Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2021 Feb 18;26(4):1064.
doi: 10.3390/molecules26041064.

Pentacyclic Triterpene Profile and Its Biosynthetic Pathway in Cecropia telenitida as a Prospective Dietary Supplement

Gustavo Gutiérrez  1 , Laura Marcela Valencia  1 , Deisy Giraldo-Dávila  2 , Marianny Y Combariza  2 , Elkin Galeano  3 , Norman Balcazar  4   5 , Aram J Panay  6 , Alejandra Maria Jerez  7 , Guillermo Montoya  1   8
Affiliations

Pentacyclic Triterpene Profile and Its Biosynthetic Pathway in Cecropia telenitida as a Prospective Dietary Supplement

Gustavo Gutiérrez et al. Molecules. .

Abstract

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.

Keywords: Cecropia telenitida; dietary supplement; pentacyclic triterpene; type 2 diabetes.

PubMed Disclaimer

Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
(A) Mass spectra of originally obtained leader fraction (DE16). (B) Mass spectra of fractions pooled (DE16-R). Ionization was carried out by MALDI (−) using DMAN as a matrix.
Figure 2
Figure 2
UPLC-APCI-MS negative mode chromatograms for DE16 and DE16-R fractions. The total ion chromatogram (TIC) spectra were obtained after peak integration and subtracting the solvent noise. Every spectrum is extracted, with each peak designated a consecutive number from 1 to 5.
Figure 3
Figure 3
A preparative chromatogram obtained by HPLC-DAD from DE16R. The 17.94 retention time molecule was identified as isoyarumic acid, 23.31 min was identified as tormentic acid, 27.47 min was identified as arjunolic acid, and 28.27 min was identified as hederagenic acid.
Figure 4
Figure 4
Presentation of pentacyclic triterpene (PT) structures found in Cecropia telenitida. Isoyarumic acid, tormentic acid, arjunolic acid, and hederagenic acid are molecules isolated and identified as an outcome of this work. The exact masses highlighted in blue show isobaric triterpenes.
Figure 5
Figure 5
Cytotoxicity of corosolic acid (CA) and DE16-R fraction on cell lines 3T3-L1, HepG2 and C2C12. The cells were seeded in 96-well plates and treated for 48H (HepG2) (A), 4 h (C2C12) (B) and 7 days (3T3-L1) (C). The cytotoxicity was evaluated by methyl thiazole tetrazolium (MTT) assay. Values are expressed as means ± SEM. ANOVA with post hoc Dunnett’s for multiple comparisons was performed. ****: p < 0.0001; ***: p < 0.001; **: p < 0.01; *: p < 0.05. n = 3.
Figure 6
Figure 6
Biosynthetic pathways to producing PTs. The underlined names refer to molecules isolated and identified for the first time in this plant. The nine molecule names bolded and italicized mark the nine PTs reported.
See this image and copyright information in PMC

References

    1. De la Torre R., Carbó M., Pujadas M., Biel S., Mesa M.D., Covas M.I., Expósito M., Espejo J.A., Sanchez-Rodriguez E., Díaz-Pellicer P., et al. Pharmacokinetics of maslinic and oleanolic acids from olive oil—Effects on endothelial function in healthy adults. A randomized, controlled, dose–response study. Food Chem. 2020;322:126676. doi: 10.1016/j.foodchem.2020.126676. - DOI - PubMed
    1. Sheng H., Sun H. Synthesis, biology and clinical significance of pentacyclic triterpenes: A multi-target approach to prevention and treatment of metabolic and vascular diseases. Nat. Prod. Rep. 2011;28:543–593. doi: 10.1039/c0np00059k. - DOI - PubMed
    1. Sharma H., Kumar P., Deshmukh R.R., Bishayee A., Kumar S. Pentacyclic triterpenes: New tools to fight metabolic syndrome. Phytomedicine. 2018;50:166–177. doi: 10.1016/j.phymed.2018.09.011. - DOI - PubMed
    1. Shi L., Zhang W., Zhou Y.Y., Zhang Y.N., Li J.Y., Hu L.H., Li J. Corosolic acid stimulates glucose uptake via enhancing insulin receptor phosphorylation. Eur. J. Pharmacol. 2008;584:21–29. doi: 10.1016/j.ejphar.2008.01.020. - DOI - PubMed
    1. Wu J.B., Kuo Y.H., Lin C.H., Ho H.Y., Shih C.C. Tormentic Acid, a major component of suspension cells of eriobotrya japonica, suppresses high-fat diet-induced diabetes and hyperlipidemia by glucose transporter 4 and amp-activated protein kinase phosphorylation. J. Agric. Food Chem. 2014;62:10717–10726. doi: 10.1021/jf503334d. - DOI - PubMed

Substances

LinkOut - more resources