Efficient synthesis of the anticancer β-elemene and other bioactive elemanes from sustainable germacrone

Barrero, Alejandro F.; Herrador, M. Mar; Moral, José F. Quı́lez del; Arteaga, Pilar; Meine, Niklas; Pérez-Morales, M. Carmen; Catalán, Julieta V.

doi:10.1039/c0ob00467g

Cited by 42 publications

(27 citation statements)

References 32 publications

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“…Germacrone treatment increases Bok expression and cytochrome c release from the mitochondria without affecting Bcl-2, Bcl-xL, Bax, and Bim protein expression and induces the cleavage of PARP and the activation of caspase-3, caspase-7, and caspase-9 ; however, the germacrone concentration required to achieve its anti-cancer properties is relatively high (i.e., nearly 200 mM) . Recently, Barrero et al (2011) reported that the synthesis of b-elemene and other bioactive elemenes is possible using germacrone as a renewable starting material and that the synthesis is achieved in only three to five steps with excellent overall yields. This finding suggests that germacrone may be used as a viable starting material for elemene synthesis.…”

Section: Germacronementioning

confidence: 99%

Anti-cancer properties of terpenoids isolated from Rhizoma Curcumae – A review

Dang

Huang

et al. 2012

Journal of Ethnopharmacology

165

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Section: Germacronementioning

confidence: 99%

Anti-cancer properties of terpenoids isolated from Rhizoma Curcumae – A review

Dang

Huang

et al. 2012

Journal of Ethnopharmacology

165

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“…39 A recent study revealed that b-elemenal was appreciably more potent than b-elemene in suppressing nonsmall cell lung cancer growth and proliferation. 39 A recent study revealed that b-elemenal was appreciably more potent than b-elemene in suppressing nonsmall cell lung cancer growth and proliferation.…”

Section: Resultsmentioning

confidence: 99%

Lanthanide-induced shift reagents enable the structural elucidation of natural products in inseparable complex mixtures – the case of elemenal from Inula helenium L. (Asteraceae)

Genčić

Radulović

2015

RSC Adv.

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The use of lanthanide complexes for resolving intricate NMR signals and, in the case of chiral ligands, for determining enantiomeric excess has progressively decreased in the last 30 years. Recently, a sesquiterpene aldehyde from Inula helenium with a possible potent antistaphylococcal activity remained unidentified due to the impossibility of separating the compound from its complex matrix available in very low amounts (ca. 5 mg). Detailed analyses of 1D and 2D NMR spectra of this original complex sample allowed access to a very limited amount of structural data for the unknown aldehyde. We decided to investigate the potential usefulness of lanthanide-induced shift reagents for the resolution and assigning of overlapped 1 H NMR signals originating from different components of this complex mixture (i.e. for a qualitative analysis). The incremental addition of tris (6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octanedionato)europium(III) (Eu(fod) 3 ) led to a simplification of the NMR spectra in terms of signal overlap and removal of chemical shift degeneracy, allowing the mining of crucial data from the shifted NMR spectra. 2D NMR spectra ( 1 H-1 H-COSY, NOESY, HSQC and HMBC) of the sample mixed with Eu(fod) 3 proved to be particularly valuable in this respect. The obtained additional information revealed that the compound in question was a rare sesquiterpeneelemenal (elema-1,3,11(13)-trien-12al). Therefore, herein we report on a new chromatography-free methodology that could be of value in structure elucidation of unknown compounds even if they are not available in a pure state. 18533014; Tel: +381 18533015 † Electronic supplementary information (ESI) available: A comparison of experimental and simulated 1 H NMR spectra of elemenal (the second order vinyl group spin system). Results of the conformational analysis of elemenal-Eu(fod) 3 complex obtained using the lanthanide probe method. See Fig. 6 The chemical shift vs. the ratio of the shift reagent and elemenal plots obtained from the incremental addition of Eu(fod) 3 to elemenal for: (a) the protons closest to the coordination site, (b) the remaining olefinic protons and (c) for the protons that resonated at the high field region.This journal is

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“…Compounds 2, 4,a nd 5 are assumed to be produced from a-cyperone or cyperol, [16b] even thoughc yclic ether moieties were not formed in 4 and 5.O nt he other hand, some isolated compoundsa re assumed to be produced by unexpected reactions. For example, compound 6 is produced from germacrone, [18d] a constituent of C. zedoaria,b ys equential reduction, etherification, cyclization, and additional Cope rearrangement [21] (Scheme3B). Compounds 7 and 8 are produced from curzerenone by sequential reduction,e therification, and bicyclization causedb yt andemM izoroki-Heck reactions (Scheme3C).…”

Section: Isolation and Structure Elucidation Of Phenolic Meroterpenoidsmentioning

confidence: 99%

Construction of a Meroterpenoid‐Like Compounds Library Based on Diversity‐Enhanced Extracts

Kikuchi

Kawai

Nakashiro

et al. 2018

Chemistry A European J

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The structural diversity of natural products and their derivatives have long contributed to the development of new drugs. However, the difficulty in obtaining compounds bearing skeletally novel structures has recently led to a decline of pharmaceutical research into natural products. This paper reports the construction of a meroterpenoid‐like library containing 25 compounds with diverse molecular scaffolds obtained from diversity‐enhanced extracts. This method constitutes an approach for increasing the chemical diversity of natural‐product‐like compounds by combining natural product chemistry and diversity‐oriented synthesis. Extensive pharmacological screening of the library revealed promising compounds for anti‐osteoporotic and anti‐lymphoma/leukemia drugs. This result indicates that the use of diversity‐enhanced extracts is an effective methodology for producing chemical libraries for the purpose of drug discovery.

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Efficient synthesis of the anticancer β-elemene and other bioactive elemanes from sustainable germacrone

Cited by 42 publications

References 32 publications

Anti-cancer properties of terpenoids isolated from Rhizoma Curcumae – A review

Anti-cancer properties of terpenoids isolated from Rhizoma Curcumae – A review

Lanthanide-induced shift reagents enable the structural elucidation of natural products in inseparable complex mixtures – the case of elemenal from Inula helenium L. (Asteraceae)

Construction of a Meroterpenoid‐Like Compounds Library Based on Diversity‐Enhanced Extracts

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