Kokusaginine and evolitrine from Acronychia pedunculata

Silva, L.B. de; Silva, U.L.L. de; Mahendran, M.; Jennings, Richard C.

doi:10.1016/0031-9422(79)80162-4

Cited by 35 publications

(14 citation statements)

References 3 publications

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confidence: 88%

“…Because of the absence of any reports in the literature concerning the constituents of Tinospora malabarica and the paucity of reports concerning the (3,4). Its mass spectrum showed a molecular ion at m/z 259 and the rest of the fragmentation pattern is identical to the reported MS of kokusaginine (3,4). The 1-H-NMR spectrum exhibited two doublets at 6 7.75 and 7.35 (two furan protons), two singlets at 64.00and 3.99 (6, 7-methoxy groups) and a singlet at 8 4.50 (4-methoxy group) identical with the reported 1H-NMR for kokusaginine (4).…”

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Isolation and Identification of Kokusaginine fromTinospora malabarica

Bowen

Motawe²

1985

Planta Med

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Melting points were determined by means of a Kofler hot plate and are uncorrected. UV spectra were determined in MeOH, IR in KBr discs, 'H-NMR were recorded in CDCI3 on a Brucker 270 MHz, tetramethylsilane was used as internal standard and MS were obtained at 70 eV. All the compounds were identified by spectroscopical properties and, with the exception of byankangelicin, were compared with authentic samples.

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Isolation and Identification of Kokusaginine fromTinospora malabarica

Bowen

Motawe²

1985

Planta Med

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“…Extracts of the leaves, bark, stems and fruits of this plant are widely used in folk medicine to treat scabies, sores and ulcers, and are reported to have antimicrobial activity, cytotoxicity and antioxidant capacity . Various compounds have been isolated and identified from A. pedunculata , including quinolone alkaloids and phenolic compounds . We previously reported the new acetophenones acrophenone A, B and C and several known acetophenone dimer compounds, such as acrovestenol and acrovestone.…”

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confidence: 99%

Acrofolione A and B, acetophenone dimers from Acronychia pendunculata, induce an apoptotic effect on human NALM-6 pre-B cell leukaemia cells

Matsui

Ito

Kato

et al. 2019

Journal of Pharmacy and Pharmacology

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Objectives We investigated the apoptotic activities of acrofolione A (1) and B (2) isolated from Acronychia pedunculata against a human pre‐B cell leukaemia cell line (NALM‐6) to explore the apoptosis‐related signalling molecules targeted by 1 and 2. Methods The apoptosis effects of 1 and 2 in NALM‐6 cells were investigated by TUNEL staining, annexin V, mitochondria membrane potential and caspase 3/7 activity. We carried out a protein array to explore the signalling molecules involved in apoptosis comprehensively. Key findings Acrofolione A (1) suppressed the growth of NALM‐6, K562 and HPB‐ALL cells (IC50 16.7 ± 1.9, 17.9 ± 0.3 and 10.1 ± 0.2 μm, respectively) more effectively than acrofolione B (2). Both compounds time‐dependently increased the number of NALM‐6 cells with abnormal nuclei, and increased the number of annexin V‐positive cells and decreased the mitochondrial membrane potential of NALM‐6 cells. Acrofolione A (1) markedly elevated caspase 3/7 activity and increased the number of TUNEL‐positive cells. Cells treated with either compound showed enhanced expression of cleaved PARP and cleaved caspase 3 and 7, and reduced survivin protein levels. Conclusions Acrofolione A (1) and B (2) may be useful in the treatment of various types of leukaemia.

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“…The respective resonances for the 13 C were extracted from the HSQC spectra at δ 123.6, 144.1, 115.2 and 59.0, respectively. According to the aforementioned signals and literature data the presence of furoquinoline alkaloids is suggested (de Silva et al 1979). A number of other features were found responsible for the discrimination of Acronychia sample groups, however, their reliable correlation with metabolites was hard to be supported.…”

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confidence: 95%

“…pedunculata have been extensively investigated by various groups resulting in a large number of literature data available concerning their chemical composition (de Silva et al 1979, Rahmani et al 1996, Cui et al 1999, Kozaki et al 2014). On the other hand, A. porteri is reported only once for the presence of three methoxyflavones (Lichius et al 1994).…”

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confidence: 99%

Phytochemical investigation of Acronychia species using NMR and LC-MS based dereplication and metabolomics approaches

