1,3 - Dioxepine and spiropyran derivatives of viomellein and other dimeric naphthopyranones from cultures of Aspergillus elegans KUFA 0015 and their antibacterial activity Author Kumla, Decha * & ICBAS-Instituto de Ciˆencias Biom´edicas Abel Salazar, Rua de Jorge Viterbo Ferreira, 228, 4050 - 313, Porto, Portugal & * & Interdisciplinary Centre of Marine and Environmental Research (CIIMAR), Terminal de Cruzeiros do Porto de Leix ˜ oes, Av. General Norton de Matos s / n, 4450 - 208, Matosinhos, Portugal Author Sousa, Emilia * & Interdisciplinary Centre of Marine and Environmental Research (CIIMAR), Terminal de Cruzeiros do Porto de Leix ˜ oes, Av. General Norton de Matos s / n, 4450 - 208, Matosinhos, Portugal & Laborat´orio de Química Orgˆanica, Departamento de Ciˆencias Químicas, Faculdade de Farm´acia, Universidade do Porto, Rua de Jorge Viterbo Ferreira, 228, 4050 - 313, Porto, Portugal Author Marengo, Alessia Department of Drug Sciences, Universita`di P´avia, C. So strada Nuova 65, 27100, Pavia, Italy Author Dethoup, Tida Department of Plant Pathology, Faculty of Agriculture, Kasetsart University, Bangkok, 10240, Thailand Author Pereira, A. J. * & ICBAS-Instituto de Ciˆencias Biom´edicas Abel Salazar, Rua de Jorge Viterbo Ferreira, 228, 4050 - 313, Porto, Portugal & * & Interdisciplinary Centre of Marine and Environmental Research (CIIMAR), Terminal de Cruzeiros do Porto de Leix ˜ oes, Av. General Norton de Matos s / n, 4450 - 208, Author Gales, Luís * & ICBAS-Instituto de Ciˆencias Biom´edicas Abel Salazar, Rua de Jorge Viterbo Ferreira, 228, 4050 - 313, Porto, Portugal & Instituto de Biologia Molecular e Celular (i 3 S-IBMC), Universidade do Porto, Rua de Jorge Viterbo Ferreira, 228, 4050 - 313, Porto, Portugal Author Freitas-Silva, Joana * & ICBAS-Instituto de Ciˆencias Biom´edicas Abel Salazar, Rua de Jorge Viterbo Ferreira, 228, 4050 - 313, Porto, Portugal & * & Interdisciplinary Centre of Marine and Environmental Research (CIIMAR), Terminal de Cruzeiros do Porto de Leix ˜ oes, Av. General Norton de Matos s / n, 4450 - 208, Matosinhos, Portugal Author Costa, Paulo M. * & ICBAS-Instituto de Ciˆencias Biom´edicas Abel Salazar, Rua de Jorge Viterbo Ferreira, 228, 4050 - 313, Porto, Portugal & * & Interdisciplinary Centre of Marine and Environmental Research (CIIMAR), Terminal de Cruzeiros do Porto de Leix ˜ oes, Av. General Norton de Matos s / n, 4450 - 208, Matosinhos, Portugal Author Mistry, Sharad Department of Chemistry, University of Leicester, University Road, Leicester, LE 7 RH, UK Author Silva, Artur M. S. Departamento de Química & QOPNA, Universidade de Aveiro, 3810 - 193, Aveiro, Portugal Author Kijjoa, Anake * & ICBAS-Instituto de Ciˆencias Biom´edicas Abel Salazar, Rua de Jorge Viterbo Ferreira, 228, 4050 - 313, Porto, Portugal & * & Interdisciplinary Centre of Marine and Environmental Research (CIIMAR), Terminal de Cruzeiros do Porto de Leix ˜ oes, Av. General Norton de Matos s / n, 4450 - 208, Matosinhos, Portugal text Phytochemistry 2021 112575 2021-01-31 181 1 15 http://dx.doi.org/10.1016/j.phytochem.2020.112575 journal article 10.1016/j.phytochem.2020.112575 1873-3700 8290910

Table 2 1 H and 13 C NMR (CDCl, 300 and 75 MHz) and HMBC assignment for 5. 3

Position	δC, type	δH, (J in Hz)	COSY	HMBC
1	171.47/171.39,	–
CO
3	76.66/76.62, CH	4.78, m	H-3, Me-3
4	34.67/34.62, CH	3.06, m	H-3, H-5
4a	134.15,/134.10,	–
C*
5	116.2, CH	6.97, s	H-4	C-4, 5a, 6, 9a,
				10a
5a	140.7, C	–
6	97.92/97.86, CH	6.67, s		C-5, 7, 8, 9a,
7	160.34/160.30, C	–
8	105.2, C	–
9	155.52/155.47, C	–
9a	108.06/108.01, C
10	162.65/162.62, C	–
, 10a	99.9, C
OMe-7	56.0, CH3	3.87, s		C-7
Me-3	20.7, CH3	1.56, d (6.4)	H-3	C-3, 4
		1.57, d (6.4)
OH-9	–	9.806, d (1.0)		C-8, 9, 9a,
9.803, d (1.0)
OH-10	–	13.89 s		C-9a, 10, 10a
		13.88, s
1′	161.68/161.60,	–
	CO
3′	74.19/74.14, CH	4.64, m	H-4′, Me-
			3′
4′	36.38/36.30, CH2	3.06, m	H-3′	C-3′, 4’a, 10’a
4’a	148.20/148.11, C
5′	116.56/116.53,	7.52, s		C-4′, 6′, 9’a, 10’a
CH
5’a	134.51/134.45, C	–
6′	180.4, CO	–
7′	158.4, C	–
8′	123.52/123.36, C	–
9′	188.7, CO	–
9’a	114.83/114.89, C	–
10′	162.97/162.93, C	–
10’a	117.82/117.92, C
OMe-7′	60.4, CH3	3.914, s		C-7′
		3.908, s
Me-3′	20.61/20.59, CH3	1.55, d (6.4)	H-3′	C-3′, 4′
		1.56, d (6.4)
OH-10′	–	13.515, s		C-9’a, 10′, 10’a
		13.500, s
1	170.99/170.88,
CO
3	75.99/75.91, CH	4.78, m	H-4
4	35.1, CH2	2.98, m	H-3, Me-3	C-3, Me-3
4a	149.5, C	–
5	115.36/115.27,	6.98, s		C-4, 6, 9a, 10a
CH
5a	141.12/141.08, C	–
6	104.15/104.11,	6.95, s		C-7, 8, 9a
CH
7	158.61/158.57, C	–
8	115.89/115.81, C
9	157.49/157.42, C
9a	112.0, C
10	163.07/162.98, C
10a	101.8, C
11	105.41/105.27,	6.08, d (4.6)		C-7, 9
	CH2	6.02, d (4.6)
		5.98, d (4.6)
OMe-7	56.1, CH3	3.89, s		C-7
Me-3	20.65/20.60, CH3	1.57, d (6.0)	H-3	C-3, 4
OH-10	–	12.962/12.933,		C-9a, 10, 10a
		s
1′	163.4, CO
3′	74.74/74.64, CH	4.71, m	H-4′, Me-
			3′
4′	36.12/35.86, CH2	3.05, m	H-3′	C-3′, Me-3′
4’a	147.76/147.54, C	–
5′	116.6, CH	7.56, s		C-4′, 6′, 9’a,
				10’a
5’a	134.82/134.51, C	–
6′	179.0, CO	–
7′	153.42/153. 31, C	–
8′	129.33/129.18, C	–
9′	186.0, CO	–
9’a	116.2, C
10′	162.58/162.52, C
10’a	116.3, C
Me-3′	20.8, CH3	1.56, d (6.0)	H-3′	C-3′, 4′
OH-10′	–	13.034/13.017,		C-9′, 9’a, 10′
		s