Fractionation of Azaphilones from Secondary Metabolites of Marine-Derived Fungus Penicillim pinophilum and Their Antibacterial Activity†

doi:10.7503/cjcu20170304

Abstract

Abstract:

Bioassay-guide fractionation of the marine-derived fungus Penicillim pinophilum led to the isolation of three azaphilones derivatives: Pinophilins G(1), Pinophilins B(2) and Sch 725680(3), which were separated by silica gel column chromatography, octadecylsilyl(ODS) column chromatography, Sephadex LH-20. Compound 1 is a new compound. The plane structure of compound 1 was determined based on HR-ESI-MS, ¹H NMR, ¹³C NMR, heteronuclear multiple bond correlation(HMBC), nuclear overhauser effect spectroscopy(NOSEY) and heteronuclear singular quantum correlation(HSQC). The absolute configuration of compound 1 was determined by comparing its experimental electronic circular dichroism(ECD) with the calculated ECD spectra using quantum methods. The results indicated that compounds 1 and 3 showed antibacterial activities against four spices of pathogenic bacteria.

Key words: Marine-derived fungus, Penicillium pinophilum, Azaphilone derivative, Absolute configuration, Antibacterial activity

CLC Number:

O629.9

TrendMD:

MA Yangyang, CAI Hui, DU Min, CAO Fei, ZHU Huajie. Fractionation of Azaphilones from Secondary Metabolites of Marine-Derived Fungus Penicillim pinophilum and Their Antibacterial Activity^†[J]. Chem. J. Chinese Universities, 2017, 38(11): 1963.

Figures/Tables 3

References 21

[1]	Shi X. L., Wang J. F., Yao H., Chem. J. Chinese Universities,2010, 31(2), 381-385
	(时晓磊, 王加付, 姚华. 高等学校化学学报, 2013, 34(2), 381-385)
[2]	Sami S., Mohamed B., Tahar M., Chem. J. Chinese Universities,2010, 31(4), 693-698
[3]	Wang W., Lee T. G., Patil R. S., Mun B., Yang I., Kim H., Hahn D., Won D. H., Lee J., Lee Y., Choi H., Nam S. J., Kang H., J. Nat. Prod., 2014, 78, 368-373
[4]	Zhao D. L., Shao C. L., Zhang Q., Wang K. L., Guan F. F., Shi T., Wang C. Y., J. Nat. Prod., 2015, 78, 2310-2314
[5]	Xu Y., Tian S. S., Yu H., Yang W. Z., Zhu H. J., Chem. J. Chinese Universities,2010, 31(6), 1107-1111
	(徐燕, 田沙沙, 俞和, 杨文智, 朱华结. 高等学校化学学报, 2015, 36(6), 1107-1111)
[6]	Gao S. S., Li X. M., Zhang Y., Li C. S., Cui C. M., Wang B. G., J. Nat. Prod., 2011, 74, 256-261
[7]	Liu Y. Y., Yang Q., Xia G. P., Huang H. B., Li H. X., Ma L., Lu Y. J., He L., Xia X. K., She Z. G., J. Nat. Prod., 2015, 78, 1816-1822
[8]	Zhang C. C., Ding S. S., Shi W. S., Cao F., Zhu H. J., Wen M. L., Nat. Prod. Res., 2017, 31, 99-103
[9]	Gao T., Cai S. Y., Xu L. L., Cao F., Zhu H. J., Chem. J. Chinese Universities,2010, 31(7), 1282-1286
	(高彤, 蔡思源, 许兰兰, 曹飞, 朱华结. 高等学校化学学报, 2016, 37(7), 1282-1286)
[10]	Zhang N., Chen Y., Jiang R., Li E., Chen X., Xi Z., Jiang X., Autophagy,2011, 7, 598-612
[11]	Xiong L., Zhu C. G., Li Y. R., Tian Y., Lin S., Yuan S. P., Hu J. F., Hou Q., J. Nat. Prod., 2011, 74, 1188-1200
[12]	Andzelm J., Wimmer E., J. Chem. Phys., 1992, 96, 1280-1303
[13]	Stratmann R. E., Burant J. C., Scuseria G. E., Frisch M. J., J. Chem. Phys., 1997, 106, 10175-10183
[14]	Zhu H.J., Organic Stereochemistry-experimental and Computational Methods, Wiley-VCH, Verlag GmbH & Co. KGaA Weimheim, 2015
[15]	Wang H., Wang J., Wu X., Shen H. Y., Luo Y., Dai H. F., Mei W. L., Chem. J. Chinese Universities,2010, 31(1), 38-43
[16]	Zhu H.J., Modern Organic Stereochemistry, Science Press of China, Beijing, 2009
	(朱华结. 现代有机立体化学, 北京: 科学出版社, 2009)
[17]	Ding S. S., Zhang C. C., Shi W. S., Liang M. M., Yang Q., Zhu H. J., Li Y., Tetrahedron Lett., 2016, 57, 75-79
[18]	Baker J., J. Comput. Chem., 1993, 14, 1085-1100
[19]	Zhu H. J., Liu L., Yang Q., Chem. J. Chinese Universities,2010, 31(8), 1559-1562
	(朱华结, 刘莉, 杨芹. 高等学校化学学报, 2015, 36(8), 1559-1562)
[20]	Yu H., Li W. X., Wang J. C., Yang Q., Wang H. J., Zhang C. C., Ding S. S., Li Y., Zhu H. J., Tetrahedron,2015, 71, 3491-3494
[21]	Hu D. B., Zhou B. D., Chem. J. Chinese Universities,2010, 31(11), 1993-1998
	(胡栋宝, 周北斗. 高等学校化学学报, 2016, 37(11), 1993-1998)

