<i>Aspergillus niger</i>: A Hundred Years of Contribution to the Natural Products Chemistry

Lima, Mary Anne S.; Oliveira, Maria da Conceição F. de; Pimenta, Antônia T. Á.; Uchôa, Paula K. S.

doi:10.21577/0103-5053.20190080

Mary Anne S. Lima ^**e-mail: mary@dqoi.ufc.br

Departamento de Química Orgânica e Inorgânica, Universidade Federal do Ceará, 60021-940 Fortaleza-CE, Brazil

Mary Anne Sousa Lima is Titular Professor at Departamento de Química Orgânica e Inorgânica from Universidade Federal do Ceará (UFC), Ceará State, Brazil. She obtained her undergraduate degree in Chemistry at the Universidade Federal do Ceará, Brazil (1991), the Master’s degree in Organic Chemistry at the Universidade Federal do Ceará, Brazil (1991-1993), PhD in Organic Chemistry at the Universidade Estadual de Campinas (UNICAMP), São Paulo State, Brazil (1995-1999), and the postdoctoral at the University of Florida, FL, USA (2015). Her scientific interests include the chemistry of plants and microorganisms.

https://orcid.org/0000-0002-3338-6347

Maria da Conceição F. de Oliveira

Departamento de Química Orgânica e Inorgânica, Universidade Federal do Ceará, 60021-940 Fortaleza-CE, Brazil

Maria C. F. Oliveira is Titular Professor at Departamento de Química Orgânica e Inorgânica from Universidade Federal do Ceará (UFC, Fortaleza-CE, Brazil). Her Master’s degree (1996) was obtained at UFC and involved the chemical investigation of plants. She concluded her doctorate (2001) at Universidade Estadual de Campinas (UNICAMP, Campinas-SP, Brazil) in Organic Synthesis. In 2013, she did a post-doctorate at The University of Arizona (Tucson-AZ, USA). Currently, she has worked with Natural Products and Biocatalysis.

Antônia T. Á. Pimenta

Departamento de Química Orgânica e Inorgânica, Universidade Federal do Ceará, 60021-940 Fortaleza-CE, Brazil

Antônia Torres Ávila Pimenta obtained her undergraduate degree in Pharmacy at Universidade Federal do Ceará (1996), Master (2004) in Organic Chemistry at Universidade Federal do Ceará and concluded the doctorate in Organic Chemistry at Universidade Federal do Ceará (2009). She is currently Adjunct Professor at Departamento de Química Orgânica e Inorgânica from Universidade Federal do Ceará. She has experience in the area of Chemistry of Natural Products, working mainly in the chemical, pharmacy and pharmacological investigation of plants and microorganisms.

Paula K. S. Uchôa

Instituto Federal de Educação, Ciência e Tecnologia do Ceará, Campus Iguatu, 63500-000 Iguatu-CE, Brazil

*e-mail: mary@dqoi.ufc.br

Mary Anne Sousa Lima

is Titular Professor at Departamento de Química Orgânica e Inorgânica from Universidade Federal do Ceará (UFC), Ceará State, Brazil. She obtained her undergraduate degree in Chemistry at the Universidade Federal do Ceará, Brazil (1991), the Master’s degree in Organic Chemistry at the Universidade Federal do Ceará, Brazil (1991-1993), PhD in Organic Chemistry at the Universidade Estadual de Campinas (UNICAMP), São Paulo State, Brazil (1995-1999), and the postdoctoral at the University of Florida, FL, USA (2015). Her scientific interests include the chemistry of plants and microorganisms.

Maria C. F. Oliveira

is Titular Professor at Departamento de Química Orgânica e Inorgânica from Universidade Federal do Ceará (UFC, Fortaleza-CE, Brazil). Her Master’s degree (1996) was obtained at UFC and involved the chemical investigation of plants. She concluded her doctorate (2001) at Universidade Estadual de Campinas (UNICAMP, Campinas-SP, Brazil) in Organic Synthesis. In 2013, she did a post-doctorate at The University of Arizona (Tucson-AZ, USA). Currently, she has worked with Natural Products and Biocatalysis.

Antônia Torres Ávila Pimenta

obtained her undergraduate degree in Pharmacy at Universidade Federal do Ceará (1996), Master (2004) in Organic Chemistry at Universidade Federal do Ceará and concluded the doctorate in Organic Chemistry at Universidade Federal do Ceará (2009). She is currently Adjunct Professor at Departamento de Química Orgânica e Inorgânica from Universidade Federal do Ceará. She has experience in the area of Chemistry of Natural Products, working mainly in the chemical, pharmacy and pharmacological investigation of plants and microorganisms.

Paula Karina Santos Uchôa

is Professor at Instituto Federal de Educação Ciência e Tecnologia do Ceará, Iguatu Campus, Ceará State, Brazil. She obtained her undergraduate degree in Industrial Chemistry at Universidade Federal do Ceará (2009), the Master’s degree in Organic Chemistry at Universidade Federal do Ceará (2011) and concluded the doctorate in Organic Chemistry (2017) at Universidade Federal do Ceará, Ceará State, Brazil. Her scientific interests includes the chemistry of natural products of plants and microorganisms.

