Acessibilidade / Reportar erro

Brasil

Revista Brasileira de Farmacognosia

Español English

Brasil

Español English

sumário « anterior atual seguinte »

Sumário

Original articles • Rev. bras. farmacogn. 29 (6) • Nov-Dec 2019 • https://doi.org/10.1016/j.bjp.2019.07.001 copy

Clathriamide, an hexapeptide isolated from the marine sponge Clathria (Clathria) nicoleae

Authorship SCIMAGO INSTITUTIONS RANKINGS

ABSTRACT

Chemical investigation of the aqueous fraction of the ethanol extract from the Brazilian endemic marine sponge Clathria (Clathria) nicoleae Vieira de Barros, Santos & Pinheiro, 2013, Microcionidae, sampled from a 55 m deep rhodolith bed at the Amazon River mouth, led to the isolation of a new hexapeptide, clathriamide (1). HP-20 resin was used to capture compound 1 from the aqueous fraction, which was purified by additional chromatographic steps. The absolute configuration of the amino acids of 1 was determined by advanced Marfey's analysis using 5-fluoro-2,4-dinitrophenyl-Nα-L-tryptophanamide. The amino acid derivatives analyzed by ultra-performance liquid chromatography coupled to a mass spectrometry using a C₈ column enabled a good chromatographic resolution of L-Ile and L-allo-Ile, previously unfeasible using C₁₈ column.

Keywords:
Porifera; Peptide; Advanced marfey's analysis; Rhodolith bed; Aqueous extract

Residue	Position	δ_c, type	δ_H (J in Hz)
L-Leu	CO	170.9, C
	α	51.7, CH	4.31, dd (9.8, 3.9)
	β	40.9, CH₂	1.80, m
	γ	25.6, CH	1.91, m
	δ	24.0, CH₃	1.12, d (6.4)
	δ'	21.8, CH₃	1.14, d (6.4)
L-Pro	CO	173.6, C
	α	61.1, CH	4.89^* * Superimposed by H2O signal.
	β	29.9, CH₂	1.83, m; 2.45, m
	γ	26.9, CH₂	2.14, m; 2.21, m
	δ	49.5, CH₂	3.58, m; 3.91, ddd (3.2,
			7.8, 9.8)
L-Hyp	CO	173.1, C
	α	61.1, CH	4.57, dd (4.7, 7.9)
	β	40.5, CH₂	2.13, m
	γ	68.4, CH	3.58, m
	δ	54.4, CH₂	3.13, dd (6.1,11.9);
			3.43, dd (5.1,11.9)
L-Phe	CO	174.1, C
	α	59.1, CH	4.44, dd (4.1,12.6)
	β	38.9, CH₂	3.27, dd (12.6,13.7);
			3.39, dd (3.9,13.7)
	aromatic	1: 139.1, C
		2: 130.4, CH	7.41, m
		3: 128.5, CH	7.32, m
		4: 130.1, CH	7.40, m
		5: 128.5, CH	7.32, m
		6: 130.4, CH	7.41, m
L-Thr	CO	172.2, C
	α	58.7, CH	4.59, d (2.7)
	β	71.4, CH	4.49, dd (2.7, 6.4)
	γ	19.3, CH₃	1.22, d (6.4)
L-Ile	CO	179.0, C
	α	62.5, CH	4.09, d (4.8)
	β	37.9, CH	1.99, m
	γ	26.1, CH₂	1.29, m; 1.57, m
	γ'	17.0, CH₃	1.02, d (6.4)
	δ	12.6, CH₃	0.98, d (7.3)

