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

Freire, Vítor F.; Slivinski, Juliano; Quintana-Bulla, Jairo I.; Moraes, Fernando C.; Paradas, Wladimir C.; Salgado, Leonardo T.; Pereira, Renato C.; Moura, Rodrigo L.; Amado-Filho, Gilberto M.; Ferreira, Antonio G.; Berlinck, Roberto G.S.

doi:10.1016/j.bjp.2019.07.001

person Vítor F. Freire

schoolInstituto de Química de São Carlos, Universidade de São Paulo, São Carlos, SP, Brazil

0000-0001-6565-1830

person Juliano Slivinski

schoolInstituto de Química de São Carlos, Universidade de São Paulo, São Carlos, SP, Brazil

0000-0002-0407-5291

person Jairo I. Quintana-Bulla

schoolInstituto de Química de São Carlos, Universidade de São Paulo, São Carlos, SP, Brazil

0000-0002-3196-7770

person Fernando C. Moraes

schoolInstituto de Pesquisas Jardim Botânico do Rio de Janeiro, Rio de Janeiro, RJ, Brazil

0000-0001-8251-6868

person Wladimir C. Paradas

schoolInstituto de Pesquisas Jardim Botânico do Rio de Janeiro, Rio de Janeiro, RJ, Brazil

person Leonardo T. Salgado

schoolInstituto de Pesquisas Jardim Botânico do Rio de Janeiro, Rio de Janeiro, RJ, Brazil

0000-0003-3215-9633

person Renato C. Pereira

schoolInstituto de Pesquisas Jardim Botânico do Rio de Janeiro, Rio de Janeiro, RJ, BrazilschoolDepartamento de Biologia Marinha, Universidade Federal Fluminense, Niteroi, RJ, Brazil

0000-0001-7576-226X

person Rodrigo L. Moura

schoolInstituto de Biologia and Laboratório de Sistemas Avançados de Gestão - Instituto Alberto Luiz Coimbra de Pós-Graduação e Pesquisa de Engenharia, Universidade Federal do Rio de Janeiro, Rio de Janeiro, RJ, Brazil

person Gilberto M. Amado-Filho

schoolInstituto de Pesquisas Jardim Botânico do Rio de Janeiro, Rio de Janeiro, RJ, Brazil 1 Deceased.

person Antonio G. Ferreira

schoolDepartamento de Química, Universidade Federal de São Carlos, São Carlos, SP, Brazil

person Roberto G.S. Berlinck *

schoolInstituto de Química de São Carlos, Universidade de São Paulo, São Carlos, SP, Brazil

0000-0003-0118-2523

person* Corresponding author.
E-mail:rgsberlinck@iqsc.usp.br (R.G. Berlinck).

Authors' contributions

FCM, WCP, LTS, RCP, RLM and GMAF contributed in collecting and identifying the sponge material. VFF, JS, JIQB and RGSB contributed for the isolation and structural elucidation of the compound. AGF contributed in the NMR data acquisition. VFF and RGSB elaborated the experimental design. RGSB supervised the laboratory work, chemicals purchase and instruments maintenance. RGSB and VFF wrote the largest portion of the manuscript. All authors have read the final manuscript and approved the submission.

Conflict of interest

All authors have none to declare

¹

Deceased.

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*
	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	2.50a	2.41a	-0.09
L-Thr	L → D	3.03a	3.99a	0.96
L-Pro	L → D	4.08a	4.63a	0.55
L-Phe	L → D	5.79a	6.88a	1.09
L-Ile	L → D	5.73a	7.11a	1.38
L-allo-Ile	L → D	5.77a	7.15a	1.38
L-Leu	L → D	5.90a	7.27a	1.37
L-Ile	L → D	17.05b
L-allo-Ile	L → D	17.49b
L-Leu	L → D	19.28b

[TFN1] ^*
Superimposed by H₂O signal.