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. 2015 Dec 11;39(3):492–513. doi: 10.1111/pce.12630

Table 1.

Phenylphenalenones isolated by HPLC and identified by 1D and 2D NMR spectroscopy and HRMS from ‘KTR’ leaves after infection with M. fijiensis strain E22

No. R t (min) Compound Chemical structure Occurrence in Musa
‘Williams’ ‘KTR’
1 74.77 2‐(4′‐Hydroxyphenyl)‐1,8‐naphthalic anhydride

chemical structure image

+ +
2 82.12 trans‐2,3‐Dihydro‐2,3‐dihydroxy‐9‐phenylphenalenone

chemical structure image

+ +
3 85.30 2‐Phenyl‐1,8‐naphthalic anhydride

chemical structure image

+ +
4 87.81 2‐Hydroxy‐4‐(4′‐hydroxyphenyl)‐1H‐phenalen‐1‐one (irenolone)

chemical structure image

+ +
5 89.35 2‐Hydroxy‐9‐(4′‐hydroxyphenyl)‐1H‐phenalen‐1‐one (hydroxyanigorufone)

chemical structure image

+ +
6 89.99 2‐Methoxy‐9‐(4′‐hydroxyphenyl)‐1H‐phenalen‐1‐one

chemical structure image

+
7 101.62 Methoxyanigorufone

chemical structure image

+
8 102.92 Dihydroxyanigorootin

chemical structure image

+ +
9 104.20 Anigorufone

chemical structure image

+ +
10 105.89 2‐Hydroxy‐9‐(4′‐methoxyphenyl)‐1H‐phenalen‐1‐one (4′‐O‐methylanigorufone)

chemical structure image

+
11 107.55 Isoanigorufone

chemical structure image

+
12 108.84 2‐Hydroxy‐4‐(4′‐methoxyphenyl)‐1H‐phenalen‐1‐one (4′‐O‐methylirenolone)

chemical structure image

+ +
13 118.98 3,3′‐bis‐Hydroxyanigorufone

chemical structure image

+ +
14 120.64 Hydroxyanigorootin

chemical structure image

+
15 121.94 Anigorootin

chemical structure image

+ +

Occurrence of the metabolites is represented by (+) or absence/not detectable (−).

HPLC, high‐performance liquid chromatography; KTR, Khai Thong Ruang; NMR, nuclear magnetic resonance; 1D, one‐dimensional; 2D, two‐dimensional.