ORCID Profile
0000-0002-2376-4260
Current Organisation
RMIT University
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Research Topics
In Research Link Australia (RLA), "Research Topics" refer to ANZSRC FOR and SEO codes. These topics are either sourced from ANZSRC FOR and SEO codes listed in researchers' related grants or generated by a large language model (LLM) based on their publications.
Top 5 Research Topics
ANZSRC Field of Research (FoR)
Medicinal and Biomolecular Chemistry | Characterisation of Biological Macromolecules | Organic Chemistry | Biological And Medical Chemistry | Separation Science | Pharmaceutical Sciences And Pharmacy | Organic Chemical Synthesis | Biologically Active Molecules | Chemical Characterisation of Materials | Structural Chemistry and Spectroscopy | Structural Biology (incl. Macromolecular Modelling) |
ANZSRC Socio-Economic Objective (SEO)
Expanding Knowledge in the Chemical Sciences | Expanding Knowledge in the Biological Sciences | Treatments (e.g. chemicals, antibiotics) | Treatments (e.g. chemicals, antibiotics) | Chemical sciences
Related Links
Publications
Chemical Profiling (HPLC-NMR & HPLC-MS), Isolation, and Identification of Bioactive Meroditerpenoids from the Southern Australian Marine Brown Alga Sargassum paradoxum
Publisher: MDPI AG
Date: 29-12-2014
DOI: 10.3390/MD13010102
Application of HPLC-NMR in the identification of plocamenone and isoplocamenone from the marine red alga Plocamium angustum
Publisher: MDPI AG
Date: 24-09-2012
DOI: 10.3390/MD10092089
Antimicrobial Evaluation of the Constituents Isolated From Macropidia fuliginosa (Hook.) Druce
Publisher: SAGE Publications
Date: 10-2019
Abstract: Six compounds previously isolated and reported from Macropidia fuliginosa were evaluated for antimicrobial activity against 11 different microbial strains, with all compounds displaying broad spectrum activity. In addition, the compounds were also assessed for their antiproliferative activity and cytotoxicity. Further investigation of M. fuliginosa has led to the discovery of a previously described acenaphthylenediol from the bulbs of the plant.
Application of HPLC-NMR for the rapid chemical profiling of a Southern Australian Sponge, Dactylospongia sp
Publisher: Wiley
Date: 02-2009
Abstract: Rapid chemical profiling of the antitumour active crude dichloromethane extract of the marine sponge, Dactylospongia sp. was undertaken. A combination of both offline (HPLC followed by NMR and MS) and on-line (on-flow and stop-flow HPLC-NMR) chemical profiling approaches was adopted to establish the exact nature of the major constituents present in the dichloromethane extract of this sponge. On-flow HPLC-NMR analysis was employed to initially identify components present in the dichloromethane extract, while stop-flow HPLC-NMR experiments were then conducted on the major component present, resulting in the partial identification of pentaprenylated p-quinol (5). Subsequent off-line RP semi-preparative HPLC isolation of 5 followed by detailed spectroscopic analysis using NMR and MS permitted the complete structure to be established. This included the first complete carbon NMR chemical shift assignment of 5 based on the heteronuclear 2-D NMR experiments, together with the first report of its antitumour activity. This study represents one of the few reports describing the application of HPLC-NMR to chemically profile secondary metabolites from a marine organism.
Chemical Composition of Salacca wallichiana
Publisher: Springer Science and Business Media LLC
Date: 07-2018
Phytochemical studies of the southern Australian marine alga, Laurencia elata
Publisher: Elsevier BV
Date: 11-2011
DOI: 10.1016/J.PHYTOCHEM.2011.06.012
Abstract: Chemical profiling of the southern Australian marine alga Laurencia elata (Rhodomelaceae) employing on-flow and stop-flow HPLC-NMR methodology followed by off-line chemical investigations resulted in the isolation of two C16 chamigrenes, cycloelatanene A and B together with three previously reported sesquiterpenes, (3Z)-chlorofucin, pacifenol and elatenyne. The chemical structures were elucidated via detailed spectroscopic analyses.
Phytochemical Investigation of the Constituents Derived from the Australian Plant Macropidia fuliginosa
Publisher: American Chemical Society (ACS)
Date: 07-07-2015
DOI: 10.1021/ACS.JNATPROD.5B00161
Abstract: A phytochemical study of the flowers and bulbs derived from the Australian plant Macropidia fuliginosa, involving hyphenated spectroscopic methodologies (HPLC-NMR and HPLC-MS), together with conventional isolation strategies, resulted in the identification of 16 constituents (1, 2, 4-17) representative of six different structural classes. Six new compounds (12-17) were identified from the bulbs of the plant. The isolated compounds were assessed for antimicrobial activity, and compound 8 was found to be more potent against P. aeruginosa than icillin.
Phytochemical Profiling and Biological Activity of the Australian Carnivorous Plant, Drosera magna
Publisher: American Chemical Society (ACS)
Date: 25-02-2021
A new lipid from an australian marine sponge, Callyspongia sp
Publisher: Wiley
Date: 06-1997
DOI: 10.1007/S11745-997-0086-0
Abstract: A specimen of the sponge Callyspongia sp. collected off the coast of New South Wales, Australia, has yielded the novel lipid (6Z, 9Z, 12Z, 15Z)-1,6,9,12,15-octadecapenten-3-one, together with (4Z, 7Z, 10Z, 13Z)-4,7,10,13-hexadecatetraenoic acid.
