Chemical composition of Helietta parvifolia and its in vitro anticholinesterase activity

Abstract

The chemical composition of the essential oil and the n-hexane (Hex), Ethyl Acetate (EtOAc) and butanol (BuOH) extracts from the leaves of Helietta parvifolia were determined by detailed GC-MS analysis, spectroscopic and spectrometric data. Eighty-four compounds were identified, revealing a furoquinoline alkaloid-rich composition. The phytochemical analysis of the extracts allowed the isolation of eigth furoquinoline alkaloids. Retention indices in GC-MS for six of this alkaloids are reported for the first time. Furoquinoline alkaloids are acethylcholinesterase inhibitors. Thus, the essential oil and extracts were submitted to this in vitro assay. The EtOAc and BuOH extracts showed potent activity, with IC of 9.7 and 12.9 μg mL, respectively. Additionaly, a correlation of their chemical constituents, established by principal component analysis (PCA) demostrated a similar profile and a high content of alkaloids. It is for these reasons that we can assume that the alkaloid content in these extracts could be responsible for their anticholinesterase activity.

Isolation and Antimacrofouling Activity of Indole and Furoquinoline Alkaloids from ‘Guatambú’ Trees (Aspidosperma australe and Balfourodendron riedelianum)

“…Kokusaginine ( 4 ) and flindersiamine ( 5 ) are furoquinoline alkaloids, and there are previous reports of antifouling compounds that have a furan ring . In particular, kokusaginine has several reported biological activities: acetylcholinesterase inhibition, insect antifeedant activity, antitumor, antiparasitic, and antibiotic . These last two biological activities may be directly related to the antifouling effect.…”

Estructura y diversidad de un matorral dominado por Helietta parvifolia (A. Gray ex Hemsl.) Benth.

“…Meléndez-Jaramillo et al (2019) señalan que H. parvifolia es una de las especies con mayor presencia en el matorral submontano del noreste de México y que se localiza en un intervalo altitudinal de 500 a 800 m.…”

Structures, Occurrences and Biosynthesis of 11,12,13-Tri-nor-Sesquiterpenes, an Intriguing Class of Bioactive Metabolites

“…In addition to the isolation of compound 4 from the EO of Juniperus species [66][67][68][69][70][71][72], pregeijerene B (4) was also isolated from the EO of two endemic Nepeta species, namely N. nuda and N. cadmea [73]; the EO of Helietta parvifolia, which exhibited anticholinesterase activity [74]; and from different species of Pimpinella [43]. This compound was also isolated from the EO of Stachys menthifolia [75], Artemisia annua [76], Calycanthus floridus L. [77] and Thottea ponmudiana [78].…”

“…All metabolites were tested for nitric oxide (NO) production inhibition in lipopolysaccharide (LPS)-activated BV-2 microglial cells, and dendryphiellin D (66), septere- The plant pathogenic fungus Septoria rudbeckiae Ellis and Halst (Mycosphaerellaceae) was isolated from the halophyte Karelinia caspia, a perennial shrub collected in the Xinjing Uyghur Autonomous Region of Western China. The study of this strain afforded 11 eremophilane sesquiterpenoids with a tri-nor-eremophilane skeleton: four known compounds, dendryphiellin B (64), C (65) and D (66) (Figure 7); and chaetopenoid F (59) (Figure 6), and seven new ones called septeremophilanes B-H (69)(70)(71)(72)(73)(74)(75). Their structures and absolute configurations were established based on spectroscopic data (NMR and HRESIMS), quantum chemical calculations and electronic circular dichroism (ECD) experiments.…”