Sesquiterpenes from Perezia longifolia

Mendoza, V.

doi:10.1021/np50055a024

Cited by 11 publications

(7 citation statements)

References 2 publications

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“…Parvifoline ( 1 ) was obtained in good yields from the roots of Acourtia humboldtii , while compounds 2 – 4 and 8 were prepared as previously reported . In order to access a series of parvifoline derivatives, the new compounds 5 – 7 and 9 – 12 were obtained by epoxidation reactions, transposition of the epoxide groups, and esterification and hydrolysis reactions.…”

Section: Resultsmentioning

confidence: 99%

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Parvifoline Derivatives as Tubulin Polymerization Inhibitors

et al. 2019

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A series of functionalized sesquiterpenoids derived from benzocyclooctene, including natural parvifoline (1), isoparvifoline (3), epoxyparvifoline (5), epoxyisoparvifoline (7), 8,12-oxyparfivoline (9), 8,14-oxyparvifoline (11), and the respective benzoyl derivatives 2, 4, 6, 8, 10, and 12, were prepared and tested for their inhibitory effect on the in vitro α,β-tubulin polymerization process. The structural analysis and characterization of the new compounds 5–7 and 9–12 were achieved by 1D and 2D NMR spectroscopy, mass spectrometry, and X-ray diffraction analysis of 6, 7, and 9. Preparation of 9 and 12 involved molecular rearrangements of the epoxide group with transannular 1,5-hydride shifts. At 10 μM compounds 1, 5, and 8 inhibited the polymerization of the α,β-tubulin heterodimer by 24%, 49%, and 90% as compared to colchicine. These compounds were subjected to docking analysis that supported their interactions in a colchicine binding site located in the α-tubulin subunit, in the pocket formed by Phe296, Pro298, Pro307, His309, Tyr312, Lys338, Thr340, Ile341, and Gln342. Competitive inhibition assays with colchicine were also performed for the three compounds, which supported their binding at the colchicine secondary site in α-tubulin. Also, evaluations of their cytotoxicity on MCF7 breast carcinoma, HeLa cervix carcinoma, and HCT 116 colon carcinoma cell lines were carried out and showed that 8 is active against the HeLa and HCT 116 cell lines with IC50 3.3 ± 0.2 and 5.0 ± 0.5 μM, respectively.

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Section: Resultsmentioning

confidence: 99%

“…Parvifoline ( 1 ) is a bicyclic sesquiterpenoid isolated in good yields from several species of the Asteraceae family, namely, Coreolepsis parvifolia , Perezia carpholepis , P. longifolia , and P. alamanii var. oolepis .…”

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confidence: 99%

Parvifoline Derivatives as Tubulin Polymerization Inhibitors

et al. 2019

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“…Its absolute configuration was resolved by the chemical correlation through its hydrogenation product that was identical to a material derived from 129 by dehydration with POCl 3 and hydrogenation [352, 353] . The (−)‐enantiomer of 138 was later isolated from several other plants [177, 349, 354–367] . Full 1 H‐ and 13 C‐NMR data in CDCl 3 and C 6 D 6 have been reported [367, 368] …”

Section: Cyclised and Rearranged Guaianesmentioning

confidence: 96%

“…[352,353] The (À)enantiomer of 138 was later isolated from several other plants. [177,349,[354][355][356][357][358][359][360][361][362][363][364][365][366][367] Full 1 H-and 13 C-NMRd ata in CDCl 3 and C 6 D 6 have been reported. [367,368]…”

Section: Compounds From J3mentioning

confidence: 97%

Germacrene A–A Central Intermediate in Sesquiterpene Biosynthesis

Dickschat

2020

Chemistry A European J

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This review summarises known sesquiterpenes whose biosyntheses proceed through the intermediate germacrene A. First, the occurrencea nd biosynthesis of germacrene Ai nN ature and its peculiar chemistry will be highlighted , followed by ad iscussion of 6-6 and 5-7 bicyclic compounds and their more complex derivatives. For each compound the absolutec onfiguration, if it is known,a nd the reasoning for its assignment is presented. 2. Germacrene A 2.1. Occurrence in Nature (À)-Germacrene A(1,S cheme 2) was first isolated in 1970 from the gorgonian Eunicea mammosa. [7] Its absolute configuration was established as (S)-(À)-1 through its Cope rearrangement to (+ +)-b-elemene (2)f or which the configurational assignment was performed by chemical correlation of (À)-elemol(3)t o (À)-2. [8, 9] Compound (À)-1 is also believed to occur in the soft coral Lobophytum, [10] andi st he alarm pheromone of the aphid Terioaphis maculata. [11, 12] In the course of this work it was noticed that the optical rotation([ a] D 25 = À26.8, c 1.0, CCl 4)w as significantly highert han initially reported ([a] D 25 = À3.2, c 14.4, CCl 4), [7] which is explainableb yapartial rearrangement of purified (À)-1 to (+ +)-2,o ra lternatively, 1 isolated from E. mammosa was not enantiomerically pure. However,the opticalrotation of (+ +)-2 ([a] D 25 =+15.1, neat) reported in this initial study [7] matches the reported value for (À)-2 ([a] D 25 = À15.8, c 0.50, CHCl 3)o btainedb yC ope rearrangement of (+ +)-1, [13] thus disfa-Scheme1.Te rpene cyclisation modes for FPP. Scheme2.Structure of 1 and its absolute configurationbyc hemicalcorrelation.

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“…The title compound parvifoline 1 along with isoparvifolinone 2 and parvifoline isovalerate 3 are sesquiterpenes, isolated from genera Coreopsis and Perezia . These are the only examples of naturally occurring compounds which contain a trimethyl benzocyclooctane structural unit.…”

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confidence: 99%