3.6. Chemical Characteristics of Compounds <italic><bold>OH–1~OH-6</bold></italic> and <italic><bold>OHR–1~OHR-16</bold></italic>
(3S,8S,Z)-Heptadeca-1,9-dien-4,6-diyne-3,8-diol ((3S,8S)-falcarindiol) OH-1): yellowish oil (1.6 g); + 213.5° (c = 0.36, CHCl_{3}); UV (CHCl_{3}) λmax (log ξ): 217 (0.81), 243 (1.39), 260 (1.75) and 286 (2.11) nm; IR (KBr) ν_{max}: 3345, 3020, 2932, 2850, 2251, 1466, 1021, 938 and 875 cm^{−1}; ^{1}H-NMR (500 MHz, CDCl_{3}): δ_{H} 0.88 (3H, t, 7.0, H-17), 1.28 (8H, m, H-13, H-14, H-15, H-16), 1.38 (2H, m, H-12), 2.10 (2H, q, 7.0, H-11), 4.94 (1H, brd, 5.0 Hz, H-3), 5.20 (1H, d, 8.5 Hz, H-8), 5.25 (1H, d, 10.0 Hz, H-1a), 5.46 (1H, ddt, 11.5, 7.5, 1.0 Hz, H-10), 5.50 (1H, ddt, 11.5, 5.0, 1.5 Hz, H-9), 5.62 (1H, dd, 17.5, 1.5 Hz, H-1b), 5.92 (1H, ddd, 17.5, 10.0, 6.0 Hz, H-2). ^{13}C-NMR (125 MHz, CDCl_{3}): δc 14.0 (C-17), 22.6 (C-15), 27.6 (C-11), 29.0 (C-12), 29.1 (C-14), 29.2(C-13), 31.7(C-16), 58.4 (C-8), 63.3 (C-3), 68.6 (C-6), 70.2 (C-5), 78.3 (C-4), 79.8 (C-7), 117.2 (C-1), 127.6 (C10), 134.4 (C-9), 135.8 (C-2).
(3S,8S,Z)-Heptadeca-9-en-4,6-diyne-3,8-diol (oplopandiol, OH-2): yellowish oil (2.5 g); + 208.6° (c = 0.28, CHCl_{3}); UV (CHCl_{3}) λmax (log ξ): 210 (1.25), 245 (1.39), 253 (2.35) and 267 (4.12) nm; IR (KBr) ν_{max}: 3350, 3015, 2934, 2860, 2250, 1468, 1025, 940 and 866 cm^{−1}; ^{1}H-NMR (500 MHz, CDCl_{3}): δ_{H }0.88 (3H, t, 7.0 Hz, H-17), 1.00 (3H, t, 7.5 Hz, H-1), 1.28 (8H, m, H-13, H-14, H-15, H-16), 1.38 (2H, m, H-12), 1.73 (2H, m, H-2), 2.09 (2H, q, 7.0 Hz, H-11), 4.38 (1H, t, 6.5 Hz, H-3), 5.19 (1H, d, 8.5 Hz, H-8), 5.51 (1H, t, 8.5 Hz, H-10), 5.59 (1H, ddt, 11.0, 7.5, 1.0 Hz, H-9). ^{13}C-NMR (125 MHz, CDCl_{3}): δc 9.3 (C-1), 14.0 (C-17), 22.5 (C-15), 27.7 (C-11), 29.1 (C-12), 29.1 (C-14), 29.3 (C-13), 30.5 (C-2), 31.7 (C-16), 58.40 (C-8), 63.9 (C-3), 68.7 (C-6), 68.8 (C-5), 79.1 (C-4), 80.7 (C-7), 127.7 (C-10), 134.3 (C-9).
(11S,16S,Z)-11,16-Dihydroxyoctadeca-9,17-dien-12,14-diynyl acetate (OH-3): yellowish oil (2.6 g); + 180.8° (c = 0.53, CHCl_{3}); UV (CHCl_{3}) λmax (log ξ): 206 (1.76), 235 (1.79), 248 (2.89) and 268 (4.42) nm; IR (KBr) ν_{max}: 3410, 2920, 2856, 2246, 1718, 1628, 1560, 1465 and 1025 cm^{−1}; ^{1}H-NMR (500 MHz, CDCl_{3}): δ_{H} 1.30 (8H, m, H-3, H-4, H-5, H-6), 1.38 (2H, m, H-7), 1.62 (2H, m, H-2), 2.05 (3H, s, COCH3), 2.10 (2H, q, 7.5 Hz, H-8), 4.06 (2H t, 7.5 Hz, H-1), 4.94 (1H, brd, 5.0 Hz, H-16), 5.19 (1H, d, 8.0 Hz, H-11), 5.24 (1H, d, 10.5 Hz, H-18a), 5.46 (1H, dd, 17.0, 1.5 Hz, H-18b), 5.51 (1H, dd, 10.5, 8.0 Hz, H-9), 5.59 (1H, ddt, 10.5, 7.5, 1.0Hz, H-10), 5.93 (1H, ddd, 17.0, 10.5, 1.5 Hz, H-17). ^{13}C-NMR (125 MHz, CDCl_{3}): δc 20.9 (COCH_{3}), 25.7 (C-2), 27.5 (C-3), 28.5 (C-5), 28.9 (C-4), 29.0 (C-6), 29.1 (C-8), 29.1 (C-7), 58.4 (C-11), 63.2 (C-16), 64.7 (C-1), 68.6 (C-13), 70.0 (C-14), 78.4 (C-15), 80.7 (C-12), 117.0 (C-18), 127.9 (C-10), 134.1 (C-9), 135.9 (C-17), 171.6 (C=O).