Amino acid DTA derivative	Order of elution	t_R, min		Δt
		L	D
4-trans-L-Hyp	D → L	2.50^a a Separation conditions: column: Waters ACQUITY BEH C18 (2.1 × 50.0 mm,1.7 μm); eluent: linear gradient 8:2 to 5:5 H2O/MeCN (+0.1% formic acid) during 8 min.; flow rate: 0.50 ml min-1.	2.41^a a Separation conditions: column: Waters ACQUITY BEH C18 (2.1 × 50.0 mm,1.7 μm); eluent: linear gradient 8:2 to 5:5 H2O/MeCN (+0.1% formic acid) during 8 min.; flow rate: 0.50 ml min-1.	-0.09
L-Thr	L → D	3.03^a a Separation conditions: column: Waters ACQUITY BEH C18 (2.1 × 50.0 mm,1.7 μm); eluent: linear gradient 8:2 to 5:5 H2O/MeCN (+0.1% formic acid) during 8 min.; flow rate: 0.50 ml min-1.	3.99^a a Separation conditions: column: Waters ACQUITY BEH C18 (2.1 × 50.0 mm,1.7 μm); eluent: linear gradient 8:2 to 5:5 H2O/MeCN (+0.1% formic acid) during 8 min.; flow rate: 0.50 ml min-1.	0.96
L-Pro	L → D	4.08^a a Separation conditions: column: Waters ACQUITY BEH C18 (2.1 × 50.0 mm,1.7 μm); eluent: linear gradient 8:2 to 5:5 H2O/MeCN (+0.1% formic acid) during 8 min.; flow rate: 0.50 ml min-1.	4.63^a a Separation conditions: column: Waters ACQUITY BEH C18 (2.1 × 50.0 mm,1.7 μm); eluent: linear gradient 8:2 to 5:5 H2O/MeCN (+0.1% formic acid) during 8 min.; flow rate: 0.50 ml min-1.	0.55
L-Phe	L → D	5.79^a a Separation conditions: column: Waters ACQUITY BEH C18 (2.1 × 50.0 mm,1.7 μm); eluent: linear gradient 8:2 to 5:5 H2O/MeCN (+0.1% formic acid) during 8 min.; flow rate: 0.50 ml min-1.	6.88^a a Separation conditions: column: Waters ACQUITY BEH C18 (2.1 × 50.0 mm,1.7 μm); eluent: linear gradient 8:2 to 5:5 H2O/MeCN (+0.1% formic acid) during 8 min.; flow rate: 0.50 ml min-1.	1.09
L-Ile	L → D	5.73^a a Separation conditions: column: Waters ACQUITY BEH C18 (2.1 × 50.0 mm,1.7 μm); eluent: linear gradient 8:2 to 5:5 H2O/MeCN (+0.1% formic acid) during 8 min.; flow rate: 0.50 ml min-1.	7.11^a a Separation conditions: column: Waters ACQUITY BEH C18 (2.1 × 50.0 mm,1.7 μm); eluent: linear gradient 8:2 to 5:5 H2O/MeCN (+0.1% formic acid) during 8 min.; flow rate: 0.50 ml min-1.	1.38
L-allo-Ile	L → D	5.77^a a Separation conditions: column: Waters ACQUITY BEH C18 (2.1 × 50.0 mm,1.7 μm); eluent: linear gradient 8:2 to 5:5 H2O/MeCN (+0.1% formic acid) during 8 min.; flow rate: 0.50 ml min-1.	7.15^a a Separation conditions: column: Waters ACQUITY BEH C18 (2.1 × 50.0 mm,1.7 μm); eluent: linear gradient 8:2 to 5:5 H2O/MeCN (+0.1% formic acid) during 8 min.; flow rate: 0.50 ml min-1.	1.38
L-Leu	L → D	5.90^a a Separation conditions: column: Waters ACQUITY BEH C18 (2.1 × 50.0 mm,1.7 μm); eluent: linear gradient 8:2 to 5:5 H2O/MeCN (+0.1% formic acid) during 8 min.; flow rate: 0.50 ml min-1.	7.27^a a Separation conditions: column: Waters ACQUITY BEH C18 (2.1 × 50.0 mm,1.7 μm); eluent: linear gradient 8:2 to 5:5 H2O/MeCN (+0.1% formic acid) during 8 min.; flow rate: 0.50 ml min-1.	1.37
L-Ile	L → D	17.05^b b Separation conditions: Waters ACQUITY BEH C8 column (2.1 × 100 mm, 1.7 μm, Waters); eluent: 73:27 H2O/MeCN (+0.1% formic acid) during 20 min.; flow rate:0.500 ml min-1.
L-allo-Ile	L → D	17.49^b b Separation conditions: Waters ACQUITY BEH C8 column (2.1 × 100 mm, 1.7 μm, Waters); eluent: 73:27 H2O/MeCN (+0.1% formic acid) during 20 min.; flow rate:0.500 ml min-1.
L-Leu	L → D	19.28^b b Separation conditions: Waters ACQUITY BEH C8 column (2.1 × 100 mm, 1.7 μm, Waters); eluent: 73:27 H2O/MeCN (+0.1% formic acid) during 20 min.; flow rate:0.500 ml min-1.

Sociedade Brasileira de Farmacognosia Universidade Federal do Paraná, Laboratório de Farmacognosia, Rua Pref. Lothario Meissner, 632 - Jd. Botânico, 80210-170, Curitiba, PR, Brasil, Tel/FAX (41) 3360-4062 - Curitiba - PR - Brazil
E-mail: revista@sbfgnosia.org.br

Acompanhe os números deste periódico no seu leitor de RSS