Microfluidic valve geometries and possibilities for flow switching in gas chromatography
Publisher: SPIE
Date: 26-12-2009
DOI: 10.1117/12.814896
Rapid Dereplication and Identification of the Bioactive Constituents from the Fungus, Leucocoprinus birnbaumii
Publisher: SAGE Publications
Date: 2015
DOI: 10.1177/1934578X1501000124
Abstract: A series of fatty acids were rapidly dereplicated and partially identified from the flowerpot fungus, Leucocoprinus birnbaumii using HPLC-NMR and HPLC-MS. Subsequent off-line isolation unequivocally established the structures, and anti-microbial testing concluded that the fatty acids displayed moderate but selective anti-microbial activity. This represents the first report of these compounds occurring in this particular terrestrial fungus.
Absolute Configuration Determination of Retroflexanone Using the Advanced Mosher Method and Application of HPLC-NMR
Publisher: MDPI AG
Date: 12-06-2018
DOI: 10.3390/MD16060205
Corrigendum to “Phenylphenalenones and oxabenzochrysenones from the Australian plant Haemodorum simulans” [Phytochemistry 95 (2013) 351–359]
Publisher: Elsevier BV
Date: 12-2013
Coproverdine, a Novel, Cytotoxic Marine Alkaloid from a New Zealand Ascidian
Publisher: American Chemical Society (ACS)
Date: 27-08-2002
DOI: 10.1021/NP010594Z
Abstract: The crude extract of a New Zealand ascidian displayed antitumor activity. Bioassay-directed fractionation yielded a novel alkaloid, coproverdine (1). The structure of 1 was assigned on the basis of detailed spectroscopic analysis. Coproverdine (1) was responsible for the antitumor activity of the crude extract.
Application of microscale-preparative multidimensional gas chromatography with nuclear magnetic resonance spectroscopy for identification of pure methylnaphthalenes from crude oils
Publisher: Elsevier BV
Date: 12-2008
DOI: 10.1016/J.CHROMA.2008.10.102
Abstract: Mass spectrometry is often insufficient to distinguish between structural isomers, requiring confirmation using NMR spectroscopy. Here, a novel preparative technique based upon capillary multidimensional gas chromatography to isolate pure volatile components from complex s les is described. The method was developed through isolation of 1,4-dimethoxybenzene (5.2 microg, 10 injections) from a peppermint essential oil. Then isomers of 1- and 2-methylnaphthalene were isolated from a complex crude oil in sufficient amounts (3.1 microg, 38 injections and 5.0 microg, 35 injections) for discrimination using (1)H NMR spectroscopy. This methodology is applicable to identify any volatile molecule in complex matrices requiring confirmation using NMR spectroscopy.
A New Furanoditerpene From a Southern Australian Marine Sponge, Thorectandra choanoides
Publisher: CSIRO Publishing
Date: 1995
DOI: 10.1071/CH9951903
Abstract: A specimen of the marine sponge Thorectandra choanoides from Bass Strait, Australia, has yielded the new furanoditerpene (7), the structure of which was secured by spectroscopic analysis.
Absolute Stereochemistry of Puupehenone and Related Metabolites
Publisher: American Chemical Society (ACS)
Date: 1996
DOI: 10.1021/NP9603838
A New Sesquiterpene Alcohol from an Antarctic sponge
Publisher: Informa UK Limited
Date: 05-1995
Phytochemical analysis of the Southern Australian marine alga, Plocamium mertensii using HPLC-NMR
Publisher: Wiley
Date: 09-2008
DOI: 10.1002/PCA.1075
Abstract: Over the last decade HPLC-NMR has become a robust analytical technique that has been applied to a wide range of studies, particularly plant extracts. There have been only a few applications of the use of HPLC-NMR to profile marine natural product extracts and no studies involving marine algae. The marine alga selected for this study belongs to the genus Plocamium, which is a well known source of polyhalogenated monoterpenes. To chemically profile the marine alga P. mertensii, using a combination of on-line (HPLC-NMR) and off-line approaches. P. mertensii was extracted with 3:1 methanol-dichloromethane and subsequently partitioned into dichloromethane and methanol-soluble fractions. The methanol partition was exclusively profiled by HPLC-NMR (on-flow, stop-flow and time-slice experiments) whilst the dichloromethane partition was investigated by conventional isolation and purification procedures. HPLC-NMR analysis of the methanol partition partially identified the presence of the major compounds 7, 13, 27 and 37, the structures of which were unequivocally elucidated by off-line characterisation of the dichloromethane partition. Two additional minor metabolites (3 and 8) present in the dichloromethane partition were only tentatively identified as these co-occurred in a mixture with compounds 7 and 13. As a result of this study a number of chemical shift reassignments were made for compound 37. This is one of the few reports describing the application of HPLC-NMR to rapidly profile or dereplicate a marine organism and the first application of HPLC-NMR to successfully profile the chemistry of a marine alga.