(11S,16S,Z)-11,16-Dihydroxyoctadeca-9-en-12,14-diynyl acetate (OH-4): yellowish oil (3.0 g); + 168.8° (c = 0.47, CHCl_{3}); UV (CHCl_{3}) λmax (log ξ): 205 (1.88), 233 (1.89), 246 (3.39) and 266 (4.05) nm; IR (KBr) ν_{max}: 3440, 2930, 2855, 2250, 1720, 1622, 1550, 1286 and 1020 cm^{−1}; ^{1}H-NMR (500 MHz, CDCl_{3}): δ_{H} 1.00 (3 H, t, 7.5 Hz, H-18), 1.30 (8H, m, H-3, H-4, H-5, H-6), 1.38 (2H, m, H-7), 1.62 (2H, m, H-2), 1.73 (2H, m, H-17), 2.05 (3H, s, COCH_{3}), 2.11 (2H, q, 7.5 Hz, H-8), 4.05 (2H, t, 7.0 Hz, H-1), 4.37 (1H, t, 6.5 Hz, H-16), 5.18 (1H, d, 8.5 Hz, H-11), 5.50 (1H, ddt, 10.6, 7.5, 1.5 Hz, H-9), 5.58 (1H, ddt, 10.6, 8.5, 1.5 Hz, H-10). ^{13}C-NMR (125 MHz, CDCl_{3}): δc 9.3 (C-18), 21.0 (COCH_{3}), 25.7 (C-2), 27.5 (C-8), 28.9 (C-6), 28.9 (C-5), 29.0 (C-4), 29.1 (C-3), 29.1 (C-7), 30.5 (C-17), 58.4 (C-11), 64.7 (C-16), 68.6 (C-1), 68.7 (C-13), 70.0 (C-14), 79.1 (C-15), 80.7 (C-12), 127.9 (C-10), 134.0 (C-9), 171.6 (C=O).
(11S,16S,Z)-Octadeca-9,17-dien-12,14-diyne-1,11,16-triol (oplopantriol A, OH-5): yellowish oil (1.8 g); +194.4° (c = 0.16, CHCl_{3}); UV (CHCl_{3}) λmax (log ξ): 226 (1.10), 255 (4.09) and 261 (3.95) nm; IR (KBr) ν_{max}: 3357, 3022, 2929, 2855, 2251, 2150, 1675, 1405 and1303 cm^{−1}. ^{1}H-NMR (500 MHz, CDCl_{3}): δ_{H} 1.31 (8H, m, H-3, H-4, H-5, H-6), 1.39 (2H, m, H-7), 1.56 (2H, m, H-2), 2.11 (2H, dq, 1.5, 7.5 Hz, H-8), 3.64 (2H, t, 7.0 Hz, H-1), 4.93 (1H, brd, 5.5 Hz, H-16), 5.19 (1H, d, 8.0 Hz, H-11), 5.22 (1H, dt, 10.0, 1.0 Hz, H-18a), 5.46 (1H, dt, 17.4, 1.0 Hz, H-18b), 5.51 (1H, ddt, 10.6, 8.2, 1.5 Hz, H-9), 5.58 (1H, ddt, 10.6, 7.3, 1.5 Hz, H-10), 5.93 (1H, ddd, 17.4, 10.0, 5.5 Hz, H-17). ^{13}C-NMR (125 MHz, CDCl_{3}): δc 25.6 (C-3), 27.5 (C-8), 28.8 (C-7), 29.0 (C-6), 29.1 (C-4), 29.2 (C-5), 32.6 (C-2), 58.5 (C-11), 63.0 (C-1), 63.3 (C-16), 68.7 (C-13), 70.1 (C-14), 78.5 (C-15), 79.8 (C-12), 117.1 (C-18), 127.9 (C-9), 134.2 (C-10), 136.0 (C-17).
(11S,16S,Z)-Octadeca-9-en-12,14-diyne-1,11,16-triol (oplopantriol B, OH-6): yellowish oil (2.5 g); + 233.0° (c = 0.3, CHCl_{3}); UV(CHCl_{3}) λmax (log ξ): 207 (1.07), 232 (1.17), 263 (3.98), and 288 (3.84) nm; IR (KBr) ν_{max}: 3355, 3021, 2930, 2856, 2232, 2143, 1656, 1463, 1305, 1095 and 1017 cm^{−1}; ^{1}H-NMR (500 MHz, CDCl_{3}): δ_{H} 1.00 (3H, s, H-18), 1.74 (2H, m, H-17),1.31 (8H, m, H-3, H-4, H-5, H-6), 1.38 (2H, m, H-7), 1.57 (2H, m, H-2), 2.11 (2H, dq, 1.5, 7.1 Hz, H-8), 3.64 (2H, t, 6.5 Hz, H-1), 4.37 (1H, t, 6.6 Hz, H-16), 5.19 (1H, d, 8.0 Hz, H-11), 5.52 (1H, ddt, 10.6, 7.5, 1.5 Hz, H-9), 5.58 (1H, ddt, 10.6, 7.3, 1.5 Hz, H-10). ^{13}C-NMR (125 MHz, CDCl_{3}): δc 9.3 (C-18), 25.6 (C-2), 27.5 (C-8), 28.8 (C-7), 29.0 (C-6), 29.1 (C-4), 29.2 (C-5), 30.6 (C-17), 32.6 (C-2), 58.5 (C-11), 63.0 (C-1), 63.8 (C-16), 68.8 (C-13), 68.8 (C-14), 80.9 (C-15), 79.1 (C-12), 128.0 (C-19), 134.1 (C-10).
