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Terpenes are the primary constituents of essential oils and are responsible for the aroma characteristics of cannabis. Together with the cannabinoids, terpenes illustrate synergic and/or entourage effect and their interactions have only been speculated in for the last few decades. Hundreds of terpenes are identified that allude to cannabis sensory attributes, contributing largely to the consumer’s experiences and market price. They also enhance many therapeutic benefits, especially as aromatherapy. To shed light on the importance of terpenes in the cannabis industry, the purpose of this review is to morphologically describe sources of cannabis terpenes and to explain the biosynthesis and diversity of terpene profiles in different cannabis chemovars.

The past five years have marked a significant evolution in terpenoid natural product research, with direct implications for marine drug discovery [...].The past five years have marked a significant evolution in terpenoid natural product research, with direct implications for marine drug discovery [...].

The interactions of plants with environment and insects are bi-directional and dynamic. Consequently, a myriad of mechanisms has evolved to engage organisms in different types of interactions. These interactions can be mediated by allelochemicals known as volatile organic compounds (VOCs) which include volatile terpenes (VTs). The emission of VTs provides a way for plants to communicate with the environment, including neighboring plants, beneficiaries (e.g., pollinators, seed dispersers), predators, parasitoids, and herbivores, by sending enticing or deterring signals. Understanding terpenoid distribution, biogenesis, and function provides an opportunity for the design and implementation of effective and efficient environmental calamity and pest management strategies. This review provides an overview of plant–environment and plant–insect interactions in the context of terpenes and terpenoids as important chemical mediators of these abiotic and biotic interactions.

[This corrects the article DOI: 10.1371/journal.pone.0287524.].

A carotenoid-derived hormonal signal that inhibits shoot branching in plants has long escaped identification. Strigolactonesare compounds thought to be derived from carotenoids and are known to trigger the germination of parasitic plant seeds andstimulate symbiotic fungi. Here we present evidence that carotenoid cleavage dioxygenase 8 shoot branching mutants of peaare strigolactone deficient and that strigolactone application restores the wild-type branching phenotype to ccd8 mutants.Moreover, we show that other branching mutants previously characterized as lacking a response to the branching inhibitionsignal also lack strigolactone response, and are not deficient in strigolactones. These responses are conserved in Arabidopsis.In agreement with the expected properties of the hormonal signal, exogenous strigolactone can be transported in shoots andact at low concentrations. We suggest that endogenous strigolactones or related compounds inhibit shoot branching inplants. Furthermore, ccd8 mutants demonstrate the diverse effects of strigolactones in shoot branching, mycorrhizalsymbiosis and parasitic weed interaction.

Shoot branching is a major determinant of plant architecture and is highly regulated by endogenous and environmental cues. Two classes of hormones, auxin and cytokinin, have long been known to have an important involvement in controlling shoot branching. Previous studies using a series of mutants with enhanced shoot branching suggested the existence of a third class of hormone(s) that is derived from carotenoids, but its chemical identity has been unknown. Here we show that levels of strigolactones, a group of terpenoid lactones, are significantly reduced in some of the branching mutants. Furthermore, application of strigolactones inhibits shoot branching in these mutants. Strigolactones were previously found in root exudates acting as communication chemicals with parasitic weeds and symbiotic arbuscular mycorrhizal fungi. Thus, we propose that strigolactones act as a new hormone class—or their biosynthetic precursors—in regulating above-ground plant architecture, and also have a function in underground communication with other neighbouring organisms. Branching out: new class of plant hormones inhibits branch formation For many years the textbooks recognized five 'classic' plant hormones: auxin, gibberellins, ethylene, cytokinin and abscisic acid. To these can be added the brassinosteroids, nitric oxide and jasmonates, among others, as phytohormones or plant growth regulators. Shoot branching is regulated by hormones, with both auxin and cytokinin playing a part. But the existence of mutants with enhanced branching in several species suggested a third factor was involved, a novel plant hormone released from the roots that prevents excessive shoot branching. Two groups now identify a class of chemical compounds called strigolactones — or one of their derivatives — as that missing hormone. Strigolactones are found in root exudates and are reduced in the branching mutants; external application of these chemicals inhibits shoot branching in the mutants. Shoot branching is regulated by hormones. Branching mutants in several plant species suggests the existence of a plant hormone that is released from the roots and prevents excessive shoot branching. This paper reports on one of two studies that show that a class of chemical compounds called strigolactones found in root exudates are reduced in the branching mutants and that external application of these chemicals inhibits shoot branching in the mutants. It is proposed that strigolactones or related metabolites are the sought after class of hormones.

