Asphaltenes are polydisperse,
compositionally complex solubility
fractions of crude oil, with a range of structural motifs that contain
two primary structural classes: molecules with single aromatic cores
(island) and bridged aromatic moieties (archipelago), each with varying
degrees of alkyl substitution (e.g., varied-length alkyl units) and
multi-heteroatom functionalities responsible for aggregate formation
through weak and strong intermolecular associations. Understanding
the link between asphaltene molecular composition and problematic
behavior, such as deposit and emulsion formation, is vital to improve
crude oils up- and downstream processes in petrochemical industries.
Some reports suggest that asphaltene precipitation occurs primarily
through self-association of polar functional groups and highlight
direct correlations between aggregate size and emulsion stability.
Here, we compare the molecular composition of whole and thin-layer
chromatography (TLC)-fractioned PetroPhase 2017 asphaltenes characterized
by Fourier transform ion cyclotron resonance mass spectrometry (FT-ICR
MS) and correlate composition to near-infrared (NIR) scattering measurements
of heptane/toluene (HepTol) dispersions. Asphaltene retention on SiO2 plates is dictated by molecular features, such as aromaticity,
heteroatom content, and degree of saturation (or content of methylene
units). The most polar molecules in PetroPhase 2017 asphaltenes are
strongly retained on SiO2 and exhibit a bimodal distribution
in compositional space (carbon number and aromaticity) characterized
by highly alkylated and highly heteroatomic (N, O, and S) species.
In contrast, the least retained compounds consist of primarily highly
aromatic, sulfur-containing species with short alkyl chains. Furthermore,
a correlation between asphaltene aggregation and emulsion stability
was observed: for the fraction that was retained the most on the silica
plate, the quicker it aggregates in HepTol and the more stable its
emulsion. Collectively, this suggests that not all asphaltenes are
the same and indicates the presence of a direct relationship between
asphaltene polarity, aggregation tendency, and emulsion stability.
Promising research over the past decades has shown that some types of pentacyclic triterpenes (PTs) are associated with the prevention of type 2 diabetes (T2D), especially those found in foods. The most abundant edible sources of PTs are those belonging to the ursane and oleanane scaffold. The principal finding is that Cecropia telenitida contains abundant oleanane and ursane PT types with similar oxygenation patterns to those found in food matrices. We studied the compositional profile of a rich PT fraction (DE16-R) and carried out a viability test over different cell lines. The biosynthetic pathway connected to the isolated PTs in C.telenitida offers a specific medicinal benefit related to the modulation of T2D. This current study suggests that this plant can assemble isobaric, positional isomers or epimeric PT. Ursane or oleanane scaffolds with the same oxygenation pattern are always shared by the PTs in C. telenitida, as demonstrated by its biosynthetic pathway. Local communities have long used this plant in traditional medicine, and humans have consumed ursane and oleanane PTs in fruits since ancient times, two key points we believe useful in considering the medicinal benefits of C. telenitida and explaining how a group of molecules sharing a closely related scaffold can express effectiveness.
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.
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