(3S,8S,Z)-Heptadeca-9-en-4,6-diyne-3,8-diyl diacetate (OHR-1): yellowish oil (210 mg); + 202.8° (c = 0.86, CHCl_{3}); UV(CHCl_{3}) λmax (log ξ): 206 (1.27), 232 (1.37), 253 (3.73), and 267 (4.12) nm; IR (KBr) ν_{max}: 3012, 2920, 2816, 2248, 1726, 1718, 1612, 1436, 1252, 1068 and 930 cm^{−1}; ^{1}H-NMR (500 MHz, CDCl_{3}): δ_{H} 0.88 (3H, t, 7.0, H-17), 1.00 (3H, t, 7.0, H-1),1.28 (8H, m, H-13, H-14, H-15, H-16), 1.38 (2H, m, H-12), 1.79 (2H, m, H-2), 2.07 (6H, s, COCH_{3}) 2.13 (2H, dq, 7.0, 1.0 Hz, H-11), 5.33 (1H, t, 6.5 Hz, H-3), 5.46 (1H, ddt, 11.0, 8.5, 1.5 Hz, H-9), 5.66 (1H, dt, 11.0, 7.5, 1.0 Hz, H-10), 6.11 (1H, dt, 8.5, 1.0 Hz, H-8). ^{13}C-NMR (125 MHz, CDCl_{3}): δc 9.2 (C-1), 14.0 (C-17), 20.8 (COCH_{3}), 20.9 (COCH_{3}), 22.6 (C-15), 27.8 (C-11), 27.8 (C-12), 29.1 (C-14), 29.1 (C-13), 29.2 (C-2), 31.7 (C-16), 60.1 (C-8), 65.2 (C-3), 69.2 (C-6), 69.3 (C-5), 76.0 (C-4), 77.3 (C-7), 123.8 (C-10), 136.4 (C-9), 169.4 (C=O), 169.7 (C=O).
(3S,8S,Z)-Heptadeca-1,9-dien-4,6-diyne-3,8-diyl diacetate (OHR-2): yellowish oil (220 mg); + 243.5° (c = 0.92, CHCl_{3}); UV (CHCl_{3}) λmax (log ξ): 208 (1.07), 228 (1.52), 248 (3.25) and 270 (3.66) nm; IR (KBr) ν_{max}: 2982, 2867, 2248, 1720, 1716, 1384, 1142, 950 and 862 cm^{−1}; ^{1}H-NMR (500 MHz, CDCl_{3}): δ_{H} 0.88 (3H, t, 7.0, H-17), 1.28 (8H, m, H-13, H-14, H-15, H-16), 1.36 (2H, m, H-12), 2.07 (3H, s, COCH_{3}), 2.09 (3H, s, COCH_{3}), 2.14 (2H, q, 7.0, H-11), 5.33 (1H, d, 10.0 Hz, H-1a), 5.46 (1H, ddt, 10.5, 8.5, 1.5Hz, H-9), 5.53 (1H, d, 17.5 Hz, H-1b), 5.66 (1H, ddt, 10.5, 7.0, 1.0 Hz, H-10), 5.84 (1H, ddd, 17.5, 10.0, 6.0 Hz, H-2), 5.90 (1H, dd, 6.0, 1.0 Hz, H-3), 6.13 (1H, d, 8.5 Hz, H-8). ^{13}C-NMR (125 MHz, CDCl_{3}): δc 14.1 (C-17), 20.8 (COCH_{3}), 20.9 (COCH_{3}), 22.6 (C-15), 27.9 (C-11), 29.0 (C-12), 29.1 (C-14), 29.1 (C-13), 31.8 (C-16), 60.0 (C-8), 64.4 (C-3), 69.1 (C-6), 70.7 (C-5), 75.1 (C-4), 77.6 (C-7), 119.7 (C-1), 123.7 (C-10), 131.9 (C-9), 136.5 (C-2), 169.4 (C=O), 169.4 (C=O).
(3S,8S,Z)-3-Hydroxyheptadeca-9-en-4,6-diyn-8-yl acetate (OHR-3): yellowish oil (60 mg); + 164.6° (c = 0.72, CHCl_{3}); UV(CHCl_{3}) λmax (log ξ): 203 (0.86), 224 (1.57), 242 (4.21), and 266 (4.58) nm; IR (KBr) ν_{max}: 3385, 3025, 2946, 2825, 2230, 1715, 1580, 1420, 1232, 1060 and 896 cm^{−1}; ^{1}H-NMR (500 MHz, CDCl_{3}): δ_{H} 0.88 (3H, t, 7.0, H-17), 1.00 (3H, t, 7.0, H-1),1.28 (8H, m, H-13, H-14, H-15, H-16), 1.38 (2H, m, H-12), 1.79 (2H, m, H-2), 2.07 (6H, s, COCH_{3}) 2.13 (2H, dq, 7.0, 1.0 Hz, H-11), 4.37 (1H, t, 6.5 Hz, H-3), 5.47 (1H, ddt, 11.0, 8.5, 1.5 Hz, H-9), 5.65 (1H, ddt, 11.0, 7.5, 1.0 Hz, H-10), 6.13 (1H, d, 8.5 Hz, H-8). ^{13}C-NMR (125 MHz, CDCl_{3}): δc 9.2 (C-1), 14.0 (C-17), 20.9 (COCH_{3}), 22.6 (C-15), 27.8 (C-11), 27.8 (C-12), 29.1 (C-14), 29.2 (C-13), 30.6 (C-2), 31.7 (C-16), 60.1 (C-8), 64.0 (C-3), 68.9 (C-6), 69.4 (C-5), 75.9 (C-4), 80.9 (C-7), 123.9 (C-10), 136.3 (C-9), 169.5 (C=O).
