Neue sesquiterpenlactone aus Aster umbellatus

Bohlmann, Ferdinand; Dutta, Lakshmi Narayan; Knauf, W.; Robinson, Harold; King, Robert M.

doi:10.1016/0031-9422(80)83195-5

Cited by 34 publications

(16 citation statements)

References 3 publications

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“…A recent review on the chemical constituents of the Lychnophorinae tribe has revealed significant variation in the occurrence of secondary metabolites in the genus Lychnophora [12]. Considering a single species, three phenomena can account for the observed differences: (a) accomplishment of a phytochemical investigation looking for a specific class of target secondary metabolites only, such as sesquiterpene lactones [13,14]; (b) performance of bioguided fractionation, which inspects a typical biological activity and may result in the isolation of a common class of secondary metabolites [15][16][17]; and (c) natural chemical variations in metabolism or presence of chemotypes [6][7][8]10].…”

Section: Introductionmentioning

confidence: 99%

A new HPLC-DAD-MS/MS method for the simultaneous determination of major compounds in the crude extract of Lychnophora salicifolia Mart. (Brazilian arnicão) leaves: Application to chemical variability evaluation

Gouvea¹,

Meloni²,

Ribeiro³

et al. 2012

Analytica Chimica Acta

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Section: Introductionmentioning

confidence: 99%

A new HPLC-DAD-MS/MS method for the simultaneous determination of major compounds in the crude extract of Lychnophora salicifolia Mart. (Brazilian arnicão) leaves: Application to chemical variability evaluation

Gouvea¹,

Meloni²,

Ribeiro³

et al. 2012

Analytica Chimica Acta

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“…Inspection of these NMR and the MS data of the compound led to the proposed eudesmanolide which was supported by the 1 H-1 H COSY and HMBC spectra of 4 ( Table 5). This compound has previously been reported from Asteraceae Aster umbellatus, 24 Mikania banisteriae 25 and Atractylodes chinensis. …”

Section: Eudesma-4(15)7(11)9-trien-12-olide (4)mentioning

confidence: 91%

Composition of the essential oil of flowers ofChloranthus spicatus (Thunb.) Makino

et al. 2006

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The composition of the essential oil of the flowers of Chloranthus spicatus (Thunb.) Makino (Chloranthaceae) was investigated using capillary GC-GC/MS, preparative GC and NMR techniques. Forty-seven compounds were identified either by comparing their retention indices and mass spectra with a library of authentic samples established under identical experimental conditions or, by isolating the compounds and deriving their structures by one-and two-dimensional NMR investigations. Thus, four minor components, viz. chloranthalactone A (0.5%), isogermafurenolide (0.7%), eudesma-4(15),7(11),9-trien-12-olide (0.5%), and 7α α α α α-hydroxyeudesm-4-en-6-one (3.3%), were isolated for the first time as constituents of the essential oil of the flowers of C. spicatus and their structures established. The major components of the oil include (Z)-β β β β β-ocimene (6.3%), allo-aromadendrene (6.2%), sarisane (2-allyl-4,5-methylenedioxyanisol, 4.2%) and selina-4(15),7(11)-diene (6.4%).

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“…It can be seen that the last compound contains fragments of the natural lactone asterolide [11] and the alkaloid vasicinone. Compounds 4, 6, and 7 were isolated pure (yields of 65%, 5, and 3, respectively).…”

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confidence: 99%

“…The cross-coupling of 1 with 2 catalyzed by Pd(OAc) 2 -(o-Tol) 3 P in DMF solution in the presence of Et 3 N formed products of arylation at the C (11,13) exo-methylene bond with the (E)-and (Z)-configurations (4,5); bis-arylation at the C (11,13) and C(4,15) bonds (6); and C(8)-epimerization of isoalantolactone and isomerization of the C (11,13) double bond (7). It can be seen that the last compound contains fragments of the natural lactone asterolide [11] and the alkaloid vasicinone.…”

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confidence: 99%

“…The structures of the products were established using spectral data. The (E)-configuration of the C (11,13) double bond in substituted lactone 4 was inferred from the presence in the 13 C NMR spectrum (single-resonance mode) of a C-H 3 J-cis coupling constant between the olefinic proton and the lactone carbonyl C atom [ 3 J = 7.0 Hz; the corresponding 3 J-trans constant for the (Z)-isomer (5) was 13.4 Hz]. The resonance for H (13) in the PMR spectrum of the (E)-isomer (4) appeared as a singlet at 7.44 ppm; for the (Z)-isomer (5), a singlet at 7.00 ppm.…”

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Synthesis of hybrid molecules containing fragments of sesquiterpene lactones and plant alkaloids

et al. 2011

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The Pd-catalyzed arylation of isoalantolactone by deoxyvasicinone and lappaconitine halides occurred with formation mainly of cross-coupling products with the (E)-configuration of the double bond. Another three compounds were isolated from the reaction of isoalantolactone with 6-bromodeoxyvasicinone. These were the lactone diarylation product, a compound with the (Z)-configuration of the double bond, and a product with a shift of the C(11,13) double bond and configuration inversion at C(8). The new compounds are interesting as potential biologically active agents.Many compounds with a "hybrid" structure containing different fragments in their molecules were observed among natural plant and marine metabolites [1,2]. In this respect the synthesis of conjugates designed by using structural analysis of natural metabolites seems logical for the discovery of pharmacologically promising agents [3]. Sesquiterpene methylenelactones exhibit various biological activities including antitumor [4], anti-inflammatory [5], and antiviral [6]. Recently interest in these natural compounds has risen sharply because of their ability to inhibit human tumor growth by activating the apoptosis mechanism that is associated with activation of the caspase cascade in such cells [7]. Therefore, the synthesis of new derivatives of D-methylene-J-lactones of natural and synthetic origin is an active research area [8].We showed previously that Pd-catalyzed cross-coupling is an efficient reaction for modifying sesquiterpene eudesmanetype D-methylene-J-lactones because it occurs with retention of the exo-methylene bond [9, 10]. Herein we report results from the reaction of isoalantolactone (1) with plant alkaloid derivatives 6-bromodeoxyvasicinone (2) (Scheme 1) and 5c-iodolappaconitine (3) (Scheme 2).

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Neue sesquiterpenlactone aus Aster umbellatus

Cited by 34 publications

References 3 publications

A new HPLC-DAD-MS/MS method for the simultaneous determination of major compounds in the crude extract of Lychnophora salicifolia Mart. (Brazilian arnicão) leaves: Application to chemical variability evaluation

A new HPLC-DAD-MS/MS method for the simultaneous determination of major compounds in the crude extract of Lychnophora salicifolia Mart. (Brazilian arnicão) leaves: Application to chemical variability evaluation

Composition of the essential oil of flowers ofChloranthus spicatus (Thunb.) Makino

Synthesis of hybrid molecules containing fragments of sesquiterpene lactones and plant alkaloids

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