Compound	Strain	Source	Reference
Asperpyrone A (1)	JV 33-48	soil	²⁸28 Akiyama, K.; Teraguchi, S.; Hamasaki, Y.; Mori, M.; Tatsumi, K.; Ohnishi, K.; Hayashi, H.; J. Nat. Prod. 2003, 66, 136.
	SCSIO Jcsw6F30	marine	²⁹29 Fang, W.; Lin, X.; Wang, J.; Liu, Y.; Tao, H.; Zhou, X.; Molecules 2016, 21, 941.
	nr	endophyte	³⁰30 Li, X. B.; Xie, F.; Liu, S. S.; Li, Y.; Zhou, J. C.; Liu, Y. Q.; Yuan, H. Q.; Lou, H. X.; Chem. Biodiversity 2013, 10, 1193.
	EN 13	marine	³¹31 Zhang, Y.; Li, X.-M.; Wang, B.-G.; J. Antibiot. 2007, 60, 204.
Asperpyrone B (2)	IFBE 003	endophyte	³²32 Song, y. c.; Li, H.; Ye, Y. H.; Shan, C. Y.; Yang, Y. M.; Tan, R. X.; FEMS Microbiol. Lett. 2004, 241, 67.
	JV 33-48	soil	²⁸28 Akiyama, K.; Teraguchi, S.; Hamasaki, Y.; Mori, M.; Tatsumi, K.; Ohnishi, K.; Hayashi, H.; J. Nat. Prod. 2003, 66, 136.
	2HL M-8	marine	³³33 Li, D.-H.; Han, T.; Guan, L.-P.; Bai, J.; Zhao, N.; Li, Z.-L.; Wu, X.; Hua, H.-M.; Nat. Prod. Res. 2016, 30, 1116.
Asperpyrone C (3)	JV 33-48	soil	²⁸28 Akiyama, K.; Teraguchi, S.; Hamasaki, Y.; Mori, M.; Tatsumi, K.; Ohnishi, K.; Hayashi, H.; J. Nat. Prod. 2003, 66, 136.
	2HL M-8	marine	³³33 Li, D.-H.; Han, T.; Guan, L.-P.; Bai, J.; Zhao, N.; Li, Z.-L.; Wu, X.; Hua, H.-M.; Nat. Prod. Res. 2016, 30, 1116.
	EN 13	marine	³¹31 Zhang, Y.; Li, X.-M.; Wang, B.-G.; J. Antibiot. 2007, 60, 204.
Asperpyrone D (4)	SCSIO Jcsw6F30	marine	²⁹29 Fang, W.; Lin, X.; Wang, J.; Liu, Y.; Tao, H.; Zhou, X.; Molecules 2016, 21, 941.
Asperpyrone D (4)	nr	endophyte	³⁰30 Li, X. B.; Xie, F.; Liu, S. S.; Li, Y.; Zhou, J. C.; Liu, Y. Q.; Yuan, H. Q.; Lou, H. X.; Chem. Biodiversity 2013, 10, 1193.
Asperpyrone E (5)	SCSIO Jcsw6F30	marine	²⁹29 Fang, W.; Lin, X.; Wang, J.; Liu, Y.; Tao, H.; Zhou, X.; Molecules 2016, 21, 941.
Aurasperone A (6)	IFBE 003	endophyte	³²32 Song, y. c.; Li, H.; Ye, Y. H.; Shan, C. Y.; Yang, Y. M.; Tan, R. X.; FEMS Microbiol. Lett. 2004, 241, 67.
	JV 33-48	soil	²⁸28 Akiyama, K.; Teraguchi, S.; Hamasaki, Y.; Mori, M.; Tatsumi, K.; Ohnishi, K.; Hayashi, H.; J. Nat. Prod. 2003, 66, 136.
	CMI-IMI 205879	endophyte	³⁴34 Ghosal, S.; Biswas, K.; Chakrabarti, D. K.; J. Agric. Food Chem. 1979, 27, 1347.
	SCSIO Jcsw6F30	marine	²⁹29 Fang, W.; Lin, X.; Wang, J.; Liu, Y.; Tao, H.; Zhou, X.; Molecules 2016, 21, 941.
	EN 13	marine	³¹31 Zhang, Y.; Li, X.-M.; Wang, B.-G.; J. Antibiot. 2007, 60, 204.
Aurasperone B (7)	MSA 773	marine	³⁵35 Leutou, A. S.; Yun, K.; Son, B. W.; Arch. Pharm. Res. 2016, 39, 806.
	SCSIO Jcsw6F30	marine	²⁹29 Fang, W.; Lin, X.; Wang, J.; Liu, Y.; Tao, H.; Zhou, X.; Molecules 2016, 21, 941.
	EN 13	marine	³¹31 Zhang, Y.; Li, X.-M.; Wang, B.-G.; J. Antibiot. 2007, 60, 204.
	C 433	endophyte	³⁶36 Bouras, N.; Mathieu, F.; Coppel, Y.; Lebrihi, A.; Nat. Prod. Res. 2005, 19, 653.
	BL-5-1	nr	³⁷37 Tanaka, H.; Wang, P. L.; Namiki, M.; Agric. Biol. Chem. 1972, 36, 2511.
Aurasperone C (8)	SCSIO Jcsw6F30	marine	²⁹29 Fang, W.; Lin, X.; Wang, J.; Liu, Y.; Tao, H.; Zhou, X.; Molecules 2016, 21, 941.
	C 433	endophyte	³⁶36 Bouras, N.; Mathieu, F.; Coppel, Y.; Lebrihi, A.; Nat. Prod. Res. 2005, 19, 653.
	BL-5-1	nr	³⁷37 Tanaka, H.; Wang, P. L.; Namiki, M.; Agric. Biol. Chem. 1972, 36, 2511.
Aurasperone D (9)	CMI-IMI 205879	endophyte	³⁴34 Ghosal, S.; Biswas, K.; Chakrabarti, D. K.; J. Agric. Food Chem. 1979, 27, 1347.
	nr	endophyte	³⁰30 Li, X. B.; Xie, F.; Liu, S. S.; Li, Y.; Zhou, J. C.; Liu, Y. Q.; Yuan, H. Q.; Lou, H. X.; Chem. Biodiversity 2013, 10, 1193.
	C 433	endophyte	³⁶36 Bouras, N.; Mathieu, F.; Coppel, Y.; Lebrihi, A.; Nat. Prod. Res. 2005, 19, 653.
Aurasperone E (10)	CMI-IMI 205879	endophyte	³⁴34 Ghosal, S.; Biswas, K.; Chakrabarti, D. K.; J. Agric. Food Chem. 1979, 27, 1347.
Aurasperone E (10)	C 433	endophyte	³⁶36 Bouras, N.; Mathieu, F.; Coppel, Y.; Lebrihi, A.; Nat. Prod. Res. 2005, 19, 653.
Aurasperone F (11)	SCSIO Jcsw6F30	marine	²⁹29 Fang, W.; Lin, X.; Wang, J.; Liu, Y.; Tao, H.; Zhou, X.; Molecules 2016, 21, 941.
Aurasperone F (11)	C 433	endophyte	³⁶36 Bouras, N.; Mathieu, F.; Coppel, Y.; Lebrihi, A.; Nat. Prod. Res. 2005, 19, 653.,³⁸38 Bouras, N.; Mathieu, F.; Coppel, Y.; Strelkov, S. E.; Lebrihi, A.; J. Agric. Food Chem. 2007, 55, 8920.
Aurasperone G (12)	C 433	endophyte	³⁸38 Bouras, N.; Mathieu, F.; Coppel, Y.; Strelkov, S. E.; Lebrihi, A.; J. Agric. Food Chem. 2007, 55, 8920.
Aurasperone H (13)	2HL M-8	marine	³³33 Li, D.-H.; Han, T.; Guan, L.-P.; Bai, J.; Zhao, N.; Li, Z.-L.; Wu, X.; Hua, H.-M.; Nat. Prod. Res. 2016, 30, 1116.
6,9-Dibromoflavasperone (14)	MSA 773	marine	³⁵35 Leutou, A. S.; Yun, K.; Son, B. W.; Arch. Pharm. Res. 2016, 39, 806.
6'-O-Demethylnigerone (15)	MRC 278	endophyte	³⁹39 Gorst-Allman, C. P.; Steyn, P. S. N.; J. Chem. Soc., Perkin Trans 1 1980, 2474.
Dianhydroaurasperone C (16)	nr	endophyte	³⁰30 Li, X. B.; Xie, F.; Liu, S. S.; Li, Y.; Zhou, J. C.; Liu, Y. Q.; Yuan, H. Q.; Lou, H. X.; Chem. Biodiversity 2013, 10, 1193.
Dianhydroaurasperone C (16)	EN 13	marine	³¹31 Zhang, Y.; Li, X.-M.; Wang, B.-G.; J. Antibiot. 2007, 60, 204.
Flavasperone (17)	MSA 773	marine	³⁵35 Leutou, A. S.; Yun, K.; Son, B. W.; Arch. Pharm. Res. 2016, 39, 806.
	CMI-IMI 205879	endophyte	³⁴34 Ghosal, S.; Biswas, K.; Chakrabarti, D. K.; J. Agric. Food Chem. 1979, 27, 1347.
	TC 1629	soil	⁴⁰40 Sakurai, M.; Kohno, J.; Yamamoto, K.; Okuda, T.; Nishio, M.; Kawano, K.; Ohnuki, T.; J. Antibiot. 2002, 55, 685.
Fonsecin (18)	MSA 773	marine	³⁵35 Leutou, A. S.; Yun, K.; Son, B. W.; Arch. Pharm. Res. 2016, 39, 806.
	TC 1629	soil	⁴⁰40 Sakurai, M.; Kohno, J.; Yamamoto, K.; Okuda, T.; Nishio, M.; Kawano, K.; Ohnuki, T.; J. Antibiot. 2002, 55, 685.
	C 433	endophyte	³⁶36 Bouras, N.; Mathieu, F.; Coppel, Y.; Lebrihi, A.; Nat. Prod. Res. 2005, 19, 653.
	SCSIO Jcsw6F30	marine	⁴¹41 Zhou, X.; Fang, W.; Tan, S.; Lin, X.; Xun, T.; Yang, B.; Liu, S.; Liu, Y.; Bioorg. Med. Chem. Lett. 2016, 26, 361.
	IBT 29019	endophyte	⁴²42 Frisvad, J. C.; Petersen, L. M.; Lyhne, E. K.; Larsen, T. O.; PLoS One 2014, 9, e94857.
Fonsecin B (19)	TC 1629	soil	⁴⁰40 Sakurai, M.; Kohno, J.; Yamamoto, K.; Okuda, T.; Nishio, M.; Kawano, K.; Ohnuki, T.; J. Antibiot. 2002, 55, 685.
Fonsecinone A (20)	IFBE 003	endophyte	³²32 Song, y. c.; Li, H.; Ye, Y. H.; Shan, C. Y.; Yang, Y. M.; Tan, R. X.; FEMS Microbiol. Lett. 2004, 241, 67.
	JV 33-48	soil	²⁸28 Akiyama, K.; Teraguchi, S.; Hamasaki, Y.; Mori, M.; Tatsumi, K.; Ohnishi, K.; Hayashi, H.; J. Nat. Prod. 2003, 66, 136.
	SCSIO Jcsw6F30	marine	²⁹29 Fang, W.; Lin, X.; Wang, J.; Liu, Y.; Tao, H.; Zhou, X.; Molecules 2016, 21, 941.
	2HL M-8	marine	³³33 Li, D.-H.; Han, T.; Guan, L.-P.; Bai, J.; Zhao, N.; Li, Z.-L.; Wu, X.; Hua, H.-M.; Nat. Prod. Res. 2016, 30, 1116.
	EN 13	marine	³¹31 Zhang, Y.; Li, X.-M.; Wang, B.-G.; J. Antibiot. 2007, 60, 204.
Fonsecinone B (21)	SCSIO Jcsw6F30	marine	²⁹29 Fang, W.; Lin, X.; Wang, J.; Liu, Y.; Tao, H.; Zhou, X.; Molecules 2016, 21, 941.
	2HL M-8	marine	³³33 Li, D.-H.; Han, T.; Guan, L.-P.; Bai, J.; Zhao, N.; Li, Z.-L.; Wu, X.; Hua, H.-M.; Nat. Prod. Res. 2016, 30, 1116.
	EN 13	marine	³¹31 Zhang, Y.; Li, X.-M.; Wang, B.-G.; J. Antibiot. 2007, 60, 204.
Fonsecinone C (22)	SCSIO Jcsw6F30	marine	²⁹29 Fang, W.; Lin, X.; Wang, J.; Liu, Y.; Tao, H.; Zhou, X.; Molecules 2016, 21, 941.
	2HL M-8	marine	³³33 Li, D.-H.; Han, T.; Guan, L.-P.; Bai, J.; Zhao, N.; Li, Z.-L.; Wu, X.; Hua, H.-M.; Nat. Prod. Res. 2016, 30, 1116.
	EN 13	marine	³¹31 Zhang, Y.; Li, X.-M.; Wang, B.-G.; J. Antibiot. 2007, 60, 204.
	SCSIO Jcsw6F30	marine	⁴¹41 Zhou, X.; Fang, W.; Tan, S.; Lin, X.; Xun, T.; Yang, B.; Liu, S.; Liu, Y.; Bioorg. Med. Chem. Lett. 2016, 26, 361.
Fonsecinone D (23)	SCSIO Jcsw6F30	marine	²⁹29 Fang, W.; Lin, X.; Wang, J.; Liu, Y.; Tao, H.; Zhou, X.; Molecules 2016, 21, 941.
	2HL M-8	marine	³³33 Li, D.-H.; Han, T.; Guan, L.-P.; Bai, J.; Zhao, N.; Li, Z.-L.; Wu, X.; Hua, H.-M.; Nat. Prod. Res. 2016, 30, 1116.
	EN 13	marine	³¹31 Zhang, Y.; Li, X.-M.; Wang, B.-G.; J. Antibiot. 2007, 60, 204.
	SCSIO Jcsw6F30	marine	⁴¹41 Zhou, X.; Fang, W.; Tan, S.; Lin, X.; Xun, T.; Yang, B.; Liu, S.; Liu, Y.; Bioorg. Med. Chem. Lett. 2016, 26, 361.
2-Hydroxydihydronigerone (24)	AKRN	endophyte	⁴³43 Happi, G. M.; Kouam, S. F.; Talontsi, F. M.; Nkenfou, C. N.; Longo, F.; Zühlke, S.; Douanla-Meli, C.; Spiteller, M.; Z. Naturforsch. B: J. Chem. Sci. 2015, 70, 625.
5,7-Dihydroxy-2-[1-(4-methoxy- 6-oxo-6H-pyran-2-yl)-2-phenylethylamino]-[1,4]naphthoquinone (25)	EN 13	marine	⁴⁴44 Zhang, Y.; Li, X. M.; Wang, C. Y.; Wang, B. G.; Chin. Chem. Lett. 2007, 18, 951.
Isoaurasperone (26)	CMI-IMI 205879	endophyte	³⁴34 Ghosal, S.; Biswas, K.; Chakrabarti, D. K.; J. Agric. Food Chem. 1979, 27, 1347.
Isoaurasperone A (27)	2HL M-8	marine	³³33 Li, D.-H.; Han, T.; Guan, L.-P.; Bai, J.; Zhao, N.; Li, Z.-L.; Wu, X.; Hua, H.-M.; Nat. Prod. Res. 2016, 30, 1116.
Isoaurasperone A (27)	nr	endophyte	³⁰30 Li, X. B.; Xie, F.; Liu, S. S.; Li, Y.; Zhou, J. C.; Liu, Y. Q.; Yuan, H. Q.; Lou, H. X.; Chem. Biodiversity 2013, 10, 1193.
Isoaurasperone F (28)	nr	endophyte	³⁰30 Li, X. B.; Xie, F.; Liu, S. S.; Li, Y.; Zhou, J. C.; Liu, Y. Q.; Yuan, H. Q.; Lou, H. X.; Chem. Biodiversity 2013, 10, 1193.
Isonigerone (29)	MRC 278	endophyte	³⁹39 Gorst-Allman, C. P.; Steyn, P. S. N.; J. Chem. Soc., Perkin Trans 1 1980, 2474.
Nigerasperone A (30)	EN 13	marine	³¹31 Zhang, Y.; Li, X.-M.; Wang, B.-G.; J. Antibiot. 2007, 60, 204.
Nigerasperone B (31)
Nigerasperone C (32)
Nigerone (33)	AKRN	endophyte	⁴³43 Happi, G. M.; Kouam, S. F.; Talontsi, F. M.; Nkenfou, C. N.; Longo, F.; Zühlke, S.; Douanla-Meli, C.; Spiteller, M.; Z. Naturforsch. B: J. Chem. Sci. 2015, 70, 625.
Nigerone (33)	MRC 278	endophyte	³⁹39 Gorst-Allman, C. P.; Steyn, P. S. N.; J. Chem. Soc., Perkin Trans 1 1980, 2474.
Rubrofusarin (34)	CMI IMI 205879	endophyte	³⁴34 Ghosal, S.; Biswas, K.; Chakrabarti, D. K.; J. Agric. Food Chem. 1979, 27, 1347.
Rubrofusarin (34)	SCSIO Jcsw6F30	marine	⁴¹41 Zhou, X.; Fang, W.; Tan, S.; Lin, X.; Xun, T.; Yang, B.; Liu, S.; Liu, Y.; Bioorg. Med. Chem. Lett. 2016, 26, 361.
Rubrofusarin B (35)	IFBE 003	endophyte	³²32 Song, y. c.; Li, H.; Ye, Y. H.; Shan, C. Y.; Yang, Y. M.; Tan, R. X.; FEMS Microbiol. Lett. 2004, 241, 67.
	TC 1629	soil	⁴⁰40 Sakurai, M.; Kohno, J.; Yamamoto, K.; Okuda, T.; Nishio, M.; Kawano, K.; Ohnuki, T.; J. Antibiot. 2002, 55, 685.
	SCSIO Jcsw6F30	marine	⁴¹41 Zhou, X.; Fang, W.; Tan, S.; Lin, X.; Xun, T.; Yang, B.; Liu, S.; Liu, Y.; Bioorg. Med. Chem. Lett. 2016, 26, 361.
nor-Rubrofusarin (36)	BL 5-1	nr	³⁷37 Tanaka, H.; Wang, P. L.; Namiki, M.; Agric. Biol. Chem. 1972, 36, 2511.
Rubrofusarin-6-O-α-D-ribofuranoside (37)	nr	endophyte	³⁰30 Li, X. B.; Xie, F.; Liu, S. S.; Li, Y.; Zhou, J. C.; Liu, Y. Q.; Yuan, H. Q.; Lou, H. X.; Chem. Biodiversity 2013, 10, 1193.
(R)-10-(3-Succinimidyl)-TMC-256A1 (38)	nr	endophyte	³⁰30 Li, X. B.; Xie, F.; Liu, S. S.; Li, Y.; Zhou, J. C.; Liu, Y. Q.; Yuan, H. Q.; Lou, H. X.; Chem. Biodiversity 2013, 10, 1193.
TMC-256A1 (39)	MSA 773	marine	³⁵35 Leutou, A. S.; Yun, K.; Son, B. W.; Arch. Pharm. Res. 2016, 39, 806.
TMC-256A1 (39)	TC 1629	soil	⁴⁰40 Sakurai, M.; Kohno, J.; Yamamoto, K.; Okuda, T.; Nishio, M.; Kawano, K.; Ohnuki, T.; J. Antibiot. 2002, 55, 685.
TMC-256C1 (40)	TC 1629	soil	⁴⁰40 Sakurai, M.; Kohno, J.; Yamamoto, K.; Okuda, T.; Nishio, M.; Kawano, K.; Ohnuki, T.; J. Antibiot. 2002, 55, 685.