(3S,8S,Z)-8-Hydroxyheptadeca-9-en-4,6-diyn-3-yl acetate (OHR-4): yellowish oil (55 mg); + 213.6° (c = 1.12, CHCl_{3}); UV(CHCl_{3}) λmax (log ξ): 205 (0.93), 222 (2.17), 245 (4.01), and 270 (4.27) nm; IR (KBr) ν_{max}: 3360, 3010, 2936, 2860, 2252, 1722, 1596, 1440, 1210, 1060 and 912 cm^{−1}; ^{1}H-NMR (500 MHz, CDCl_{3}): δ_{H} 0.88 (3H, t, 7.0, H-17), 1.02 (3H, t, 7.0, H-1), 1.28 (8H, m, H-13, H-14, H-15, H-16), 1.38 (2H, m, H-12), 1.79 (2H, m, H-2), 2.07 (3H, s, COCH_{3}) 2.13 (2H, dq, 7.0, 1.0 Hz, H-11), 5.19 (1H, d, 8.0 Hz, H-8), 5.34 (1H, t, 6.5 Hz, H-3), 5.48 (1H, ddt, 11.0, 8.5, 1.5 Hz, H-9), 5.63 (1H, dt, 11.0, 7.5, 1.0 Hz, H-10). ^{13}C-NMR (125 MHz, CDCl_{3}): δc 9.2 (C-1), 14.0 (C-17), 20.8 (COCH_{3}), 22.6 (C-15), 27.7 (C-11), 27.9 (C-12), 29.1 (C-14), 29.2 (C-13), 29.3 (C-2), 31.8 (C-16), 58.7 (C-8), 65.3 (C-3), 69.2 (C-6), 69.3 (C-5), 76.0 (C-4), 79.4 (C-7), 127.8 (C-10), 134.7 (C-9), 169.5 (C=O).
(3S,8S,Z)-3-Hydroxyheptadeca-1,9-dien-4,6-diyn-8-yl acetate (OHR-5): yellowish oil (30 mg); + 230.2° (c = 0.91, CHCl_{3}); UV(CHCl_{3}) λmax (log ξ): 210 (1.56), 228 (3.17), 242 (4.31), and 265 (4.45) nm; IR (KBr) ν_{max}: 3422, 2981, 2258, 1716, 1584, 1432, 1226, 1030 and 990 cm^{−1}; ^{1}H-NMR (500 MHz, CDCl_{3}): δ_{H} 0.89 (3H, t, 7.0, H-17), 1.27 (8H, m, H-13, H-14, H-15, H-16), 1.38 (2H, m, H-12), 2.07 (3H, s, COCH_{3}), 2.14 (2H, q, 7.0, H-11), 4.93 (1H, d, 6.0 Hz, H-3), 5.27 (1H, d, 10.0 Hz, H-1a), 5.46 (1H, ddt, 10.5, 8.5, 1.5Hz, H-9), 5.50 (1H, d, 17.5 Hz, H-1b), 5.66 (1H, ddt, 10.5, 7.0, 1.0 Hz, H-10), 5.84 (1H, ddd, 17.5, 10.0, 6.0 Hz, H-2), 6.14 (1H, d, 8.5 Hz, H-8). ^{13}C-NMR (125 MHz, CDCl_{3}): δc 14.1 (C-17), 20.9 (COCH_{3}), 22.6 (C-15), 27.9 (C-11), 29.0 (C-12), 29.1 (C-14), 29.2 (C-13), 31.8 (C-16), 60.0 (C-8), 64.4 (C-3), 69.2 (C-6), 70.9 (C-5), 75.5 (C-4), 77.7 (C-7), 117.4 (C-1), 123.8 (C-10), 131.9 (C-9), 136.5 (C-2), 169.4 (C=O).
