2012
DOI: 10.1021/np300544a
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Antibacterial Butenolides from the Korean Tunicate Pseudodistoma antinboja

Abstract: Six new (1, 2, and 5-8) and three known (3, 4, and 9) butenolide metabolites were isolated from the tunicate Pseudodistoma antinboja by activity-guided fractionations. The structures were elucidated by combined NMR and MS spectroscopic methods. These compounds were evaluated for their antibacterial activity, and most of them exhibited moderate to significant activity that selectively targeted Gram-positive strains and did not exhibit cytotoxicity in the MTT assay at 100 μM. Cadiolides 5-9 in particular exhibit… Show more

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Cited by 75 publications
(81 citation statements)
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“…13 C-NMR (CDCl 3 ): 56.2 (MeO); 111.8 (C(6));1 12.9 (C(3)); 113.0 (C(5'));1 13.7 (C(3'));1 19.5 (C(1'));1 24.5 (q, J(C,F) ¼ 270.5,CF 3 ); 126.0 (q, J(C,F) ¼ 3.7,C(3'',5''));131.0 (J(C,F) ¼ 32.4,C(4''));131.0 (C(2'',6''));132.8 (C(6')); 135.0 (C(4'));136.0 (C(1''));148.9 (C(5)); 150.9 (C(4));1 56.0 (C(2'));164.7 (C(2)).M S: 506 (30 (6) HÀC(6'')). 13 C-NMR(CDCl 3 ): 56.2 (MeO); 112.0 (C(3))* 1 ); 112.1 (C(6));1 13.0 (C(5'))* 1 ); 113.6 (C(3'));1 19.5 (C(1'));1 25.8 (C(2''));1 28.1 (C(5''));1 30.8 (C(4''));1 32.2 (C(6''));1 32.3 (C(1''));1 33.1 (C(6'));1 33.3 (C(3''));1 35.0 (C(4'));1 48.1 (C(5)); 151.1 (C(4));1 56.0 (C(2'));165.1 (C(2)).MS: 518 (9 (6));6.97 (d, J(3',4') ¼ 9.0, HÀC(3'));7 .27 -7. 40 (m,H ÀC(3'',4'',5''));7 .44 (d, J(6',4') ¼ 2.4, HÀC(6'));7 .63 (dd, J(4',3') ¼ 9.0, J(4',6') ¼ 2.4, HÀC(4')); 8.22 (dd, J(6'',4'') ¼ 7.…”
Section: Experimental Partmentioning
confidence: 99%
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“…13 C-NMR (CDCl 3 ): 56.2 (MeO); 111.8 (C(6));1 12.9 (C(3)); 113.0 (C(5'));1 13.7 (C(3'));1 19.5 (C(1'));1 24.5 (q, J(C,F) ¼ 270.5,CF 3 ); 126.0 (q, J(C,F) ¼ 3.7,C(3'',5''));131.0 (J(C,F) ¼ 32.4,C(4''));131.0 (C(2'',6''));132.8 (C(6')); 135.0 (C(4'));136.0 (C(1''));148.9 (C(5)); 150.9 (C(4));1 56.0 (C(2'));164.7 (C(2)).M S: 506 (30 (6) HÀC(6'')). 13 C-NMR(CDCl 3 ): 56.2 (MeO); 112.0 (C(3))* 1 ); 112.1 (C(6));1 13.0 (C(5'))* 1 ); 113.6 (C(3'));1 19.5 (C(1'));1 25.8 (C(2''));1 28.1 (C(5''));1 30.8 (C(4''));1 32.2 (C(6''));1 32.3 (C(1''));1 33.1 (C(6'));1 33.3 (C(3''));1 35.0 (C(4'));1 48.1 (C(5)); 151.1 (C(4));1 56.0 (C(2'));165.1 (C(2)).MS: 518 (9 (6));6.97 (d, J(3',4') ¼ 9.0, HÀC(3'));7 .27 -7. 40 (m,H ÀC(3'',4'',5''));7 .44 (d, J(6',4') ¼ 2.4, HÀC(6'));7 .63 (dd, J(4',3') ¼ 9.0, J(4',6') ¼ 2.4, HÀC(4')); 8.22 (dd, J(6'',4'') ¼ 7.…”
Section: Experimental Partmentioning
confidence: 99%
“…11 (d, J(3',4') ¼ 9.0, HÀC(3'));7 .36 (d, J(2'',3'') ¼ J(6'',5'') ¼ 8.4, HÀC(2'',6''));7 .46 (dd, J(4',3') ¼ 9.0, J(4',6') ¼ 2.7,H ÀC(4'));7 .67 (d, J(6',4') ¼ 2.7,HÀC(6'));8.01 (d, J(3'',2'') ¼ J(5'',6'') ¼ 8.4, HÀC(3'',5'')). 13 C-NMR((D 6 )acetone): 41.6 (C(7)); 55.2 (MeO); 93.8 (C(4));113.2 (C(3'));120.6 (C(1'));121.5 (C(6)); 122.6(C(3'',5''));124.5 (C(5'));128.9 (C(6'));130.8 (C(4'));131.7 (C(2'',6''));143.1 (C(1''));147.1 (C(4'')); 149.6 (C(5)); 155.4 (C(2'));158.1 (C(3)). MS:453 (14 (7)); 3.49 (AB, J AB ¼ 14.1,H b ÀC (7)); 3.77 (s,MeO);…”
mentioning
confidence: 99%
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“…[1][2][3] Butyrolactones were mainly found as metabolites from fungi and high plants in nature. 4 They appeal to medicinal chemists because of their pronounced pharmacological effects including antibacterial, 5,6 anti-tumor, 7,8 anti-inflammatory, 9,10 anti-virus, 11,12 and the like. In previous studies, some butyrolactones were isolated from the fermentation products of fungus Aspergillus.…”
Section: Introductionmentioning
confidence: 99%
“…In the case of isomers 34, the ROESY spectra unequivocally identified the (Z)-isomer by the presence of two ROE cross-peaks of H-5 with H-2Ј,6Ј and H-2ЈЈ,6ЈЈ. The location of the methoxyl group at C-4ЈЈ was assigned by the ROESY correlations between the methoxyl protons and H-5ЈЈ [35].…”
Section: Stereochemistrymentioning
confidence: 96%