Multiple component isolation in preparative multidimensional gas chromatography with characterisation by mass spectrometry and nuclear magnetic resonance spectroscopy
Publisher: Elsevier BV
Date: 07-2009
DOI: 10.1016/J.CHROMA.2009.06.006
Abstract: The preparative scale isolation of multiple components from an essential oil matrix is described using multidimensional gas chromatography (prep-MDGC) which allows their further characterisation by mass spectrometry and nuclear magnetic resonance (NMR) spectroscopy. Menthol, linalyl acetate, carvone and geraniol were isolated in idually, and were also collected in various combinations. It was demonstrated to be possible to collect multiple selected components from numerous repeat injections of the s le, to permit increased mass recovery from an external cryotrap collection device. Peak retention times remained reproducible (<0.3s) over the repeated injections and switching events. This methodology may be utilised to confirm peak identity or to produce unique mixed-component reference standards, for instance to allow their identification in other s les using GC/MS, or identify them in comprehensive two-dimensional gas chromatography (GCxGC) analysis.
A Bioactive Diterpene from Smallanthus sonchifolius
Publisher: SAGE Publications
Date: 10-2008
DOI: 10.1177/1934578X0800301016
Abstract: The dichloromethane extract of the air-dried leaves and freeze-dried tubers of Smallanthus sonchifolius afforded ent-kaurenoic acid (1). The structure of 1 was elucidated by extensive 1D and 2D NMR spectroscopy and was found to exhibit significant analgesic and anti-inflammatory activities. Ent-kaurenoic acid (1), dissolved in dimethylsulfoxide, also displayed potential anti-diabetes and anti-toxicity activity. In addition, 1 showed low antimicrobial activities against E. coli, P. aeruginosa, S. aureus, C. albicans and T. mentagrophytes, but was found to be inactive against B. subtilis and A. niger.
Chemical Constituents of Hoya buotii Kloppenb
Publisher: Journal of Applied Pharmaceutical Science
Date: 2015
Pen-Enabled, Real-Time Student Engagement for Teaching in STEM Subjects
Publisher: American Chemical Society (ACS)
Date: 28-06-2017
Spongiaquinone Revisited: Structural and Stereochemical Studies on Marine Sesquiterpene/Quinones From a Southern Australian Marine Sponge, Spongia sp.
Publisher: CSIRO Publishing
Date: 1993
DOI: 10.1071/CH9931245
Abstract: A chemical investigation of a large purple sponge, Spongia sp., from the Great Australian Bight, resulted in the isolation of a new sesquiterpene/quinone (8), together with the known compounds dehydrocyclospongiaquinone-1 (4) and spongiaquinone (2). The last compound was also isolated as the potassium salt (9), this being the first recorded account of a naturally occurring marine sesquiterpene/quinone salt. The structure for (8) was assigned by detailed spectroscopic analysis. A re-investigation into the stereostructure of spongiaquinone (2) resulted in the first unambiguous assignment of absolute stereochemistry, and uncovered the peculiar chiroptical properties of spongiaquinone (2) and its potassium salt (9).
Dereplication and Chemotaxonomical Studies of Marine Algae of the Ochrophyta and Rhodophyta Phyla
Publisher: MDPI AG
Date: 30-04-2015
DOI: 10.3390/MD13052714
Natural Compounds from the Marine Brown Alga Caulocystis cephalornithos with Potent In Vitro-Activity against the Parasitic Nematode Haemonchus contortus
Publisher: MDPI AG
Date: 09-07-2020
Abstract: Eight secondary metabolites (1 to 8) were isolated from a marine sponge, a marine alga and three terrestrial plants collected in Australia and subsequently chemically characterised. Here, these natural product-derived compounds were screened for in vitro-anthelmintic activity against the larvae and adult stages of Haemonchus contortus (barber’s pole worm)—a highly pathogenic parasitic nematode of ruminants. Using an optimised, whole-organism screening system, compounds were tested on exsheathed third-stage larvae (xL3s) and fourth-stage larvae (L4s). Anthelmintic activity was initially evaluated on these stages based on the inhibition of motility, development and/or changes in morphology (phenotype). We identified two compounds, 6-undecylsalicylic acid (3) and 6-tridecylsalicylic acid (4) isolated from the marine brown alga, Caulocystis cephalornithos, with inhibitory effects on xL3 and L4 motility and larval development, and the induction of a “skinny-straight” phenotype. Subsequent testing showed that these two compounds had an acute nematocidal effect (within 1–12 h) on adult males and females of H. contortus. Ultrastructural analysis of adult worms treated with compound 4 revealed significant damage to subcuticular musculature and associated tissues and cellular organelles including mitochondria. In conclusion, the present study has discovered two algal compounds possessing acute anthelmintic effects and with potential for hit-to-lead progression. Future work should focus on undertaking a structure-activity relationship study and on elucidating the mode(s) of action of optimised compounds.
5-epi-Isospongiaquinone, a New Sesquiterpene/Quinone Antibiotic from an Australian Marine Sponge, Spongia hispida
Publisher: American Chemical Society (ACS)
Date: 11-1992
DOI: 10.1021/NP50089A012
Abstract: An Australian marine sponge, Spongia hispida, has been found to contain a new sesquiterpene/quinone identified by detailed spectroscopic analysis and chemical derivatization as the antibiotic 5-epi-isospongiaquinone [3]. The complete stereostructure for 3 was determined by detailed spectroscopic analysis and chemical correlation with the known marine natural product isospongiaquinone [2]. Co-occurring with 3 was an ethylated analogue, 5-epi-homoisospongiaquinone [4], which was speculated to be an artifact of the isolation process. A revised structure 15 for the known marine metabolite, smenorthoquinone [13], is also presented.