(3S,8S,Z)-8-Hydroxyheptadeca-1,9-dien-4,6-diyn-3-yl acetate (OHR-6): yellowish oil (45 mg); + 210.8° (c = 0.51, CHCl_{3}); UV(CHCl_{3}) λmax (log ξ): 208 (1.36), 226 (2.57), 248 (4.31), and 268 (4.48) nm; IR (KBr) ν_{max}: 3380, 3012, 2252, 1718, 1560, 1482, 1216, 1024 and 990 cm^{−1}; ^{1}H-NMR (500 MHz, CDCl_{3}): δ_{H} 0.89 (3H, t, 7.0, H-17), 1.27 (8H, m, H-13, H-14, H-15, H-16), 1.38 (2H, m, H-12), 2.09 (3H, s, COCH_{3}), 2.11 (2H, q, 7.0, H-11), 5.19 (1H, d, 6.0 Hz, H-3), 5.33 (1H, d, 10.0 Hz, H-1a), 5.48 (1H, ddt, 10.5, 8.5, 1.5Hz, H-9), 5.51 (1H, d, 17.5 Hz, H-1b), 5.60 (1H, ddt, 10.5, 7.0, 1.0 Hz, H-10), 5.86 (1H, ddd, 17.5, 10.0, 6.0 Hz, H-2), 5.91 (1H, d, 8.5 Hz, H-8). ^{13}C-NMR (125 MHz, CDCl_{3}): δc 14.0 (C-17), 20.8 (COCH_{3}), 22.6 (C-15), 27.9 (C-11), 29.0 (C-12), 29.1 (C-14), 29.2 (C-13), 31.8 (C-16), 58.6 (C-8), 64.4 (C-3), 68.6 (C-6), 70.8 (C-5), 74.8 (C-4), 80.1 (C-7), 119.7 (C-1), 127.6 (C-10), 132.0 (C-9), 134.7 (C-2), 169.4 (C=O).
(11S,16S,Z)-Octadeca-9-en-12,14-diyne-1,11,16-triyl triacetate (OHR-7): yellowish oil (180 mg); + 185.4° (c = 0.41, CHCl_{3}); UV(CHCl_{3}) λmax (log ξ): 205 (0.76), 223 (1.35), 240 (3.21), and 265 (4.05) nm; IR (KBr) ν_{max}: 2985, 2258, 1723, 1716, 1585, 1477, 1238, 1028 and 954 cm^{−1}; ^{1}H-NMR (500 MHz, CDCl_{3}): δ_{H} 1.00 (3 H, t, 7.5 Hz, H-18), 1.29 (8H, m, H-3, H-4, H-5, H-6), 1.37 (2H, m, H-7), 1.61 (2H, m, H-2), 1.79 (2H, m, H-17), 2.04 (3H, s, COCH_{3}), 2.07 (6H, s, 2 × COCH_{3}), 2.13 (2H, q, 7.5 Hz, H-8), 4.05 (2H, t, 7.0 Hz, H-1), 5.33 (1H, t, 6.5 Hz, H-16), 5.47 (1H, ddt, 10.6, 7.5, 1.5 Hz, H-9), 5.66 (1H, ddt, 10.6, 8.5, 1.5 Hz, H-10), 6.13 (1H, d, 8.5 Hz, H-11). ^{13}C-NMR (125 MHz, CDCl_{3}): δc 9.2 (C-18), 20.8 (COCH_{3}), 20.9 (COCH_{3}), 21.0 (COCH_{3}), 25.8 (C-2), 27.8 (C-8), 28.6 (C-6), 28.9 (C-5), 29.0 (C-4), 29.1 (C-3), 29.1 (C-7), 29.3 (C-17), 60.0 (C-11), 64.6 (C-16), 65.1 (C-1), 69.2 (C-13), 69.3 (C-14), 75.9 (C-15), 77.2 (C-12), 123.8 (C-10), 136.2 (C-9), 169.4 (C=O), 169.7 (C=O), 171.2 (C=O).
(11S,16S,Z)-Octadeca-9,17-dien-12,14-diyne-1,11,16-triyl triacetate (OHR-8): yellowish oil (175 mg); + 236.7° (c = 0.61, CHCl_{3}); UV(CHCl_{3}) λmax (log ξ): 210 (1.46), 228 (2.15), 246 (3.71), and 274 (4.65) nm; IR (KBr) ν_{max}: 2968, 2257, 1720, 1718, 1562, 1457, 1318, 1016 and 946 cm^{−1}; ^{1}H-NMR (500 MHz, CDCl_{3}): δ_{H} 1.29 (8H, m, H-3, H-4, H-5, H-6), 1.37 (2H, m, H-7), 1.62 (2H, m, H-2), 2.04 (3H, s, COCH3), 2.07 (3H, s, COCH3), 2.10 (3H, s, COCH3), 2.13 (2H, q, 7.5 Hz, H-8), 4.05 (2H t, 7.5 Hz, H-1), 5.33 (1H, d, 10.5 Hz, H-18a), 5.46 (1H, dt, 10.5, 7.5 Hz, Hz, H-9), 5.53 (1H, dd, 17.5, 1.5 Hz, H-18b), 5.66 (1H, ddt, 10.5, 7.5, 1.0Hz, H-10), 5.85 (1H, ddd, 17.0, 10.0, 1.5 Hz, H-17), 5.90 (1H, brd, 5.0 Hz, H-16), 6.13 (1H, d, 8.0 Hz, H-11). ^{13}C-NMR (125 MHz, CDCl_{3}): δc 20.8 (COCH_{3}), 20.9 (COCH_{3}), 20.9 (COCH_{3}), 25.8 (C-2), 27.8 (C-3), 28.6 (C-5), 29.0 (C-4), 29.0 (C-6), 29.1 (C-8), 29.2 (C-7), 60.0 (C-11), 64.3 (C-16), 64.6 (C-1), 69.1 (C-13), 70.7 (C-14), 75.1 (C-15), 76.7 (C-12), 119.7 (C-18), 123.7 (C-10), 131.9 (C-9), 136.3 (C-17), 169.3(C=O), 169.4 (C=O), 171.6 (C=O).
