ORCID Profile
0009-0008-6804-3572
Current Organisation
University of Wollongong
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Publisher: American Chemical Society (ACS)
Date: 17-04-2009
DOI: 10.1021/NP900030Y
Abstract: Three known compounds, stemofoline (1), (2'S)-hydroxystemofoline (2), and (11Z)-1',2'-didehydrostemofoline (3), along with two new alkaloids, stemaphylline (4) and stemaphylline-N-oxide (5), have been isolated from a root extract of Stemona aphylla. The structures of these alkaloids were determined on the basis of their spectroscopic data. The analysis of the crude dichloromethane extract by GC-MS in the EIMS mode showed the presence of alkaloids 1-4, the alkaloid 11, and stilbostemin R (12). The crude dichloromethane extract and 4 were tested for their comparative biological activities. The results of their acetylcholinesterase (AChE) inhibitory activities showed that the crude extract had higher activity than that of 4. The insecticidal properties of the crude extract and 4, using a topical application, showed that 4 had an activity similar to the positive control, methomyl, whereas the crude extract had much lower activity. Their antimicrobial activity against Escherichia coli ATCC 25922, Staphylococcus aureus ATCC 25923, Pseudomonas auruginosa ATCC 27853, and Candida albicans ATCC 90028 was weak (MIC 62.5-125 microg/mL, MBC 125-250 microg/mL, MFC 125 microg/mL) but much higher than that of the crude extract.
Publisher: American Chemical Society (ACS)
Date: 28-08-2004
DOI: 10.1021/NP049791Z
Abstract: Two new dihydrostemofoline alkaloids, 11(S),12(R)-dihydrostemofoline (3) and stemoburkilline (4), along with stemofoline (1) and 2'-hydroxystemofoline (2) have been isolated from a root extract of Stemona burkillii Prain. The structure and relative configuration of 3 have been determined via spectroscopic data and from comparison with synthetic 11(S),12(S)-dihydrostemofoline (5). The configuration of the exo-cyclic alkene group in 4 is tentively assigned as E on the basis of mechanistic considerations.
Publisher: American Chemical Society (ACS)
Date: 24-09-2003
DOI: 10.1021/NP030387U
Publisher: American Chemical Society (ACS)
Date: 17-02-2009
DOI: 10.1021/NP800806B
Abstract: The semisynthesis of the Stemona alkaloids (3'R)-stemofolenol (1), (3'S)-stemofolenol (2), methylstemofoline (3), and (3'S)-hydroxystemofoline (5) and the unnatural analogues (11E)-methylstemofoline (15) and 3'R-hydroxystemofoline (11) has been achieved starting from (11Z)-1',2'-didehydrostemofoline (4). This synthesis allowed, for the first time, access to diastereomerically enriched s les of 1 and 2 and the assignment of their absolute configurations at C-3'. These compounds were obtained in sufficient quantities to allow for their biological testing. In a quantitative assay as AChE inhibitors, (11Z)-1',2'-didehydrostemofoline (4) and (3'S)-hydroxystemofoline (5) were found to be the most active.
Publisher: American Chemical Society (ACS)
Date: 07-03-2014
DOI: 10.1021/NP400978X
Abstract: Four new stichoneurine-type alkaloids, stichoneurines F and G (1-2) and sessilistemonamines E and F (3-4), have been isolated from the root extracts of Stichoneuron caudatum. The structures and relative configurations of these alkaloids have been determined by spectroscopic methods and molecular modeling experiments. Compounds 1-4 were tested for their acetylcholinesterase (AChE) inhibitory activities against human AChE. Compound 3 showed significant inhibitory activity with an IC50 value of 9.1±0.15 μM.
