Acetophenones and terpenoids from Senecio Gallicus

Urones, Julio G.; Teresa, J. De Pascual; Marcos, Isidro S.; Moro, Rosalina F.; Barcala, Pilar Basabe; Cuadrado, Ma Josè Sexmero

doi:10.1016/s0031-9422(00)82360-2

Cited by 30 publications

(32 citation statements)

References 9 publications

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“…12) [14], (1b,9b)-caryolane-1,9-diol (= (1R,2S,5R,8S,9S)-4,4,8-trimethyltricyclo[6.3.1.0 2,5 ]dodecane-1, 9-diol; 13) [15], (2b,9a)-clovane-2b,9a-diol (= (3S,3aS,6R,7R,9aS)-decahydro-1,1,7-trimethyl-3a,7methano-3aH-cyclopentacyclooctene-3,6-diol; 14) [15], (3S,5R,8R)-3,5-dihydroxymegastigma-6,7-dien-9-one (= (3R)-4-((2R,4S)-2,4-dihydroxy-2,6,6-trimethylcyclohexylidene)but-3-en-2-one; 15) [16] [17], 7,11,15-trimethyl-3-methylidenehexadecane-1,2diol (16) [18] [19], (3b,24RS)-cycloart-25-ene-3,24-diol (= (3b)-9,19-cyclolanost-25ene-3,24-diol; 17) [20] [21], and cycloaudenyl palmitate (= hexadecanoic acid (3b)-24-methyl-9,19-cylcolanost-25-en-3-yl ester; 18) [22] [23].…”

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confidence: 99%

Terpenoids from Eupatorium fortuneiTurcz

Jiang¹,

Li²,

Pan³

et al. 2006

Helvetica Chimica Acta

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Four new terpenoids, namely, rel-(1R,2S,3R,4R,6S)-p-menthane-1,2,3,6-tetrol (1), rel-(1R,2R,3R,4S,6S)-p-menthane-1,2,3,6-tetrol (2), 9-hydroxythymol 3-O-angelate (3), and (3b,20R)-20hydroxylanost-25-en-3-yl palmitate (4), together with fourteen known compounds, were isolated from the AcOEt part of the MeOH extracts of Eupatorium fortunei. In addition, two other monoterpenoids, 'acetone thymol-8,9-diyl ketal' (19) and 8-methoxy-9-hydroxythymol 3-O-angelate (20) were also obtained which were probably artifacts but have never been reported in the literature. The structures of the new compounds, including their relative configurations, were established by an extensive study of their spectral data, especially 1D-and 2D-NMR. The cytotoxic activity of the new compounds against human hepatoma (SMMC-7721), human leukemia (HL-60), and human hepatocyte (LO 2 ) cells was investigated.1. Introduction. -The genus Eupatorium (Compositae) consists of about 1200 species, with 14 species widely distributed in China [1], of which 8 species have long been used as Chinese folk medicines [2], especially Eupatorium fortunei. This species has been used as a diuretic and detoxifying drug [3] in China for the treatment of a dropsy, chill, and fever. In continuation of our search for bioactive compounds from species of the family of Compositae [4] [5], we studied the whole plant of E. fortunei. The petroleum ether, AcOEt, and BuOH extracts of the initially obtained MeOH extract of E. fortune were firstly tested for their antitumor activities against human hepatoma (SMMC-7721) and human leukemia (HL-60) cells, establishing cytotoxicity of the AcOEt extract (see below, Table 3). Therefore, we investigated the AcOEt extract and succeeded isolating of four new terpenoids 1 -3 and 4, together with the fourteen known compounds 5 -18. Furthermore, two new monoterpenoids, 19 and 20, were also obtained which were probably artifacts. These new compounds were investigated for the cytotoxic activities against SMMC-7721, HL-60, and human hepatocyte (LO 2 ) cells, revealing that compounds 1, 2, 19, and 20 were cytotoxic against HL-60 cell. We report here on the isolation and structural elucidation of these compounds and the cytotoxicity-assay results. Results andDiscussion. -The known compounds were identified by comparing their spectral data (MS, IR, 1 H-and 13 C-NMR) with those reported in the literature, i.e., as thymol (= 5-methyl-2-(1-methylethyl)phenol; 5) [6], 7-hydroxythymol (= 5-(hydroxymethyl)-2-(1-methylethyl)phenol; 6) [7] [8], 9-hydroxythymol (= 2-(2-hy-

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confidence: 99%

Terpenoids from Eupatorium fortuneiTurcz

Jiang¹,

Li²,

Pan³

et al. 2006

Helvetica Chimica Acta

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“…In addition to the nine new compounds ( 1 – 9 ), six known sesquiterpenoids ( 10 – 16 ) and 4-hydroxyacetophenone ( 17 ) were also isolated and identified by comparison with published spectroscopic and physical data as 1α-hydroxy and 1β-hydroxy dehydrofukinones ( 10 , 11 ), dehydrofukinone ( 12 ), ligudicins A and C ( 13 , 14 ), 11-hydroxyeremophil-6,9-dien-8-one ( 15 ), and istanbulin A ( 16 ) . The presence of 4-hydroxyacetophenone and derivatives has been reported in several Senecio species. ,, …”

Section: Resultsmentioning

confidence: 97%

“…34 The presence of 4hydroxyacetophenone and derivatives has been reported in several Senecio species. 29,35,36 The occurrence of pyrrolizidine alkaloids has been reported in most Senecio species. For this reason, 200 gr of the aerial part of S. volckmannii was processed using a specific methodology for their extraction.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Phytochemical Study of Senecio volckmannii Assisted by CASE-3D with Residual Dipolar Couplings and Isotropic ¹H/¹³C NMR Chemical Shifts

et al. 2018

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“…They are important constituents of essential oils, which have many applications as medicine and also in soap and perfume formulations [126]. The sesquiterpenes of the genus Senecio can mainly be devided into 17 groups: [81] eremophilanes, cacalols, bisabolanes, eudesmanes, oplopanes, germacranes, phomalairdanes, caryophyllanes, humulanes, presilphiperfolanes, aromadendranes, himachalanes, africananes, pentalenanes, bakkanes, valeranes, and benzofuranes. The biosyn- [115] thetic routes to these sesquiterpenes and their biogenetic relationships are shown in Schemes 2 to 5.…”

Section: Pyrrolizidine Alkaloidsmentioning

confidence: 99%