Amphilectane Diterpenes from <i>Salvia sclarea</i>: Biosynthetic Considerations

Laville, Rémi; Castel, Cécilia; Filippi, Jean‐Jacques; Delbecque, Claire; Audran, Arthur; Garry, Pierre-Philippe; Legendre, Laurent; Fernández, Xavier

doi:10.1021/np2004177

Cited by 15 publications

(12 citation statements)

References 30 publications

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“…ex Fischer from Kandavan, northern Tehran in Iran[15] and Sigesbeckia jorullensis Kunth (Asteraceae) from North-East of Hamburg, German[16]. It was also detected in Lagochilus cabulicus Benth (Lamiaceae) (19.4%); an aromatic plant from Wakhan Corridor in Afghanistan used by the Wakhi and Kyrgyz peoples[17]. Additionally, it was found in very small amounts in Salvia sclarea Clary (Lamiaceae) (1.1%) from France[18] and Salvia reuterana Boiss (Lamiaceae) (0.3%) from Iran[19].…”

mentioning

confidence: 99%

Chemical Variation and Implications on Repellecy Activity of Tephrosia vogelii (Hook f.) Essential Oils Against Sitophilus zeamais Motschulsky

Kerebba¹,

Oyedeji²,

Boyer³

et al. 2020

Preprint

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Chemical variability in the components of T. vogelii essential oils from eastern Uganda was identified using principal component analysis (PCA) and Agglomerative hierarchical clustering (AHC). Based on the profiles of the compounds of farnesene family three chemotypes were found: farnesol (chemotype 1), springene (β- Springene and α-Springene) and the β-Farnesene were distinctive in chemotype 2 and a mixed variety of farnesol and the Springene. In the three cases, alkybenzenes; o-xylene, m-xylene and ethylbenzene were significant components in the oil. 1,4-dihydroxy-p-menth-2-ene, 5,9-undecadien-2-one, 6,10-dimethyl, and 3-cyclohexen-1-carboxaldehyde,3,4-dimethyl were other prominent constituents. The yields of the essential oils did not vary significantly however the chemical composition varied with harvesting time during the rainy and dry seasons. In choice repellency tests, chemotype 1 and chemotype 2 were more active against Sitophilus zeamais than mixed chemotype. Farnesol was found to be effective only at a higher concentration as a repellent against S. zeamais. However, further study that aims to optimize and standardize the varieties and harvesting period needed for recommendation to smallhold farmers.

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confidence: 99%

Chemical Variation and Implications on Repellecy Activity of Tephrosia vogelii (Hook f.) Essential Oils Against Sitophilus zeamais Motschulsky

Kerebba¹,

Oyedeji²,

Boyer³

et al. 2020

Preprint

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“…Within Lamiaceae, there are reports of nonlabdane-related diterpenes from other species, for example cembranoid diterpenes from Anisomeles indica (Chen et al, 2008) and Isodon sculponeatus (Li et al, 2009), and the unusual diterpenoids from Salvia sclarea and Leucosceptrum canum ( Fig. 1) (Laville et al, 2012;Luo et al, 2012). Determining whether the cyclisation of these diterpenes is catalysed by plastidial TPS-a enzymes and, if so, whether those enzymes are encoded by orthologs of PvHVS would help to answer the question of how rare of an event a substrate or compartment change is for a TPS, and whether it occurred multiple times within Lamiaceae.…”

Section: Compartment and Substrate Switching Among Plant Tpssmentioning

confidence: 99%

“…As biosynthetic pathways for labdanerelated diterpenoids in Lamiaceae have already received considerable attention, we decided to focus on a more unusual skeleton. Of the five options (Laville et al, 2012;Luo et al, 2012;Lou et al, 2014), we chose to investigate the biosynthesis of the vulgarisane skeleton ( Fig. 1) from Prunella vulgaris because live plants were accessible and there was high-quality transcriptome data available for both root and leaf tissue (Xiao et al, 2013;Boachon et al, 2018).…”

Section: Introductionmentioning

confidence: 99%

Promiscuous terpene synthases from Prunella vulgaris highlight the importance of substrate and compartment switching in terpene synthase evolution

et al. 2019

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Summary The mint family (Lamiaceae) is well documented as a rich source of terpene natural products. More than 200 diterpene skeletons have been reported from mints, but biosynthetic pathways are known for just a few of these. We crossreferenced chemotaxonomic data with publicly available transcriptomes to select common selfheal ( Prunella vulgaris ) and its highly unusual vulgarisin diterpenoids as a case study for exploring the origins of diterpene skeletal diversity in Lamiaceae. Four terpene synthases (TPS) from the TPS‐a subfamily, including two localised to the plastid, were cloned and functionally characterised. Previous examples of TPS‐a enzymes from Lamiaceae were cytosolic and reported to act on the 15‐carbon farnesyl diphosphate. Plastidial TPS‐a enzymes using the 20‐carbon geranylgeranyl diphosphate are known from other plant families, having apparently arisen independently in each family. All four new enzymes were found to be active on multiple prenyl‐diphosphate substrates with different chain lengths and stereochemistries. One of the new enzymes catalysed the cyclisation of geranylgeranyl diphosphate into 11‐hydroxy vulgarisane, the likely biosynthetic precursor of the vulgarisins. We uncovered the pathway to a rare diterpene skeleton. Our results support an emerging paradigm of substrate and compartment switching as important aspects of TPS evolution and diversification.

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“…Recently two amphilectane diterpenes, salviatriene A and salviatriene B have been isolated from n-hexane extract of the full bloom stage calyx of S. sclarea. These diterpene molecules are considered as the first representatives of this family to be described from the plant kingdom [25]. The current research programme was undertaken as part of our on-going research programme based on bioprospection of natural products [26][27][28][29][30][31][32].…”

Section: Advances In Biomedicine and Pharmacy (An International Journmentioning

confidence: 99%

Chemical constituents of Salvia sclarea from Kashmir (India).

Rahman¹

2017

Adv. Biomed. Pharma

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Salvia sclarea (Lamiaceae) commonly known as clarysage, is a medicinally important herb showing broad range of biological activities. This plant is mainly known because of its pleasantly smelling essential oils rich in linalool and linalyl acetate. In addition to linalool and linalyl acetate (major essential oil secondary metabolites), the peculiar aromatic note of the essential oil is because of the minor constituents including α-terpineol, geranyl acetate, (E)-caryophyllene, limonene, thymol, nerol, geranyl acetate etc. Phytochemical investigation of the aerial parts of this plant yielded nine compounds i.e. β-sitosterol, α-amyrin, ursolic acid, oleanolic acid, betulinic acid, sclareol, salvigenin, acacetin and norartocarpetin. The structures of these compounds have been established by spectroscopic methods (UV, IR, 1 H NMR, 13 C NMR and MS) in light of literature. Structure of ursolic acid has also been established by HMBC experiments. Ursolic acid, oleanolic acid, betulinic acid, salvigenin, acacetin and norartocarpetin are reported for the first time from this plant.

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Amphilectane Diterpenes from Salvia sclarea: Biosynthetic Considerations

Cited by 15 publications

References 30 publications

Chemical Variation and Implications on Repellecy Activity of Tephrosia vogelii (Hook f.) Essential Oils Against Sitophilus zeamais Motschulsky

Chemical Variation and Implications on Repellecy Activity of Tephrosia vogelii (Hook f.) Essential Oils Against Sitophilus zeamais Motschulsky

Promiscuous terpene synthases from Prunella vulgaris highlight the importance of substrate and compartment switching in terpene synthase evolution

Chemical constituents of Salvia sclarea from Kashmir (India).

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