Isolation, finding or discovery of novel anticancer agents is very important for cancer treatment, and seaweeds are one of the largest producers of chemically active metabolites with valuable cytotoxic properties, and therefore can be used as new chemotherapeutic agents or source of inspiration to develop new ones. Identification of the more potent and selective anticancer components isolated from brown, green and red seaweeds, as well as studies of their mode of action is very attractive and constitute a small but relevant progress for pharmacological applications. Several researchers have carried out in vitro and in vivo studies in various cell lines and have disclosed the active metabolites among the terpenoids, including carotenoids, polyphenols and alkaloids that can be found in seaweeds. In this review the type of metabolites and their cytotoxic or antiproliferative effects will be discussed additionally their mode of action, structure-activity relationship and selectivity will also be revealed. The diterpene dictyolactone, the sterol cholest-5-en-3β,7α-diol and the halogenated monoterpene halomon are among the reported compounds, the ones that present sub-micromolar cytotoxicity. Additionally, one dimeric sesquiterpene of the cyclolaurane-type, three bromophenols and one halogenated monoterpene should be emphasized because they exhibit half maximal inhibitory concentration (IC50) values between 1–5 µM against several cell lines.

Background It is well known that aromatic essential oils extracted from the heartwood of Santalum album L. have wide economic value. However, little is known about the role of terpenoids in response to various adverse environmental stresses as other plants do in the form of signals during plant-environment interactions. Results In this study, trace amounts of volatiles consisting of α-santalene, epi -β-santalene, β-santalene, α-santalol, β-santalol, ( E )-α-bergamotene, ( E )-β-farnesene and β-bisabolene were found in the leaves of mature S. album trees. We identified more than 40 candidate terpene synthase (TPS) unigenes by mining publicly-available RNA-seq data and characterized the enzymes encoded by three cDNAs: one mono-TPS catalyzes the formation of mostly α-terpineol, and two multifunctional sesqui-TPSs, one of which produces ( E )-α-bergamotene and sesquisabinene as major products and another which catalyzes the formation of ( E )-β-farnesene, ( E )-nerolidol and ( E,E )-farnesol as main products. Metabolite signatures and gene expression studies confirmed that santalol content is closely related with santalene synthase (SaSSY) transcripts in heartwood, which is key enzyme responsible for santalol biosynthesis. However, the expression of three new SaTPS genes differed significantly from SaSSY in the essential oil-producing heartwood. Increased activities of antioxidant enzymes, superoxide dismutase, catalase, peroxidase and ascorbate peroxidase, were detected in different tissues of S. album plants after applying 1 mM methyl jasmonate (MeJA) and 1 mM salicylic acid (SA), or exposure to 4°C, 38°C and high light intensity. MeJA and SA dramatically induced the expression of SaTPS1 and SaTPS2 in leaves. SaTPS1 to 3 transcripts were differentially activated among different tissues under adverse temperature and light stresses. In contrast, almost all SaSSY transcripts decreased in response to these environmental stresses, unlike SaTPS1 to 3 . Conclusions Multifunctional enzymes were biochemically characterized, including one chloroplastic mono-TPS and two cytosolic sesqui-TPSs in sandalwood. Our results suggest the ecological importance of these three new SaTPS genes in defensive response to biotic attack and abiotic stresses in S. album .

Terpenoids have extensive pharmacological activities and are extensively applied in the pharmaceutical, cosmetic, and food industries. Increasing the structural diversity of terpenoids would expand their potential applications.Noncanonical backbones can be generated by coexpressing the canonical mevalonate pathway and C-methyltransferases, or the lepidopteran mevalonate pathway, in engineered strains.The design and chemical synthesis of farnesyl pyrophosphate analogs to create unnatural terpenoids promises two advantages: it complements other methods of terpene synthesis and bypasses the task of engineering entire metabolic pathways to produce alternative substrates in vivo.The artificial metalloenzyme Ir(Me)-porphyrin IX CYP119 allows cyclopropanation of limonene to synthesize high titers of unnatural products with high diastereoselectivity. Terpenoids display chemical and structural diversities as well as important biological activities. Despite their extreme variability, the range of these structures is limited by the scope of natural products that canonically derive from interconvertible five-carbon (C5) isoprene units. New approaches have recently been developed to expand their structural diversity. This review systematically explores the combinatorial biosynthesis of noncanonical building blocks via the coexpression of the canonical mevalonate (MVA) pathway and C-methyltransferases (C-MTs), or by using the lepidopteran mevalonate (LMVA) pathway. Unnatural terpenoids can be created from farnesyl diphosphate (FPP) analogs by chemobiological synthesis and terpene cyclopropanation by artificial metalloenzymes (ArMs). Advanced technologies to accelerate terpene biosynthesis are discussed. This review provides a valuable reference for increasing the diversity of valuable terpenoids and their derivatives, as well as for expanding their potential applications. Terpenoids display chemical and structural diversities as well as important biological activities. Despite their extreme variability, the range of these structures is limited by the scope of natural products that canonically derive from interconvertible five-carbon (C5) isoprene units. New approaches have recently been developed to expand their structural diversity. This review systematically explores the combinatorial biosynthesis of noncanonical building blocks via the coexpression of the canonical mevalonate (MVA) pathway and C-methyltransferases (C-MTs), or by using the lepidopteran mevalonate (LMVA) pathway. Unnatural terpenoids can be created from farnesyl diphosphate (FPP) analogs by chemobiological synthesis and terpene cyclopropanation by artificial metalloenzymes (ArMs). Advanced technologies to accelerate terpene biosynthesis are discussed. This review provides a valuable reference for increasing the diversity of valuable terpenoids and their derivatives, as well as for expanding their potential applications.