Unusual cyclic terpenoids with terminal pendant prenyl moieties: from occurrence to synthesis

Kulciţki, Veaceslav; Harghel, Petru; Ungur, Nicon

doi:10.1039/c4np00081a

Cited by 11 publications

(9 citation statements)

References 176 publications

(195 reference statements)

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“…Consistent with this, the signal due to H–C(10) ax was a broad multiplet ( w 1/2 = 17.0 Hz) in the 1 H‐NMR spectrum whereas axial Me(14) resonated at δ (C) 15.8 in the 13 C‐NMR spectrum (see Supporting Information ). This stereochemical assignment was further supported by comparing spectroscopic data of 1 with those reported in the literature for marine diterpenoid models exhibiting a similar structural architecture and substitution pattern ( i.e . sphaerococcenol A, bromophycolide J).…”

Section: Resultssupporting

confidence: 69%

“…Monocyclic diterpenoids with a double pendant prenylation are not common in nature. In particular, in marine organisms, a few examples have been reported from anaspidean molluscs and algae . Biogenetically, they should derive from a cyclization of the open chain C 20 precursor, initiated specifically at the internal double bond and involving only two C=C bonds …”

Section: Resultsmentioning

confidence: 99%

“…In particular, in marine organisms, a few examples have been reported from anaspidean molluscs and algae. [34] Biogenetically, they should derive from a cyclization of the open chain C 20 precursor, initiated specifically at the internal double bond and involving only two C=C bonds. [34] Compound 3, named spurillin B, had the molecular formula C 20 H 34 O exhibiting two rings and two C=C bonds, as evidenced by analysis of MS and NMR data.…”

Section: Resultsmentioning

confidence: 99%

See 2 more Smart Citations

Chemistry of Two Distinct Aeolid Spurilla Species: Ecological Implications

Ciavatta

García-Matucheski

Carbone

et al. 2017

Chemistry & Biodiversity

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The lipophilic extracts of two marine aeolid nudibranch molluscs of the genus Spurilla collected in distinct geographical areas have been chemically analyzed. The Et O extracts of the nudibranchs were dominated by the presence of usual fatty acids and sterols and contained terpenoid compounds 1 - 3 as minor metabolites. Spurillin A (1) and spurillin B (3) were new molecules whereas cis-γ-monocyclofarnesol (2) was already reported in the literature as a synthesis product. Interestingly, bursatellin (4), previously isolated from anaspidean molluscs of the genus Bursatella, was found in the butanol extract of both Spurilla species. Compounds 1 - 4 were not detected in the extracts of the sea-anemone preys collected together with the molluscs.

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Section: Resultssupporting

confidence: 69%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Chemistry of Two Distinct Aeolid Spurilla Species: Ecological Implications

Ciavatta

García-Matucheski

Carbone

et al. 2017

Chemistry & Biodiversity

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“…To date, various kinds of Kv1.5 modulators have been disclosed, herein, we summarize the molecular structures and functionality of different types of Kv1.5 modulators with their chemical structure as follows (Table 1, Figure 2). As shown in Table 1, the existing Kv1.5 modulators can be divided into four categories: clinical cardiovascular drugs (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14), other clinical drugs (15)(16)(17)(18)(19)(20)(21)(22)(23)(24)(25)(26)(27)(28), drugs in development (29)(30)(31)(32)(33)(34)(35)(36)(37), and natural products (38)(39)(40)(41)(42)(43)(44)(45)(4...…”

Section: Summarization Of Models and Mechanisms Of Kv15 Modulatorsmentioning

confidence: 99%

“…As for other clinical drugs, CNS agents include: donepezil (15), which is generally used as an anti-Alzheimer's agent; paroxetine (16), fluoxetine (17), and sertraline (18), which are usually used as antidepressant agents; and bupivacaine (23), propofol (24), midazolam (25), tolbutamide (26), and benzocaine (27), which are utilized as anesthetic agents. hERGs (human ether-à-go-go-related genes) are widely associated with CNS diseases [16][17][18], thus it is not strange that active CNS agents can effectively modulate Kv1.5 according to the homology of the protein.…”

Section: Summarization Of Models and Mechanisms Of Kv15 Modulatorsmentioning

confidence: 99%

Challenges Faced with Small Molecular Modulators of Potassium Current Channel Isoform Kv1.5

Zhao

Ruan

et al. 2019

Biomolecules

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The voltage-gated potassium channel Kv1.5, which mediates the cardiac ultra-rapid delayed-rectifier (IKur) current in human cells, has a crucial role in atrial fibrillation. Therefore, the design of selective Kv1.5 modulators is essential for the treatment of pathophysiological conditions involving Kv1.5 activity. This review summarizes the progress of molecular structures and the functionality of different types of Kv1.5 modulators, with a focus on clinical cardiovascular drugs and a number of active natural products, through a summarization of 96 compounds currently widely used. Furthermore, we also discuss the contributions of Kv1.5 and the regulation of the structure-activity relationship (SAR) of synthetic Kv1.5 inhibitors in human pathophysiology. SAR analysis is regarded as a useful strategy in structural elucidation, as it relates to the characteristics that improve compounds targeting Kv1.5. Herein, we present previous studies regarding the structural, pharmacological, and SAR information of the Kv1.5 modulator, through which we can assist in identifying and designing potent and specific Kv1.5 inhibitors in the treatment of diseases involving Kv1.5 activity.

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Terpenoids from Essential Oils

Pragadheesh

Bisht

Chanotiya

2020

Kirk-Othmer Encyclopedia of Chemical Technology

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Essential oils contain terpenoids and phenylpropanoids as major constituents. Terpene‐bearing aromatic plants play an important role in food, flavor, and fragrance. Essential oils rarely reach the consumers in their natural composition. They are adjusted to meet either the desired quality or specification of a legal regulatory body such as BIS and ISO. The adulterants can be inexpensive synthetic or essential oils of another origin, which ultimately leads to a variable product with less demand. In this article, chiral differentiation using enantioselective gas chromatographic technique is described for high‐value chiral terpenes identified in essential oils. The technique is based on the separation of enantiomers in different cyclodextrin‐coated fused silica capillary columns. The chiral distribution of citronellol enantiomers in Rosa damascena and Cympbopogon winterianus showed the presence of opposite images in each oil. R. damascena contained (−)‐citronellol, whereas (+)‐citronellol was recorded in citronella oil. (+)‐Linalool was a unique feature of Lippia alba . On the contrary, Ocimum basilicum possessed pure (−)‐linalool. Camphor was separated in Ocimum spp. and Cinnamomum camphora with exclusive presence of (+)‐enantiomer. Limonene, menthone, menthol, and menthyl acetate were identified as pure (−)‐enantiomers, whereas isomenthone, neomenthol, pulegone, and piperitone as pure (+)‐enantiomers in Indian menthol mint and peppermint oils, respectively. The usefulness of unique chiral signatures in setting up regulatory guidelines for the most traded essential oils is also discussed.

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Unusual cyclic terpenoids with terminal pendant prenyl moieties: from occurrence to synthesis

Cited by 11 publications

References 176 publications

Chemistry of Two Distinct Aeolid Spurilla Species: Ecological Implications

Chemistry of Two Distinct Aeolid Spurilla Species: Ecological Implications

Challenges Faced with Small Molecular Modulators of Potassium Current Channel Isoform Kv1.5

Terpenoids from Essential Oils

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