Application of Networking Approaches to Assess the Chemical Diversity, Biogeography, and Pharmaceutical Potential of Verongiida Natural Products
Publisher: MDPI AG
Date: 18-10-2021
DOI: 10.3390/MD19100582
Abstract: This study provides a review of all isolated natural products (NPs) reported for sponges within the order Verongiida (1960 to May 2020) and includes a comprehensive compilation of their geographic and physico-chemical parameters. Physico-chemical parameters were used in this study to infer pharmacokinetic properties as well as the potential pharmaceutical potential of NPs from this order of marine sponge. In addition, a network analysis for the NPs produced by the Verongiida sponges was applied to systematically explore the chemical space relationships between taxonomy, secondary metabolite and drug score variables, allowing for the identification of differences and correlations within a dataset. The use of scaffold networks as well as bipartite relationship networks provided a platform to explore chemical ersity as well as the use of chemical similarity networks to link pharmacokinetic properties with structural similarity. This study paves the way for future applications of network analysis procedures in the field of natural products for any order or family.
HPLC-NMR and HPLC-MS Profiling and Bioassay-Guided Identification of Secondary Metabolites from the Australian Plant Haemodorum spicatum
Publisher: American Chemical Society (ACS)
Date: 19-06-2015
DOI: 10.1021/NP500905G
Abstract: Phytochemical dereplication was undertaken on the bioactive crude CH2Cl2 extract of the bulbs of the Australian plant Haemodorum spicatum employing HPLC-NMR and HPLC-MS methodologies. Subsequent bioassay-guided isolation resulted in the identification of two new phenylphenalenones [haemoxiphidone (8) and haemodoronol (17)] and two new chromenes [haemodordione (13) and haemodordiol (16)], together with seven previously described compounds. Antimicrobial testing showed that the compounds displayed selective antibacterial activity. Most noteworthy were the activities displayed by several of the compounds against multi-drug-resistant Pseudomonas aeruginosa.
Phytochemical Profiling and Biological Testing of the Constituents of the Australian Plant Haemodorum brevisepalum
Publisher: American Chemical Society (ACS)
Date: 15-11-2021
DOI: 10.1021/ACS.JNATPROD.1C00509
Abstract: Phytochemical profiling was undertaken on the crude extracts of the bulbs, stems, and the fruits of
Application of the Crystalline Sponge Method to Revise the Structure of the Phenalenone Fuliginone
Publisher: MDPI AG
Date: 30-01-2017
Hericium erinaceus (Bull.: Fr) Pers. cultivated under tropical conditions: isolation of hericenones and demonstration of NGF-mediated neurite outgrowth in PC12 cells via MEK/ERK and PI3K-Akt signaling
Publisher: Royal Society of Chemistry (RSC)
Date: 2014
DOI: 10.1039/C4FO00452C
Abstract: Hericium erinaceus is an edible and medicinal mushroom used traditionally to improve memory.
Cometins (A-C), New Furanosesterterpenes From an Australian Marine Sponge, Spongia sp.
Publisher: CSIRO Publishing
Date: 1992
DOI: 10.1071/CH9921255
Abstract: The known marine furanosesterterpene furospinosulin-1 (1), together with three new furanosesterterpenes, namely cometin-A (2), cometin-B (3) and cometin-C (4), were isolated from a marine sponge, Spongia sp., collected during commercial trawling operations in the Great Australian Bight. The structures of these metabolites were determined by detailed spectroscopic analysis and chemical derivatization . The antibiotic property of the crude ethanol extract of this sponge was attributed solely to the furanosesterterpene tetronic acid cometin -A (2).
Chemical constituents of the lichen, Candelaria concolor: A complete NMR and chemical degradative investigation
Publisher: Informa UK Limited
Date: 10-07-2009
DOI: 10.1080/14786410802682536
Abstract: A detailed chemical and spectroscopic investigation of the terrestrial lichen Candelaria concolor has yielded several lichenic metabolites belonging to the pulvinic acid series, as well as several depside derivatives including pulvinic dilactone (1), vulpinic acid (4) and calycin (5). The chemical transformation of 1 to pulvinic acid (3) is reported for the first time, as is the conversion of atranorin (6) to 5-chloroatranorin (7) and then finally to 5,5'-dichloroatranorin (8) under very mild conditions. Also presented is the complete 1D and 2D NMR assignment for compounds 1, 3, 4, 5 and 8, including partial NMR chemical shift assignments for the unstable depside (7). Previously, these metabolites had only been partially assigned by NMR spectroscopy.
Chemical Constituents of Hoya cagayanensis C. M. Burton
Publisher: Journal of Applied Pharmaceutical Science
Date: 2017
Axinellamines A−D, Novel Imidazo−Azolo−Imidazole Alkaloids from the Australian Marine Sponge Axinella sp.