Compound	Strain	Source	Reference
Asnipyrone A (41)	MA 132	marine	⁴⁶46 Liu, D.; Li, X. M.; Meng, L.; Li, C. S.; Gao, S. S.; Shang, Z.; Proksch, P.; Huang, C. G.; Wang, B. G.; J. Nat. Prod. 2011, 74, 1787.
Asnipyrone B (42)	MA 132	marine
Aspergillusol (43)	EN 13	marine	⁴⁷47 Zhang, Y.; Li, X. M.; Feng, Y.; Wang, B. G.; Nat. Prod. Res. 2010, 24, 1036.
Campyrone A (44)	nr	endophyte	⁴⁸48 Li, X. B.; Li, Y. L.; Zhou, J. C.; Yuan, H. Q.; Wang, X. N.; Lou, H. X.; J. Asian Nat. Prod. Res. 2015, 17, 182.
Campyrone A (44)	CAFT 160	endophyte	⁴⁹49 Talontsi, F. M.; Tatong, M. D. K.; Michel, D.; Dittrich, B.; Douanla-Meli, C.; Laatsch, H.; Tetrahedron 2013, 69, 7147.
Campyrone B (45)	CAFT 160	endophyte	⁴⁹49 Talontsi, F. M.; Tatong, M. D. K.; Michel, D.; Dittrich, B.; Douanla-Meli, C.; Laatsch, H.; Tetrahedron 2013, 69, 7147.
Campyrone B (45)	nr	endophyte	⁴⁸48 Li, X. B.; Li, Y. L.; Zhou, J. C.; Yuan, H. Q.; Wang, X. N.; Lou, H. X.; J. Asian Nat. Prod. Res. 2015, 17, 182.
Campyrone C (46)	CAFT 160	endophyte	⁴⁹49 Talontsi, F. M.; Tatong, M. D. K.; Michel, D.; Dittrich, B.; Douanla-Meli, C.; Laatsch, H.; Tetrahedron 2013, 69, 7147.
Campyrone C (46)	nr	endophyte	⁴⁸48 Li, X. B.; Li, Y. L.; Zhou, J. C.; Yuan, H. Q.; Wang, X. N.; Lou, H. X.; J. Asian Nat. Prod. Res. 2015, 17, 182.
4-(Hydroxymethyl)-5-hydroxy-2H-pyran-2-one (47)	AKRN	endophyte	⁴³43 Happi, G. M.; Kouam, S. F.; Talontsi, F. M.; Nkenfou, C. N.; Longo, F.; Zühlke, S.; Douanla-Meli, C.; Spiteller, M.; Z. Naturforsch. B: J. Chem. Sci. 2015, 70, 625.
4-(Hydroxymethyl)-5,6-dihydro-pyran-2-one (48)	nr	endophyte	⁴⁸48 Li, X. B.; Li, Y. L.; Zhou, J. C.; Yuan, H. Q.; Wang, X. N.; Lou, H. X.; J. Asian Nat. Prod. Res. 2015, 17, 182.
Isopyrophen (49)	EN 13	marine	⁴⁷47 Zhang, Y.; Li, X. M.; Feng, Y.; Wang, B. G.; Nat. Prod. Res. 2010, 24, 1036.
Nafuredin (50)	FT 0054	marine	⁵⁰50 Ui, H.; Shiomi, K.; Yamaguchi, Y.; Masuma, R.; Nagamitsu, T.; Takano, D.; Sunazuka, T.; Namikoshi, M.; Omura, S.; J. Antibiot. 2001, 54, 234.
Nigerapyrone A (51)	MA 132	marine	⁴⁶46 Liu, D.; Li, X. M.; Meng, L.; Li, C. S.; Gao, S. S.; Shang, Z.; Proksch, P.; Huang, C. G.; Wang, B. G.; J. Nat. Prod. 2011, 74, 1787.
Nigerapyrone B (52)
Nigerapyrone C (53)
Nigerapyrone D (54)
Nigerapyrone E (55)
Nigerapyrone F (56)
Nigerapyrone G (57)
Nigerapyrone H (58)
Pyrophen (59)	AKRN	endophyte	⁴³43 Happi, G. M.; Kouam, S. F.; Talontsi, F. M.; Nkenfou, C. N.; Longo, F.; Zühlke, S.; Douanla-Meli, C.; Spiteller, M.; Z. Naturforsch. B: J. Chem. Sci. 2015, 70, 625.
	UCSC 4-1212	marine	⁵¹51 Varoglu, M.; Crews, P.; J. Nat. Prod. 2000, 63, 41.
	ATCC 36533	nr	⁵²52 Barnes, C. L.; Steiner, J. R.; Torres, E.; Pacheco, R.; Marquez, H.; J. Peptide Protein Res. 1990, 36, 292.
	EN 13	marine	⁴⁷47 Zhang, Y.; Li, X. M.; Feng, Y.; Wang, B. G.; Nat. Prod. Res. 2010, 24, 1036.
Walterolactone (60)	nr	endophyte	⁴⁸48 Li, X. B.; Li, Y. L.; Zhou, J. C.; Yuan, H. Q.; Wang, X. N.; Lou, H. X.; J. Asian Nat. Prod. Res. 2015, 17, 182.