Publisher: Elsevier BV
Date: 06-2012
Publisher: Elsevier BV
Date: 12-2013
DOI: 10.1016/J.JEP.2013.09.052
Abstract: The aerial components of Meconopsis simplicifolia (D. Don) Walpers are indicated in Bhutanese traditional medicine for treating malaria, coughs and colds, and the infections of the liver, lung and blood. This study is to validate the ethnopharmacological uses of this plant and also identify potent antimalarial drug leads through bioassays of its crude extracts and phytochemical constituents. Meconopsis simplicifolia (D. Don) Walpers was collected from Bhutan and its crude MeOH extract was subjected to acid-base fractionation. Through repeated extractions, separations and spectroscopic analysis, the alkaloids obtained were identified and tested for their antimalarial and cytotoxicity activities. Phytochemical studies resulted in the isolation of one new protoberberine type alkaloid which we named as simplicifolianine and five known alkaloids: protopine, norsanguinarine, dihydrosanguinarine, 6-methoxydihydrosanguinarine and oxysanguinarine. Among the five of the alkaloids tested, simplicifolianine showed the most potent antiplasmodial activities against the Plasmodium falciparum strains, TM4/8.2 (chloroquine-antifolate sensitive strain) and K1CB1 (multidrug resistant strain) with IC50 values of 0.78 μg/mL and 1.29 μg/mL, respectively. The compounds tested did not show any significant cytotoxicity activities against human oral carcinoma KB cells and normal Vero cells of African kidney epithelial cells. This study validated the traditional uses of the plant for the treatment of malaria and identified a new alkaloid, simplicifolianine as a potential antimalarial drug lead.
Publisher: Wiley
Date: 31-12-2021
Publisher: Elsevier BV
Date: 06-2014
DOI: 10.1016/J.JINORGBIO.2014.02.012
Abstract: Recent studies showed that the metal-coordinated non-steroidal anti-inflammatory drug (NSAID), copper indomethacin, reduced aberrant crypt formation in the rodent colon cancer model, while also exhibiting gastrointestinal sparing properties. In the present study, the stability and biological activity of three BiNSAIDs of the general formula [Bi(L)3]n, where L=diflunisal (difl), mefenamate (mef) or tolfenamate (tolf) were examined. NMR spectroscopy of high concentrations of BiNSAIDs (24h in cell medium, 37°C) indicated that their structural stability and interactions with cell medium components were NSAID specific. Assessment of cell viability using the [3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-tetrazolium]bromide (MTT) assay showed that the toxicity ranking of the BiNSAIDs paralleled those of the respective free NSAIDs: diflH<mefH<tolfH. While the IC50 values of the BiNSAIDs (ranging between 16 and 81μM) were lower than the free NSAIDs, it was apparent that the toxicity of the BiNSAIDs was due to the molar ratio of the three NSAID molecules contained in the BiNSAIDs, with the exception of [Bi(difl)3]. The highest cellular bismuth content was observed following treatment with [Bi(tolf)3]. Since NMR studies indicated that [Bi(tolf)3] was the most stable BiNSAID and that cellular uptake of bismuth correlated with structural stability it appears that bismuth uptake is assisted by the NSAID. Microprobe SR-XRF imaging showed that the intracellular fate of bismuth was independent of the specific BiNSAID treatment whereby all BiNSAID-treated cells showed bismuth accumulation in the cytoplasm within 24-h exposure. The size and location of the hot spots (0.3-5.8μm(2)), were consistent with cellular organelles such as lysosomes.
Publisher: Elsevier BV
Date: 07-2018
DOI: 10.1016/J.JCIS.2018.03.015
Abstract: Processing conditions deeply affect the mechanical, chemical and biological properties of elastomeric based nanocomposites. In this work, multi-walled carbon nanotubes (MWCNTs) were dispersed in poly(glycerol sebacate) (PGS) prepolymer, followed by curing under vacuum at 120 °C. It was observed an increase of the water contact angle with the amount of MWCNTs added, as well as the tensile strength and Young modulus, without compromising the elastomeric behaviour of the pristine PGS matrix. The cross-linking degree was determined by the Flory-Rehner swelling method and through the mechanical rubber elasticity model, and an increase of more than six-fold was observed, which demonstrates the chemical conjugation between the MWCNTs and the PGS polymer chains, resulting in stiff and elastomeric nanocomposites. Finally, in vitro cell culture of adult mouse hypothalamus neurons A59 cells showed good support for cell viability and stimulation for axons and dendrites growth. The unique features of these nanocomposites make them promise for biomedical applications, as soft tissue substrates with tailored mechanical properties.
