Summary
Brianolide (1), a new antiinflammatory diterpenoid of the briarein class, possessing a β substituent at C-12 (R), has been isolated from the Okinawan gorgonianBriareum sp. Its structure has been established from spectral data in conjunction with a single crystal X-ray analysis.
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CD (MeOH)Δɛ220−1.52; IR (KBr)v max 3490, 2980, 2950, 2850, 1780, 1760, 1740, 1720, 1480, 1250, 1230, 1100, 1070, 1020, 930, and 740 cm−1.
IR (K Br)v max 3500, 2980, 2925, 2850, 1780, 1740, 1370, 1220, 1100, 1020, and 750 cm−1; FABMS (glycerol as matrix)m/z 557 (M++H) (Found: M++H, 557.1797. Cacl. for C26O11Cl: M+H, 557.1789).
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The relative stereochemistry at C-12 might be assigned by the vicinal coupling values between H-12 and H-13 to be α (J=4 ∼ 6 Hz) of β (J=∼0 Hz).
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Kobayashi, J., Cheng, J.F., Nakamura, H. et al. Structure and stereochemistry of brianolide, a new antiinflammatory diterpenoid from the Okinawan gorgonianBriareum sp.. Experientia 47, 501–502 (1991). https://doi.org/10.1007/BF01959955
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DOI: https://doi.org/10.1007/BF01959955