Elsevier

Phytochemistry

Volume 28, Issue 6, 1989, Pages 1613-1615
Phytochemistry

Antifungal phloroglucinol derivatives and lipophilic flavonoids from Helichrysum decumbens

https://doi.org/10.1016/S0031-9422(00)97809-9Get rights and content

Abstract

From the aerial parts of Helichrysum decumbens, three new antifungal phloroglucinol derivatives have been identified. Their structures have been established by UV, IR, EIMS, FAB-MS, 1H NMR and 13C NMR techniques. In addition, the highly methylated flavonoids 3,5-dihydroxy-6,7,8-trimethoxyflavone, 5,7-dihydroxy-3,6,8-trimethoxy-flavone and 3,5-dihydroxy-6,7-dimethoxyflavone have been detected, the latter being a new naturally occurring compound. The phloroglucinols prevented the growth of Cladosporium herbarum in a bio-assay. These secondary metabolises are externally deposited on the plant surfaces.

References (10)

  • J. Jakupovic et al.

    Phytochemistry

    (1986)
  • F. Bohlmann et al.

    Phytochemistry

    (1980)
  • F.A. Tomás-Barberán et al.

    Phytochemistry

    (1988)
  • I. Kouno et al.

    Phytochemistry

    (1985)
  • F. Bohlmann et al.

    Phytochemistry

    (1979)
There are more references available in the full text version of this article.

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