Occurrence and biosynthesis of plant sesterterpenes (C25), a new addition to terpene diversity

Chen, Qingwen; Li, Jianxu; Ma, Yihua; Yuan, Weiliang; Zhang, Peng; Wang, Guodong

doi:10.1016/j.xplc.2021.100184

Cited by 13 publications

(13 citation statements)

References 47 publications

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“…Salvia is one of the few genera in the Lamiaceae family that produces sesterterpenoids ( Qingwen et al, 2021 ). To date, more than 130 species of Salvia have been phytochemically studied.…”

Section: Resultsmentioning

confidence: 99%

“…Sesterterpenes show many interesting pharmacological properties, including cytotoxicity, anti-microbial, anti-angiogenic activities, antibioﬁlm, and platelet aggregation inhibition ( Rustaiyan et al, 2007 ; Cabanillas et al, 2018 ). The genus Salvia is one of the few genera in the Lamiaceae family that produces sesterterpenes ( Qingwen et al, 2021 ). Many of these Salvia species are medicinal plants included in some pharmacopoeias, and are also used for alimentary and cosmetic purposes.…”

Section: Introductionmentioning

confidence: 99%

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New Sesterterpenoids from Salvia mirzayanii Rech.f. and Esfand. Stereochemical Characterization by Computational Electronic Circular Dichroism

et al. 2022

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Phytochemical investigation on the acetone extract of Salvia mirzayanii Rech. f. and Esfand. aﬀorded seven new isoprenoids including six new sesterterpenoids salvimirzacolide A-F (1–6), and one new nor-diterpenoid (7). Their structures were established by comprehensive spectroscopic and spectrometric data analysis (1D and 2D NMR, HRMS) and DP4+ NMR chemical shift probability calculation technique. Moreover, the absolute conﬁguration of compounds was determined by using electronic circular dichroism spectroscopy. Evaluation of antiproliferative properties of compounds isolated against four human melanoma cancer cells displayed no cytotoxic activity at the concentration range used.

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“…Salvia is one of the few genera in the Lamiaceae family that produces sesterterpenoids ( Qingwen et al, 2021 ). To date, more than 130 species of Salvia have been phytochemically studied.…”

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

New Sesterterpenoids from Salvia mirzayanii Rech.f. and Esfand. Stereochemical Characterization by Computational Electronic Circular Dichroism

et al. 2022

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“…The formation mechanism of compounds 1 and 2 is clearly different from those of reported plant sester-TPSs using either the type A (C 1 –IV–V, cyclization between C 1 -cation, C 14 -C 15 olefin [double bond IV], and C 18 -C 19 olefin [double bond V] of GFDP) or type B (C 1 –III–IV, cyclization between C 1 -cation, C 10 -C 11 olefin [double bond III], and C 14 -C 15 olefin [double bond IV] of GFDP) cyclization route ( Huang et al., 2017 ; Minami et al., 2018 ; Chen et al., 2020 , 2021 ) ( Figure 6 ). According to the catalytic mechanism of the monoterpenoid and sesquiterpenoid products of CcTPS1 delineated in previous enzymological studies, the linear prenyl diphosphate precursors probably undergo an ionization–isomerization–reionization process to form cation A with different chain lengths.…”

Section: Discussionmentioning

confidence: 99%

An extremely promiscuous terpenoid synthase from the Lamiaceae plant Colquhounia coccinea var. mollis catalyzes the formation of sester-/di-/sesqui-/mono-terpenoids

Jin

Luo

et al. 2021

Plant Communications

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Terpenoids are the largest class of natural products with complex structures and extensive bioactivities; their scaffolds are generated by diverse terpenoid synthases (TPSs) from a limited number of isoprenoid diphosphate precursors. Promiscuous TPSs play important roles in the evolution of terpenoid chemodiversity, but they remain largely unappreciated. Here, an extremely promiscuous terpenoid synthase (CcTPS1) of the TPS-b subfamily was cloned and functionally characterized from a leaf-specific transcriptome of the Lamiaceae plant Colquhounia coccinea var. mollis . CcTPS1 is the first sester-/di-/sesqui-/mono-TPS identified from the plant kingdom, accepting C 25 /C 20 /C 15 /C 10 diphosphate substrates to generate a panel of sester-/di-/sesqui-/mono-terpenoids. Engineered Escherichia coli expressing CcTPS1 produced three previously unreported terpenoids (two sesterterpenoids and a diterpenoid) with rare cyclohexane-containing skeletons, along with four sesquiterpenoids and one monoterpenoid. Their structures were elucidated by extensive nuclear magnetic resonance spectroscopy. Nicotiana benthamiana transiently expressing CcTPS1 also produced the diterpenoid and sesquiterpenoids, demonstrating the enzyme’s promiscuity in planta . Its highly leaf-specific expression pattern combined with detectable terpenoid products in leaves of C . coccinea var. mollis and N. benthamiana expressing CcTPS1 suggested that CcTPS1 was mainly responsible for diterpenoid and sesquiterpenoid biosynthesis in plants. CcTPS1 expression and the terpenoid products could be induced by methyl jasmonate, suggesting their possible role in plant–environment interaction. CcTPS1 was localized to the cytosol and may differ from mono-TPSs in subcellular compartmentalization and substrate tolerance. These findings will greatly aid our understanding of plant TPS evolution and terpenoid chemodiversity; they also highlight the enormous potential of transcriptome mining and heterologous expression for the exploration of unique enzymes and natural products hidden in plants.

