Chapter 12. Triterpene/Steroid Glycoconjugates: Natural Occurrence, Synthesis and Biological Activities

2017 ◽  
pp. 326-373 ◽  
Author(s):  
Stefan Schwarz ◽  
Nuno M. Xavier ◽  
René Csuk ◽  
Amélia P. Rauter
Keyword(s):  
Biological Activities ◽  
Natural Occurrence

scholarly journals Effects of Terpenes and Terpenoids of Natural Occurrence in Essential Oils on Vascular Smooth Muscle and on Systemic Blood Pressure: Pharmacological Studies and Perspective of Therapeutic Use

2020 ◽  
Author(s):  
Ana Carolina Cardoso-Teixeira ◽  
Klausen Oliveira-Abreu ◽  
Levy Gabriel de Freitas Brito ◽  
Andrelina Noronha Coelho-de-Souza ◽  
José Henrique Leal-Cardoso
Keyword(s):  
Blood Pressure ◽  
Smooth Muscle ◽  
Vascular Smooth Muscle ◽  
Biological Activities ◽  
Systemic Blood Pressure ◽  
Potential Effect ◽  
Natural Occurrence ◽  
Systemic Blood ◽  
Vascular Beds ◽  
Chemical Groups

Terpenes are a class of chemical compounds with carbon and hydrogen atoms in their structure. They can be classified into several classes according to the quantity of isoprene units present in its structure. Terpenes can have their structure modified by the addition of various chemical radicals. When these molecules are modified by the addition of atoms other than carbon and hydrogen, they become terpenoids. Terpenes and terpenoids come from the secondary metabolism of several plants. They can be found in the leaves, fruits, stem, flowers, and roots. The concentration of terpenes and terpenoids in these organs can vary according to several factors such as the season, collection method, and time of the day. Several biological activities and physiological actions are attributed to terpenes and terpenoids. Studies in the literature demonstrate that these molecules have antioxidant, anticarcinogenic, anti-inflammatory, antinociceptive, antispasmodic, and antidiabetogenic activities. Additionally, repellent and gastroprotective activity is reported. Among the most prominent activities of monoterpenes and monoterpenoids are those on the cardiovascular system. Reports on literature reveal the potential effect of monoterpenes and monoterpenoids on systemic blood pressure. Studies show that these substances have a hypotensive and bradycardic effect. In addition, the inotropic activity, both positive and negative, of these compounds has been reported. Studies also have shown that some monoterpenes and monoterpenoids also have a vasorelaxing activity on several vascular beds. These effects are attributed, in many cases to the blocking of ion channels, such as voltage-gated calcium channels. It can also be observed that monoterpenes and monoterpenoids can have their effects modulated by the action of the vascular endothelium. In addition, it has been shown that the molecular structure and the presence of chemical groups influence the potency and efficacy of these compounds on vascular beds. Here, the effect of several monoterpenes and monoterpenoids on systemic blood pressure and vascular smooth muscle will be reported.

Fusaproliferin, beauvericin and enniatins: occurrence in food – a review

2012 ◽  
Vol 5 (1) ◽  
pp. 71-81 ◽  
Author(s):  
A. Santini ◽  
G. Meca ◽  
S. Uhlig ◽  
A. Ritieni
Keyword(s):  
Maximum Concentration ◽  
Biological Activities ◽  
Northern Europe ◽  
Natural Occurrence ◽  
High Prevalence ◽  
Occasional Occurrence ◽  
Food And Feed ◽  
The Mediterranean ◽  
Reported Data ◽  
Feed Safety