Publisher: American Chemical Society (ACS)
Date: 02-03-2004
DOI: 10.1021/NP034066U
Abstract: A new pentacyclic Stemona alkaloid, stemocurtisinol (3), with a pyrido[1,2-a]azepine A,B-ring system, and the known pyrrolo[1,2-a]azepine alkaloid oxyprotostemonine (4) have been isolated from a root extract of S. curtisii. The structure and relative stereochemistry of stemocurtisinol was determined by spectral data interpretation and X-ray crystallography. This compound is a diastereoisomer of oxystemokerrin and has the opposite configuration at C-4 and C-19. The in idual alkaloid components showed significant larvicidal activity (IC(50) 4-39 ppm) on mosquito larvae (Anopheles minimus HO).
Publisher: American Chemical Society (ACS)
Date: 12-11-2005
DOI: 10.1021/NP050361Y
Abstract: Six new stemofoline alkaloids, (2'R)-hydroxystemofoline (5), (3'R)-stemofolenol (6), (3'S)-stemofolenol (7), 1',2'-didehydrostemofoline-N-oxide (8), the first C(19) stemofoline alkaloid, methylstemofoline (9), and the first glycosidated Stemona alkaloid, stemofolinoside (10), and three known alkaloids, (2'S)-hydroxystemofoline (2), (11Z)-1',2'-didehydrostemofoline (3), and (11E)-1',2'-didehydrostemofoline (4), have been isolated from a root extract of an unidentified Stemona species. The structure and relative configuration of these new alkaloids have been determined by spectral data interpretation and from semisynthetic studies.
Publisher: American Chemical Society (ACS)
Date: 27-06-2013
DOI: 10.1021/NP400268D
Abstract: Eight new compounds, fimbricalyxs B-D (1-3), fimbricalyxanhydrides A and B (4, 5), and fimbricalyxlactones A-C (6-8), together with three known compounds, trigonostemone (9), 3,6,9-trimethoxyphenanthropolone (10), and fimbricalyx A (11), were isolated from the roots of Strophioblachia fimbricalyx. The structures of the new compounds were elucidated on the basis of their spectroscopic data and, in the case of compounds 2, 4, and 7, confirmed by single-crystal X-ray crystallographic analysis. Compounds 1-4 and 8 were evaluated for their cytotoxicity (KB, MCF7, and NCI-H187 cancer cells) and antiplasmodial activity (Plasmodium falciparum, K1 multidrug-resistant strain). Fimbricalyx B (1) exhibited potent antiplasmodial activity with an IC50 value of 0.019 μM, while 4 was cytotoxic toward NCI-H187 cancer cells and showed antiplasmodial activities with IC50 values of 5.7 and 3.9 μM, respectively. In addition, the X-ray structure of 10 and the antiplasmodial activity of 11 are reported herein for the first time.
Publisher: American Chemical Society (ACS)
Date: 04-11-2010
DOI: 10.1021/NP100474Y
Abstract: The isolation of two new Stemona alkaloids, 1-hydroxyprotostemonine and stemocurtisine N-oxide, and a new benzofuran, stemofuran L, from the root extracts of Stemona curtisii is reported. The major known alkaloids from this plant extract, stemocurtisine, stemocurtisinol, and oxyprotostemonine, were also isolated along with oxystemokerrine N-oxide. The nonalkaloid components of this extract included a new benzofuran derivative, stemofuran L, the known stemofurans F, J, and K, dihydro-γ-tocopherol, and stigmasterol. Stemocurtisine and stemocurtisinol were converted to their respective N-oxides by oxidation. Stemocurtisine was converted to a tetracyclic derivative by oxidative cleavage of the γ-butyrolactone ring, while stemocurtisinol gave a novel lactam derivative by oxidative cleavage of the C-4 side chain under basic conditions. The acetylcholinesterase inhibitory activities of some known and new alkaloids and their derivatives are also reported. All were 10-20 times less active as acetylcholinesterase inhibitors than the pyrrolo[1,2-a]azepine Stemona alkaloids stemofoline and 1',2'-didehydrostemofoline. None of the stemofuran compounds showed significant antibacterial or antifungal activities.