Κουλούρα¹

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Medicinal plants constitute an unfailing source of compounds (natural products –NPs) utilised in medicine for the prevention and treatment of various deceases. Theintroduction of new technologies and methods in the field of natural products chemistryenabled the development of high throughput methodologies for the chemical compositiondetermination of plant extracts, evaluation of their properties and the exploration of theirpotentials as drug candidates. Lately, metabolomics, an integrated approach incorporatingthe advantages of modern analytical technologies and the power of bioinformatics hasbeen proven an efficient tool in systems biology. In particular, the application ofmetabolomics for the discovery of new bioactive compounds constitutes an emerging fieldin natural products chemistry.In this context, Acronychia genus of Rutaceae family was selected based on its wellknowntraditional use as antimicrobial, antipyretic, antispasmodic and anti-inflammatorytherapeutic agent. Modern chromatographic, spectrometric and spectroscopic methodswere utilised for the exploration of their metabolite content following three basic axis: a)phytochemical investigation, identification of secondary metabolites and evaluation of theirbiological properties, b) development of analytical methods for identification ofacetophenones (chemotaxonomic markers of the genus) and dereplication strategies forthe chemical characterisation of extracts and c) application of metabolomic methodologies(LC-MS & NMR) for comparative analysis (between different species, origins, organs),chemotaxonomic studies (between species) and compound-activity correlations.Bioinformatics and sophisticated statistical tools were employed especially towards thelatter methodology. In particular:The application of various analytical and chromatographic techniques (LC-PDA, -ELSD, -HRMS, SFC-UV, HRNMR; chiral separation, FCPC) enabled the phytochemical exploration and isolation of numerous NPs (alkaloids, lignans, terpenoids). Among them,several acetophenones, an important and interesting class for the genus (Acronychia-typeacetophenones-AtA) from A. pedunculata were isolated and identified. Their particularstructural characteristics compelled their detailed and unabigious structural investigation. In addition, the evaluation of their pharmacological properties, including antimicrobial,cytotoxic (against human tumour cell lines) and anti-inflammatory activity, of all isolated AtAwas assessed in vitro.The small number of Acronychia-type acetophenones (AtA) despite their importantpharmacological profile, the limited information regarding their identification as well as thelow number of species investigated so far, led to the development of an identification anddereplication strategy for further exploration of AtA in complex mixtures. In particular, aUPLC-HRMS & HRMSn method was developed and applied for the detailed and accurateidentification thereof. Fragmentation patterns and certain ion motifs enabled theconstruction of decision trees for AtA identification and a MS nomenclature scheme wassuggested. Moreover, this methodology was utilised for the analysis of different A.pedunculata extracts enabling the dereplication of known AtA and the discovery ofpotentially new ones. This approach, having taken advantage of state of the art analyticalplatforms and concepts, could be incorporated for the investigation of other complexmixtures and plant extracts.NMR and UPLC-HRMS-based metabolomics (metabolic profiling) were used for theinvestigation of various Acronychia species and organs, from different geographical origin.Dereplication tools were also employed for the characterization of their chemical profiles.Statistical models were developed for the comparison of the different extracts revealingorgan- and species-specific biomarkers. Moreover, discrimination models allowed theidentification of certain compounds giving new insight into chemotaxonomic issues.Specific strategies were established for the identification of the revealed biomarkersincluding statistical integration of datasets obtained from both platforms. Statisticalcorrelation of the analytical and pharmacological data resulted in the development of a methodology for tracking bioactive metabolites in extracts without any prior purification.This approach provides a novel tool for the drug discovery in natural products field.Overall, the combination of these different approaches comprises a complete andcomprehensive study of Acronychia species and important knowledge was obtainedconcerning their metabolite composition and pharmacological profile. Metabolomics wereproved a promising tool in modern pharmacognosy and phytochemistry while betterinsight into the utilisation of new approaches in natural products drug discovery processwas obtained.

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Kokusaginine and evolitrine from Acronychia pedunculata

Cited by 35 publications

References 3 publications

Isolation and Identification of Kokusaginine fromTinospora malabarica

Isolation and Identification of Kokusaginine fromTinospora malabarica

Acrofolione A and B, acetophenone dimers from Acronychia pendunculata, induce an apoptotic effect on human NALM-6 pre-B cell leukaemia cells

Phytochemical investigation of Acronychia species using NMR and LC-MS based dereplication and metabolomics approaches

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