Compound	Strain	Source	Reference
7-Deacetoxyyanutone A (61)	BR 1001	mutant strain	⁵³53 Holm, D. K.; Petersen L. M.; Klitgaard, A.; Knudsen, P. B.; Jarczynska, Z. D.; Nielsen, K. F.; Gotfredsen, C. H.; Larsen, T. O.; Mortensen, U. H.; Chem. Biol. 2014, 21, 519.
22-Deacetylyanuthone A (62)	F 97S11	marine	⁵⁴54 Bugni, T. S.; Abbanat, D.; Bernan, V. S.; Maiese, W. M.; Greenstein, M.; Van Wagoner, R. M. V.; Ireland, C. M.; J. Org. Chem. 2000, 65, 7195.
1-Hydroxyyanuthone A (63)
1-Hydroxyyanuthone C (64)
Yanuthone A (65)
Yanuthone B (66)
Yanuthone C (67)
Yanuthone D (68)
Yanuthone E (69)
Yanuthone F (70)	BR 1001	mutant strain	⁵³53 Holm, D. K.; Petersen L. M.; Klitgaard, A.; Knudsen, P. B.; Jarczynska, Z. D.; Nielsen, K. F.; Gotfredsen, C. H.; Larsen, T. O.; Mortensen, U. H.; Chem. Biol. 2014, 21, 519.
Yanuthone G (71)
Yanuthone H (72)
Yanuthone I (73)
Yanuthone J (74)
Yanuthone K (75)	KB 1001	mutant strain	⁵⁵55 Petersen, L. M.; Holm, D. K.; Knudsen, P. B.; Nielsen, K. F.; Gotfredsen, C. H.; Mortensen, U. H.; Larsen, T. O.; J. Antibiot. 2015, 68, 201.
Yanuthone L (76)
Yanuthone M (77)
Yanuthone X1 (78)	BR 1001	mutant strain	⁵³53 Holm, D. K.; Petersen L. M.; Klitgaard, A.; Knudsen, P. B.; Jarczynska, Z. D.; Nielsen, K. F.; Gotfredsen, C. H.; Larsen, T. O.; Mortensen, U. H.; Chem. Biol. 2014, 21, 519.
Yanuthone X2 (79)	KB 1001	mutant strain	⁵⁵55 Petersen, L. M.; Holm, D. K.; Knudsen, P. B.; Nielsen, K. F.; Gotfredsen, C. H.; Mortensen, U. H.; Larsen, T. O.; J. Antibiot. 2015, 68, 201.

