Colouring Matters of Australian Plants. XVIII. Constituents of Anigozanthos rufus

Abstract

Four new phenylphenalenone pigments have been isolated from Anigozanthos rufus Labill. and their structures have been determined. The known compound 2-phenylnaphthalic anhydride was also isolated from the plant. The synthesis of one of the new pigments, and of some related compounds, is described.

Phenylphenalenones and related natural products from Wachendorfia thyrsiflora L.

“…Furthermore, lachnanthocarpone (7) was found in the roots of Wachendorfia paniculata (Edwards, 1974 1 R 1 , R 3 , R 4 , R 5 = H, R 2 , R 6 = OH 4 R 1 , R 2 , R 5 , R 6 = H, R 3 = OCH 3 , R 4 = OH 5 R 1 , R 2 , R 5 , R 6 = H, R 3 , R 4 = OH 7 R 1 , R 2 , R 3 , R 5 , R 6 = H, R 4 = OH 10 R 1 , R 2 , R 3 , R 4 , R 5 , R 6 = H 11 R 1 = CH 3 , R 2 , R 3 , R 4 , R 5 , R 6 = H 21 R 1 , R 3 , R 4 = H, R 2 , R 5 , R 6 = OH 23 R 1 , R 2 , R 3 , R 4 , R 5 = H, R 6 =OH 24 R 1 , R 2 , R 3 , R 4 = H, R 5 , R 6 = OH 25 R 1 , R 3 , R 4 , R 5 , R 6 = H, R 2 = OH Compound 7 was isolated from W. paniculata (Edwards, 1974). extracts identified, in addition to 4-6, 2-phenylnaphthalic anhydride (8) (Cooke and Thomas, 1975), and the (6''-O-allophanyl)-glucoside 9, which was first found in Xiphidium caeruleum (Opitz et al, 2002a).…”

“…Based on the above NMR data and combined with MS data (see Section 4), the structure of compound 21 was elucidated as 2,4-dihydroxy-9-(3,4-dihydroxyphenyl)-1H-phenalen-1-one. The other seven known compounds were determined by 1 H NMR and/or 2D NMR spectroscopy, mass spectrometry, and comparison with reported data as thyrsiflorin (1) (Dora et al, 1991), haemofluorone B (22) (Cooke and Dagley, 1979), anigorufone (10), hydroxyanigorufone (23), dihydroxyanigorufone (24) (Cooke and Thomas, 1975), 4-hydroxyanigorufone (25), and anigorootin (6) (Hö lscher and Schneider, 1999).…”

Synthesis of [phenyl‐13C6]lachnanthocarpone and other 13C‐labelled phenylphenalenones

“…Labelled anigorufone 19 ( 13 C-2) and 4 0 -methoxyanigorufone 20 ( 13 C-8) were synthesized starting from perinaphthenone (9). [U- 13 C]bromophenol and [1-…”

Chemical constituents from the aerial parts of Musella lasiocarpa

“…The known compounds were identified by comparison of their spectroscopic data with published values, as rel-(3S,4aR,10bR)-3-(4′-hydroxyphenyl)-8-hydroxy-9-methoxy-4a, 5,6,10b-tetrahydro-3H-naphtho[2,1-b]pyran (1, musellarin A), 7 2-hydroxy-9-(4′-hydroxyphenyl)-1H-phenalen-1-one (6, hydroxyanigorufone), 15 2-methoxy-9-(4′-hydroxyphenyl)-1H-phenalen-1-one (7), 8 2-hydroxy-9-(3′,4′-dihydroxyphenyl)-1H-phenalen-1-one (8, dihydroxyanigorufone), 15 2-hydroxy-4-(3′,4′-dihydroxyphenyl)-1H-phenalen-1-one (11), 16 2-hydroxy-4-(4′-methoxyphenyl)-1H-phenalen-1-one (12), 17 (4E,6E)-1,7-bis(4-hydroxyphenyl)-hepta-4,6-dien-3-one (14), 18 (4E,6E)-1-(3′,4′-dihydroxyphenyl)-7-(4′′-hydroxyphenyl)-hepta-4,6-dien- 20 Previously, a number of phenylphenalenones with moderate cytotoxic effects against P388 murine leukemia cell line were reported from Haemodorum simplex. 21 In this study, except for 13, 16, and 17, the other compounds were evaluated for cytotoxicity against five human tumor cell lines (HL-60, SMMC-7721, A-549, MCF-7, and SW480) using the MTT method.…”