Phenylphenalenones and oxabenzochrysenones from the Australian plant Haemodorum simulans

Phytochemical Profiling and Biological Testing of the Constituents of the Australian Plant Haemodorum brevisepalum

“…The HPLC chromatogram of the eighth fraction of the methanolic extract of the bulbs exhibited a number of chromatographic peaks with a λ max of 525 nm, suggesting OBCs were present within this fraction (Figure S154, Supporting Information). The major component of this fraction ( t R = 17.32 min, 3 , see Figure S155, Supporting Information) was isolated and subsequently elucidated via dereplication, primarily on the basis of comparison with other known OBCs isolated throughout this study ( 23 – 26 ) and reported previously in the literature. − , Its identity was determined as the previously reported oxabenzochrysenone 5-methoxy-1 H -naphtho­[2,1,8- mna ]­xanthen-1-one ( 3 ) . Of interest was the fact that this purified compound crystallized as thin orange plates upon refrigeration at −20 °C.…”

“…These characteristic UV profiles are indicative of the PhPs (λ max > 400 nm), OBCs (λ max > 500 nm), and PBICs (λ max < 400 nm); see Figures S135–S137, Supporting Information . The λ max values are used only as a guide to support the tentative structure class, since closely related compounds, such as the OBCOs, are also possible, for example, compound 1 . − ,, Diagnostic 13 C NMR chemical shifts for the carbonyl C-1 of the PhP (δ C ∼180), OBC (δ C ∼175), and PBIC (δ C ∼165) structure classes were supported by gHMBCAD correlations from nearby protons throughout the study (see Figures S138–S140, Supporting Information).…”

“…simulans , as well as H . spicatum ). − As part of our continuing efforts to profile plants of the Haemodorum genus, the present investigation involved a comprehensive phytochemical screening of the previously unstudied Australian endemic plant H . brevisepalum .…”

“…The complete NMR spectra for the 13 unreported compounds and the derivative are presented in Figures S4–S133, Supporting Information. The 17 previously reported compounds were identified as follows: four oxabenzochrysenone aglycones, 5-methoxy-1 H -naphtho­[2,1,8- mna ]­xanthen-1-one ( 3 ), 5-hydroxy-1 H -naphtho­[2,1,8- mna ]­xanthen-1-one ( 23 ), 5-hydroxy-2-methoxy-1 H -naphtho­[2,1,8- mna ]­xanthen-1-one ( 24 ), and 2,5-dimethoxy-1 H -naphtho­[2,1,8- mna ]­xanthen-1-one ( 25 ); an oxabenzochrysenone glycoside, haemodoroxychrysenose ( 26 ); two flavonol glycosides, quercetin-3- O -β- d -glucopyranoside ( 15 ) and quercetin-3- O -[β- d -glucopyranosyl-(1→6)-β- d -glucopyranoside] ( 16 ); three phenylbenzoisochromenone glycosides, 5-hydroxy-6- O -(β- d -glucopyranosyl)-7-phenyl-3 H -benzo­[ de ]­isochromen-1-one ( 17 ), 6- O -(β- d -glucopyranosyl)-(3 R/S )-3,5-dihydroxy-7-phenyl-3 H -benzo­[ de ]­isochromen-1-one ( 21 ), and 6- O -(β- d -glucopyranosyl)-(3 R/S )-3-carboxy-5-hydroxy-7-phenyl-3 H -benzo­[ de ]­isochromen-1-one ( 22 ); four phenylbenzoisochromenone aglycones, haemodordiol ( 27 ), 6-hydroxy-(3 R/S )-3,5-dimethoxy-7-phenyl-3 H -benzo­[ de ]­isochromen-1-one ( 28 ), 5-hydroxy-(3 R/S )-3,6-dimethoxy-7-phenyl-3 H -benzo­[ de ]­isochromen-1-one ( 29 ), and haemodorone ( 30 ); as well as two phenylphenalenone glycosides, lachnanthoside ( 19 ) and dilatrin ( 20 ) . Finally, any isolated compounds obtained in sufficient mass quantities and stability were evaluated for their antimicrobial and anthelmintic activity, with moderate activity observed against Staphylococcus aureus MRSA and slight activity observed against Pseudomonas aeruginosa and Candida albicans (Figure S134, Supporting Information).…”

Antimicrobial Evaluation of the Constituents Isolated From Macropidia fuliginosa (Hook.) Druce

“…In recent years, the Marine and Terrestrial Natural Product (MATNAP) research group has been extensively investigating the chemistry of plants that belong to the Haemodoraceae family. 1 -4 As part of our continuing efforts to chemically profile Australian plants derived from this family, Macropidia fuliginosa (Hook.) Druce, commonly known as the Black Kangaroo paw which is an endemic species of Western Australia, was recently investigated, with 16 compounds being reported from the bulbs and flowers of the plant.…”