Taxonomic Insights and Its Type Cyclization Correlation of Volatile Sesquiterpenes in Vitex Species and Potential Source Insecticidal Compounds: A Review

Abstract

Sesquiterpenes (SS) are secondary metabolites formed by the bonding of 3 isoprene (C5) units. They play an important role in the defense and signaling of plants to adapt to the environment, face stress, and communicate with the outside world, and their evolutionary history is closely related to their physiological functions. This review considers their presence and extensively summarizes the 156 sesquiterpenes identified in Vitex taxa, emphasizing those with higher concentrations and frequency among species and correlating with the insecticidal activities and defensive responses reported in the literature. In addition, we classify the SS based on their chemical structures and addresses cyclization in biosynthetic origin. Most relevant sesquiterpenes of the Vitex genus are derived from the germacredienyl cation mainly via bicyclogermacrene and germacrene C, giving rise to aromadrendanes, a skeleton with the highest number of representative compounds in this genus, and 6,9-guaiadiene, respectively, indicating the production of 1.10-cyclizing sesquiterpene synthases. These enzymes can play an important role in the chemosystematics of the genus from their corresponding routes and cyclizations, constituting a new approach to chemotaxonomy. In conclusion, this review is a compilation of detailed information on the profile of sesquiterpene in the Vitex genus and, thus, points to new unexplored horizons for future research.

Phytochemical Profile, Preliminary Toxicity, and Antioxidant Capacity of the Essential Oils of Myrciaria floribunda (H. West ex Willd.) O. Berg. and Myrcia sylvatica (G. Mey) DC. (Myrtaceae)

“…This EO consists only of sesquiterpenes, which generally have high toxicity [ 122 , 123 ]. Many sesquiterpenes have shown promising potential for use as raw materials or additives in bioinsecticides, natural repellents, and biopesticides due to their high toxicities [ 124 , 125 , 126 ].…”

A comprehensive review of ethnomedicinal approaches, phytochemical analysis, and pharmacological potential of Vitex trifolia L.

“…β -caryophyllene ( 202 ), a volatile sesquiterpene commonplace across numerous Vitex species, has been consistently identified in V. trifolia , as referenced in nine previous studies, commanding a majority presence in five of these—specifically within the EOs derived from leaves and flowers ( Suksamrarn et al, 1991 ; Musa et al, 2022 ). This metabolite has a defensive role in many plants, released in both direct and indirect defence mechanisms against insect and pathogens ( Barreto et al, 2021 ). Moreover, 1,8-cineole ( 197 ) features prominently in V. trifolia essential oils.…”

Phytochemistry and Pharmacology of Sesquiterpenoids from Atractylodes DC. Genus Rhizomes

“…Sesquiterpenoids are well known as major constituents of essential oils and play important ecological roles in the plants’ interactions with pollinators and predators to adapt to the environment [ 146 ]. In previous reports, atractylon and β -eudesmol were toxic to fruit flies (LD 50 = 1.63 and 2.65 μg/adult, respectively), while the crude oil of A. lancea had an LD 50 value of 2.44 μg/adult [ 49 ].…”

“…Kamauchi et al [48] obtained 2-oxo-hinesol (140), 2-oxo-12-hydroxy-hinesol (141), and 2-oxo-15-hydroxy-hinesol (142) from A. lancea fermented by marine fungus. Eight new spirovetivane-type sesquiterpenoids (143)(144)(145)(146)(147)(148)(149)(150) were identified from the n-BuOH section of an aqueous EtOH extraction of A. lancea using NMR, MS, and ECD data [17]. The spirovetivane-type sesquiterpenoids from genus Atractylodes DC.…”