Ceanothane and oleanane-type triterpenes from Talguenea quinquenervia have insecticidal activity against Cydia pomonella, Tenebrio molitor and Drosophila melanogaster

Quiroz, Soledad; Cespedes‐Acuña, Carlos L.; Alderete, Joel B.; Alarcón, Julio

doi:10.1016/j.indcrop.2015.06.003

Cited by 17 publications

(15 citation statements)

References 35 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…et Hook) (Rhamnaceae) is a shrub or small tree distributed throughout the central‐southern zone of Chile . Previous studies of the aerial part of the plant have reported a set of pentacyclic triterpenes and alkaloids with a benzylisoquinoline skeleton . In this family, the presence of compounds such as polyphenols, triterpenes, aromatics, flavonoids, and cyclopeptide, aporphines and benzylisoquinoline alkaloids is characteristic .…”

Section: Introductionmentioning

confidence: 99%

Identification of structurally diverse alkaloids in Talguenea quinquinervia (gill. Et hook) by liquid chromatography/electrospray ionisation tandem mass spectroscopy and insecticidal activity

Quiroz-Carreño

Cespedes‐Acuña

Seigler

et al. 2019

Phytochemical Analysis

View full text Add to dashboard Cite

Introduction Talguenea quinquinervia has been used in folk medicine and to dye wool, and the main constituents are alkaloids and triterpenes. Identification of these type of compounds in this specie is a necessary step to understand the biological properties. Objective To evaluate the relationship between the chemical composition of root from T. quinquinervia and its insecticidal properties using liquid chromatography electrospray ionisation tandem mass spectrometry (LC‐ESI‐MS/MS). Methods Alkaloids were extracted using Soxhlet extraction with methanol. Total extract was partitioned at pH 2 and 12 to enrich alkaloid constituents and to remove interferences. The separation of alkaloids in the Talguenea extract was performed on a C18 column using gradient elution and their tandem mass spectra were obtained by quadrupole time‐of‐flight tandem mass spectrometry (QTOF‐MS/MS) to perform accurate mass measurements of fragment ions for the alkaloid constituents. Results Several types of alkaloids were separated and identified by LC‐ESI‐MS/MS. The structural assignment of individual alkaloids was performed based on convergence of MS/MS spectral data, pH partitioning behaviour, LC retention behaviour, and accurate mass measurements. The pH partition of the extract provided structural information about unknown alkaloids extracted from T. quinquinervia. A total of 20 compounds were identified and tentatively characterised, and of these 15 alkaloids were reported for the first time in the investigated T. quinquinervia. Conclusion The chemical profiling of alkaloids in T. quinquinervia with different origins was performed for the first time and provided diagnostic ions for diverse alkaloids in T. quinquinervia. Insecticidal activity observed can be explain by the presence of alkaloid and pentacyclic triterpenes on the fractions assayed.

show abstract

Section: Introductionmentioning

confidence: 99%

Identification of structurally diverse alkaloids in Talguenea quinquinervia (gill. Et hook) by liquid chromatography/electrospray ionisation tandem mass spectroscopy and insecticidal activity

Quiroz-Carreño

Cespedes‐Acuña

Seigler

et al. 2019

Phytochemical Analysis

View full text Add to dashboard Cite

show abstract

“…Our results indicate that these compounds are involved in interference of sclerotization and moulting (Quiroz et al 2015). These triterpenes showed to have selective effects on the pre-emergence metabolism of the insect and selectivity towards Lepidoptera and Diptera, but not to coleoptera.…”

Section: Insecticidal Activitymentioning

confidence: 64%

“…Some taxa from Americas such as Rhamnaceae members are toxic to insects, fungi and several bacteria strains, and these effects has been associated with the presence of alkaloids, phenolics and terpenes. The methanol extract from the roots of T. quinquenervia afforded 9 triterpenes which belong to lupane, oleanane, ursane, sterol and ceanothane groups, these compounds showed insecticidal effects (Tables 3, 4) (Quiroz et al 2015).…”