Compound	Strain	Source	Reference
Beauvericin (80)	DS 3.1	mutant strain	⁵⁶56 Boecker, S.; Storm, D.; Meyer, V.; Richter, L.; Zobel, S.; Wanka, F.; Süßmuth, R.; Mühlenweg, A.; WO 2015/140315 A2 2015.
Enniantin B (81)	DS 3.1	mutant strain
Malformin A1 (82)	nr	endophyte	³⁰30 Li, X. B.; Xie, F.; Liu, S. S.; Li, Y.; Zhou, J. C.; Liu, Y. Q.; Yuan, H. Q.; Lou, H. X.; Chem. Biodiversity 2013, 10, 1193.
	BRF 074	marine	⁵⁷57 Uchoa, P. K. S.; Pimenta, A. T. A.; Braz-Filho, R.; Oliveira, M. C. F.; Saraiva, N. N.; Rodrigues, B. S. F.; Pfenning, L. H.; Abreu, L. M.; Wilke, D. V.; Florêncio, K. G. D.; Lima, M. A. S.; Nat. Prod. Res. 2017, 31, 2599.
	nr	air	⁵⁸58 Yoshizawa, T.; Tsuchiya, Y.; Morooka, N.; Sawada, Y.; Agric. Biol. Chem. 1975, 39, 1325.
	56-39	soil	⁵⁹59 Kim, S. Y.; Cho, A.; Kim, K. W.; Oh, S.; J. Plant Biol. 2004, 47, 254.
	F 7586	nr	⁶⁰60 Koizumi, Y.; Nagai, K.; Gao, L.; Koyota, S.; Yamaguchi, T.; Natsui, M.; Imai, Y.; Hasumi, K.; Sugiyama, T.; Kuba, K.; Sci. Rep. 2018, 8, 5472.
Malformin A2 (83)	56-39	soil	⁶¹61 Kim, K. W.; Sugawara, F.; Yoshida, S.; Murofushi, N.; Takahashi, N.; Curtis, R. W.; Biosci. Biotechnol. Biochem. 1993, 57, 240.
Malformin A3 (84)
Malformin A4 (85)
Malformin B1a (86)	56-30	soil	⁶²62 Kim, K. W.; Sugawara, F.; Uzawa, J.; Yoshida, S.; Murofushi, N.; Takahashi, N.; Curtis, R. W.; Kanai, M.; Tetrahedron Lett. 1991, 32, 6715.
Malformin B1b (87)
Malformin B2 (88)
Malformin B3 (89)
Malformin B4 (90)
Malformin B5 (91)
Malformin C (92)	SCSIO Jcsw6F30	marine	⁴¹41 Zhou, X.; Fang, W.; Tan, S.; Lin, X.; Xun, T.; Yang, B.; Liu, S.; Liu, Y.; Bioorg. Med. Chem. Lett. 2016, 26, 361.
	UCSC94-1212	marine	⁵¹51 Varoglu, M.; Crews, P.; J. Nat. Prod. 2000, 63, 41.
	FKI 2342	soil	⁶³63 Hagimori, K.; Fukuda, T.; Hasegawa, Y.; Omura, S.; Tomoda, H.; Biol. Pharm. Bull. 2007, 30, 1379.
	nr	endophyte	⁶⁴64 Kobbe, B.; Cushman, M.; Wogan, G. N.; Demain, A. L.; Appl. Environ. Microbiol. 1977, 33, 996.
	AN-1	endophyte	⁶⁵65 Anderegg, R. J.; Biemann, K.; Biichi, G.; Cushman, M.; J. Am. Chem. Soc. 1976, 98, 3365.
	nr	endophyte	⁶⁶66 Mikušová, P.; Sulyok, M.; Santini, A.; Šrobárová, A.; Phytopathol. Mediterr. 2014, 53, 311.

Compound	Strain	Source	Reference
Pyranonigrin A (93)	LL-LV 3020	marine	⁶⁹69 Schlingmann, G.; Taniguchi, T.; He, H.; Bigelis, R.; Yang, H. Y.; Koehn, F. E.; Carter, G. T.; Berova, N.; J. Nat. Prod. 2007, 70, 1180.
Pyranonigrin A (93)	CBX 146 2002	marine	⁷⁰70 Hiort, J.; Maksimenka, K.; Reichert, M.; Perovic-Ottstadt, S.; Lin, W. H.; Wray, V.; Steube, K.; Schaumann, K.; Weber, H.; Proksch, P.; Ebel, R.; Müller, W. E. G.; Bringmann, G.; J. Nat. Prod. 2004, 67, 1532.
Pyranonigrin B (94)	CBX 146 2002	marine	⁷⁰70 Hiort, J.; Maksimenka, K.; Reichert, M.; Perovic-Ottstadt, S.; Lin, W. H.; Wray, V.; Steube, K.; Schaumann, K.; Weber, H.; Proksch, P.; Ebel, R.; Müller, W. E. G.; Bringmann, G.; J. Nat. Prod. 2004, 67, 1532.
Pyranonigrin C (95)
Pyranonigrin D (96)
Pyranonigrin E1 (97)	A 1179	mutant strain	⁷¹71 Yamamoto, T.; Tsunematsu, Y.; Noguchi, H.; Hotta, K.; Watanabe, K.; Org. Lett. 2015, 17, 4992.
Pyranonigrin E2 (98)	NBRC 5374	nr	⁷²72 Riko, R.; Nakamura, H.; Shindo, K.; J. Antibiot. 2014, 67, 179.
Pyranonigrin F (99)	A 1179	mutant strain	⁷¹71 Yamamoto, T.; Tsunematsu, Y.; Noguchi, H.; Hotta, K.; Watanabe, K.; Org. Lett. 2015, 17, 4992.
Pyranonigrin G (100)
Pyranonigrin H (101)
Pyranonigrin I (102)
Pyranonigrin J (103)
Pyranonigrin K (104)
Pyranonigrin S (105)	LL-LV 3020	marine	⁶⁹69 Schlingmann, G.; Taniguchi, T.; He, H.; Bigelis, R.; Yang, H. Y.; Koehn, F. E.; Carter, G. T.; Berova, N.; J. Nat. Prod. 2007, 70, 1180.