Publisher: American Chemical Society (ACS)
Date: 14-01-1999
DOI: 10.1021/JO981034G
Abstract: Four imidazo-azolo-imidazole alkaloids, axinellamines A-D, have been isolated from an Australian marine sponge, Axinella sp. (order: Halichondrida: family: Axinellidae). These compounds contain a unique perhydrocyclopenta-imidazo-azolo-imidazole carbon skeleton. Three of these compounds had bactericidal activity against Helicobacter pylori at 1000 &mgr M.
Morphological and genetic diversity of Momordica cochinchinenesis (Cucurbitaceae) in Vietnam and Thailand
Publisher: Springer Science and Business Media LLC
Date: 12-03-2016
Selected applications of NMR spectroscopy
Publisher: CRC Press
Date: 13-10-2014
DOI: 10.1201/B17535
Cycloelatanene A and B: absolute configuration determination and structural revision by the crystalline sponge method
Publisher: Royal Society of Chemistry (RSC)
Date: 2017
DOI: 10.1039/C6SC04288K
Abstract: The crystalline sponge method revealed the absolute configuration of cycloelatanene A and B.
NMR spectroscopy: Structure elucidation of cycloelatanene A: A natural product case study
Publisher: Humana Press
Date: 2013
DOI: 10.1007/978-1-62703-577-4_8
Abstract: The structure elucidation of new secondary metabolites derived from marine and terrestrial sources is frequently a challenging task. The hurdles include the ability to isolate stable secondary metabolites of sufficient purity that are often present in <0.5 % of the dry weight of the s le. This usually involves a minimum of several chromatographic purification steps. The second issue is the stability of the compound isolated. It must always be assumed when dealing with the isolation of natural products that the compound may rapidly degrade during and/or after the isolation, due to sensitivity to light, air oxidation, and/or temperature. In this way, precautions need to be taken, as much as possible to avoid any such chemical inter-conversions and/or degradations. Immediately after purification, the next step is to rapidly acquire all analytical spectroscopic data in order to complete the characterization of the isolated secondary metabolite(s), prior to any possible decomposition. The final hurdle in this multiple step process, especially in the acquisition of the NMR spectroscopic and other analytical data (mass spectra, infrared and ultra-violet spectra, optical rotation, etc.), is to assemble the structural moieties/units in an effort to complete the structure elucidation. Often ambiguity with the elucidation of the final structure remains when structural fragments identified are difficult to piece together on the basis of the HMBC NMR correlations or when the relative configuration cannot be unequivocally identified on the basis of NOE NMR enhancements observed. Herein, we describe the methodology used to carry out the structure elucidation of a new C16 chamigrene, cycloelatanene A (5) which was isolated from the southern Australian marine alga Laurencia elata (Rhodomelaceae). The general approach and principles used in the structure determination of this compound can be applied to the structure elucidation of other small molecular weight compounds derived from either natural or synthetic sources.
Lamellarins O and P: New Aromatic Metabolites From the Australian Marine Sponge Dendrilla cactos
Publisher: CSIRO Publishing
Date: 1994
DOI: 10.1071/CH9941919
Abstract: A specimen of Dendrilla cactos collected during trawling operations in Bass Strait, Australia, has yielded two new alkaloids, lamellarin-O (17) and lamellarin-P (18). Both these metabolites are ex les of the lamellarin structure class, previously reported from tunicates and a mollusc however, in these ex les the pyrrole ring system is not fused to adjacent aromatic rings. The structures of (17) and (18) were secured by spectroscopic analysis and partial synthesis.
Pinastric acid revisited: A complete NMR and X-ray structure assignment
Publisher: Informa UK Limited
Date: 04-2007
DOI: 10.1080/14786410701194484
Abstract: Chemical investigation of a terrestrial lichen has yielded the pulvinic acid derivative pinastric acid (4). The structure of 4 was secured by detailed spectroscopic analysis as well as via a single X-ray diffraction study. This is the first report of the X-ray structure and 2D NMR assignment of pinastric acid (4). Pinastric acid (4) displayed antitumour, antiviral and antimicrobial (both antibacterial and antifungal) activities. Whilst the antiviral and antimicrobial activities are consistent with previous findings of 4 this is the first report of the antitumour properties for the compound.
Naphthalene aglycones and glycosides from the australian medicinal plant, dianella callicarpa
Publisher: Georg Thieme Verlag KG
Date: 25-05-2009
Abstract: The crude extract of the roots from the Australian medicinal plant Dianella callicarpa (Liliaceae) displayed significant antimicrobial and antiviral activities. This prompted a chemical investigation, resulting in the isolation of the new naphthalene glycoside, dianellose (10), together with dianellin (1), dianellidin (2), dianellinone (3), stellalderol (9) and 5-hydroxydianellin (11). The structures for compounds 1, 9 and 10 were secured by detailed spectroscopic analyses, while compounds 2, 3 and 11 were identified on the basis of comparisons to literature data. Whilst the chemistry of the genus Dianella has previously been investigated, we report the first isolation of stellalderol (9) from this genus, together with the chemical and biological evaluation of the callicarpa species. Biological evaluation of the isolated compounds established that 2 showed antiviral and mild antimicrobial properties and that compounds 1, 9 and 10 displayed moderate antitumour activities.