(11S,16S,Z)-16-Hydroxyoctadeca-9,17-dien-12,14-diyne-1,16-diyl diacetate (OHR-9): yellowish oil (110 mg); + 285.2° (c = 1.01, CHCl_{3}); UV(CHCl_{3}) λmax (log ξ): 208 (1.40), 226 (3.15), 245 (4.81), and 268 (4.55) nm; IR (KBr) ν_{max}: 3348, 3014, 2988, 2254, 1722, 1710, 1486, 1380, 1258, 1016 and 885 cm^{−1}; ^{1}H-NMR (500 MHz, CDCl_{3}): δ_{H} 1.29 (8H, m, H-3, H-4, H-5, H-6), 1.37 (2H, m, H-7), 1.62 (2H, m, H-2), 2.04 (3H, s, COCH3), 2.07 (3H, s, COCH3), 2.13 (2H, q, 7.5 Hz, H-8), 4.05 (2H t, 7.5 Hz, H-1), 5.19 (1H, d, 8.0 Hz, H-11), 5.34 (1H, d, 10.5 Hz, H-18a), 5.50 (1H, dt, 10.5, 7.5 Hz, Hz, H-9), 5.52 (1H, dd, 17.5, 1.5 Hz, H-18b), 5.62 (1H, ddt, 10.5, 7.5, 1.0Hz, H-10), 5.86 (1H, ddd, 17.0, 10.0, 1.5 Hz, H-17), 5.90 (1H, brd, 5.0 Hz, H-16). ^{13}C-NMR (125 MHz, CDCl_{3}): δc 20.8 (COCH_{3}), 20.9 (COCH_{3}), 25.8 (C-2), 27.8 (C-3), 28.6 (C-5), 29.0 (C-4), 29.0 (C-6), 29.1 (C-8), 29.2 (C-7), 58.6 (C-11), 64.3 (C-16), 64.6 (C-1), 68.6 (C-13), 70.8 (C-14), 74.9 (C-15), 80.1 (C-12), 119.7 (C-18), 127.7 (C-10), 132.0 (C-9), 134.6 (C-17), 169.4(C=O), 171.3 (C=O).
(11S,16S,Z)-16-Hydroxyoctadeca-9,17-dien-12,14-diyne-1,11-diyl diacetate (OHR-10): yellowish oil (110 mg); + 285.2° (c = 1.01, CHCl_{3}); UV(CHCl_{3}) λmax (log ξ): 208 (1.40), 226 (3.15), 245 (4.81), and 268 (4.55) nm; IR (KBr) ν_{max}: 3348, 3014, 2988, 2254, 1722, 1710, 1486, 1380, 1258, 1016 and 885 cm^{−1}; ^{1}H-NMR (500 MHz, CDCl_{3}): δ_{H} 1.26 (8H, m, H-3, H-4, H-5, H-6), 1.41 (2H, m, H-7), 1.61 (2H, m, H-2), 2.04 (3H, s, COCH3), 2.07 (3H, s, COCH3), 2.13 (2H, q, 7.5 Hz, H-8), 4.05 (2H t, 7.5 Hz, H-1), 4.94 (1H, brd, 5.0 Hz, H-16), 5.25 (1H, d, 10.5 Hz, H-18a), 5.50 (1H, dt, 10.5, 7.5 Hz, Hz, H-9), 5.55 (1H, dd, 17.5, 1.5 Hz, H-18b), 5.65 (1H, ddt, 10.5, 7.5, 1.0Hz, H-10), 5.96 (1H, ddd, 17.0, 10.0, 1.5 Hz, H-17), 6.13 (1H, d, 8.0 Hz, H-11). ^{13}C-NMR (125 MHz, CDCl_{3}): δc 20.8 (COCH_{3}), 21.0 (COCH_{3}), 25.8 (C-2), 27.8 (C-3), 28.6 (C-5), 29.0 (C-4), 29.0 (C-6), 29.1 (C-8), 30.4 (C-7), 58.6 (C-11), 64.3 (C-16), 64.6 (C-1), 68.6 (C-13), 70.8 (C-14), 74.9 (C-15), 80.1 (C-12), 117.3 (C-18), 123.9 (C-10), 130.8 (C-9), 136.2 (C-17), 169.5 (C=O), 171.3 (C=O).
(11S,16S,Z)-11-Hydroxyoctadeca-9-en-12,14-diyne-1,16-diyl diacetate (OHR-11): yellowish oil (30 mg); + 225.4° (c = 1.01, CHCl_{3}); UV(CHCl_{3}) λmax (log ξ): 205 (0.76), 223 (1.35), 240 (3.21), and 265 (4.05) nm; IR (KBr) ν_{max}: 3310, 2985, 2258, 1723, 1716, 1585, 1477, 1238, 1028 and 954 cm^{−1}; ^{1}H-NMR (500 MHz, CDCl_{3}): δ_{H} 0.89 (3 H, t, 7.5 Hz, H-18), 1.28 (8H, m, H-3, H-4, H-5, H-6), 1.38 (2H, m, H-7), 1.62 (2H, m, H-2), 1.78 (2H, m, H-17), 2.04 (3H, s, COCH_{3}), 2.09 (3, s, COCH_{3}), 2.13 (2H, q, 7.5 Hz, H-8), 4.05 (2H, t, 7.0 Hz, H-1), 5.33 (1H, t, 6.5 Hz, H-16), 5.47 (1H, ddt, 10.6, 7.5, 1.5 Hz, H-9), 5.66 (1H, ddt, 10.6, 8.5, 1.5 Hz, H-10), 5.90 (1H, d, 8.5 Hz, H-11). ^{13}C-NMR (125 MHz, CDCl_{3}): δc 9.2 (C-18), 20.8 (COCH_{3}), 20.9 (COCH_{3}), 25.8 (C-2), 27.8 (C-8), 28.6 (C-6), 28.9 (C-5), 29.0 (C-4), 29.1 (C-3), 29.1 (C-7), 29.3 (C-17), 60.0 (C-11), 64.6 (C-16), 65.1 (C-1), 69.2 (C-13), 69.5 (C-14), 75.6 (C-15), 77.6 (C-12), 126.1 (C-10), 134.3 (C-9), 169.4 (C=O), 171.2 (C=O).
