Natural sesquiterpenoids

Fraga, Braulio M.

doi:10.1039/a705676a

Cited by 25 publications

(9 citation statements)

References 259 publications

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“…Plant species belonging to the family Asteraceae are known for their content of sesquiterpenes which have been reported to serve as toxic or feeding deterrents to insect herbivores . In the present studies, two sesquiterpene lactones, alantolactone and isoalantolactone isolated from I. racemosa , exerted a growth‐inhibiting effect on S. litura .…”

Section: Discussionmentioning

confidence: 99%

Impact of sesquiterpenes from Inula racemosa (Asteraceae) on growth, development and nutrition of Spodoptera litura (Lepidoptera: Noctuidae)

Kaur

Kumar

Upendrabhai

et al. 2016

Pest Management Science

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Section: Discussionmentioning

confidence: 99%

Impact of sesquiterpenes from Inula racemosa (Asteraceae) on growth, development and nutrition of Spodoptera litura (Lepidoptera: Noctuidae)

Kaur

Kumar

Upendrabhai

et al. 2016

Pest Management Science

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“…Basidiomycetes have an inherent ability to produce terpenoids, which is the largest and most diverse class of natural products (Quin et al ., ; Schmidt‐Dannert, ). A wide variety of sesquiterpenoids with an extensive repertoire of backbone structures have been isolated and characterized (Stadler et al ., ; Shiono et al ., ; Kim et al ., ; Li et al ., ; Yoshikawa et al ., ; Kramer and Abraham, ; Fraga, ). A rich history of biochemical studies on sesquiterpene metabolism has established a general scheme that structural diversity of sesquiterpenoids is accomplished by concomitant actions of both sesquiterpene synthases (STSs) and terpene‐modifying enzymes, such as cytochrome P450 monooxygenases (P450s) (Christianson, ; Quin et al ., ; Weitzel and Simonsen, ).…”

Section: Introductionmentioning

confidence: 99%

Insight into metabolic diversity of the brown‐rot basidiomycete Postia placenta responsible for sesquiterpene biosynthesis: semi‐comprehensive screening of cytochrome P450 monooxygenase involved in protoilludene metabolism

Ichinose

Kitaoka

2018

Microbial Biotechnology

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SummaryA wide variety of sesquiterpenoids have been isolated from basidiomycetes, and their bioactive properties have attracted significant attention in an effort to understand biosynthetic machineries. As both sesquiterpene synthases and cytochrome P450 monooxygenases play key roles in the diversification of sesquiterpenoids, it is important to widely and mutually understand their biochemical properties. In this study, we performed genome‐wide annotation and functional characterization of sesquiterpene synthases from the brown‐rot basidiomycete Postia placenta. Using RT‐PCR, we isolated 16 sesquiterpene synthases genes as full‐length cDNAs. Heterologous expression revealed that the sesquiterpene synthases could produce a series of sesquiterpene scaffolds with distinct metabolic profiles. Based on metabolic studies, we identified 25 sesquiterpene scaffolds including Δ6‐protoilludene produced by the sesquiterpene synthases. In particular, a protoilludene synthase from the brown‐rot basidiomycete was characterized for the first time. Furthermore, we conducted a semi‐comprehensive functional screening of cytochrome P450 monooxygenases from P. placenta to elucidate biosynthetic machineries involved in metabolisms of Δ6‐protoilludene. Coexpression of protoilludene synthase and 184 isoforms of cytochrome P450 monooxygenases enabled the identification of CYP5344B1, CYP5348E1 and CYP5348J3, which catalysed the hydroxylation reaction of Δ6‐protoilludene to produce Δ6‐protoilludene‐8‐ol and Δ6‐protoilludene‐5‐ol. Furthermore, structural isomers of Δ7‐protoilludene‐6‐ol were obtained from incubation of Δ6‐protoilludene‐8‐ol in acidic culture medium.

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“…Kayser and Kolodziej () reported that position of alcoholic group affect the fungicidal activity of compound. Hence it can be concluded hydroxyl groups was perquisite for toxicity and position of hydroxyl group was most important as the enzyme‐alcohol complex formed in stereo‐specific manner and compounds with hydroxyl groups showed high solubility in water causing more toxicity (Fraga, ). Daucone showed fungicidal activity due to the presence of ketone group.…”

Section: Resultsmentioning

confidence: 99%

Antifungal potential and structure activity relationship of carrot seed constituents

et al. 2019

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The aim of this study was to evaluate in vitro antifungal potential of carrot seed extracts, its essential oil, different fractions, isolated compounds, and their derivatives against three phytopathogenic rice fungi (Fusarium moniliforme, Bipolaris oryzae, and Rhizoctonia solani) using poisoned food technique. Carrot seed essential oil was extracted using hydrodistillation method and extracts were prepared using different solvents viz. dichloromethane, hexane, and methanol. The pure compounds daucene, carotol, and daucol were isolated using column chromatography and derivatized using different reagents. The study demonstrated that antifungal potential of all tested compounds varied in a dose dependent manner. Structure activity relationship of isolated and derivatized compounds showed that polar moieties possessed more antifungal potential as compared to non‐polar moieties. The results suggested that carrot seed methanol extract and carotol possessed strong antifungal potential as compared to other components tested. Practical applications Phytopathogenic fungi are the major problems causing harmful damage to the rice crop. Only available control of these diseases is synthetic fungicides but their repeated use led to serious environmental issues, residual toxicity, and development of resistance. Therefore, it's better to find some natural alternatives. The current study was conducted to evaluate in vitro antifungal potential of carrot seed essential oil, its constituents and extracts against phytopathogenic fungi of rice. The methanol extract and carotol possessed highest antifungal potential which might be due to their polar nature. This information may add a new dimensions to biological activity of these natural molecules mainly in the field of agriculture as fungal diseases are found to be associated with major losses in agriculture. Hence these compounds can act as natural antifungal agents against rice fungi.

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Natural sesquiterpenoids

Abstract: For Abstract see ChemInform Abstract in Full Text.

Cited by 25 publications

References 259 publications

Impact of sesquiterpenes from Inula racemosa (Asteraceae) on growth, development and nutrition of Spodoptera litura (Lepidoptera: Noctuidae)

Impact of sesquiterpenes from Inula racemosa (Asteraceae) on growth, development and nutrition of Spodoptera litura (Lepidoptera: Noctuidae)

Insight into metabolic diversity of the brown‐rot basidiomycete Postia placenta responsible for sesquiterpene biosynthesis: semi‐comprehensive screening of cytochrome P450 monooxygenase involved in protoilludene metabolism

Antifungal potential and structure activity relationship of carrot seed constituents

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