Biochemistry of Terpenoids: Monoterpenes, Sesquiterpenes, Diterpenes, Sterols, Cardiac Glycosides and Steroid Saponins

Gershenzon, Jonathan; Kreis, Wolfgang; Roberts, Jeremy A.; Evan, David; McManus, Michael T.; Rose, Jocelyn K. C.

doi:10.1002/9781119312994.apr0016

Cited by 28 publications

(27 citation statements)

References 324 publications

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“…In Vitro Assays Demonstrate That ZmTps21 Is a Largely Product-Specific b-Selinene Synthase ZmTps21 lacks a predicted N-terminal transit peptide, suggesting that the enzyme is not targeted to plastids, as is typical of monoterpene and diterpene synthases, but instead remains cytosolic, consistent with predictions for a sesquiterpene synthase (Gershenzon and Kreis, 1999). To obtain additional support for the hypothesis that Mo17 ZmTps21 is a b-selinene synthase, heterologous expression was performed in E. coli and the resulting protein extract was incubated with the precursor substrate FPP.…”

Section: Identification Of A-and B-selinene-derived Products As Inducmentioning

confidence: 53%

Selinene Volatiles Are Essential Precursors for Maize Defense Promoting Fungal Pathogen Resistance

et al. 2017

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To ensure food security, maize (Zea mays) is a model crop for understanding useful traits underlying stress resistance. In contrast to foliar biochemicals, root defenses limiting the spread of disease remain poorly described. To better understand belowground defenses in the field, we performed root metabolomic profiling and uncovered unexpectedly high levels of the sesquiterpene volatile b-selinene and the corresponding nonvolatile antibiotic derivative b-costic acid. The application of metabolite-based quantitative trait locus mapping using biparental populations, genome-wide association studies, and nearisogenic lines enabled the identification of terpene synthase21 (ZmTps21) on chromosome 9 as a b-costic acid pathway candidate gene. Numerous closely examined b-costic acid-deficient inbred lines were found to harbor Zmtps21 pseudogenes lacking conserved motifs required for farnesyl diphosphate cyclase activity. For biochemical validation, a full-length ZmTps21 was cloned, heterologously expressed in Escherichia coli, and demonstrated to cyclize farnesyl diphosphate, yielding b-selinene as the dominant product. Consistent with microbial defense pathways, ZmTps21 transcripts strongly accumulate following fungal elicitation. Challenged field roots containing functional ZmTps21 alleles displayed b-costic acid levels over 100 mg g 21 fresh weight, greatly exceeding in vitro concentrations required to inhibit the growth of five different fungal pathogens and rootworm larvae (Diabrotica balteata). In vivo disease resistance assays, using ZmTps21 and Zmtps21 near-isogenic lines, further support the endogenous antifungal role of selinene-derived metabolites. Involved in the biosynthesis of nonvolatile antibiotics, ZmTps21 exists as a useful gene for germplasm improvement programs targeting optimized biotic stress resistance.

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Section: Identification Of A-and B-selinene-derived Products As Inducmentioning

confidence: 53%

Selinene Volatiles Are Essential Precursors for Maize Defense Promoting Fungal Pathogen Resistance

et al. 2017

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“…They are phytochemicals, or plant chemicals, possessing detergent properties and make foam when mixed with water [11]. In fact, saponins are classified as steroidal, triterpenoidal or alkaloidal depending on the nature of the aglycone [12]. The aglycone parts of saponins are generally oligosaccharides [13].…”

Section: Introductionmentioning

confidence: 99%

Production of Saponin Biosurfactant from Glycyrrhiza glabra as an Agent for Upgrading Heavy Crude Oil

Hajimohammadi

Hosseini

Amani

et al. 2016

J Surfact & Detergents

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Saponins are the main group of phytogenic biosurfactants extracted from plants. One of the significant applications of these compounds is upgrading and viscosity reduction of heavy crude oil water in oil (W/O) emulsions. In this research, use of saponin extracted from Glycyrrhiza glabra was investigated for viscosity reduction of heavy crude oil and upgrading its API properties. The extracted saponin was characterized using Fourier transform infrared (FTIR) and nuclear magnetic resonance (NMR) spectroscopy. Phase behavior analysis demonstrated a reduction in initial viscosity and improved API gravity of the heavy oil from 2350 mPa·s and 19 to 900 mPa·s and 27, respectively. In addition, the emulsification index (E24) was found to be 98 % at a saponin concentration of 8 % w/v. It was observed that the emulsions were stable in the pH range of 5.5–13, temperature from 30 to 80 °C and salinity up to 6 % w/v of NaCl solution. Average diameter of W/O droplets evaluated by dynamic light scattering (DLS) were in the range of 10–15 µm. The results obtained from the present research revealed that the extracted saponin improved the physical characteristics of heavy crude oil. We propose the use of saponin as a potential alternative to conventional emulsifiers for upgrading heavy crude oil in petroleum industry.

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“…The next stage occurs during a series of cyclizations driven by TPS. The pentanol isoprene units C5H8 can produce very different terpenoid metabolite constituents (Gershenzon and Kreis 1999;Monson 2013;Lange and Rios-Estepa 2014). In the pine resin biosynthesis pathway, the TPS, such as DXS, DXR, HDR, IPPI, IPPS, GPPS, FPPS, and GGPPS, were able to participate in the resin terpene production progress.…”

Section: Differential Gene Expression In Resin Biosynthetic Pathwaymentioning

confidence: 99%

Transcriptome Analyses to Reveal Genes Involved in Terpene Biosynthesis in Resin Producing Pine Tree Pinus kesiya var. langbianensis

et al. 2018

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Pinus kesiya var. langbianensis is an important resin resource tree that belongs to the Pinaceae family. It produces a higher yield of resin per year compared to the rest of the pine trees from the same habitat. To identify genes that may be involved in this high resin yield production, the bark transcriptomes of P. kesiya var. langbianensis and a P. kesiya that produce a normal volume of resin were sequenced using RNA-Seq, and their gene expression profiles were compared in regards to specific interest in the resin synthetic metabolism pathways. The results showed that a total of 68,881 transcripts were assembled, 180 of which were involved in terpene metabolism. Surprisingly, in both the transcriptome analysis and the quantitative fluorescent polymerase chain reaction (QF-PCR), nine genes involved in resin biosynthesis were shown to be significantly down-regulated in P. kesiya. In addition, this study provided numerous gene candidates for the further study of resin production in pine trees.

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Biochemistry of Terpenoids: Monoterpenes, Sesquiterpenes, Diterpenes, Sterols, Cardiac Glycosides and Steroid Saponins

Abstract: The sections in this article areThe Basic Pathway of Terpenoid Biosynthesis and the Formation and Function ofC5‐C20Terpenoid MetabolitesSterols, Cardiac Glycosides and Steroid SaponinsAcknowledgements

Cited by 28 publications

References 324 publications

Selinene Volatiles Are Essential Precursors for Maize Defense Promoting Fungal Pathogen Resistance

Selinene Volatiles Are Essential Precursors for Maize Defense Promoting Fungal Pathogen Resistance

Production of Saponin Biosurfactant from Glycyrrhiza glabra as an Agent for Upgrading Heavy Crude Oil

Transcriptome Analyses to Reveal Genes Involved in Terpene Biosynthesis in Resin Producing Pine Tree Pinus kesiya var. langbianensis

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