Meroditerpenoids from the southern Australian marine brown alga Sargassum fallax
Publisher: Elsevier BV
Date: 2009
DOI: 10.1016/J.PHYTOCHEM.2008.12.007
Abstract: Chemical investigation of the southern Australian marine brown alga Sargassum fallax resulted in the isolation of three meroditerpenoids fallahydroquinone, fallaquinone and fallachromenoic acid together with the previously reported compounds sargaquinone [isolated and identified in a mixture with sargaquinoic acid], sargahydroquinoic acid, sargaquinoic acid and sargachromenol. As a result of this study the complete 2D NMR characterisation for sargaquinoic acid and sargahydroquinoic acid can now be reported for the first time. All structures were elucidated by detailed spectrometric analysis. Sargaquinoic acid and sargahydroquinoic acid displayed moderate antitumour activity.
Distribution, biosynthesis, and biological activity of phenylphenalenone-type compounds derived from the family of plants, Haemodoraceae
Publisher: Royal Society of Chemistry (RSC)
Date: 2019
DOI: 10.1039/C8NP00067K
Abstract: This review provides a summary of the current state of research concerning the unique specialised metabolites from Haemodoraceae.
RECENT ADVANCEMENTS IN HPLC-NMR AND APPLICATIONS FOR NATURAL PRODUCT PROFILING AND IDENTIFICATION
Publisher: Informa UK Limited
Date: 08-2011
Linear and Cyclic C18 Terpenoids from the Southern Australian Marine Brown Alga Cystophora moniliformis
Publisher: American Chemical Society (ACS)
Date: 08-2008
DOI: 10.1021/NP800201C
Abstract: Chemical investigation of the Southern Australian marine brown alga Cystophora moniliformis resulted in the isolation of two new cyclic epimeric terpene diols, moniliforminol A (25) and moniliforminol B (26), a new linear farnesylacetone derivative (27), and the previously described terpenoids 19-24. This study also resulted in the first complete 2D NMR characterization for compounds 21 to 24 as well as the first report of 24 as a natural product. All structures were elucidated by detailed spectroscopic analysis, with the relative configurations of 25 and 26 being established by selective 1D NOE NMR experiments. The absolute configuration of 26 was assigned on the basis of circular dichroism (CD), which also permitted that of 25 to be tentatively assigned.
β-Carboline Alkaloids from a New Zealand Marine Bryozoan, Cribricellina Cribraria
Publisher: Informa UK Limited
Date: 2003
DOI: 10.1080/1057563021000001063
Abstract: The crude extract of a New Zealand marine bryozoan Cribricellina cribraria was examined and resulted in the isolation of the previously described, 6-hydroxyharman (1) and the new beta-carboline metabolite, 8-hydroxyharman (2).
Bromophenolics from the Red Alga Polysiphonia decipiens
Publisher: MDPI AG
Date: 26-08-2019
DOI: 10.3390/MD17090497
Abstract: The isolation and the structure determination of a new bromophenolic compound, polysiphonol (10), as well as five previously reported compounds, (4–8), from the red alga Polysiphonia decipiens is reported. In addition, the absolute configuration of the natural product rhodomelol (8) could be unequivocally confirmed for the first time, and on biosynthetic grounds, the absolute configuration of polysiphonol (10) was tentatively suggested. Compounds 4–8 were evaluated for their antibacterial activity against both Gram-positive and Gram-negative bacteria, but none of the compounds showed any appreciable activity.
Determination of the Absolute Configuration of the Pseudo‐Symmetric Natural Product Elatenyne by the Crystalline Sponge Method
Publisher: Wiley
Date: 14-01-2016
Abstract: Elatenyne is a marine natural product that was isolated in 1986. Despite its simple 2,2'-bifuranyl backbone, its relative structure was only recently determined. The absolute configuration of elatenyne has still not been unequivocally confirmed because of its pseudo-meso core structure, which results in a specific rotation, [α]D , of almost zero. In this work, the structure of natural elatenyne was determined by the crystalline sponge method and the use of a porous coordination network (a crystalline sponge) capable of absorbing organic guests in the sponge, the absorbed guests are ordered and crystallographically observable. The crystalline sponge could differentiate between the two very similar alkyl side chains, and the absolute structure of elatenyne was thus reliably determined. The total amount required for the experiments was only approximately 100 μg, and the majority (95 μg) could be recovered after the experiments.
Lamellarins Q and R: New Aromatic Metabolites From an Australian Marine Sponge, Dendrilla cactos
Publisher: CSIRO Publishing
Date: 1995
DOI: 10.1071/CH9951491
Abstract: A specimen of Dendrilla cactos collected off the coast of New South Wales, Australia, has yielded two new alkaloids, lamellarins Q (19) and R (20), the structures of which were secured by spectroscopic analysis and by chemical derivatization.
Bioactive Marine Alkaloids
Publisher: Bentham Science Publishers Ltd.
Date: 07-2000
Evaluation of cytotoxic and apoptotic activities of Clinacanthus nutans (Burm. f.) Lindau leaves against D24 human melanoma cells
Publisher: Elsevier BV
Date: 09-2019
Phenylphenalenones from the Australian plant Haemodorum simplex
Publisher: American Chemical Society (ACS)
Date: 06-05-2009
DOI: 10.1021/NP900016H
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.
