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Original Articles

Algicidal Activity of Glycerolipids from Brown Alga Ishige sinicola toward Red Tide Microalgae

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Pages 372-374 | Received 30 Aug 2011, Accepted 18 Oct 2011, Published online: 22 May 2014

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  • 7) A MeOH (2 L) extract (47.60 g) of air-dried and powdered I. sinicola (1042 g) was partitioned between water (400 mL) and CH2Cl2 (700 mL). Part of the CH2Cl2 extract (12.99 g of 23.80 g) was chromatographed over Diaion HP-20, using gradient elution from 40% to 100% MeOH, to yield five fractions (Fr 1 to Fr 5), in which Fr 3 and Fr 4 were active. The Fr 3 was then chromatographed on Chromatorex ODS DM1020T using gradient elution from 85% to 100% MeOH, to yield an active fraction (Fr 3-3, 62.5 mg) which was separated by HPLC (Cosmosil 5C18 MS-II, 20×250 mm, 80% CH3CN), and subsequent reversed-phase TLC (Merck, RP-18, 90% MeOH) to yield compound 5 (4.5 mg). Part of Fr 4 (1.33 g of 3.71 g) was separated by silica gel chromatography, using a hexane-EtOAc gradient (1:1 to 0:1), and subsequent HPLC (Cosmosil 5C18 MS-II, 90% CH3CN) to yield compounds 1 (11.6 mg), 2 (5.2 mg), 3 (23.0 mg), and 4 (6.5 mg).
  • 8) Colorless oil, [α]D 25 −10.3° (c 0.58, MeOH). NMR δH (400 MHz, CDCl3): 0.89 (3H, t, J=6.8 Hz), 1.30 (8H, m), 1.70 (2H, m), 2.09 (4H, m), 2.37 (2H, t, J=7.8 Hz), 2.81 (6H, m), 3.60 (1H, dd, J=11.7, 5.8 Hz), 3.70 (1H, dd, J=11.7, 3.9 Hz), 3.93 (1H, m), 4.15 (1H, dd, J=11.7, 6.8 Hz), 4.21 (1H, dd, J=11.7, 4.4 Hz), 5.38 (8H, m).
  • 9) Colorless oil, [α]D 25 −5.4° (c 0.52, MeOH). NMR δH (400 MHz, CDCl3): 0.98 (3H, t, J=7.6 Hz), 1.41 (2H, m), 1.66 (2H, m), 2.08 (4H, m), 2.37 (2H, t, J=7.3 Hz), 2.83 (6H, m), 3.60 (1H, dd, J=11.7, 5.8 Hz), 3.70 (1H, dd, J=11.7, 4.3 Hz), 3.94 (1H, m), 4.15 (1H, dd, J=11.7, 5.8 Hz), 4.21 (1H, dd, J=11.7, 5.3 Hz), 5.38 (8H, m).
  • 10) Colorless oil, [α]D 25 −3.9° (c 0.77, MeOH). NMR δH (400 MHz, CDCl3) 0.89 (3H, t, J=6.8 Hz), 1.31 (14H, m), 1.61 (2H, m), 2.05 (4H, m), 2.35 (2H, t, J=7.7 Hz), 2.77 (2H, t, J=6.4 Hz), 3.59 (1H, dd, J=11.7, 5.8 Hz), 3.69 (1H, dd, J=11.7, 3.9 Hz), 3.93 (1H, m), 4.14 (1H, dd, J=11.7, 5.8 Hz), 4.20 (1H, dd, J=11.7, 4.3 Hz), 5.36 (4H, m).
  • 11) Colorless oil, [α]D 25 −2.5° (c 0.65, MeOH). NMR δH (400 MHz, CDCl3) 0.88 (3H, t, J=6.8 Hz), 1.29 (22H, m), 1.63 (2H, m), 2.02 (4H, m), 2.35 (2H, t, J=7.6 Hz), 3.60 (1H, dd, J=11.7, 5.8 Hz), 3.70 (1H, dd, J=11.7, 3.9 Hz), 3.93 (1H, m), 4.15 (1H, dd, J=11.7, 5.8 Hz), 4.21 (1H, dd, J=11.7, 4.3 Hz), 5.35 (2H, m).
  • 12) Colorless oil, [α]D 22 +48.1° (c 0.54, MeOH). NMR δH (600 MHz, CD3OD) 0.89 (3H, t, J=7.0 Hz), 1.30 (24H, m), 1.61 (2H, quint, J=7.5 Hz), 2.36 (2H, t, J=7.5 Hz), 2.90 (1H, dd, J=14.3, 9.3 Hz), 3.07 (1H, dd, J=9.8, 9.0 Hz), 3.35 (1H, dd, J=14.3, 2.0 Hz), 3.38 (1H, m), 3.40 (1H, dd, J=9.1, 3.8 Hz), 3.64 (1H, t, J=9.1 Hz), 4.05 (1H, dd, J=10.2, 3.5 Hz), 4.09 (3H, m), 4.19 (1H, dd, J=13.8, 6.3 Hz), 4.77 (1H, d, J=3.8 Hz).
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