Compound	Strain	Source	Reference
Asperazine (106)	nr	endophyte	⁴⁸48 Li, X. B.; Li, Y. L.; Zhou, J. C.; Yuan, H. Q.; Wang, X. N.; Lou, H. X.; J. Asian Nat. Prod. Res. 2015, 17, 182.
	UCSC 94-1212	marine	⁵¹51 Varoglu, M.; Crews, P.; J. Nat. Prod. 2000, 63, 41.
	nr	marine	⁷³73 Varoglu, M.; Corbett, T. H.; Valeriote, F. A.; Crews, P.; J. Org. Chem. 1997, 62, 7078.
Asperazine A (107)	nr	endophyte	⁴⁸48 Li, X. B.; Li, Y. L.; Zhou, J. C.; Yuan, H. Q.; Wang, X. N.; Lou, H. X.; J. Asian Nat. Prod. Res. 2015, 17, 182.
Cyclo-(D-Phe-L-Trp) (108)	nr	endophyte
Cyclo-(L-Pro-L-Leu) (109)	BRF 074	marine	⁵⁷57 Uchoa, P. K. S.; Pimenta, A. T. A.; Braz-Filho, R.; Oliveira, M. C. F.; Saraiva, N. N.; Rodrigues, B. S. F.; Pfenning, L. H.; Abreu, L. M.; Wilke, D. V.; Florêncio, K. G. D.; Lima, M. A. S.; Nat. Prod. Res. 2017, 31, 2599.
Cyclo-(L-Pro-L-Phe) (110)
Cyclo-(L-Pro-L-Tyr) (111)
Cyclo-(L-Trp-L-Ile) (112)	EN 13	marine	⁴⁷47 Zhang, Y.; Li, X. M.; Feng, Y.; Wang, B. G.; Nat. Prod. Res. 2010, 24, 1036.
Cyclo-(L-Trp-L-Phe) (113)	EN 13	marine
Cyclo-(L-Trp-L-Trp) (114)	nr	endophyte	⁴⁸48 Li, X. B.; Li, Y. L.; Zhou, J. C.; Yuan, H. Q.; Wang, X. N.; Lou, H. X.; J. Asian Nat. Prod. Res. 2015, 17, 182.
Cyclo-(L-Trp-L-Tyr) (115)	EN 13	marine	⁴⁷47 Zhang, Y.; Li, X. M.; Feng, Y.; Wang, B. G.; Nat. Prod. Res. 2010, 24, 1036.
Cyclo-(trans-4-hydroxy-L-Pro-L-Leu) (116)	BRF 074	marine	⁵⁷57 Uchoa, P. K. S.; Pimenta, A. T. A.; Braz-Filho, R.; Oliveira, M. C. F.; Saraiva, N. N.; Rodrigues, B. S. F.; Pfenning, L. H.; Abreu, L. M.; Wilke, D. V.; Florêncio, K. G. D.; Lima, M. A. S.; Nat. Prod. Res. 2017, 31, 2599.
Cyclo-(trans-4-hydroxy-L-Pro-L-Phe) (117)	BRF 074	marine

Compound	Strain	Source	Reference
Asperitaconic acid A (118)	LS 11	marine	⁷⁵75 Ding, L.; Li, T.; Liao, X.; He, S.; Xu, S.; J. Antibiot. 2018, 71, 902.
Asperitaconic acid B (119)
Asperitaconic acid C (120)
Hexylitaconic acid (121)	UCSCm 94-1212	marine	⁵¹51 Varoglu, M.; Crews, P.; J. Nat. Prod. 2000, 63, 41.
Hexylitaconic acid (121)	K 88	soil	⁷⁶76 Isogai, A.; Washizu, M.; Kondo, K.; Murakoshi, S.; Suzuki, A.; Agric. Biol. Chem. 1984, 48, 2607.
Itaconic acid (122)	AB1 13	mutant	⁷⁷77 Li, A.; Pfelzer, N.; Zuijderwijk, R.; Punt, P.; BMC Biotechnol. 2012, 12, 57.,⁷⁸78 Hossain, A. H.; Li, A.; Brickwedde, A.; Wilms, L.; Caspers, M.; Overkamp, K.; Punt, P. J.; Microb. Cell Fact. 2016, 15, 130.
Tensyuic acid A (123)	FKI 2342	soil	⁷⁹79 Hasegawa, Y.; Fukuda, T.; Hagimori, K.; Tomoda, H.; Omura, S.; Chem. Pharm. Bull. 2007, 55, 1338.
Tensyuic acid B (124)
Tensyuic acid C (125)
Tensyuic acid D (126)
Tensyuic acid E (127)
Tensyuic acid F (128)

Compound	Strain	Source	Reference
6,11-Epoxy-isodaucane (129)	AB1.13	mutant strain	⁸¹81 Priegnitz, B. E.; Brandt, U.; Pahirulzaman, K. A. K.; Dickschat, J. S.; Fleibner, A.; Eukaryotic Cell 2015, 14, 602.
Geosmin (130)
Germacra-[1(10)E,5E]-dien-11-ol (131)
Germacrene D (132)
(1S,6S,10S)-6,10-Dimethylbicyclo[4.4.0]dec-2-en-4-one (133)
(6S,10S)-6,10-Dimethylbicyclo[4.4.0]dec-1-en-3-one (134)
2-Methylisoborneol (135)
(8S,10S)-8,10-Dimethyl-1 (9)-octalin (136)
β-Copaene (137)
β-Ylangene (138)

Compound	Strain	Source	Reference
(22E,24R)-5α,8α-Epidioxyergosta-6,22-dien-3β-ol (139) (22E,24R)-Ergosta-4,6,8(14),22-tetraen-3-one (140) (22E,24R)-Ergosta-5,7,22-trien-3β-ol (141) (22E,24R)-Ergosta-7,22-dien-3β,5α,6β-triol (142) Ergosterimide (143)	EN 13	endophyte	⁸²82 Zhang, Y.; Li, X. M.; Proksch, P.; Wang, B. G.; Steroids 2007, 72, 723.
Nigerasterol A (144) Nigerasterol B (145)	MA 132	endophyte	⁸³83 Liu, D.; Li, X. M.; Li, C. S.; Wang, B. G.; Helv. Chim. Acta 2013, 96, 1055.

Compound	Strain	Source	Reference
Bicoumanigrin A (152)	CBX 146 2002	marine	⁷⁰70 Hiort, J.; Maksimenka, K.; Reichert, M.; Perovic-Ottstadt, S.; Lin, W. H.; Wray, V.; Steube, K.; Schaumann, K.; Weber, H.; Proksch, P.; Ebel, R.; Müller, W. E. G.; Bringmann, G.; J. Nat. Prod. 2004, 67, 1532.
Demethylkotanin (153)	nr	nr	⁸⁵85 Oveden, S. P. B.; Sberna, G.; Tait, R. M.; Wildman, H. G.; Patel, R.; Li, B.; Steffy, K.; Nguyen, N.; Meurer-Grimes, B. M.; J. Nat. Prod. 2004, 67, 2093.
Kotanin (154)	ATCC 36626	nr	⁸⁶86 Stothers, J. B.; Stoessl, A.; Can. J. Chem. 1988, 66, 2816.
Orlandin (155)	ATCC 36626	nr	⁸⁶86 Stothers, J. B.; Stoessl, A.; Can. J. Chem. 1988, 66, 2816.
	ATCC 36626	endophyte	⁸⁷87 Cutler, H. G.; Crumley, F. G.; Cox, R. H.; Hernandez, O.; Cole, R. J.; Dorner, J. W.; J. Agric. Food Chem. 1979, 27, 592.

Compound	Strain	Source	Reference
Asperenone (156)	NRRL 3	nr	⁸⁸88 Jefferson Jr., W. E.; Biochemistry 1967, 6, 3479.
	CFTRI 1105	nr	⁸⁹89 Rao, K. C. S.; Divakar, S.; Rao, A. G. A.; Karanth, N. G.; Suneetha, W. J.; Krishnakantha, T. P.; Sattur, A. P.; Biotechnol. Lett. 2002, 24, 1967.
	ATCC 9029	nr	⁹⁰90 Rabache, M.; Neumann, J.; Lavollay, J.; Phytochemistry 1974, 13, 637.
Aspergillin (157)	nr	nr	⁹¹91 Ray, A. C.; Eakin, R. E.; Appl. Microbiol. 1975, 30, 909.
Asperrubrol (158)	ATCC 9029	nr	⁹⁰90 Rabache, M.; Neumann, J.; Lavollay, J.; Phytochemistry 1974, 13, 637.
Cycloleucomelone (159)	CBX 146 2002	marine	⁷⁰70 Hiort, J.; Maksimenka, K.; Reichert, M.; Perovic-Ottstadt, S.; Lin, W. H.; Wray, V.; Steube, K.; Schaumann, K.; Weber, H.; Proksch, P.; Ebel, R.; Müller, W. E. G.; Bringmann, G.; J. Nat. Prod. 2004, 67, 1532.