(11S,16S,Z)-16-Hydroxyoctadeca-9-en-12,14-diyne-1,11-diyl diacetate (OHR-12): yellowish oil (80 mg); + 241.4° (c = 1.21, CHCl_{3}); UV(CHCl_{3}) λmax (log ξ): 204 (0.86), 225 (1.25), 242 (3.61), and 266 (4.15) nm; IR (KBr) ν_{max}: 3326, 2986, 2252, 1720, 1715, 1565, 1447, 1232, 1120 and 880 cm^{−1}; ^{1}H-NMR (500 MHz, CDCl_{3}): δ_{H} 1.00 (3 H, t, 7.5 Hz, H-18), 1.29 (8H, m, H-3, H-4, H-5, H-6), 1.38 (2H, m, H-7), 1.62 (2H, m, H-2), 1.74 (2H, m, H-17), 2.04 (3H, s, COCH_{3}), 2.07 (3, s, COCH_{3}), 2.15 (2H, q, 7.5 Hz, H-8), 4.06 (2H, t, 7.0 Hz, H-1), 4.37 (1H, t, 6.5 Hz, H-16), 5.48 (1H, ddt, 10.6, 7.5, 1.5 Hz, H-9), 5.66 (1H, ddt, 10.6, 8.5, 1.5 Hz, H-10), 6.13 (1H, d, 8.5 Hz, H-11). ^{13}C-NMR (125 MHz, CDCl_{3}): δc 9.2 (C-18), 20.8 (COCH_{3}), 20.9 (COCH_{3}), 25.8 (C-2), 27.6 (C-8), 28.6 (C-6), 28.9 (C-5), 29.0 (C-4), 29.1 (C-3), 29.3 (C-7), 30.6(C-17), 58.6 (C-11), 64.0 (C-16), 65.4 (C-1), 68.7 (C-13), 69.5 (C-14), 75.7 (C-15), 81.1 (C-12), 124.0 (C-10), 136.1 (C-9), 169.4 (C=O), 171.4 (C=O).
(3S,8S,Z)-18-Hydroxyoctadeca-9-en-4,6-diyne-3,8-diyl diacetate (OHR-13): yellowish oil (20 mg); + 168.6° (c = 0.50, CHCl_{3}); UV(CHCl_{3}) λmax (log ξ): 206 (0.56), 226 (1.55), 242 (2.86), and 265 (3.84) nm; IR (KBr) ν_{max}: 3410, 3020, 2252, 1718, 1714, 1562, 1460, 1235, 1022 and 950 cm^{−1}; ^{1}H-NMR (500 MHz, CDCl_{3}): δ_{H} 1.00 (3 H, t, 7.5 Hz, H-1), 1.28 (8H, m, H-13, H-14, H-15, H-16), 1.37 (2H, m, H-12), 1.61 (2H, m, H-17), 1.79 (2H, m, H-2), 2.04 (3H, s, COCH_{3}), 2.09 (3H, s, COCH_{3}), 2.13 (2H, q, 7.5 Hz, H-11), 4.08 (2H, t, 7.0 Hz, H-18), 5.33 (1H, t, 6.5 Hz, H-3), 5.47 (1H, ddt, 10.6, 7.5, 1.5 Hz, H-10), 5.66 (1H, ddt, 10.6, 8.5, 1.5 Hz, H-9), 6.13 (1H, d, 8.5 Hz, H-8). ^{13}C-NMR (125 MHz, CDCl_{3}): δc 9.2 (C-1), 20.8 (COCH_{3}), 21.0 (COCH_{3}), 25.8 (C-17), 27.8 (C-11), 28.6 (C-13), 28.9 (C-14), 29.0 (C-15), 29.1 (C-16), 29.1 (C-12), 29.3 (C-2), 60.0 (C-8), 64.6 (C-3), 65.1 (C-18), 69.1 (C-6), 69.2 (C-5), 75.7 (C-4), 77.5 (C-7), 123.6 (C-9), 136.1 (C-10), 169.4 (C=O), 169.7 (C=O).
