Molecular and Functional Evolution of the Spermatophyte Sesquiterpene Synthases

Liang, Dongmei; Li, Weiguo; Xia, Yan; Caiyin, Qinggele; Zhao, Guang‐Rong; Qiao, Jianjun

doi:10.3390/ijms22126348

Cited by 7 publications

(5 citation statements)

References 60 publications

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“…The removal of the diphosphate anion converts (E,E)‐farnesyl diphosphate to the farnesyl cation, which is sequentially isomerised to the nerolildyl cation. The nerolildyl cation is cyclised to the bisabolyl cation at C6‐C1, which leads to the formation of (−)‐α‐bisabolol ( 1 ), a bisabolene‐type sesquiterpene [81,82] . The farnesyl cation undergoes cyclisation to form the (E,E)‐germacradienyl cation at C10‐C1.…”

Section: Resultsmentioning

confidence: 99%

“…The nerolildyl cation is cyclised to the bisabolyl cation at C6-C1, which leads to the formation of (À )-α-bisabolol (1), a bisabolene-type sesquiterpene. [81,82] The farnesyl cation undergoes cyclisation to form the (E,E)-germacradienyl cation at C10-C1. Two elemene-type sesquiterpenes -elemol (2) and α-elemol (3) -are produced from the (E,E)-germacradienyl cation through the thermal rearrangement of (+)-hedycaryol (Figure 12).…”

Section: Monocyclic Sesquiterpenesmentioning

confidence: 99%

“…Two elemene-type sesquiterpenes -elemol (2) and α-elemol (3) -are produced from the (E,E)-germacradienyl cation through the thermal rearrangement of (+)-hedycaryol (Figure 12). [82][83][84]…”

Section: Monocyclic Sesquiterpenesmentioning

confidence: 99%

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Sesquiterpenoids Isolated from the Rhizomes of Genus Atractylodes

Kim

2022

Chemistry & Biodiversity

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Atractylodes plants have been used in traditional herbal medicine to treat gastrointestinal diseases and contain various chemical compounds. Sesquiterpenoids are the most important therapeutic compounds in Atractylodes rhizomes. Based on studies reported from 2000 to 2022, we classified sesquiterpenoids by their chemical skeletons and original resources. Moreover, we discussed their biosynthesis and physicochemical and pharmacological features. We reported sesquiterpenoids with skeletal moieties, such as monocyclic sesquiterpenes (bisabolene-and elemene-type), bicyclic sesquiterpenes (eudesmane-, isopterocarpolone-, hydroxycarissone-, eremophilane-, bisesquiterpenoid-, guaiane-and spirovetivane-type and eudesmane lactones) and tricyclic sesquiterpenes (cyperene-and patchoulene-type), with their biosynthetic pathways, chemical modifications and in vivo metabolites. The pharmacological activities of sesquiterpenoids as anti-inflammatory, anti-tumor, anti-diabetic and anti-microbial and for treating gastrointestinal disorders have been reported for this genus.

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Section: Resultsmentioning

confidence: 99%

Section: Monocyclic Sesquiterpenesmentioning

confidence: 99%

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Sesquiterpenoids Isolated from the Rhizomes of Genus Atractylodes

Kim

2022

Chemistry & Biodiversity

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“…Sesquiterpenoids are the most complex terpenoids and play vital roles in plant physiological processes [ 25 ]. Artemisinin is a representative sesquiterpenoid that is extracted from A. annua .…”

Section: Discussionmentioning

confidence: 99%

Promoter variations in DBR2-like affect artemisinin production in different chemotypes of Artemisia annua

Wang,

Wu,

Xiang

et al. 2023

Horticulture Research

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Artemisia annua is the only known plant source of the potent antimalarial artemisinin, which occurs as the low- and high-artemisinin producing (LAP and HAP) chemotypes. Nevertheless, the different mechanisms of artemisinin producing between these two chemotypes were still not fully understood. Here, we performed a comprehensive analysis of genome resequencing, metabolome, and transcriptome data to systematically compared the difference in the LAP chemotype JL and HAP chemotype HAN. Metabolites analysis revealed that 72.18% of sesquiterpenes was highly accumulated in HAN compared to JL. Integrated omics analysis found a DBR2-Like (DBR2L) gene may be involved in artemisinin biosynthesis. DBR2L was highly homologous with DBR2, belonged to ORR3 family, and had the DBR2 activity of catalyzing artemisinic aldehyde to dihydroartemisinic aldehyde. Genome resequencing and promoter cloning revealed that complicated variations existed in DBR2L promoters among different varieties of A. annua, and were clustered into three variation types. The promoter activity of diverse variant types showed obvious differences. Furthermore, the core region (-625 to 0) of the DBR2L promoter was identified and candidate transcription factors involved in DBR2L regulation were screened. Thus, the result indicates that DBR2L is another key enzyme involved in artemisinin biosynthesis. The promoter variation in DBR2L affects its expression level, thereby may result in the different yield of artemisinin in varieties of A. annua. It provides a novel insight into the mechanism of artemisinin-producing difference in LAP and HAP chemotypes of A. annua, and will assist in a high yield of artemisinin in A. annua.

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“…The first step of the sesquiterpene synthesis begins with the ionization of farnesyl diphosphate to farnesyl cation. Also, the formation of nerolidyl cation via isomerization can occur from farnesyl cation ( Liang et al., 2021 ; Kirschning et al., 2022 ). Two routes are known for the synthesis of diterpenes and the main enzymes for synthesis are diterpene synthases.…”

Section: Secondary Metabolitesmentioning

confidence: 99%

Production of secondary metabolites using tissue culture-based biotechnological applications

et al. 2023

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Plants are the sources of many bioactive secondary metabolites which are present in plant organs including leaves, stems, roots, and flowers. Although they provide advantages to the plants in many cases, they are not necessary for metabolisms related to growth, development, and reproduction. They are specific to plant species and are precursor substances, which can be modified for generations of various compounds in different plant species. Secondary metabolites are used in many industries, including dye, food processing and cosmetic industries, and in agricultural control as well as being used as pharmaceutical raw materials by humans. For this reason, the demand is high; therefore, they are needed to be obtained in large volumes and the large productions can be achieved using biotechnological methods in addition to production, being done with classical methods. For this, plant biotechnology can be put in action through using different methods. The most important of these methods include tissue culture and gene transfer. The genetically modified plants are agriculturally more productive and are commercially more effective and are valuable tools for industrial and medical purposes as well as being the sources of many secondary metabolites of therapeutic importance. With plant tissue culture applications, which are also the first step in obtaining transgenic plants with having desirable characteristics, it is possible to produce specific secondary metabolites in large-scale through using whole plants or using specific tissues of these plants in laboratory conditions. Currently, many studies are going on this subject, and some of them receiving attention are found to be taken place in plant biotechnology and having promising applications. In this work, particularly benefits of secondary metabolites, and their productions through tissue culture-based biotechnological applications are discussed using literature with presence of current studies.

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Molecular and Functional Evolution of the Spermatophyte Sesquiterpene Synthases

Cited by 7 publications

References 60 publications

Sesquiterpenoids Isolated from the Rhizomes of Genus Atractylodes

Sesquiterpenoids Isolated from the Rhizomes of Genus Atractylodes

Promoter variations in DBR2-like affect artemisinin production in different chemotypes of Artemisia annua

Production of secondary metabolites using tissue culture-based biotechnological applications

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