compounds through a series of study by classical separation methods, for example Octadecyl Silane(ODS) and Sephadex LH-20. Two new compounds 2-(2',4',6'-trihydroxy phenyl)benzene-(7-hydroxy-5-methyl) chromone(1) and (E)-4-hydroxy-3-[(4-hydroxy-3-methylbut-2-en-1-yl)oxy] benzoic acid(2) were obtained. The structures were elucidated using mass spectrometry(MS), one demensional nuclear magnetic resonance spectroscopy(1D NMR), heteronuclear multiple bond correlation(HMQC), heteronuclear single quanturn correlation(HMBC) and rotating-frame overhauser effect spectroscopy(ROESY). Other two known compounds 2-(2'-hydroxypropyl)-5-methyl-7-hydroxychromone(3) and (3R, 4S)-8-hydroxy-3,4,5- trime-thyl-6-oxo-4,6-dihydro-3H-isochromene-7-carboxylic acid(4) were obtained. Compounds 2 to 4 exhibited some 2,2-diphenyl-1-picrylhydrazyl(DPPH) antioxidant activity.

Key words: Fungi, Aspergillus aculeatus, Nuclear magnetic resonance spectroscopy(NMR), Flavanoid, Antioxidant activity

CLC Number:

O629.9

TrendMD:

XU Yan, TIAN Shasha, YU He, YANG Wenzhi, ZHU Huajie. Isolation and Identification of Two New Compounds from Aspergillus Aculeatus^†[J]. Chem. J. Chinese Universities, 2015, 36(6): 1107.

Figures/Tables 5

References 21

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C atom	¹³C NMR(150 MHz, DMSO-d₆), δ	¹H NMR(600 MHz, DMSO-d₆), δ	HMBC
C2	164.5(C)
C3	112.1(CH)	6.21(Overlap, 1H)	C2, C4, C4a, C1'
C4	182.2(C)
C4a	111.7(C)
C5	139.4(C)
C6	109.2(CH)	6.21(Overlap, 1H)	C4, C4a , C9
C7	157.5(C)
C8	100.8(CH)	6.28(d, J=1.9 Hz, 1H)	C4a , C6, C7, C8a
C8a	160.3(C)
C9	20.3(CH₃)	2.14(s, 3H)	C4a , C5, C6
C1'	104.2(C)
C2'	162.0(C)
C3'	99.3(CH)	6.21(Overlap, 1H)	C2, C4, C1'
C4'	164.8(C)
C5'	94.3(CH)	6.35(d, J=1.9 Hz, 1H)	C1', C4', C6'
C6'	158.7(C)

C atom	¹³C NMR(150 MHz, DMSO-d₆), δ	¹H NMR(600 MHz, DMSO-d₆), δ	HMBC
C2	164.5(C)
C3	112.1(CH)	6.21(Overlap, 1H)	C2, C4, C4a, C1'
C4	182.2(C)
C4a	111.7(C)
C5	139.4(C)
C6	109.2(CH)	6.21(Overlap, 1H)	C4, C4a , C9
C7	157.5(C)
C8	100.8(CH)	6.28(d, J=1.9 Hz, 1H)	C4a , C6, C7, C8a
C8a	160.3(C)
C9	20.3(CH₃)	2.14(s, 3H)	C4a , C5, C6
C1'	104.2(C)
C2'	162.0(C)
C3'	99.3(CH)	6.21(Overlap, 1H)	C2, C4, C1'
C4'	164.8(C)
C5'	94.3(CH)	6.35(d, J=1.9 Hz, 1H)	C1', C4', C6'
C6'	158.7(C)

C atom	¹³C NMR(150 MHz, CD₃OD), δ	¹H NMR(600 MHz, CD₃OD), δ	HMBC
C1	121.8(C)
C2	114.5(CH)	7.58(d, J=1.8 Hz, 1H)	C1, C3, C4, C6, C13
C3	146.1(C)
C4	151.6(C)
C5	114.6(CH)	6.86(d, J=7.8 Hz, 1H)	C1, C2, C3, C4, C13
C6	124.0(CH)	7.56(dd, J=7.8, 1.8 Hz, 1H)	C2, C4, C13
C8	65.3(CH₂)	4.75(d, J=6.3 Hz, 2H)	C3, C9, C10, C11, C12
C9	119.3(CH)	5.78(t, J=6.3 Hz, 1H)	C10, C11, C12
C10	140.1(C)
C11	66.4(CH₂)	4.01(s, 2H)	C9, C10,C12
C12	12.6(CH₃)	1.78(s, 3H)	C9, C10, C11
C13	168.7(C)

C atom	¹³C NMR(150 MHz, CD₃OD), δ	¹H NMR(600 MHz, CD₃OD), δ	HMBC
C1	121.8(C)
C2	114.5(CH)	7.58(d, J=1.8 Hz, 1H)	C1, C3, C4, C6, C13
C3	146.1(C)
C4	151.6(C)
C5	114.6(CH)	6.86(d, J=7.8 Hz, 1H)	C1, C2, C3, C4, C13
C6	124.0(CH)	7.56(dd, J=7.8, 1.8 Hz, 1H)	C2, C4, C13
C8	65.3(CH₂)	4.75(d, J=6.3 Hz, 2H)	C3, C9, C10, C11, C12
C9	119.3(CH)	5.78(t, J=6.3 Hz, 1H)	C10, C11, C12
C10	140.1(C)
C11	66.4(CH₂)	4.01(s, 2H)	C9, C10,C12
C12	12.6(CH₃)	1.78(s, 3H)	C9, C10, C11
C13	168.7(C)