(3S,8S,Z)-18-Hydroxyoctadeca-1,9-dien-4,6-diyne-3,8-diyl diacetate (OHR-14): yellowish oil (30 mg); + 236.7° (c = 0.61, CHCl_{3}); UV(CHCl_{3}) λmax (log ξ): 210 (1.46), 228 (2.15), 246 (3.71), and 274 (4.65) nm; IR (KBr) ν_{max}: 3380, 3010, 2252, 1718, 1713, 1568, 1438, 1310, 1016 and 890 cm^{−1}; ^{1}H-NMR (500 MHz, CDCl_{3}): δ_{H} 1.31 (8H, m, H-13, H-14, H-15, H-16), 1.38 (2H, m, H-12), 1.61 (2H, m, H-17), 2.04 (3H, s, COCH3), 2.07 (3H, s, COCH3), 2.14 (2H, q, 7.5 Hz, H-11), 4.09 (2H t, 7.5 Hz, H-17), 5.33 (1H, d, 10.5 Hz, H-1a), 5.46 (1H, dt, 10.5, 7.5 Hz, Hz, H-10), 5.53 (1H, dd, 17.5, 1.5 Hz, H-1b), 5.66 (1H, ddt, 10.5, 7.5, 1.0Hz, H-9), 5.85 (1H, ddd, 17.0, 10.0, 1.5 Hz, H-2), 5.90 (1H, brd, 5.0 Hz, H-3), 6.13 (1H, d, 8.0 Hz, H-8). ^{13}C-NMR (125 MHz, CDCl_{3}): δc 20.8 (COCH_{3}), 20.9 (COCH_{3}), 25.8 (C-17), 27.8 (C-16), 28.6 (C-14), 29.0 (C-15), 29.0 (C-13), 29.1 (C-11), 29.2 (C-12), 60.0 (C-8), 64.3 (C-3), 64.6 (C-18), 69.1 (C-6), 70.7 (C-5), 75.1 (C-4), 76.7 (C-7), 119.7 (C-1), 123.7 (C-9), 131.9 (C-10), 136.3 (C-2), 169.3(C=O), 169.4 (C=O).
(3S,8S,Z)-3,18-Dihydroxyoctadeca-1,9-dien-4,6-diyn-8-yl acetate (OHR-15): yellowish oil (16 mg); + 216.8° (c = 0.26, CHCl_{3}); UV(CHCl_{3}) λmax (log ξ): 206 (0.86), 228 (2.35), 247 (3.75), and 270 (4.25) nm; IR (KBr) ν_{max}: 3460, 3010, 2250, 1716, 1562, 1442, 1320, 1038 and 860 cm^{−1}; ^{1}H-NMR (500 MHz, CDCl_{3}): δ_{H} 1.31 (8H, m, H-13, H-14, H-15, H-16), 1.37 (2H, m, H-12), 1.61 (2H, m, H-17), 2.07 (3H, s, COCH3), 2.14 (2H, q, 7.5 Hz, H-11), 4.09 (2H t, 7.5 Hz, H-17), 4.33 (1H, brd, 5.0 Hz, H-3), 5.33 (1H, d, 10.5 Hz, H-1a), 5.48 (1H, dt, 10.5, 7.5 Hz, Hz, H-10), 5.52 (1H, dd, 17.5, 1.5 Hz, H-1b), 5.66 (1H, ddt, 10.5, 7.5, 1.0Hz, H-9), 5.92 (1H, ddd, 17.0, 10.0, 1.5 Hz, H-2), 6.13 (1H, d, 8.0 Hz, H-8). ^{13}C-NMR (125 MHz, CDCl_{3}): 20.9 (COCH_{3}), 25.8 (C-17), 27.8 (C-16), 28.6 (C-14), 29.0 (C-15), 29.0 (C-13), 29.1 (C-11), 29.2 (C-12), 61.3 (C-8), 63.3 (C-3), 64.6 (C-18), 69.1 (C-6), 70.6 (C-5), 75.6 (C-4), 79.8 (C-7), 119.7 (C-1), 127.8 (C-10), 132.1 (C-9), 136.4 (C-2), 169.4 (C=O).
(3S,8S,Z)-3,18-Dihydroxyoctadeca-1,9-dien-4,6-diyn-3-yl acetate (OHR-16): yellowish oil (20 mg); + 176.4° (c = 0.16, CHCl_{3}); UV(CHCl_{3}) λmax (log ξ): 203 (0.75), 225 (2.10), 248 (2.65), and 266 (4.86) nm; IR (KBr) ν_{max} :3410, 3022, 2258, 1720, 1582, 1432, 1360, 1024 and 860 cm^{−1}; ^{1}H-NMR (500 MHz, CDCl_{3}): δ_{H} 1.31 (8H, m, H-13, H-14, H-15, H-16), 1.37 (2H, m, H-12), 1.61 (2H, m, H-17), 2.04 (3H, s, COCH3), 2.14 (2H, q, 7.5 Hz, H-11), 4.09 (2H t, 7.5 Hz, H-17), 5.13 (1H, d, 8.0 Hz, H-8) 5.33 (1H, d, 10.5 Hz, H-1a), 5.48 (1H, dt, 10.5, 7.5 Hz, Hz, H-10), 5.52 (1H, dd, 17.5, 1.5 Hz, H-1b), 5.68 (1H, ddt, 10.5, 7.5, 1.0Hz, H-9), 5.90 (1H, brd, 5.0 Hz, H-3), 5.92 (1H, ddd, 17.0, 10.0, 1.5 Hz, H-2). ^{13}C-NMR (125 MHz, CDCl_{3}): 20.9 (COCH_{3}), 25.8 (C-17), 27.8 (C-16), 28.6 (C-14), 29.0 (C-15), 29.0 (C-13), 29.1 (C-11), 29.2 (C-12), 61.3 (C-8), 63.3 (C-3), 64.6 (C-18), 69.1 (C-6), 70.6 (C-5), 75.5 (C-4), 77.8 (C-7), 117.2 (C-1), 129.2 (C-10), 134.4 (C-9), 136.4 (C-2), 169.3 (C=O).