본 논문에서는 연황색 오일인 (2S)-1-O- \( \beta \)-D-galactopyranosyl-2,3-dilinoleoyl glycerol과 연녹색 오일인 (2S)-1-O- \( \beta \)-D-galactopyranosyl-2,3-dipalmitoyl glycerol를 소개한다.
<p>화합물 1 ((2S)-1-O- \( \beta \)-D-galactopyranosyl-2,3-dilinoleoyl glycerol): 연황색 오일 \( \left(\mathrm{CH}_{3} \mathrm{OH}\right) ; \quad[\alpha]_{\mathrm{D}}^{25}+26.0^{\circ}(c=0.10, \mathrm{MeOH}) ; \) negative FAB-mass spectrometry (MS) \( m / z \quad 777[\mathrm{M}-]^{-} \); infrared spectro-scopy (IR) \( (\mathrm{KBr}, \mu) 3383,1723,1612 \mathrm{~cm}^{-1} ;{ }^{1} \mathrm{H} \)-nuclear magnetic resonance (NMR) (\(400 \mathrm{MHz}\), \( \left.\mathrm{CD}_{3} \mathrm{OD}, \delta_{\mathrm{H}}\right) 5.40-5.30 \) (\(8\mathrm{H}\), overlapped, H-9",9"',10",10"',12",12"',13",13"'), \( 5.30 \) (1H, m, H-2), \( 4.46(1 \mathrm{H}, \mathrm{dd}, J=10.8,2.8, \quad \mathrm{H}-3 \mathrm{a}), 4.24(1 \mathrm{H}, \mathrm{d}, J=8.0 \), \( \left.\mathrm{H}^{\prime} 1^{\prime}\right), 4.18(1 \mathrm{H}, \quad \mathrm{dd}, \quad J=10.8,6.8, \quad \mathrm{H}-3 \mathrm{~b}), 3.86 \) (1H, dd, \( J=10.4,5.4 \), H-1a), \( 3.79\left(1 \mathrm{H}, \mathrm{m}, \mathrm{H}-4^{\prime}\right), 3.75 \) (1H, m, H-\( \left.5^{\prime}\right), 3.71 \) (2H, overlapped, \( \left.\mathrm{H}^{\prime}-6^{\prime}\right), 3.64 \) (1H, dd, \( J=10.4,6.0 \), H-1b), \( 3.49 \) (1H, overlapped, H-2',3'), \( 2.80 \) (4H, overlapped, \( \mathrm{H}-11,11), 2.32 \) (2H, overlapped, \( \mathrm{H}-2), 2.31 \) (2H, overlapped, \( \mathrm{H}-2), \quad 2.06 \quad\left(8 \mathrm{H}, \quad\right. \) overlapped, \( \left.\mathrm{H}-8^{\prime \prime}, 8^{\prime \prime \prime}, 14 ", 144^{\prime \prime}\right), \quad 1.59 \quad(4 \mathrm{H} \), overlapped, \( \mathrm{H}-3,3), 1.32-1.26(28 \mathrm{H} \), overlapped, \( \mathrm{H}-4-7,4-7 \), \( \left.15-17, \quad 15-17^{\prime \prime \prime}\right), \quad 0.97 \quad\left(6 \mathrm{H}, \quad \mathrm{t}, \quad J=8.0, \quad \mathrm{H}-18^{\prime \prime}, 18^{\prime \prime}\right) ; \quad{ }^{13} \mathrm{C}-\mathrm{NMR} \) \( \left(100 \mathrm{MHz}, \quad \mathrm{CD}_{3} \mathrm{OD}, \quad \delta_{\mathrm{C}}\right) 175.5 \) (C-1"), \( 175.3 \) (C-1"'), \( 131.1 \) \( \left(\mathrm{C}-9\right. \) "), \( 131.0 \quad\left(\mathrm{C}-9^{\prime \prime}\right), \quad 129.2 \quad\left(\mathrm{C}-12^{\prime \prime}, 12^{\prime \prime \prime}, 13^{\prime \prime}, 13^{\prime \prime}\right), 128.8 \quad(\mathrm{C}- \) \( \left.10^{\prime \prime}, 10^{\prime \prime \prime}\right), \quad 105.2\left(\mathrm{C}-1^{\prime}\right), 74.7 \quad\left(\mathrm{C}-3^{\prime}\right), 