Sesquiterpenoids from <i>Nectandra megapotamica</i> (Lauraceae)

Oliveira, Carolina Q.; Morandini, Liziane B.; Pedroso, Marcelo; T., Alexandre; Silva, Ubiratan F.; Mostardeiro, Marco A.; Dalcol, Ionara I.; Morel, Ademir F.

doi:10.5935/0103-5053.20160141

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Articles • J. Braz. Chem. Soc. 28 (1) • Jan 2017 • https://doi.org/10.5935/0103-5053.20160141 copy

Sesquiterpenoids from Nectandra megapotamica (Lauraceae)

Authorship SCIMAGO INSTITUTIONS RANKINGS

Five sesquiterpenoid oxides, named nectandrene A, B, C, D, and E, were isolated from the essential oil of the leaves of Nectandra megapotamica. Their structures were elucidated by spectroscopic analysis, and the relative configurations were proposed by their nuclear Overhauser effect (NOESY) spectrum. Three of these isolated compounds displayed significant antimicrobial activity; the compound most active had minimal inhibitory concentration (MIC) values between 3.12 and 25.0 μg mL^-1 against some tested bacteria, and antifungal activity with MIC values between 12.5 and 25.0 μg mL^-1.

Keywords:
Nectandra megapotamica; Lauraceae; sesquiterpenoid spectroscopic analysis; antimicrobial activity

Proton position	1^b b 400 MHz;	2^b b 400 MHz;	3^b b 400 MHz;	4^c c 600 MHz.	5^b b 400 MHz;
Proton position	(mult., J) / Hz	(mult., J) / Hz	(mult., J) / Hz	(mult., J) / Hz	(mult., J) / Hz
2, CH₂	4.04, dd (8.5, 7.8) 3.29, dd (8.5, 8.2)	4.02, dd (8.5, 8.2) 3.29, dd (8.5; 8.0)	4.03, dd (8.0, 8.4) 3.30, dd (8.4, 8.8)	3.96, dd (7.8, 7.5) 3.18, dd (8.4, 7.5)	4.13, dd (8.8, 8.0) 3.30, dd (8.8, 9.2)
3, CH	2.25, m	2.20, m	2.26, m	1.85, m	2.33, m
3a, CH	1.89, m	1.98, m	1.86, m	1.72, m	1.77, m
4, CH₂	1.87, m 1.65, m	1.89, m 1.65, m	1.86, m 1.81, m	1.93, m 1.44, m	1.75, m 1.68, m
5, CH₂ (1-3, 5), CH (4)	1.35/1.32, m	1.34/1.30, m	1.52/1.21, m	4.92, brs	1.36/1.35, m
6, CH₂	1.29/1.20, m	1.26/1.22, m			1.28/1.26, m
7, CH₂ (1, 2, 4, 5), CH (3)	1.58, m	2.05/1.74, m	1.90, d (10.7)	2.20/1.89, m	1.35/1.18, m
7a, CH	–	–	4.28, dd (10.7, 7.2)
8, CH₂ (1, 4, 5), CH (2, 3)	2.34/2.0, m	5.34, brs	5.76, dd (17.4, 10.9)	2.10, m	1.78/1.42, m
9, CH (3), CH₂ (4)	–	–	4.88, dd (10.9, 1.2)/4.86, dd (17.4, 1.2)	2.47/1.74, m
9a, CH	1.79, d (10.4)	1.90, m			1.42, d (11.2)
9b, CH	4.27, dd (10.4, 7.2)	4.05, m			4.45, dd (11.2, 7.2)
10, CH₂ (1, 3) CH₃ (2, 5)	4.92, d (1.5) 4.77, d (1.5)	1.82, brs	4.99, brs 4.71, brs		1.30, s
11, CH (4), CH₃ (1, 2, 5)	0.73, brs	0.79, brs		4.85, d (10.2)	0.84, brs
11a, CH				4.54, dd (10.2, 7.5)
12, CH₃	0.99, d (6.4)	1.00, d (6.5, 3.0)	1.76, brs	1.43, brs	1.0, d (6.5)
13, CH₃	–	–	0.97, brs	1.50, brs
14, CH₃	–	–	1.05, d (6.8)	1.06, d (7.2

Position	1^b b 400 MHz;	2^b b 400 MHz;	3^c c 600 MHz.	4^c c 600 MHz.	5^b b 400 MHz;
2, CH₂	73.7	73.0	73.5	73.6	73.4
3, CH	34.6	35.6	34.8	44.1	34.7
3a, CH	45.0	47.1	53.3	50.9	45.6
4, CH₂	19.5	20.4	20.4	38.18	41.4
5, CH₂ (1-3, 5); CH (4)	36.6	37.9	33.9	125.8	39.2
5a, C	36.8	33.6			35.4
6, CH₂ (1, 2, 5); C (3, 4)	41.9	35.3	40.7	139.5	19.4
7, CH₂ (1, 2, 4, 5); CH (3)	23.6	22.9	44.8	40.0	19.6
7a, CH	–	–	79.3
8, CH₂ (1, 4, 5); CH (2, 3)	37.6	122.1	148.7	25.7	41.8
9, C (1, 2, 5); CH (3); CH₂ (4)	147.1	135.3	113.6	32.9	72.3
9a, CH	51.6	45.9			52.1
9b, CH	76	79.2			79.9
10, C (4); CH₂ (1, 3); CH₃ (2, 5)	107.3	23.2	109.7	133.5	24.0
11, C (3); CH (4); CH₃ (1, 2, 5)	16.4	15.9	144.4	127.7	18.1
11a, CH				76.7
12, CH₃	15.6	16.4	25.0	21.0	15.8
13, CH₃	–	–	17.2	17.0
14, CH₃	–	–	15.5	17.2

Bacteria^a a ATCC (American Type Culture Collection);	Compound
	1		2		5		Antibiotic^b b cloramphenicol for bacteria and nystatin for fungi; nt: not tested; MIC: minimal inhibitory concentration; MBC and MFC: minimal lethal concentration for bacteria and for fungi, respectively.
	MIC / (µg mL^-1)	MBC / (µg mL^-1)	MIC / (µg mL^-1)	MBC / (µg mL^-1)	MIC / (µg mL^-1)	MBC / (µg mL^-1)	MIC / (µg mL^-1)
Staphylococcus aureus	6.25	100	3.12	100	25.0	100	3.12
Staphylococcus epidermidis	25.0	200	12.5	> 200	nt	nt	3.12
Bacillus subtilis	25.0	200	12.5	200	25.0	100	3.12
Staphylococcus saprophyticus	25.0	200	12.5	200	nt	nt	3.12
Streptococcus pyogenes	12.5	200	12.5	200	nt	nt	3.12
Escherichia coli	25.0	200	12.5	200	25.0	100	3.12
Shiguella sonnei	25.0	200	12.5	200	25.0	25.0	3.12
Pseudomonas aeruginosa	25.0	200	12.5	> 200	25.0	25.0	3.12
Yeasts^a a ATCC (American Type Culture Collection);	MIC	MFC	MIC	MFC	MIC	MFC	MIC
Candida albicans	25.0	100	12.5	25.0	> 100	nt	6.25
Candida tropicalis	25.0	100	25.0	25.0	25.0	50.0	6.25
Cryptococcus neoformans	25.0	100	12.5	25.0	25.0	25.0	10.3
Saccharomyces cerivisiae	25.0	200	12.5	25.0	25.0	25.0	5.15

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