Publisher: Wiley
Date: 14-05-2020
Publisher: Elsevier BV
Date: 11-2013
Publisher: Elsevier BV
Date: 04-2013
Publisher: Elsevier BV
Date: 05-2014
Publisher: Springer Science and Business Media LLC
Date: 11-05-2023
DOI: 10.1038/S41467-023-38384-X
Abstract: Aqueous Zn-ion batteries have attracted increasing research interest however, the development of these batteries has been hindered by several challenges, including dendrite growth, Zn corrosion, cathode material degradation, limited temperature adaptability and electrochemical stability window, which are associated with water activity and the solvation structure of electrolytes. Here we report that water activity is suppressed by increasing the electron density of the water protons through interactions with highly polar dimethylacetamide and trimethyl phosphate molecules. Meanwhile, the Zn corrosion in the hybrid electrolyte is mitigated, and the electrochemical stability window and the operating temperature of the electrolyte are extended. The dimethylacetamide alters the surface energy of Zn, guiding the (002) plane dominated deposition of Zn. Molecular dynamics simulation evidences Zn 2+ ions are solvated with fewer water molecules, resulting in lower lattice strain in the NaV 3 O 8 ·1.5H 2 O cathode during the insertion of hydrated Zn 2+ ions, boosting the lifespan of Zn|| NaV 3 O 8 ·1.5H 2 O cell to 3000 cycles.
Publisher: American Chemical Society (ACS)
Date: 23-04-2010
DOI: 10.1021/NP100137H
Abstract: Semisynthesis of the known Stemona alkaloids oxystemofoline (7) and methoxystemofoline (8) has been achieved starting from (11Z)-1',2'-didehydrostemofoline (6), which confirmed their structures and absolute configurations. The synthesis of (1'R)-hydroxystemofoline (9) helped establish this compound as a natural product from Stemona aphylla. (1'S)-Hydroxystemofoline (10) and a number of related analogues were also prepared. In a TLC bioautographic assay, 9 was found to be the most active acetylcholinesterase inhibitor, but it was not as active as galanthamine.
Publisher: American Chemical Society (ACS)
Date: 11-06-2003
DOI: 10.1021/NP020612S
Abstract: A new pentacyclic stemona alkaloid, stemocurtisine (2), with a novel pyrido[1,2-a]azapine A,B-ring system, has been isolated from a root extract of Stemona curtisii. The structure and relative stereochemistry was determined by spectral data interpretation and X-ray crystallography.
Publisher: Wiley
Date: 07-11-2000
Publisher: Elsevier BV
Date: 03-2015
Publisher: American Chemical Society (ACS)
Date: 30-01-2009
DOI: 10.1021/NP800755P
Abstract: Semisynthesis studies starting from (11Z)-1',2'-didehydrostemofoline (4) indicated that the known Stemona alkaloid stemoburkilline is the Z-isomer and not the E-isomer as initially reported. The semisynthesis involved conversion of (11Z)-1',2'-didehydrostemofoline (4) to 11(S),12(S)-dihydrostemofoline (3) followed by a stereoselective base-catalyzed ring-opening reaction to give (Z)-stemoburkilline (8). The same product was obtained using a similar synthetic protocol starting from isostemofoline (6) via a based-catalyzed ring-opening reaction of 11(S),12(R)-dihydrostemofoline (1). A re-examination of the crude root extracts of Stemona burkillii Prain and further NOE studies established stemoburkilline as the Z-isomer (8).
Publisher: Elsevier BV
Date: 07-2017
DOI: 10.1016/J.FITOTE.2017.06.002
Abstract: Three new 2-phenylnaphthalene derivatives, cherrevenaphthalenes A-C (1-3), and a new polyoxygenated cyclohexene derivative, (-)-uvaribonol F (4) together with six known compounds, 5-10, were isolated from the stem and root extracts of Uvaria cherrevensis (Annonaceae). The structures of all isolated compounds were elucidated by spectroscopic analysis. The structures of 3 and 4 were further confirmed by single crystal X-ray diffraction methods. Compound 2 exhibited modest antiplasmodial activity against the P. falciparum stains TM4/8.2 and K1CB1 with IC
Publisher: SAGE Publications
Date: 06-2013
DOI: 10.1177/1934578X1300800603
Abstract: A study of the hitherto unreported Stichoneuron halabalensis Inthachub led to the characterization of the known compounds (+)-α-tocopherol and ( R)-(+)-goniothalamin four known Stemona alkaloids, bisdehydoxystemoninine A (1), stemoninine (2), sessilistemonamine C (3) and sessilistemonamine A (4) and three new alkaloids, stichoneurine C (5), D (6) and E (7). The structures of these compounds were determined on the basis of their spectroscopic data. Alkaloid 7 showed significant inhibitory activity against electric eel acetylcholinesterase (AChE) (IC 50 5.90±0.084 μM), while goniothalamin and compounds 1 and 2 showed significant inhibitory activities against human AChE (IC 50 7.24±0.52, 5.52±0.13 and 3.74±0.09 μM, respectively).