The present review summarises data on the prevalence and concentration of fusaproliferin, beauvericin and enniatins in small grains, maize and processed grain-based foods. These fungal secondary metabolites possess interesting biological activities and are presently often referred to as 'emerging mycotoxins'. They have been considered as less important since they are likely not of acute toxicity. However, their high prevalence in foodstuffs, occasionally in higher mg/kg concentrations, warrants an assessment of their true importance for food (and feed) safety. Thorough surveys that determine the contamination of raw and processed foods with fusaproliferin, beauvericin and enniatins are still scarce and are generally limited to Northern Europe and the Mediterranean. The reported data suggest a connection between the observed concentrations and climate. The data further suggest that humans might be exposed continuously to low levels of enniatins as these compounds were of particularly high prevalence in the surveys. The highest concentrations of enniatins were reported from Spain and Northern Africa (maximum concentration of enniatin A1 814 mg/kg in rice from the Spanish market), while concentrations were significantly lower in Northern Europe (maximum concentration of enniatin B 18.3 mg/kg in wheat from Finland). Beauvericin appears to be of low significance in grains from cooler climates while it has been reported to occur at concentrations of tens of mg/ kg in Southern Europe and Morocco (maximum concentration 59 mg/kg in maize from Morocco). Fusaproliferin has been least investigated. Several reports from the Mediterranean show its occasional occurrence up to 19.6 mg/ kg in rice from Morocco, while its natural occurrence in cooler climates seems to be more rare.

scholarly journals Isolation and Potential Biological Applications of Haloaryl Secondary Metabolites from Macroalgae

Marine Drugs ◽  
2019 ◽  
Vol 17 (2) ◽  
pp. 73 ◽  
Author(s):  
Ana Jesus ◽  
Marta Correia-da-Silva ◽  
Carlos Afonso ◽  
Madalena Pinto ◽  
Honorina Cidade
Keyword(s):  
Secondary Metabolites ◽  
Green Algae ◽  
Red Algae ◽  
Biological Activities ◽  
Marine Organisms ◽  
Natural Occurrence ◽  
Biological Applications ◽  
Naphthalene Derivatives

Macroalgae have been reported as an important source of halogenated aromatic secondary metabolites, being the majority of these derivatives isolated from red algae. Halophenols and haloindoles are the most common haloaryl secondary metabolites isolated from these marine organisms. Nevertheless, some halogenated aromatic sesquiterpenes and naphthalene derivatives have also been isolated. Most of these secondary metabolites showed interesting biological activities, such as antitumor, antimicrobial, antidiabetic, and antioxidant. This review describes in a systematic way the distribution and natural occurrence of halogenated aromatic secondary metabolites from extracts of red, brown, and green algae, as well as biological activities reported for these compounds.

ChemInform Abstract: Triterpene/Steroid Glycoconjugates: Natural Occurrence, Synthesis and Biological Activities

ChemInform ◽  
2012 ◽  
Vol 43 (24) ◽  
pp. no-no
Author(s):  
Stefan Schwarz ◽  
Nuno M. Xavier ◽  
Rene Csuk ◽  
Amelia P. Rauter
Keyword(s):  
Biological Activities ◽  
Natural Occurrence

Beta-lapachone: Natural occurrence, physicochemical properties, biological activities, toxicity and synthesis

2021 ◽  
Vol 186 ◽  
pp. 112713
Author(s):  
Camila Luiz Gomes ◽  
Victor de Albuquerque Wanderley Sales ◽  
Camila Gomes de Melo ◽  
Rosali Maria Ferreira da Silva ◽  
Rodolfo Hideki Vicente Nishimura ◽  
...  
Keyword(s):  
Physicochemical Properties ◽  
Biological Activities ◽  
Natural Occurrence

ChemInform Abstract: Natural Occurrence, Biological Activities and Synthesis of 8-, 9-, and 11-Membered Ring Lactones

ChemInform ◽  
2009 ◽  
Vol 40 (25) ◽  
Author(s):  
Helena M. C. Ferraz ◽  
Fernanda I. Bombonato ◽  
Myrian K. Sano ◽  
Luiz S. Jr. Longo
Keyword(s):  
Biological Activities ◽  
Membered Ring ◽  
Natural Occurrence

scholarly journals Biocatalysis in the Chemistry of Lupane Triterpenoids

Molecules ◽  
2021 ◽  
Vol 26 (8) ◽  
pp. 2271
Author(s):  
Jan Bachořík ◽  
Milan Urban
Keyword(s):  
Organic Synthesis ◽  
Biological Activities ◽  
Natural Occurrence ◽  
Chemical Transformations ◽  
Large Space ◽  
Lupane Triterpenoids ◽  
Current State ◽  
State Of Research ◽  
Living Organisms ◽  
Derivatives Of

