Spergulagenic Acid A: Isolation and single crystal structure elucidation

Montoya, Guillermo; Gutiérrez, Gustavo; Vries, R. de; Ellena, Javier; Panay, Aram J.

doi:10.1016/j.molstruc.2018.07.032

Cited by 5 publications

(10 citation statements)

References 24 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Spergulagenic acid (84), a pentacyclic triterpene used in medicine, was found in diverse plant families [258]. Until now, three spergulagenic acid glycosides (Table 11) were identified in quinoa [217,256], though spergulagenic acid as the aglycone has not been isolated from quinoa.…”

Section: Spergulagenic Acid Derivatives and Their Biological Activitimentioning

confidence: 99%

Quinoa Secondary Metabolites and Their Biological Activities or Functions

Lin

Han

et al. 2019

Molecules

View full text Add to dashboard Cite

Quinoa (Chenopodium quinoa Willd.) was known as the “golden grain” by the native Andean people in South America, and has been a source of valuable food over thousands of years. It can produce a variety of secondary metabolites with broad spectra of bioactivities. At least 193 secondary metabolites from quinoa have been identiﬁed in the past 40 years. They mainly include phenolic acids, ﬂavonoids, terpenoids, steroids, and nitrogen-containing compounds. These metabolites exhibit many physiological functions, such as insecticidal, molluscicidal and antimicrobial activities, as well as various kinds of biological activities such as antioxidant, cytotoxic, anti-diabetic and anti-inﬂammatory properties. This review focuses on our knowledge of the structures, biological activities and functions of quinoa secondary metabolites. Biosynthesis, development and utilization of the secondary metabolites especially from quinoa bran were prospected.

show abstract

Section: Spergulagenic Acid Derivatives and Their Biological Activitimentioning

confidence: 99%

Quinoa Secondary Metabolites and Their Biological Activities or Functions

Lin

Han

et al. 2019

Molecules

View full text Add to dashboard Cite

show abstract

“…The laboratory has kept the SA standard previously isolated due to being not commercially available, and organic molecules isolation becomes easier having a reference material. Extraction protocol for PTs dealing with the same vegetal material was reported using a semi-pilot extraction plant coupled with and automated flash and low-pressure chromatography systems [10]. A MALDI-TOF support the choice of extracts having the major amount of SA, as shown in Figure 1, since thin layer chromatography of crude extracts has made us take wrong decisions.…”

Section: Sa Extraction and Purificationmentioning

confidence: 99%

“…The roots collected (5 kg) were dried at 45 • C for six days and later powdered using a disc sander and disposed at the 20 L percolator tank from a semi-pilot extraction plant. The vegetal material was extracted with 10 L of the following n-hexane, dichloromethane/ethyl acetate, ethyl acetate, ethyl acetate/methanol, and methanol solvents [10]. For every solvent system, the extraction process was maintained under constant temperature (40 • C) and continuous stirring rate (90 rpm) for 8 h.…”

Section: Purification Of Sa From Cecropia Telenitida Rootsmentioning

confidence: 99%

“…In contrast, the distribution of Cecropia telenitida [8], retrieved from the TROPICOS database (Missouri Botanical Garden), shows how this species is limited to the central and northern sections of the Andes (Venezuela, Colombia, Ecuador, and north of Peru). Despite the fact that C. telenitida has not been abundantly studied in terms of its chemistry and bioactivity, the genus has some phytochemical descriptions [7,[9][10][11][12], and our research group has reported pentacyclic triterpenes (PT) as chemotaxonomic markers in the roots of Cecropia genus.…”

Section: Introductionmentioning

confidence: 99%

“…Serjanic acid (SA) is a PT identified in nature making part of complex glycosides mixtures from Chenopodium quinoa and Phytolacca genus without a detailed description of its potential properties [30,31]. SA is a noncommercialized molecule also present in Cecropia telenitida roots, and a standard protocol was developed to obtain a sufficient amount to support animal assays [10].…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Serjanic Acid Improves Immunometabolic Markers in a Diet-Induced Obesity Mouse Model

et al. 2020

Self Cite

View full text Add to dashboard Cite

Plant extracts from Cecropia genus have been used by Latin-American traditional medicine to treat metabolic disorders and diabetes. Previous reports have shown that roots of Cecropia telenitida that contains serjanic acid as one of the most prominent and representative pentacyclic triterpenes. The study aimed to isolate serjanic acid and evaluate its effect in a prediabetic murine model by oral administration. A semi-pilot scale extraction was established and serjanic acid purification was followed using direct MALDI-TOF analysis. A diet induced obesity mouse model was used to determine the impact of serjanic acid over selected immunometabolic markers. Mice treated with serjanic acid showed decreased levels of cholesterol and triacylglycerols, increased blood insulin levels, decreased fasting blood glucose and improved glucose tolerance, and insulin sensitivity. At transcriptional level, the reduction of inflammation markers related to adipocyte differentiation is reported.

show abstract