Publisher: Royal Society of Chemistry (RSC)
Date: 2015
DOI: 10.1039/C5CC02901E
Abstract: Compatible with various common solvents, a new electrolyte salt NaDFOB has been studied, which enables excellent reversible capacity and high rate capability when used in Na/Na 0.44 MnO 2 half cells.
Publisher: American Chemical Society (ACS)
Date: 02-12-2010
DOI: 10.1021/NP100668S
Abstract: A new stemofoline alkaloid, (2'S)-hydroxy-(11S,12R)-dihydrostemofoline (3), new stemofurans M-R (8-13), and known compounds stemofoline (1), (2'S)-hydroxystemofoline (2), stemofuran E (4), stemofuran F (5), stemofuran J (6), and stilbostemin F (7) have been isolated from the root extracts of Stemona aphylla. The structures and relative configurations of these new compounds have been determined by spectroscopic data interpretation and from semisynthetic studies. These natural and semisynthetic alkaloids were tested for acetylcholinesterase inhibitory activities and were found to be 10-20 times less active than 1',2'-didehydrostemofoline itself. Stemofurans 4, 6, 8, 11, and 13 were tested for their antibacterial and antifungal activities. Three of these showed antibacterial activities against MRSA with MIC values of 15.6 μg/mL.
Publisher: SAGE Publications
Date: 10-2006
DOI: 10.1177/1934578X0600101001
Abstract: Two new tuberostemonine alkaloids, tuberostemonine L (3) and tuberostemonine M (4) and a new stemofoline alkaloid, (3′S)-hydroxystemofoline (5), along with two known alkaloids, (2′S)-hydroxystemofoline (1) and neotuberostemonine (2) have been isolated from a root extract of an unidentified Stemona species (Stemona sp.). The structure and relative configuration of these new alkaloids has been determined by spectral data interpretation, while the 3′S configuration of 5 was determined from NMR analysis of its (R)- and (S)-Mosher esters.
Publisher: CSIRO Publishing
Date: 2000
DOI: 10.1071/CH99108
Abstract: Caerin 4.1 (GLWQK5IKSAA10GDLAS15GIEVG20IKS-NH2) is an antibiotic peptide isolated from the Australian tree frog Litoria caerulea. Unlike caerin 1.1, the major peptide isolated from this species, caerin 4.1 has a narrow spectrum of antibiotic activity, e.g. it shows selective activity against Pasteurella haemolytica and Escherichia coli. Caerin 4.1 consists of 23 amino acid residues and is comparable in size with other wide-spectrum antibiotic peptides isolated from Australian hibians, e.g. caerin 1.1 and maculatin 1.1. An n.m.r. study in trifluoroethanol/water indicates that caerin 4.1 forms an hipathic α-helix with distinct hydrophilic and hydrophobic zones. Two regions of well defined helicity (from Gln4 to Ala10 and from Ile17 to Ile21) are separated by a central helical region of greater conformational variability. The enhanced disorder in this region arises from the presence of two central glycine residues at positions 11 and 16. However, the degree of disorder and hence flexibility is much less than in caerin 1.1 where central proline residues are present instead. This reduced central flexibility may account for the narrow spectrum of biological activity of caerin 4.1, i.e. because biological membranes of the various bacteria have different composition and topology, their optimal interaction with the relatively rigid caerin 4.1 peptide is not possible.
No related grants have been discovered for Wilford Lie.