Compound	Strain	Source	Reference
Agglomerin F (164)	ATCC 1015	nr	⁹⁴94 Yang, X. L.; Awakawa, T.; Wakimoto, T.; Abe, I.; ChemBioChem 2014, 15, 1578.
Anominine (165)	IBT 29019	endophyte	⁷⁴74 Frisvad, J. C.; Lars, L. H.; Møller, L. L. H.; Larsen, T. O.; Kumar, R.; Arnau, J.; Appl. Microbiol. Biotechnol. 2018, 102, 9481.
Antafumicin A (166)	NH-401	nr	⁹⁵95 Fujimoto, Y.; Miyagawa, H.; Tsurushima, T.; Irie, H.; Okamura, K.; Ueno, T.; Biosci. Biotechnol. Biochem. 1993, 57, 1222.
Antafumicin B (167) Asperaldin (168)	CFR-1046	nr	⁹⁶96 Rao, K. C. S.; Divakar, S.; Srinivas, M.; Babu, K. N.; Karanth, N. G.; Sattur, A. P.; J. Antibiot. 2003, 56, 173.
Asperic acid (169)	UCSC 94-1212	marine	⁵¹51 Varoglu, M.; Crews, P.; J. Nat. Prod. 2000, 63, 41.
Aspernigerin (170)	IFB E003	endophyte	⁹⁷97 Shen, L.; Ye, Y.-H.; Wang, X.-T.; Zhu, H.-L.; Xu, C.; Song, Y.-C.; Li, H.; Tan, R.-X.; Chem. - Eur. J. 2006, 12, 4393.
Aspernigrin A (171)	CBX 146 2002 SCSIO Jcsw6F30	marine marine	⁷⁰70 Hiort, J.; Maksimenka, K.; Reichert, M.; Perovic-Ottstadt, S.; Lin, W. H.; Wray, V.; Steube, K.; Schaumann, K.; Weber, H.; Proksch, P.; Ebel, R.; Müller, W. E. G.; Bringmann, G.; J. Nat. Prod. 2004, 67, 1532. ⁴¹41 Zhou, X.; Fang, W.; Tan, S.; Lin, X.; Xun, T.; Yang, B.; Liu, S.; Liu, Y.; Bioorg. Med. Chem. Lett. 2016, 26, 361.
Aspernigrin B (172)	CBX 146 2002	marine	⁷⁰70 Hiort, J.; Maksimenka, K.; Reichert, M.; Perovic-Ottstadt, S.; Lin, W. H.; Wray, V.; Steube, K.; Schaumann, K.; Weber, H.; Proksch, P.; Ebel, R.; Müller, W. E. G.; Bringmann, G.; J. Nat. Prod. 2004, 67, 1532.
	SCSIO Jcsw6F30	marine	⁴¹41 Zhou, X.; Fang, W.; Tan, S.; Lin, X.; Xun, T.; Yang, B.; Liu, S.; Liu, Y.; Bioorg. Med. Chem. Lett. 2016, 26, 361.
Aspernigrin C (173)	SCSIO Jcsw6F30	marine	⁴¹41 Zhou, X.; Fang, W.; Tan, S.; Lin, X.; Xun, T.; Yang, B.; Liu, S.; Liu, Y.; Bioorg. Med. Chem. Lett. 2016, 26, 361.
Aspernigrin D (174)	SCSIO Jcsw6F30	marine	⁴¹41 Zhou, X.; Fang, W.; Tan, S.; Lin, X.; Xun, T.; Yang, B.; Liu, S.; Liu, Y.; Bioorg. Med. Chem. Lett. 2016, 26, 361.
Atromentin (175)	LL-LV 3020	marine	⁶⁹69 Schlingmann, G.; Taniguchi, T.; He, H.; Bigelis, R.; Yang, H. Y.; Koehn, F. E.; Carter, G. T.; Berova, N.; J. Nat. Prod. 2007, 70, 1180.
Averufin (176)	MF 16	marine	⁹³93 Wu, Z. J.; Ouyang, M. A.; Su, R. K.; Guo, Y. X.; Chin. J. Chem. 2008, 26, 759.
5-Benzofuran carboxylic acid-6-formyl methyl ester (177)	nr	endophyte	⁹⁸98 Siddiqui, B. S.; Ismail, F. A.; Gulzar, T.; Begum, S.; Nat. Prod. Res. 2003, 17, 355.
2-Carboxymethyl-3-hexylmaleic acid anhydride (178)	A. niger 5 No. 22	nr	⁹⁹99 Almassi, F.; Ghisalberti, E. L.; Rowland, C. Y.; J. Nat. Prod. 1994, 57, 833.
Carlosic acid (179) Carlosic acid methyl ether (180)	ATCC 1015	nr	⁹⁴94 Yang, X. L.; Awakawa, T.; Wakimoto, T.; Abe, I.; ChemBioChem 2014, 15, 1578.
Chlovalicin (181)	BRF 074	marine	⁵⁷57 Uchoa, P. K. S.; Pimenta, A. T. A.; Braz-Filho, R.; Oliveira, M. C. F.; Saraiva, N. N.; Rodrigues, B. S. F.; Pfenning, L. H.; Abreu, L. M.; Wilke, D. V.; Florêncio, K. G. D.; Lima, M. A. S.; Nat. Prod. Res. 2017, 31, 2599.
FK17-P2a (182)	ATCC 1015	mutant strain	⁸⁴84 Zabala, A. O.; Xu, W.; Chooi, Y. H.; Tang, Y.; Chem. Biol. 2012, 19, 1049.
Funalenone (183)	FO 5904	soil	¹⁰⁰100 Inokoshi, J.; Shiomi, K.; Masuma, R.; Tanaka, H.; Yamada, H.; Omura, S.; J. Antibiot. 1999, 52, 1095.
Furan ester derivative (184)	BRF 074	marine	⁵⁷57 Uchoa, P. K. S.; Pimenta, A. T. A.; Braz-Filho, R.; Oliveira, M. C. F.; Saraiva, N. N.; Rodrigues, B. S. F.; Pfenning, L. H.; Abreu, L. M.; Wilke, D. V.; Florêncio, K. G. D.; Lima, M. A. S.; Nat. Prod. Res. 2017, 31, 2599.
Dihydrocarolic acid (185)	AM 410	soil	¹⁰¹101 Alvi, K. A.; Nair, B. G.; Rabenstein, J.; Davis, G.; Baker, D. D.; J. Antibiot. 2000, 53, 110.
10,23-Dihydro-24,25-dehydroaflavinine (186)	IBT 29019	endophyte	⁴²42 Frisvad, J. C.; Petersen, L. M.; Lyhne, E. K.; Larsen, T. O.; PLoS One 2014, 9, e94857.
4-(3'(R)-Hydroxybutyl)-3,5,5, trimethyl-cyclohex-2-en-1-one (187)	nr	endophyte	⁹⁸98 Siddiqui, B. S.; Ismail, F. A.; Gulzar, T.; Begum, S.; Nat. Prod. Res. 2003, 17, 355.
8,10,12-Trihydroxy-9-methoxy-7α-methyl-7,7α,12α,13-tetrahydrobenzocycloheptaoxocin-6-one (188)	nr	endophyte	¹⁰²102 Elfita; Muharni; Munawar; Aryani, S.; Indones. J. Chem. 2012, 12, 195.
5,8-Dihydroxy-9-octadecenoic acid (189)	KCCM 60318	nr	¹⁰³103 Lee, M. Y.; Park, H. M.; Son, G. H.; Lee, C. H.; J. Microbiol. Biotechnol. 2013, 23, 932.
p-Hydroxyphenylacetic acid (190) Kojic acid (191)	AKRN	endophyte	⁴³43 Happi, G. M.; Kouam, S. F.; Talontsi, F. M.; Nkenfou, C. N.; Longo, F.; Zühlke, S.; Douanla-Meli, C.; Spiteller, M.; Z. Naturforsch. B: J. Chem. Sci. 2015, 70, 625.
p-Methoxyphenylacetic acid (192)	nr	endophyte	¹⁰⁴104 Nair, M. G.; Burke, B. A.; Phytochemistry 1988, 27, 3169.
Methyl (Z)-4-{[(Z)-1-(hydroxymethyl)-2-phenyl-1-ethenyl] amino}-4-oxo-2-butenoate (193)	Ta 1	nr	¹⁰⁵105 Yuan, W.; Zhu, H.; Cheng, K.; Huang, Z.; Qin, Y.; Yang, J.; Zhu, P.; Nat. Prod. Res. 2006, 20, 573.
2-Methylene-3-hexyl-butanedioic acid (194) 2-Methylene-3-(6-hydroxyhexyl)-butanedioic acid (195)	A. niger 5 No. 22	nr	⁹⁹99 Almassi, F.; Ghisalberti, E. L.; Rowland, C. Y.; J. Nat. Prod. 1994, 57, 833.
2-(2'-Methyl,4'-hydroxyphenyl)2-(4''-hydroxyphenyl)-propane (196)	CFTRI 1105	nr	¹⁰⁶106 Rao, K. C. S.; Divakar, S.; Rao, A. G. A.; Karanth, N. G.; Sattur, A. P.; Appl. Microbiol. Biotechnol. 2002, 58, 539.
Methyl 3-methyl-8-hydroxy-4-decenoate (197)	nr	endophyte	¹⁰⁴104 Nair, M. G.; Burke, B. A.; Phytochemistry 1988, 27, 3169.
2-Methylpropan-1-ol (198)	nr	nr	¹⁰⁷107 Borjesson, T. S.; Stollman, U. M.; Schnurer, J. L.; J. Agric. Food Chem. 1993, 41, 2104.
Nidurufin (199)	MF 16	marine	⁹³93 Wu, Z. J.; Ouyang, M. A.; Su, R. K.; Guo, Y. X.; Chin. J. Chem. 2008, 26, 759.
Nigerazine A (200) Nigerazine B (201)	I 639	soil	¹⁰⁸108 Iwamoto, T.; Hirota, A.; Shima, S.; Sakai, H.; Isogai, A.; Agric. Biol. Chem. 1985, 49, 3323.
Nigerloxin (202)	CFR-W 105	nr	¹⁰⁹109 Rao, K. C. S.; Divakar, S.; Babu, K. N.; Rao, A. G. A.; Karanth, N. G.; Sattur, A. P.; J. Antibiot. 2002, 55, 789.,¹¹⁰110 Suresha, B. S.; Srinivasan, K.; Curr. Eye Res. 2013, 38, 1064.
Nigragillin (203)	IBT 29019	endophyte	⁴²42 Frisvad, J. C.; Petersen, L. M.; Lyhne, E. K.; Larsen, T. O.; PLoS One 2014, 9, e94857.
1-Octen-3-ol (204)	nr	nr	¹⁰⁷107 Borjesson, T. S.; Stollman, U. M.; Schnurer, J. L.; J. Agric. Food Chem. 1993, 41, 2104.
1-Octen-3-one (205)	AB1.13	nr	⁸¹81 Priegnitz, B. E.; Brandt, U.; Pahirulzaman, K. A. K.; Dickschat, J. S.; Fleibner, A.; Eukaryotic Cell 2015, 14, 602.
Penitricin D (206)	AM 410	soil	¹⁰¹101 Alvi, K. A.; Nair, B. G.; Rabenstein, J.; Davis, G.; Baker, D. D.; J. Antibiot. 2000, 53, 110.
Phenoxyacetic acid (207) Phenylacetic acid (208)	nr	endophyte	¹⁰⁴104 Nair, M. G.; Burke, B. A.; Phytochemistry 1988, 27, 3169.
2-Phenylethanol (209)	nr JUBT 3M	endophyte endophyte	¹⁰⁴104 Nair, M. G.; Burke, B. A.; Phytochemistry 1988, 27, 3169. ¹¹¹111 Wani, M. A.; Sanjana, K.; Kumar, D. M.; Lal, D. K.; J. Basic Microbiol. 2010, 50, 110.
Pseurotin A (210) Pseurotin D (211)	BRF 074	marine	⁵⁷57 Uchoa, P. K. S.; Pimenta, A. T. A.; Braz-Filho, R.; Oliveira, M. C. F.; Saraiva, N. N.; Rodrigues, B. S. F.; Pfenning, L. H.; Abreu, L. M.; Wilke, D. V.; Florêncio, K. G. D.; Lima, M. A. S.; Nat. Prod. Res. 2017, 31, 2599.
Tensidol A (212)	FKI 2342	soil	¹¹²112 Fukuda, T.; Hasegawa, Y.; Hagimori, K.; Yamaguchi, Y.; Masuma, R.; Tomoda, H.; Omura, S.; J. Antibiot. 2006, 59, 480.
Tensidol B (213)	IBT 29019 FKI 2342	endophyte soil	⁴²42 Frisvad, J. C.; Petersen, L. M.; Lyhne, E. K.; Larsen, T. O.; PLoS One 2014, 9, e94857. ¹¹²112 Fukuda, T.; Hasegawa, Y.; Hagimori, K.; Yamaguchi, Y.; Masuma, R.; Tomoda, H.; Omura, S.; J. Antibiot. 2006, 59, 480.