Pentacyclic triterpenes are important representatives of natural products that exhibit a wide variety of biological activities. These activities suggest that these compounds may represent potential medicines for the treatment of cancer and viral, bacterial, or protozoal infections. Naturally occurring triterpenes usually have several drawbacks, such as limited activity and insufficient solubility and bioavailability; therefore, they need to be modified to obtain compounds suitable for drug development. Modifications can be achieved either by methods of standard organic synthesis or with the use of biocatalysts, such as enzymes or enzyme systems within living organisms. In most cases, these modifications result in the preparation of esters, amides, saponins, or sugar conjugates. Notably, while standard organic synthesis has been heavily used and developed, the use of the latter methodology has been rather limited, but it appears that biocatalysis has recently sparked considerably wider interest within the scientific community. Among triterpenes, derivatives of lupane play important roles. This review therefore summarizes the natural occurrence and sources of lupane triterpenoids, their biosynthesis, and semisynthetic methods that may be used for the production of betulinic acid from abundant and inexpensive betulin. Most importantly, this article compares chemical transformations of lupane triterpenoids with analogous reactions performed by biocatalysts and highlights a large space for the future development of biocatalysis in this field. The results of this study may serve as a summary of the current state of research and demonstrate the potential of the method in future applications.

scholarly journals Chemistry of trisindolines: natural occurrence, synthesis and bioactivity

RSC Advances ◽  
2021 ◽  
Vol 11 (41) ◽  
pp. 25381-25421
Author(s):  
First Ambar Wati ◽  
Mardi Santoso ◽  
Ziad Moussa ◽  
Sri Fatmawati ◽  
Arif Fadlan ◽  
...  
Keyword(s):  
Biological Activities ◽  
Structure Activity Relationship ◽  
Activity Relationship ◽  
Natural Occurrence ◽  
Structure Activity

This in-depth review of trisindolines covers their natural occurrence in addition to several routes of synthesis and catalysts used. The biological activities of trisindolines have been discussed with a special emphasis on the structure–activity relationship.

scholarly journals Natural Occurrence, Bioactivity and Biosynthesis of Elaiophylin Analogues

Molecules ◽  
2019 ◽  
Vol 24 (21) ◽  
pp. 3840 ◽  
Author(s):  
Min Gui ◽  
Meng-xue Zhang ◽  
Wen-hui Wu ◽  
Peng Sun
Keyword(s):  
Metabolic Engineering ◽  
Small Molecule ◽  
Biological Activities ◽  
Ischemia Reperfusion ◽  
Genome Mining ◽  
Small Molecule Inhibitor ◽  
Natural Occurrence ◽  
Preclinical Trial ◽  
Molecule Inhibitor ◽  
Inhibitory Activities

Elaiophylins belong to a special family of 16-membered macrodiolides with C2-symmetry. They have exhibited remarkable biological activities, such as antimicrobial, anthelmintic, anticancer, immunosuppressive, anti-inflammatory, antiviral, and α-glucosidase inhibitory activities. A member of elaiophylins, efomycin M, is as a specific small molecule inhibitor of selectin in preclinical trial for the treatment of psoriasis, ischemia-reperfusion, and allergy. The biosynthetic investigation of elaiophylins has uncovered a unique thioesterase, which is responsible for the formation of C2-symmetric diolide. We herein summarize the natural occurrence, bioactivity, and biosynthesis of elaiophylins covering the literatures from 1959 to 2019. Hopefully, this review will inspire further research interests of these compounds and encourage the discovery of new analogues by metabolic engineering or genome mining.

Sign in / Sign up

Export Citation Format

Share Document