Natural Products of Marine Macroalgae from South Eastern Australia, with Emphasis on the Port Phillip Bay and Heads Regions of Victoria
Publisher: MDPI AG
Date: 28-02-2020
DOI: 10.3390/MD18030142
Abstract: Marine macroalgae occurring in the south eastern region of Victoria, Australia, consisting of Port Phillip Bay and the heads entering the bay, is the focus of this review. This area is home to approximately 200 different species of macroalgae, representing the three major phyla of the green algae (Chlorophyta), brown algae (Ochrophyta) and the red algae (Rhodophyta), respectively. Over almost 50 years, the species of macroalgae associated and occurring within this area have resulted in the identification of a number of different types of secondary metabolites including terpenoids, sterols/steroids, phenolic acids, phenols, lipids olyenes, pheromones, xanthophylls and phloroglucinols. Many of these compounds have subsequently displayed a variety of bioactivities. A systematic description of the compound classes and their associated bioactivities from marine macroalgae found within this region is presented.
Targeted Isolation of Antibiotic Brominated Alkaloids from the Marine Sponge Pseudoceratina durissima Using Virtual Screening and Molecular Networking
Publisher: MDPI AG
Date: 29-08-2022
DOI: 10.3390/MD20090554
Abstract: Many targeted natural product isolation approaches rely on the use of pre-existing bioactivity information to inform the strategy used for the isolation of new bioactive compounds. Bioactivity information can be available either in the form of prior assay data or via Structure Activity Relationship (SAR) information which can indicate a potential chemotype that exhibits a desired bioactivity. The work described herein utilizes a unique method of targeted isolation using structure-based virtual screening to identify potential antibacterial compounds active against MRSA within the marine sponge order Verongiida. This is coupled with molecular networking-guided, targeted isolation to provide a novel drug discovery procedure. A total of 12 previously reported bromotyrosine-derived alkaloids were isolated from the marine sponge species Pseudoceratina durissima, and the compound, (+)-aeroplysinin-1 (1) displayed activity against the MRSA pathogen (MIC: µg/mL). The compounds (1–3, 6 and 9) were assessed for their central nervous system (CNS) interaction and behavioral toxicity to zebrafish (Danio rerio) larvae, whereby several of the compounds were shown to induce significant hyperactivity. Anthelmintic activity against the parasitic nematode Haemonchus contorutus was also evaluated (2–4, 6–8).
Professor Frances Separovic AO
Publisher: CSIRO Publishing
Date: 2020
DOI: 10.1071/CHV73N3_FO
Method for small-molecule discovery based on microscale-preparative multidimensional gas chromatography isolation with nuclear magnetic resonance spectroscopy
Publisher: American Chemical Society (ACS)
Date: 23-07-2008
DOI: 10.1021/AC8007847
Abstract: Absolute chemical identification requires obtaining a pure compound followed by structure elucidation using spectroscopic techniques, principally NMR spectroscopy and mass spectrometry. Classical isolation techniques suffer from insufficient resolution for complex s les, requiring time-consuming fractionation in multiple steps. Here, a novel preparative technique based upon capillary column multidimensional gas chromatography (MDGC) with 2D NMR to resolve, isolate, and identify pure volatile components from a complex s le is described. As a model application, geraniol was isolated from an essential oil matrix using MDGC and quantitatively resolved from 15 partially coeluting compounds from the first column. Geraniol was recovered from 10 (8.6 microg) and 100 injections (77.6 microg purity >99%) for subsequent NMR analysis at 500 and 800 MHz (with cryoprobe). Proton and gCOSY NMR experiments were successfully performed at 12.3 microg/mL (10 injections), while gHSQC and gHMBC NMR experiments were obtained at 110.8 microg/mL (100 injections). This approach is applicable to the biodiscovery of volatile molecular species or, indeed, any volatile compound in a complex matrix that requires confirmation of component identity.
Correction to Phytochemical Profiling and Biological Activity of the Australian Carnivorous Plant, Drosera magna
Publisher: American Chemical Society (ACS)
Date: 23-06-2021
Comparison of cytotoxicity between extracts of Clinacanthus nutans (Burm. f.) Lindau leaves from different locations and the induction of apoptosis by the crude methanol leaf extract in D24 human melanoma cells
Publisher: Springer Science and Business Media LLC
Date: 20-09-2016
Comparative analysis of carotenoid content in Momordica cochinchinensis (Cucurbitaceae) collected from Australia, Thailand and Vietnam
Publisher: Springer Science and Business Media LLC
Date: 06-06-2017
HPLC–NMR and HPLC–MS investigation of antimicrobial constituents in Cystophora monilifera and Cystophora subfarcinata
Publisher: Elsevier BV
Date: 09-2015
DOI: 10.1016/J.PHYTOCHEM.2015.06.014
Abstract: The crude dichloromethane extracts of the marine brown algae Cystophora monilifera and Cystophora subfarcinata were subjected to phytochemical profiling. This enabled the structures of both new and known phloroglucinols to be dereplicated and proposed using HPLC-NMR and HPLC-MS. Subsequent isolation confirmed the presence of four new and eight previously reported compounds. Five of the isolated phloroglucinols displayed selective antimicrobial activity.
