Elsevier

Phytochemistry

Volume 44, Issue 1, January 1997, Pages 167-172
Phytochemistry

Plant chemistry
Bibenzyl derivatives from the orchid Bulbophyllum protractum

https://doi.org/10.1016/S0031-9422(96)00402-5Get rights and content

Abstract

Two new bibenzyl derivatives were isolated from the orchid Bulbophyllum protractum and designated bulbophyllin and bulbophyllidin. In addition batatasin-III (3,3′-dihydroxy-5-methoxy bibenzyl), 3,3′,5-trimethoxybibenzyl, aloifol-I (3′,4-dihydroxy-3,5-dimethoxybibenzyl), 3,3′-dimethoxy-4,5-methylenedioxybibenzyl, flavidin (2,7-dihydroxy-9,10-dihydro-5H-phenanthro[4,5-bcd]pyran), dihydroconiferyl alcohol, stigmasterol and sitosterol were isolated. The structures of bulbophyllin and bulbophyllidin were established as 2,3′-dihydroxy-3-methoxy-4,5-methylenedioxybibenzyl and 2,3′-dihydroxy-3,5-dimethoxybibenzyl, respectively, from spectral and chemical evidence.

References (32)

  • P.L. Majumder et al.

    Phytochemistry

    (1991)
  • P.L. Majumder et al.

    Phytochemistry

    (1993)
  • P.L. Majumder et al.

    Phytochemistry

    (1993)
  • P.L. Majumder et al.

    Phytochemistry

    (1990)
  • P.L. Majumder et al.

    Phytochemistry

    (1991)
  • P.L. Majumder et al.

    Phytochemistry

    (1982)
  • P.L. Majumder et al.

    Phytochemistry

    (1990)
  • P.L. Majumder et al.

    Phytochemistry

    (1990)
  • P.L. Majumder et al.

    Phytochemistry

    (1991)
  • P.L. Majumder et al.

    Phytochemistry

    (1990)
  • P.L. Majumder et al.

    Tetrahedron

    (1990)
  • P.L. Majumder et al.

    Tetrahedron

    (1988)
  • P.L. Majumder et al.

    Phytochemistry

    (1988)
  • P.L. Majumder et al.

    Phytochemistry

    (1989)
  • P.L. Majumder et al.

    Phytochemistry

    (1996)
  • P.L. Majumder et al.

    Phytochemistry

    (1995)
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