Picrotoxane sesquiterpenoids: chemistry, chemo- and bio-syntheses and biological activities

Shi, Qiang-Qiang; Tang, Jiang‐Jiang; Gao, Jin‐Ming

doi:10.1039/d2np00049k

Cited by 19 publications

(5 citation statements)

References 230 publications

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“…Sesquiterpenes, with their 15-carbon backbone derived from three isoprene units, exhibit a remarkable diversity in chemical structures and shapes, making them a significant class of terpene known for various structures and functions [ 129 ]. These compounds, found in numerous plants, contribute to the unique scents and flavors of many essential oils and have notable biological activities, including the antimalaria drug artemisinin.…”

Section: Applications Of Tpf In Microbial Production Of Terpenesmentioning

confidence: 99%

Two-Phase Fermentation Systems for Microbial Production of Plant-Derived Terpenes

Li,

Liu,

Xiang

et al. 2024

Molecules

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Microbial cell factories, renowned for their economic and environmental benefits, have emerged as a key trend in academic and industrial areas, particularly in the fermentation of natural compounds. Among these, plant-derived terpenes stand out as a significant class of bioactive natural products. The large-scale production of such terpenes, exemplified by artemisinic acid—a crucial precursor to artemisinin—is now feasible through microbial cell factories. In the fermentation of terpenes, two-phase fermentation technology has been widely applied due to its unique advantages. It facilitates in situ product extraction or adsorption, effectively mitigating the detrimental impact of product accumulation on microbial cells, thereby significantly bolstering the efficiency of microbial production of plant-derived terpenes. This paper reviews the latest developments in two-phase fermentation system applications, focusing on microbial fermentation of plant-derived terpenes. It also discusses the mechanisms influencing microbial biosynthesis of terpenes. Moreover, we introduce some new two-phase fermentation techniques, currently unexplored in terpene fermentation, with the aim of providing more thoughts and explorations on the future applications of two-phase fermentation technology. Lastly, we discuss several challenges in the industrial application of two-phase fermentation systems, especially in downstream processing.

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Section: Applications Of Tpf In Microbial Production Of Terpenesmentioning

confidence: 99%

Two-Phase Fermentation Systems for Microbial Production of Plant-Derived Terpenes

Li,

Liu,

Xiang

et al. 2024

Molecules

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“…Polycyclic frameworks are not only commonly found in biologically active molecules and natural products [ 1 , 2 , 3 , 4 , 5 ], but they also have the potential to provide structural foundations for fragment-based drug discovery [ 6 , 7 , 8 , 9 , 10 ]. The ring-fusion strategy has been one of the most powerful methods for efficiently constructing polycyclic frameworks [ 11 , 12 , 13 , 14 , 15 , 16 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Benzofuro[3,2-b]indol-3-one Derivatives via Dearomative (3 + 2) Cycloaddition of 2-Nitrobenzofurans and para-Quinamines

Yuan,

Zeng,

Zhang

et al. 2024

Molecules

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An efficient dearomative (3 + 2) cycloaddition of para-quinamines and 2-nitrobenzofurans has been developed. This reaction proceeds smoothly under mild conditions and affords a series of benzofuro[3,2-b]indol-3-one derivatives in good to excellent yields (up to 98%) with perfect diastereoselectivities (all cases > 20:1 dr). The scale-up synthesis and versatile derivatizations demonstrate the potential synthetic application of the protocol. A plausible reaction mechanism is also proposed to account for the observed reaction process. This work represents the first instance of the N-triggered dearomative (3 + 2) cycloaddition of 2-nitrobenzofurans.

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“…Since picrotoxin, which is a poisonous compound composed of a 1:1 mixture of picrotoxinin ( 1 ) and picrotin ( 2 ), was found in Menispermum cocculus in 1818, more than 130 picrotoxane-type natural products have been isolated (Figure ). Because 1 is a strong antagonist of the γ-aminobutyric acid (GABA) receptor, resulting in excitatory effects in the central nervous system, 1 is frequently used as a chemical tool for investigations in neurobiology . Picrotoxane-type sesquiterpenes bear a cis -hydrindane skeleton as a common structure, and its bicyclic core is highly oxy-functionalized with hydroxy groups, lactones, and epoxides.…”

mentioning

confidence: 99%

Total Synthesis of (+)-Coriamyrtin via a Desymmetrizing Strategy Involving a 1,3-Cyclopentanedione Moiety

et al. 2023

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We describe the total synthesis of (+)-coriamyrtin, which bears a highly functionalized cis-hydrindane skeleton and is a widely known neurotoxin of the Coriariaceae family. Our synthetic strategy involves the highly stereoselective construction of the cishydrindane skeleton via a desymmetrizing strategy involving a 1,3cyclopentanedione moiety using an intramolecular aldol reaction and the formation of the 1,3-diepoxide moiety of coriamyrtin through the elaborate functionalization of the cyclopentane ring in the bicyclic structure. P icrotoxane-type sesquiterpenes are widely distributed in plants, such as Coriariaceae, Orchidaceae, and Menispermaceae. 1 Since picrotoxin, which is a poisonous compound composed of a 1:1 mixture of picrotoxinin (1) and picrotin (2), was found in Menispermum cocculus in 1818, more than 130 picrotoxane-type natural products have been isolated (Figure 1). 2 Because 1 is a strong antagonist of the γ-

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Picrotoxane sesquiterpenoids: chemistry, chemo- and bio-syntheses and biological activities

Abstract: This review summarizes a total of 132 picrotoxane sesquiterpenoids to date, focusing on their structural diversity, chemo- and bio-syntheses, and biological activities.

Cited by 19 publications

References 230 publications

Two-Phase Fermentation Systems for Microbial Production of Plant-Derived Terpenes

Two-Phase Fermentation Systems for Microbial Production of Plant-Derived Terpenes

Synthesis of Benzofuro[3,2-b]indol-3-one Derivatives via Dearomative (3 + 2) Cycloaddition of 2-Nitrobenzofurans and para-Quinamines

Total Synthesis of (+)-Coriamyrtin via a Desymmetrizing Strategy Involving a 1,3-Cyclopentanedione Moiety

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