A Historical overview of natural products in drug discovery
Publisher: MDPI AG
Date: 16-04-2012
Phenylphenalenones and oxabenzochrysenones from the Australian plant Haemodorum simulans
Publisher: Elsevier BV
Date: 11-2013
DOI: 10.1016/J.PHYTOCHEM.2013.07.019
Abstract: Chemical investigation of the Australian plant Haemodorum simulans (Haemodoraceae) resulted in the isolation of two new phenylphenalenones, haemoxiphidone and haemodordioxolane from the bulbs together with the first report of an oxabenzochrysenone glycoside, haemodoroxychrysenose from the aerial parts of the plant. Also isolated were two previously described phenylphenalenones 5,6-dimethoxy-7-phenyl-1H,3H-naphtho[1,8-cd]pyran-1,3-dione and haemodorone and two oxabenzochrysenones 5-hydroxyl-2-methoxy-1H-naphtho[2,1,8-mna]xanthen-1-one and 5-methoxy-1H-naphtho[2,1,8-mna]xanthen-1-one. The X-ray structure of the phenylphenalenone 5,6-dimethoxy-7-phenyl-1H,3H-naphtho[1,8-cd]pyran-1,3-dione was secured for the first time. All compounds were deduced by detailed spectroscopic analyses. HPLC-NMR chemical profiling of an enriched fraction containing a mixture of haemodordioxolane and 5,6-dimethoxy-7-phenyl-1H,3H-naphtho[1,8-cd]pyran-1,3-dione facilitated the partial identification of these secondary metabolites. The structure previously assigned as xiphidone in our initial studies of this plant was re-assigned as the new isomer haemoxiphidone.
Contextualizing Learning Chemistry in First-Year Undergraduate Programs: Engaging Industry-Based Videos with Real-Time Quizzing
Publisher: American Chemical Society (ACS)
Date: 18-05-2017
Exploring resveratrol dimers as virulence blocking agents – Attenuation of type III secretion in Yersinia pseudotuberculosis and Pseudomonas aeruginosa
Publisher: Springer Science and Business Media LLC
Date: 07-02-2020
DOI: 10.1038/S41598-020-58872-0
Abstract: Bacterial infections continue to threaten humankind and the rapid spread of antibiotic resistant bacteria is alarming. Current antibiotics target essential bacterial processes and thereby apply a strong selective pressure on pathogenic and non-pathogenic bacteria alike. One alternative strategy is to block bacterial virulence systems that are essential for the ability to cause disease but not for general bacterial viability. We have previously show that the plant natural product (-)-hopeaphenol blocks the type III secretion system (T3SS) in the Gram-negative pathogens Yersinia pseudotuberculosis and Pseudomonas aeruginosa . (-)-Hopeaphenol is a resveratrol tetramer and in the present study we explore various resveratrol dimers, including partial structures of (-)-hopeaphenol, as T3SS inhibitors. To allow rapid and efficient assessment of T3SS inhibition in P. aeruginosa , we developed a new screening method by using a green fluorescent protein reporter under the control of the ExoS promoter. Using a panel of assays we showed that compounds with a benzofuran core structure i.e. viniferifuran, dehydro elopsin B, anigopreissin A, dehydro-δ-viniferin and resveratrol-piceatannol hybrid displayed significant to moderate activities towards the T3SS in Y. pseudotuberculosis and P. aeruginosa .
Limit of detection studies for application to natural product identification using high performance liquid chromatography coupled to nuclear magnetic resonance spectroscopy
Publisher: Elsevier BV
Date: 2015
DOI: 10.1016/J.CHROMA.2014.11.074
Abstract: In the pursuit of new natural products, the demand to rapidly identify compounds present, in ever decreasing amounts, in complex crude extracts has become a limiting factor. Despite improvements in HPLC-NMR hardware and pulse sequences, no extensive limit of detection (LOD) investigations have been reported for the acquisition of 2D NMR spectroscopic experiments acquired through HPLC-NMR. In this study the LOD for five key 1D and 2D NMR spectroscopic experiments have been established, using two reference compounds, including the on-flow (WET 1D proton), stop-flow (WET1D proton), gCOSY, HSQCAD and gHMBCAD NMR experiments. The LOD for all of the NMR experiments were within the range of 700ng to 1mg for the set of fixed experimental parameters implemented. For principle components in a complex multi-component mixture, this would allow for in situ compound identification. HPLC-NMR analysis was employed to investigate the principle components present in a marine brown alga crude extract, Cystophora subfarcinata.
Corymbones A and B, Phloroglucinols with Thyrotropin Releasing Hormone Receptor 2 Binding Affinity from the Flowers of Corymbia peltata
Publisher: American Chemical Society (ACS)
Date: 16-04-2008
DOI: 10.1021/NP0706567
Abstract: High-throughput screeing of a plant and marine invertebrate extract library to find natural products with rat thytotropin releasing hormone receptor 2 binding affinity led to the isolation of two new active acylphloroglucinols, corymbones A and B (1 and 2) from flowers of the Queensland tree Corymbia peltata. Their structures were assigned from interpretation of 2D NMR and high-resolution ESIMS data. Compounds 1 and 2 showed rat TRH receptor 2 binding affinity with IC 50 values of 23 and 19 microM, respectively.
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