Section: Insecticidal Activitymentioning

confidence: 99%

“…To the best our knowledge, this was the first report about the isolation of ceanothane triterpenes type from this plant All extracts tested had insecticidal activity, the most active being those that contain alkaloids. From the most active fraction, it was possible to identify the known alkaloids coclaurine, armepavine and Nmethylcoclaurine (Alarcon et al 2011(Alarcon et al , 2015.…”

Section: Insecticidal Activitymentioning

confidence: 99%

See 1 more Smart Citation

Chemical constituents and biological activities of South American Rhamnaceae

Alarcón

Cespedes‐Acuña

2015

Phytochem Rev

View full text Add to dashboard Cite

Secondary metabolites have diverse functions into plants. These functions are products of the coevolution which result in synthesis of constitutive and/or induced chemical defense generated for protection against to different phytopathogenic attack. Many phytochemical studies are biodirected with the aim of finding biopesticides of botanical origins. Some taxa of Americas such as Rhamnaceae family are toxic to insects, fungi and several bacteria strains, and these effects has been associated with the presence of alkaloids, phenolics and terpenes. The natural compounds that have been isolated represent a valuable resource for future studies of plant chemical defense and the role of these substances in chemical ecology.Here are show recent advances in the phytochemistry and biological activities of selected members of Rhamnaceae from Latin-America.

show abstract

“…2 zizyberanalic acid (17), 15 ceanothic acid (18), 16 oleanolic acid (19), 16 maslinic acid (20), 17 3-O-cis-ρ-coumaroyl-maslinic acid (21), 17 and 3-O-trans-ρ-coumaroyl-maslinic acid (22), 17 were isolated and identified as a by spectroscopic experiments, NMR and MS, and comparison with reported data (Fig. 1).…”

mentioning

confidence: 88%

Studies on the Chemical Constituents from the Seeds of Zizyphus jujuba var. inermis

et al. 2017

View full text Add to dashboard Cite

-This study analyzed the seeds of Zizyphus jujuba var. inermis commonly used as a remedy in traditional Chinese medicine, in order to determine its various biologically active compounds. Through process 3-pentadecylcatechol, ρ-menth-8-ene, and γ-bisabolene were isolated and identified for the first time which are urushiol, monoterpenoidal, and sesquiterpenoidal compounds, respectively. Also, found were another sesquiterpenoidal compounds, vomifoliol, and four steroidal compounds, β-sitosterol, stigmasterol, stigmasta-5,23-dien-3β-ol, and stigmast-4-en-3-one. In addition, fourteen triterpenoidal compounds were isolated and identified. These were lupeol, betulinic acid, betulinaldehyde, alphitolic acid, 3-O-cis-ρ-coumaroyl-alphitolic acid, 3-O-trans-ρ-coumaroylalphitolic acid, 2-O-cis-ρ-coumaroyl-alphitolic acid, 2-O-trans-ρ-coumaroyl-alphitolic acid, zizyberanalic acid, ceanothic acid, oleanolic acid, maslinic acid, 3-O-cis-ρ-coumaroyl-maslinic acid, and 3-O-trans-ρ-coumaroylmaslinic acid. The structures were identified by comparing of the spectroscopic experiments, NMR and MS, and then compared that reported data, respectively. Three extracts of water, methanol, and chloroform from the seeds showed a weak anti-proliferative effect, anti-microbial activity, and anti-oxidant effect, respectively.

show abstract

Ceanothane and oleanane-type triterpenes from Talguenea quinquenervia have insecticidal activity against Cydia pomonella, Tenebrio molitor and Drosophila melanogaster

Cited by 17 publications

References 35 publications

Identification of structurally diverse alkaloids in Talguenea quinquinervia (gill. Et hook) by liquid chromatography/electrospray ionisation tandem mass spectroscopy and insecticidal activity

Identification of structurally diverse alkaloids in Talguenea quinquinervia (gill. Et hook) by liquid chromatography/electrospray ionisation tandem mass spectroscopy and insecticidal activity

Chemical constituents and biological activities of South American Rhamnaceae

Studies on the Chemical Constituents from the Seeds of Zizyphus jujuba var. inermis

Contact Info

Product

Resources

About