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Symbioramide, a novel Ca2+-ATPase activator from the cultured dinoflagellateSymbiodinium sp.

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Summary

A novel sphingosine derivative, symbioramide, has been isolated from the laboratory-cultured dinoflagellateSymbiodinium sp. as a sarcoplasmic reticulum (SR) Ca2+-ATPase activator, and its structure elucidated to be1 on the basis of spectral and chemical means.

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References

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  11. Colorless crystals, mp 105–107°C; [α] 22D + 5.8° (c=1, CHCl3); IR (KBr) 3270, 1650, 1535, 1470, and 1070 cm−1;1H NMR (CDCl3) δ 0.89 (6H, t,J=7.0 Hz; H3-18 and H3-18′), 1.28 (50H, br s), 2.10 (2H, q,J=7.3 Hz; H2-5′), 3.81 (3H, m; H-1, H-2, and H-3), 4.05 (1H, d,J=11.3 Hz; H′-1), 4.54 (1H, d,J=7.3 Hz; H-2′), 5.57 (1H, dd,J=15.3 and 7.3 Hz; H-3′), 5.92 (1H, dt,J=15.3 and 7.3 Hz; H-4′), and 7.01 (1H, d,J=7.2 Hz; NH); FABMS (positive ion, thioglycerol as a matrix)m/z 582 (M+H)+; EIMSm/z 328 (fragment a), 310, 284, 270, and 253; Foundm/z 328.2860, Calcd for C19H38O3N: fragment a, 328.2851.

  12. White solids, mp 75–78°C;1H NMR (CDCl3) δ 0.89 (6H, t,J=6.9 Hz; H3-18 and H3-18′), 1.26 (50H, br s), 2.05 (3H, s; Ac), 2.08 (3H, s; Ac), 2.18 (3H, s; Ac), 4.04 (1H, m; H-1), 4.32 (1H, m; H′-1), 4.36 (1H, m; H-2), 4.91 (1H, m; H-3), 5.49 (1H, d,J=7.2 Hz; H-2′), 5.53 (1H, m; H-3′), 5.91 (1H, dt,J=14.5 and 6.7 Hz; H-4′), and 6.55 (1H, d,J=8.8 Hz; NH);13C NMR (CDCl3) δ 14.00 q (2C), 20.59 q, 20.83 q, 20.89 q, 22.58 t, 25.28 t, 28.61 t, 29.14 t, 29.38 t, 29.61 t (19C), 31.42 t, 31.83 t, 32.24 t, 50.68 d, 62.09 t, 73.86 d, 74.44 d, 122.90 d, 137.65 d, 168.44 s (2C), 169.73 s, and 170.67 s; FABMS (positive ion, thioglycerol as a matrix)m/z 708 (M+H)+; EIMSm/z 412 (fragmenta), 370, 352, and 310; Foundm/z 412.3078. Calcd for C23H42O5N: fragmenta, 412.3063.

  13. White solids, mp 57–59°C;1H NMR (CDCl3) δ 0.88 (6H, t,J=6.9 Hz; H3-18 and H3-18′), 1.25 (50H, br s), 1.76 (1H, m; H-4), 1.86 (1H, m; H′-4), 2.05 (2H, q,J=7.1 Hz; H2-5′), 4.44 (1H, dd,J=11.5 and 4.0 Hz; H-1), 4.55 (1H, dd,J=11.5 and 5.6 Hz; H′-1), 4.60 (1H, m; H-2), 5.24 (1H, m; H-3), 5.64 (1H, dd,J=15.4 and 7.1 Hz; H-3′), 5.75 (1H, d,J=7.1 Hz; H-2′), 5.98 (1H, dt,J=15.4 and 7.1 Hz; H-4′), 7.04 (1H, d,J=8.6 Hz; NH), 7.40, 7.49, 7.52, 7.60, 7.71, and 7.86 (each 2H, d,J=8.5 Hz; aromatic protons); FABMS (positive ion, thioglycerol as a matrix)m/z 1134, 1132, 1130, and 1128 (M+H)+.

  14. Colorless oil; [α] 28D −16° (c=1, CHCl3);1H NMR (CDCl3) δ 0.81 (3H, t,J=6.9 Hz; H3-18′), 1.18 (24H, br s), 1.99 (2H, q,J=7.2 Hz; H2-5′), 2.77 (1H, d,J=5.9 Hz; OH-2′), 4.54 (1H, t,J=5.9 Hz; H-2′), 5.43 (1H, dd,J=15.3 and 5.9 Hz; H-3′), and 5.81 (1H, dt,J=15.3 and 7.2 Hz; H-4′); EIMSm/z 253 (M−COOMe)+.

  15. White crystals, mp 92–94°C [lit.3 mp 100.5–101°C]; [α] 22D +14° (c=0.1, CHCl3) [lit.3 [α]D+15.7° (c=0.86, CHCl3)];1H NMR (CDCl3) δ 0.89 (3H, t,J=6.9 Hz; H3-18), 1.27 (26H, br s), 1.60 (2H, m; H2-4), 2.10 (3H, s; Ac), 2.07 (3H, s; Ac), 2.08 (3H, s; Ac), 4.07 (1H, dd,J=11.6 and 3.9 Hz; H-1), 4.25 (1H, dd,J=11.6 and 6.1 Hz; H′-1), 4.40 (1H, m; H-2), 4.91 (1H, m; H-3), 5.84 (1H, d,J=9.0 Hz; NH); EIMSm/z 428 (M+1), 368, 294, and 144.

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Authors and Affiliations

  1. Mitsubishi Kasei Institute of Life Sciences, Minamiooya, 194, Machida, Tokyo, Japan

    J. Kobayashi, M. Ishibashi, H. Nakamura & Y. Ohizumi

  2. Faculty of Pharmacy, Meijo University, 468, Nagoya, Japan

    Y. Hirata

  3. Division of General Education, University of the Ryukyus, 903-01, Okinawa, Japan

    T. Yamasu

  4. Cancer Research Institute, Kanazawa University, 920, Kanazawa, Japan

    T. Sasaki

Authors
  1. J. Kobayashi
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  2. M. Ishibashi
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  3. H. Nakamura
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  4. Y. Hirata
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  5. T. Yamasu
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  6. T. Sasaki
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  7. Y. Ohizumi
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Acknowledgments. We thank Ms M. Hamashima and Ms A. Muroyama for their technical assistance.

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Kobayashi, J., Ishibashi, M., Nakamura, H. et al. Symbioramide, a novel Ca2+-ATPase activator from the cultured dinoflagellateSymbiodinium sp.. Experientia 44, 800–802 (1988). https://doi.org/10.1007/BF01959173

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