Compound	Strain	Source	Reference
Fumonisin B2 (214)	nr	endophyte	¹¹⁴114 Mogensen, J. M.; Frisvad, J. C.; Thrane, U.; Nielsen, K. F.; J. Agric. Food Chem. 2010, 58, 954.
	NRRL 326	nr	¹¹⁵115 Mansson, M.; Klejnstrup, M. L.; Phipps, R. K.; Nielsen, K. F.; Frisvad, J. C.; Gotfredsen, C. H.; Larsen, T. O.; J. Agric. Food Chem. 2010, 58, 949.
	NRRL 3122	mutant strain	¹¹⁶116 Frisvad, J. C.; Smedsgaard, J.; Samson. R. A.; Larsen, T. O.; Thrane, U.; J. Agric. Food Chem. 2007, 55, 9727.
	nr	endophyte	⁶⁶66 Mikušová, P.; Sulyok, M.; Santini, A.; Šrobárová, A.; Phytopathol. Mediterr. 2014, 53, 311.
Fumonisin B4 (215)	nr	endophyte	¹¹⁴114 Mogensen, J. M.; Frisvad, J. C.; Thrane, U.; Nielsen, K. F.; J. Agric. Food Chem. 2010, 58, 954.
Fumonisin B6 (216)	NRRL 326	nr	¹¹⁵115 Mansson, M.; Klejnstrup, M. L.; Phipps, R. K.; Nielsen, K. F.; Frisvad, J. C.; Gotfredsen, C. H.; Larsen, T. O.; J. Agric. Food Chem. 2010, 58, 949.
Gliotoxin (217)	nr	nr	¹¹⁷117 Lewis, R. E.; Wiederhold, N. P.; Lionakis, M. S.; Prince, R. A.; Kontoyiannis, D. P.; J. Clin. Microbiol. 2005, 43, 6120.
Ochratoxin A (218)	nr	endophyte	⁶⁶66 Mikušová, P.; Sulyok, M.; Santini, A.; Šrobárová, A.; Phytopathol. Mediterr. 2014, 53, 311.
Ochratoxin a (219)	IBT 28144	nr	¹¹⁸118 Sorensen, L. M.; Lametsch, R.; Andersen, M. R.; Nielsen, P. V.; Frisvad, J. C.; BMC Microbiol. 2009, 9, 255.
Ochratoxin b (220)	nr	nr	¹¹⁹119 Nielsen, K. F.; Mogensen, J. M.; Johansen, M.; Larsen, T. O.; Frisvad, J. C.; Anal. Bioanal. Chem. 2009, 395, 1225.

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Aspergillus niger: A Hundred Years of Contribution to the Natural Products Chemistry