Phenylphenalenones from the Australian Plant Haemodorum simplex

Abstract

Chemical investigation of the Australian plant Haemodorum simplex resulted in the isolation of three new phenylphenalenones, haemodorone (10), haemodorol (11), and haemodorose (12), together with the previously reported compounds 5, dilatrin (6), and xiphidone (8). The first complete 2D NMR characterization for all of the compounds isolated, including several chemical shift reassignments for dilatrin (6), is reported. In addition this is one of the few reports to discuss the isolation of new phenylphenalenones from an Australian medicinal plant. The crude extract of both the bulbaceous and aerial components of the plant exhibited varying degrees of antibacterial, antifungal, and antiviral activity, and only the bulbs displayed potent cytotoxic activity.

HPLC-NMR and HPLC-MS Profiling and Bioassay-Guided Identification of Secondary Metabolites from the Australian Plant Haemodorum spicatum

“…Of significance is the fact that the bulbs of H. spicatum are reported to have been used as a traditional medicine by the Australian Aborigines to treat dysentery. 38 The present investigation on the bulbs of H. spicatum has yielded two new [(haemoxiphidone (8) and haemodoronol (17)] and two previously reported phenylphenalenones (2 and 15), four known oxabenzochrysenones (1, 5, 11, and 12), and two new [haemodordione (13) and haemodordiol (16)] chromenes as well as a reported (3) chromene. For three (2,5, and 11) of the known compounds identified, this represents their first occurrence as natural products.…”

“…2,17,[27][28][29]39,40 Off-line isolation and subsequent characterization of peak D (Figure 1) confirmed this component to be the new phenylphenalenone haemoxiphidone (8), which was isolated as an orange solid. This particular compound was concurrently isolated within the research group from a separate Haemodorum species.…”

Nuclear Magnetic Resonance Spectroscopy for Structural Characterization of Bioactive Compounds

“…involving 1D ( 1 H, 13 C, and DEPT spectra) and 2D (COSY, HSQC, and HMBC spectra) NMR experiments [68]. Similar studies on the marine alga Laurencia filiformis led to the identification of the new potential antimicrobial compounds cycloisoallolaurinterol 55 and isoallolaurinterol 56 from their crude extract as well as the in situ monitoring of the chemical conversion between them [69] (Figure 7.24).…”

Chemical constituents from the aerial parts of Musella lasiocarpa

“…The molecular formula C 21 Figure 1). The HMBC correlations from H-3 at δ H 5.05 (1H, br s) to C-4a (δ C 68.1, d), C-2′ (δ C 112.1, d), and C-6′ (δ C 121.3, d) suggested the presence of a tetrahydropyran unit bearing an aromatic ring connected to C-3.…”

“…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. 22 Cisplation was used as the positive control.…”