Aquatolide. A new type of humulane-related sesquiterpene lactone

Feliciano, Arturo San; Medarde, Manuel; Corral, José M. Miguel del; Aramburu, A.; Gordaliza, Marina; Barrero, Alejandro F.

doi:10.1016/s0040-4039(00)99142-1

Cited by 44 publications

(50 citation statements)

References 3 publications

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“…In 1989, San Feliciano et al 76 isolated a novel sesquiterpene lactone from the hexane extracts of Asteriscus aquaticus, named aquatolide, to which structure 152 was proposed based on spectroscopic studies, mainly homo-and heteronuclear two-dimensional NMR correlations ( Figure 30). In 2012, Tantillo and co-workers 77 computed NMR chemical shifts for structure 152 at the CPCM/mPW1PW91/6-311+G(2d,p)//B3LYP/6-31+G(d,p) level of theory, and although the proposed structure was consistent with all the reported experimental data, including NOE, the calculated chemical shifts for the proposed structure deviated from the experimental data available for the natural product.…”

Section: Aquatolidementioning

confidence: 99%

Computer-Guided Total Synthesis of Natural Products. Recent Examples and Future Perspectives

Della‐Felice¹,

Pilli²,

Sarotti³

2018

J. Braz. Chem. Soc.

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Quantum chemical calculations of nuclear magnetic resonance (NMR) shifts and coupling constants have been extensively employed in recent years mainly to facilitate structural elucidation of organic molecules. When the results of such calculations are used to determine the most likely structure of a natural product in advance, guiding the subsequent synthetic work, the term "computer-guided synthesis" could be coined. This review article describes the most relevant examples from recent literature, highlighting the scope and limitations of this merged computational/experimental approach as well.

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Section: Aquatolidementioning

confidence: 99%

Computer-Guided Total Synthesis of Natural Products. Recent Examples and Future Perspectives

Della‐Felice¹,

Pilli²,

Sarotti³

2018

J. Braz. Chem. Soc.

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“…( À)-Asteriscunolide A[(À)-1], isolated from Asteriscus aquaticus along with cis-trans isomers (À)-asteriscunolides B-D [(À)- [2][3][4], is the first elucidated sesquiterpene lactone containing ah umulane skeleton, known as ah umulanolide [1] (Figure 1A). ( À)-Asteriscunolide A[(À)-1], isolated from Asteriscus aquaticus along with cis-trans isomers (À)-asteriscunolides B-D [(À)- [2][3][4], is the first elucidated sesquiterpene lactone containing ah umulane skeleton, known as ah umulanolide [1] (Figure 1A).…”

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confidence: 99%

“…Thes ame plant also afforded tricyclic (+ +)-asteriscanolide [(+ +)-5], [2] and its tetradehydro analogue (+ +)-tetradehydroasteriscanolide [(+ +)-6]w as isolated from A. graveolens. [4] Thestructure of (+ +)-aquatolide was originally assigned by NMR analysis as 7a,w hich consists of at etracyclic 5/4/4/7-ring system with an unusual embedded [2]-ladderane motif.L ater, its structure was revised based on quantum chemical NMR calculations and X-ray crystallography of the re-isolated sample by Shaw and Tantillo. [4] Thestructure of (+ +)-aquatolide was originally assigned by NMR analysis as 7a,w hich consists of at etracyclic 5/4/4/7-ring system with an unusual embedded [2]-ladderane motif.L ater, its structure was revised based on quantum chemical NMR calculations and X-ray crystallography of the re-isolated sample by Shaw and Tantillo.…”

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Total Syntheses of (+)‐Aquatolide and Related Humulanolides

et al. 2019

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The short, efficient total synthesis of (+ +)-aquatolide was achieved by ab iomimetic transannular [2+ +2] photocycloaddition, and provides the first example of constructing a5 /5/4/8-ring system from asteriscunolides.F urthermore,t he reaction leading to a5 /4/4/7-ring system, the originally proposed structure of aquatolide,w as also developed. This strategy achieved syntheses of five more humulanolides,( À)asteriscunolides A, C, D, and I, and (+ +)-tetradehydroasteriscanolide.Supportinginformation and the ORCID identification number(s) for the author(s) of this article can be found under: https://doi.org/10.1002/anie.201904404. Angewandte ChemieZuschriften Scheme 1. Construction of the asteriscunolide skeleton. DDQ = 2,3dichloro-5,6-dicyano-1,4-benzoquinone, DMSO = dimethylsulfoxide, LiHMDS = lithium bis(trimethylsilyl)amide, MPM = 4-methoxyphenylmethyl, THF = tetrahydrofuran.

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“…A considerable attention has been given to the genus Asteriscus from which mainly sesquiterpenes have been reported. Asteriscunolides A-D were previously isolated from the aerial parts of some Asteriscus species such as A. aquaticus 3 and A. vogelii 4 . Other sesquiterpene lactones such as asteriscanolide and aquatolide were obtained from the hexane extract of A. aquaticus 3,5 .…”

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confidence: 99%

“…Asteriscunolides A-D were previously isolated from the aerial parts of some Asteriscus species such as A. aquaticus 3 and A. vogelii 4 . Other sesquiterpene lactones such as asteriscanolide and aquatolide were obtained from the hexane extract of A. aquaticus 3,5 . Flavonoids 6,7 , bisabolone hydroperoxides 8 as well as farnesol and thymol derivatives 9 were also described as constituents of extracts from Asteriscus plants and reported to possess antimicrobial and hypoglycemic activities 6,7 , whereas Asteriscunolides C and D have shown phytotoxic activities and the last one also exhibited cytotoxic effects 4 .…”

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confidence: 99%

Chemical composition, Antimicrobial and anti-acetylcholinesterase activities of essential oils from the Tunisian Asteriscus maritimus (L.) Less

et al. 2012

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Abstract:The chemical composition, the acetylcholinesterase inhibitory effect and the antimicrobial activity of the Tunisian Asteriscus maritimus (L.) Less essential oils obtained from flowers, leaves and stems were investigated. According to the GC and GC-MS analysis results, 45 (99.32%), 34 (94%) and 29 compounds (94.95%) were identified, respectively. In the essential oils extracted from the flowers and leaves of A. maritimus, oxygenated sesquiterpenes were abundantly found (57.82 and 46.39%, respectively). Hexdecanoic acid was detected in an important amount in leaves and stems (30.35 and 49.18%, respectively), while β-eudesmol (24.25%), menthyl acetate (17.03%) and pentadecanal (15.38%) were the most abundant constituents in flowers. To evaluate the in vitro antimicrobial activity, all volatiles were tested against some bacterial and fungal agents. It was found that only the volatile oil from flowers exhibited interesting antibacterial and antifungal activities. When screened for their anti-acetylcholinesterase activity, essential oil from flowers exhibited the highest activity (IC 50 =95 µg/mL). To our knowledge, this is the first report of acetylcholinesterase inhibition and antimicrobial activity of the Tunisian A. maritimus essential oils.

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Aquatolide. A new type of humulane-related sesquiterpene lactone

Cited by 44 publications

References 3 publications

Computer-Guided Total Synthesis of Natural Products. Recent Examples and Future Perspectives

Computer-Guided Total Synthesis of Natural Products. Recent Examples and Future Perspectives

Total Syntheses of (+)‐Aquatolide and Related Humulanolides

Chemical composition, Antimicrobial and anti-acetylcholinesterase activities of essential oils from the Tunisian Asteriscus maritimus (L.) Less

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