Monoterpenes and Sesquiterpenes of Essential Oils from Psidium Species and Their Biological Properties

Abstract

Psidium (Myrtaceae) comprises approximately 266 species, distributed in tropical and subtropical regions of the world. Psidium taxa have great ecological, economic, and medicinal relevance due to their essential oils’ chemical diversity and biological potential. This review reports 18 Psidium species growing around the world and the chemical and biological properties of their essential oils. Chemically, 110 oil records are reported with significant variability of volatile constituents, according to their seasonality and collection sites. Monoterpenes and sesquiterpenes with acyclic (C10 and C15), p-menthane, pinane, bisabolane, germacrane, caryophyllane, cadinane, and aromadendrane skeleton-types, were the primary constituents. The essential oils showed various biological activities, including antioxidant, antifungal, antibacterial, phytotoxic, larvicidal, anti-inflammatory, and cytotoxic properties. This review contributes to the Psidium species rational and economic exploration as natural sources to produce new drugs.

Chemical Composition and Variability of the Volatile Components of Myrciaria Species Growing in the Amazon Region

“…The primary data retrieved from the databases included information related to the article title, authors’ names, keywords, and citation information, including the reference lists. In this way, a cluster was generated relating the main keywords and their links with others used less frequently in the searches [ 4 ].…”

“…The species of Myrtaceae stand out for their economic potential for wood exploitation, a source of ornamental plants, and edible fruits [ 3 ]. In addition, the Myrtaceae species are essential oil-producers which show a chemical variability of cyclic mono- and sesquiterpenes, composed by p -menthane, pinane, bisabolane, germacrane, caryophyllane, cadinane, and aromadendrane skeletons in Psidium genus [ 4 ], and caryophyllane, germacrane, and pinane in Eugenia and Syzygium genera [ 5 ]. Myrtaceae essential oils have many applications in the pharmaceutical, food, and cosmetic industries because of their antifungal, antibacterial, cytotoxic, and insecticidal properties [ 6 ].…”

“…Due to the chemical and biological relevance of Myrtaceae species, some reviews of volatile compounds and essential oils of some genera of Myrtaceae have been published in recent years. Among them are Eugenia , Syzygium [ 5 ], and Psidium [ 4 ]. In addition, another review has addressed one hundred volatile samples of Myrtaceae species, including four samples of Myrciaria [ 11 ].…”

Triterpenoids as Reactive Oxygen Species Modulators of Cell Fate

“… 22 Farnesyl diphosphate and geranylgeranyl diphosphate can then condense in a “head-to-head” mode or tail-to-tail addition to form precursors such as squalene to complex sterols. 22 While these precursors undergo a series of reactions mediated by enzymes, such as late-stage oxidations, carbocation mediated alkyl shifts, and intramolecular cyclization reactions, a representative for antcamphorol triterpenoid was recently reported. 22 A plausible biosynthetic pathway of the triterpenoid family member antcamphorol was proposed as depicted in Figure 4 .…”

“… 22 While these precursors undergo a series of reactions mediated by enzymes, such as late-stage oxidations, carbocation mediated alkyl shifts, and intramolecular cyclization reactions, a representative for antcamphorol triterpenoid was recently reported. 22 A plausible biosynthetic pathway of the triterpenoid family member antcamphorol was proposed as depicted in Figure 4 . Starting with the hydroxylation of the D-ring via bio-oxidation, followed by a unique acid-promoted methyl-migration and the consequent olefin formation, the molecular scaffold of antcamphorol can be derived from its precursor lanosterol, and the late-stage oxidation and cyclization of the D-ring side chain of the advanced intermediate (species d, Figure 4 ) furnished the tetrahydrofuran moiety of antcamphorol triterpenoid.…”