C atom	¹³C NMR(150 MHz, DMSO-d₆), δ	¹H NMR(600 MHz, DMSO-d₆), δ	HMBC	COSY
1	69.5, CH₂	3.90, dd(13.4, 10.9)	4a, 8, 8a
		4.52, dd(10.9, 5.2)	3, 4a, 8a
3	158.9, C
4	110.8, CH	6.13, s	3, 4a, 5, 8a, 10
4a	151.2, C
5	120.3, CH	5.92, s	4, 7, 8a
6	197.3, C
7	75.1, C
8	76.5, CH	5.31, d(9.9)	1, 4a, 7, 8a, 9, 1'	8a
8a	36.2, CH	3.48, m		8
9	19.6,CH₃	1.32, s	6, 7
10	137.9, CH	7.06, d(15.5)	3, 4, 11, 12	11
11	124.8,CH	6.37, d(15.5)	3, 10, 12	10
12	169.7, C
1'	171.9, C
2'	105.6, C
3'	166.0, C
4'	101.9, CH	6.20, d(2.0)	1', 2',3', 6'
5'	164.2, C
6'	112.8, CH	6.27, d(2.0)	1', 2', 4', 8'
7'	145.0, C
8'	24.6, CH₃	2.58, s	1', 2', 3', 6', 7'

C atom	¹³C NMR(150 MHz, DMSO-d₆), δ	¹H NMR(600 MHz, DMSO-d₆), δ	HMBC	COSY
1	69.5, CH₂	3.90, dd(13.4, 10.9)	4a, 8, 8a
		4.52, dd(10.9, 5.2)	3, 4a, 8a
3	158.9, C
4	110.8, CH	6.13, s	3, 4a, 5, 8a, 10
4a	151.2, C
5	120.3, CH	5.92, s	4, 7, 8a
6	197.3, C
7	75.1, C
8	76.5, CH	5.31, d(9.9)	1, 4a, 7, 8a, 9, 1'	8a
8a	36.2, CH	3.48, m		8
9	19.6,CH₃	1.32, s	6, 7
10	137.9, CH	7.06, d(15.5)	3, 4, 11, 12	11
11	124.8,CH	6.37, d(15.5)	3, 10, 12	10
12	169.7, C
1'	171.9, C
2'	105.6, C
3'	166.0, C
4'	101.9, CH	6.20, d(2.0)	1', 2',3', 6'
5'	164.2, C
6'	112.8, CH	6.27, d(2.0)	1', 2', 4', 8'
7'	145.0, C
8'	24.6, CH₃	2.58, s	1', 2', 3', 6', 7'