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“…Sesterterpenes (C 25 ) are a class of terpenoid compounds that have been frequently reported from bacteria, fungi, lichens, insects, marine invertebrates (particularly marine sponges), and some higher plant families such as Asteraceae, Lamiaceae, Lobariaceae, Gentianaceae, and Pteridaceae. Sesterterpenoids are among the most interesting classes of specialized metabolites since they possess relevant biological and pharmacological activities [ 50 ]. Sesterterpenoids reported from plants of the genus Salvia possess a prenyllabdane skeleton ( Figure 4 ) [ 51 ], all containing a γ-lactone ring.…”

Section: Sesterterpenoidsmentioning

confidence: 99%

“…Moreover, phylogenetic analysis of plant TPS sequences clearly showed that functional sesterTPSs evolved from the TPS-a subfamily, the members of which always utilize GPP and/or FPP as substrates. However, since plant sesterTPSs have been identified only from Brassicaceae, it is still unclear whether the sesterTPSs from other plant species, such as Lamiaceae, evolved from the TPS-a subfamily or from other TPS subfamilies [ 50 ].…”

Section: Sesterterpenoidsmentioning

confidence: 99%

Uncommon Terpenoids from Salvia Species: Chemistry, Biosynthesis and Biological Activities

et al. 2022

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The search for new bioactive compounds from plant sources has been and continues to be one of the most important fields of research in drug discovery. However, Natural Products research has continuously evolved, and more and more has gained a multidisciplinary character. Despite new developments of methodologies and concepts, one intriguing aspect still persists, i.e., different species belonging to the same genus can produce different secondary metabolites, whereas taxonomically different genera can produce the same compounds. The genus Salvia L. (Family Lamiaceae) comprises myriad distinct medicinal herbs used in traditional medicine worldwide that show different pharmacological activities due to the presence of a variety of interesting specialized metabolites, including mono-, sesqui-, di-, sester-, tri-, tetra-, and higher terpenoids as well as phenylpropanoids, phenolic acid derivatives, lignans, flavonoids, and alkaloids. We herein summarize the research progress on some uncommon terpenoids, isolated from members of the genus Salvia, which are well recognized for their potential pharmacological activities. This review also provides a current knowledge on the biosynthesis and occurrence of some interesting phytochemicals from Salvia species, viz. C23-terpenoids, sesterterpenoids (C25), dammarane triterpenoids (C30), and uncommon triterpenoids (C20+C10). The study was carried out by searching various scientific databases, including Elsevier, ACS publications, Taylor and Francis, Wiley Online Library, MDPI, Springer, Thieme, and ProQuest. Therefore, 106 uncommon terpenoids were identified and summarized. Some of these compounds possessed a variety of pharmacological properties, such as antibacterial, antiviral, antiparasitic, cytotoxic and tubulin tyrosine ligase inhibitory activities. Due to the lack of pharmacological information for the presented compounds gathered from previous studies, biological investigation of these compounds should be reinvestigated.

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Occurrence and biosynthesis of plant sesterterpenes (C25), a new addition to terpene diversity

Cited by 13 publications

References 47 publications

New Sesterterpenoids from Salvia mirzayanii Rech.f. and Esfand. Stereochemical Characterization by Computational Electronic Circular Dichroism

New Sesterterpenoids from Salvia mirzayanii Rech.f. and Esfand. Stereochemical Characterization by Computational Electronic Circular Dichroism

An extremely promiscuous terpenoid synthase from the Lamiaceae plant Colquhounia coccinea var. mollis catalyzes the formation of sester-/di-/sesqui-/mono-terpenoids

Uncommon Terpenoids from Salvia Species: Chemistry, Biosynthesis and Biological Activities

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