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 4 1 H and 13 C NMR (CDCl, 500 and 125 MHz) and HMBC assignment for 7. 3

Position	δC, type	δH, (J in Hz)	COSY	HMBC
a Observed by HMBC correlation.
1	161.85/161.79,	–
CO
3	74.2, CH	4.68, m	H-4, Me-
			3
4	36.07, CH2	2.98, m	H-3	C-3, Me-3
4a	149.5, C	–
5	116.9, CH	6.58, s		C-4, 6, 9a, 10a
5a	135.52/135.44,	–
C
6	97.9, CH	5.82, s		C-5, 8, 9a
7	160.84/160.79,	–
C
8	61.29/61.21, C	–
9	197.0, CO a	–
9a	111.38/111.25,	–
C
10	164.93/164.88,	–
C
10a	109.05/109.02,	–
	C
11	82.96/82.92,	5.07, d (9.3)/5.06,		C-7, 8, 8′, 9
	CH2	d (9.3)
		4.97, d (9.3)/4.96,
		d (9.3)
Me-3	20.6, CH3	1.54, d (6.2)	H-3	C-3, 4
OMe-7	56.40/56.38,	3.820/3.817, s		C-7
	CH3
OH-10	–	13.07, brs		C-9a, 10, 10a
1′	161.85/161.79,	–
	CO
3′	74.76/74.68,	4.68, m	H-4′, Me-
	CH		3′
4′	35.94/35.80,	3.03, m	H-3′	C-3′, Me-3′
	CH2
4’a	147.71/147.57,	–
	C
5′	117.0, CH	7.50, s		C-4′, 6′, 9’a,
				10’a
5’a	135.52/135.44,	–
	C
6′	176.59/176.53,	–
	CO
7′	145.7, C	–
8′	127.94/127.87,	–
	C
9′	183.2, CO	–
9’a	115.56/115.49,	–
	C
10′	162.77/162.70,	–
C
10’a	117.76/117.58,	–
	C
Me-3′	20.7, CH3	1.55, d (6.2)	H-3′	C-3, 4
OH-10′	–	12.760/12.752, s		H-9’a, 10′,
				10’a