74.4\left(\mathrm{C}-5^{\prime}\right), 72.3 \) (C-2'), \( 71.7(\mathrm{C}-2), 70.2\left(\mathrm{C}-4^{\prime}\right), 67.7(\mathrm{C}-1), 66.2(\mathrm{C}-3), 62.2 \) (C-6'), \( 35.1\left(\mathrm{C}-2^{\prime \prime}\right), 34.9\left(\mathrm{C}-2^{\prime \prime}\right), 33.1\left(\mathrm{C}-14^{\prime \prime}, 14^{\prime \prime \prime}\right), 30.7-30.2 \) (C-4"-7",4"'-7"',15"-17", \( 15^{\prime \prime \prime}-17 \) "'"), \( 28.1 \quad(\mathrm{C}-8,8), 26.4(\mathrm{C}-11,11), 26.0 \) \( (\mathrm{C}-3,3), 14.7(\mathrm{C}-18,18) ; \mathrm{GC}-\mathrm{MS} \mathrm{t}_{\mathrm{R}}=12.96 \) min (linoleic acid methyl ester).</p><p>화합물 \(2\) ((2S)-1-O- \( \beta \)-D-galactopyranosyl-2,3-dipalmitoyl glycerol): 연녹색 오일 \( \left(\mathrm{CH}_{3} \mathrm{OH}\right) ;[\alpha]_{\mathrm{D}}^{25}+26.4^{\circ}(c=0.10, \mathrm{MeOH}) \); positive FAB-MS \( m / z 731[\mathrm{M}+\mathrm{H}]^{+} ; \quad \mathrm{IR}(\mathrm{KBr}, \mu) 3383,1723 \mathrm{~cm}^{-1} \); \( { }^{1} \mathrm{H}-\mathrm{NMR}\left(400 \mathrm{MHz}, \mathrm{CD}_{3} \mathrm{OD}, \delta_{\mathrm{H}}\right) ; 5.30(1 \mathrm{H}, \mathrm{m}, \mathrm{H}-2), 4.46 \) \( (1 \mathrm{H}, \mathrm{dd}, J=10.4,2.8 \mathrm{~Hz}, \mathrm{H}-3 \mathrm{a}), 4.23(1 \mathrm{H}, \mathrm{d}, J=8.0 \mathrm{~Hz}, \mathrm{H}- \) 1'), \( 4.18(1 \mathrm{H}, \mathrm{dd}, J=10.4,6.8 \mathrm{~Hz}, \mathrm{H}-3 \mathrm{~b}), 3.86(1 \mathrm{H}, \mathrm{dd} \), \( J=10.2,4.2 \mathrm{~Hz}, \mathrm{H}-1 \mathrm{a}), 3.79(1 \mathrm{H}, \mathrm{m}, \mathrm{H}-4 \) ) \( ) 3.75(1 \mathrm{H}, \mathrm{m} \),\( \left.\mathrm{H}-5^{\prime}\right), 3.71\left(2 \mathrm{H}\right. \), overlapped, \( \left.\mathrm{H}-6^{\prime}\right), 3.64 \) (1H, dd, \( J=10.2 \),\( 6.0 \mathrm{~Hz}, \mathrm{H}-\mathrm{lb}), 3.50 \) (2H, overlapped, \( \left.\mathrm{H}-2^{\prime}, 3^{\prime}\right), 2.32(2 \mathrm{H} \), overlapped, H-2"), \( 2.31 \) (2H, overlapped, H-2"'), \( 1.59 \) (4H, overlapped, \( \left.\mathrm{H}-3^{\prime \prime}, 3^{\prime \prime}\right) \), 1.34-1.25 (48H, overlapped, H-4"-15", H-4"'-15"'), \( 0.89 \) (6H, t, \( J=8.0, \quad \mathrm{H}-16 ", 16 " 16) ;{ }^{13} \mathrm{C}-\mathrm{NMR} \) (100\( \left.\mathrm{MHz}, \mathrm{CD}_{3} \mathrm{OD}, \delta_{\mathrm{C}}\right) 175.7 \) (C-1"), \( 175.3 \) (C-1"'), 105.2 (C-1'), 74.7 (C-3'), 74.4 (C-5'), \( 72.3 \) (C-2'), \( 71.7 \) (C-2), \( 70.2 \) (C-4'), 67.7 (C-1), 66.2 (C-3), 62.2 (C-6'), 34.9 (C-2"), 34.8 (C-2"'), 33.1 (C-14",14"'), 30.8-30.1 (C-4"-13",4"'-13"'), 26.0 (C-3",3"'), 23.7(C-15",15"'), 14.4 (C-16",16"'); GC-MS \(\mathrm{t}_{\mathrm{R}}=11.06 \) min (palmitic acid).</p>