Isolation and Structure Revision of Pepluane Diterpenoids from Euphorbia peplus

Hohmann, Judit; Günther, Gábor; Vasas, Andrea; Kálmán, A; Argay, Gyula

doi:10.1021/np980319l

Cited by 27 publications

(34 citation statements)

References 4 publications

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“…36 A conformational study showed that pepluane possesses a relatively rare ring D conformation, which probably led to the misinterpretation of the NMR data. 36 The challenging 3D determination of some jatrophane esters may also be exemplified by a study by Hohmann and associates, in which the relative configuration of esulatin C could not be assigned. 34 The high flexibility of the macrocyclic part of this compound was one of the explanations made.…”

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confidence: 99%

Advanced Structural Determination of Diterpene Esters Using Molecular Modeling and NMR Spectroscopy

et al. 2015

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Three new jatrophane esters (1-3) were isolated from Euphorbia amygdaloides ssp. semiperfoliata, including an unprecedented macrocyclic jatrophane ester bearing a hemiketal substructure, named jatrohemiketal (3). The chemical structures of compounds 1-3 and their relative configurations were determined by spectroscopic analysis. The absolute configuration of compound 3 was determined unambiguously through an original strategy combining NMR spectroscopy and molecular modeling. Conformational search calculations were performed for the four possible diastereomers 3a-3d differing in their C-6 and C-9 stereocenters, and the lowest energy conformer was used as input structure for geometry optimization. The prediction of NMR parameters ((1)H and (13)C chemical shifts and (1)H-(1)H coupling constants) by density functional theory (DFT) calculations allowed identifying the most plausible diastereomer. Finally, the stereostructure of 3 was solved by comparison of the structural features obtained by molecular modeling for 3a-3d with NMR-derived data (the values of dihedral angles deduced from the vicinal proton-proton coupling constants ((3)JHH) and interproton distances determined by ROESY). The methodology described herein provides an efficient way to solve or confirm structural elucidation of new macrocyclic diterpene esters, in particular when no crystal structure is available.

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confidence: 99%

Advanced Structural Determination of Diterpene Esters Using Molecular Modeling and NMR Spectroscopy

et al. 2015

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“…The acetylated vicinal diol (C-8 and C-9) found in all known pepluans, can be explained by an enzymatic epoxidation in D8(9) followed by an opening of the epoxide as shown in Fig. 11 (Hohmann et al 1999a;Jakupovic et al 1998c).…”

Section: Pepluane and Paralianementioning

confidence: 96%

“…The results showed the importance of functionality and structure of the D-ring for the activity and its possible involvement in the inhibition of NF-jB activation as follows ( compounds exhibited inhibitory effects on LPSinduced NO production which possessed lipophilic substituents such as benzoyl, nicotinoyl and decadienoyl moieties with IC 50 values ranging from 0.7 to 46.5 lM in RAW 264.7 macrophages (Lee et al 2016). Wan et al (2016a, b) isolated paralianones A-D (66-69) and pepluanols A-H (52-56, 58, 62, and 63), along with five known compounds 72 (Jakupovic et al 1998b), 59 (Hohmann et al 1999a), 60 (Hohmann et al 2000a), 61 (Hohmann et al 1999b), and pepluanone (57) (Corea et al 2005b), from E. peplus.The isolated compounds were tested for inhibitory activity on LPS-stimulated NO production in RAW264.7 macrophage cell line. Compounds 68, 69, 62, 72, and 61 displayed inhibitory effects on NO inhibition, with IC 50 values of 33.7, 38.3, 36.6, 29.9, and 37.1 lM, respectively.…”

Section: Anti-inflammatory Activitymentioning

confidence: 99%

Jatrophane and rearranged jatrophane-type diterpenes: biogenesis, structure, isolation, biological activity and SARs (1984–2019)

et al. 2020

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Diterpene compounds specially macrocyclic ones comprising jatrophane, lathyrane, terracinolide, ingenane, pepluane, paraliane, and segetane skeletons occurring in plants of the Euphorbiaceae family are of considerable interest in the context of natural product drug discovery programs. They possess diverse complex skeletons and a broad spectrum of therapeutically relevant biological activities including anti-inflammatory, anti-chikungunya virus, anti-HIV, cytotoxic, and multidrug resistance-reversing activities as well as curative effects on thrombotic diseases. Among macrocyclic diterpenes of Euphorbia, the discovery of jatrophane and modified jatrophane diterpenes with a wide range of structurally unique polyoxygenated polycyclic derivatives and as a new class of powerful inhibitors of P-glycoprotein has opened new frontiers for research studies on this genus. In this review, an attempt has been made to give in-depth coverage of the articles on the naturally occurring jatrophanes and rearranged jatrophane-type diterpenes isolated from species belonging to the Euphorbiaceae family published from 1984 to March 2019, with emphasis on the biogenesis, isolation methods, structure, biological activity, and structureactivity relationship.

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“…The phytochemical investigation of E. peplus was started in our department in 1999, and 13 diterpenes ( 9 , 12 , Figure 3; 20 – 27 , 30 – 32 , Figure 5) with different skeletons (pepluane, jatrophane and ingenane) were isolated from the whole plant 2,57,58. Three diterpenes ( 20 – 22 ) have a pepluane skeleton and differ only in the esterification.…”

Section: Isolation Of Diterpenesmentioning

confidence: 99%

“…In the pepluanes, the geminal dimethyl groups (originating from a cembrene‐casbane source) are absent, because one of them (C‐18) is incorporated in a six‐membered ring. On the basis of our X‐ray examinations, the structure of 20 was revised with regard to the absolute stereochemistry at C‐8 and C‐9 57…”

Section: Isolation Of Diterpenesmentioning

confidence: 99%

Diterpenes from European Euphorbia Species Serving as Prototypes for Natural‐Product‐Based Drug Discovery

et al. 2012

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A nanotemplate surface that functions as a regular array of traps for molecules such as naphthalocyanine (see picture) is provided by a nanomesh of hexagonal BN on Rh(111), which has now been identified as a single, complete monolayer. The 2‐nm‐sized pores form at regions where the layer binds strongly to the underlying metal, while the regular network of mesh wires corresponds to regions where the layer is not bonded to the substrate.

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Isolation and Structure Revision of Pepluane Diterpenoids from Euphorbia peplus

Cited by 27 publications

References 4 publications

Advanced Structural Determination of Diterpene Esters Using Molecular Modeling and NMR Spectroscopy

Advanced Structural Determination of Diterpene Esters Using Molecular Modeling and NMR Spectroscopy

Jatrophane and rearranged jatrophane-type diterpenes: biogenesis, structure, isolation, biological activity and SARs (1984–2019)

Diterpenes from European Euphorbia Species Serving as Prototypes for Natural‐Product‐Based Drug Discovery

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