Five New Insecticidal Sesquiterpenoids from Celastrus angulatus

Wu, Wenjun; Wang, Mingan; Zhu, Jiang; Zhou, Wenming; Hu, Zhaonong; Ji, Zhiqin

doi:10.1021/np0004193

Cited by 77 publications

(66 citation statements)

References 8 publications

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“…-Microtropis fokienensis Dunn (Celastraceae) is a small shrub that grows in high-altitude forests throughout southern China and Taiwan [1]. Various dihydroagarofuranoid sesquiterpenes [2] [3], sesquiterpene alkaloids [4], and triterpenes [5] [6] are widely distributed in plants of the family Celastraceae. Many of these compounds exhibit insecticidal [2], anti-inflammatory [3], anti-AIDS [5], and antitumor [5] [6] activities.…”

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confidence: 99%

“…Various dihydroagarofuranoid sesquiterpenes [2] [3], sesquiterpene alkaloids [4], and triterpenes [5] [6] are widely distributed in plants of the family Celastraceae. Many of these compounds exhibit insecticidal [2], anti-inflammatory [3], anti-AIDS [5], and antitumor [5] [6] activities. In our continuing studies on the antitubercular constituents of Formosan plants, over 400 species have been screened so far for their in vitro antituberculosis activities, and M. fokienensis has been found to be one of the active species.…”

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confidence: 99%

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A New Dihydroagarofuranoid Sesquiterpene from Microtropis fokienensis with Antituberculosis Activity

Chou¹,

Chen²,

Sung³

et al. 2007

Chemistry & Biodiversity

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A new dihydroagarofuran-based sesquiterpene, 8-acetoxymutangin (1), was isolated from the stems of Microtropis fokienensis, together with eight known compounds, including mutangin (2). Their structures were determined through in-depth spectroscopic and mass-spectrometric analyses. Among the isolated compounds, 1 exhibited potent in vitro antituberculosis activity, with an MIC value of 10.0 microg/ml against Mycobacterium tuberculosis 90-221387, which is considerably better than that of mutangin (2). The activity of 1 lies in the same range as that of the clinic drug ethambutol (MIC 6.25 microg/ml), despite completely different chemical structures, which indicates different modes of action.

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confidence: 99%

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confidence: 99%

A New Dihydroagarofuranoid Sesquiterpene from Microtropis fokienensis with Antituberculosis Activity

Chou¹,

Chen²,

Sung³

et al. 2007

Chemistry & Biodiversity

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“…90°. [8][9][10] From the NOESY spectrum of 1, the strong correlation between H-7/H-9 and H-9/H-13 indicated the presence of cis-orientation of H-9. Thus, compound 1 was identified as 1S,13-diacetyloxy-4S-hydroxy-6R-(3-)furancarbonyloxy-9S-cinnamoyloxy-b-dihydroagarofuran.…”

Section: Resultsmentioning

confidence: 99%

“…The cou- pling constant, J 8,9 ϭ6.0 Hz suggested that H-8 and H-9 have a different orientation. 9,10) The stereochemistry for H-8 and H-9 was determined from the NOESY spectrum, which showed cross-peaks between H-7/H-8, H-7/H-9, H-8/H-13 and H-9/H-13, suggesting that H-8 is axial and H-9 is equatorial, respectively. The locations of the ester groups were also identified by the HMBC cross-peaks between H-8 and the benzoate carbonyl signal at d 165.3, H-9 and the (3-)furancarboxylate carbonyl at d 161.9, the H-13 and the acetate carbonyl at d 170.4, and H-1 and H-6 between 2-methylbutanoate carbonyl groups at d 174.5 and 175.1, respectively.…”

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Two New Sesquiterpene Polyesters from the Seeds of Euonymus nanoides LOES.

Wang

Tian

2006

CHEMICAL & PHARMACEUTICAL BULLETIN

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Plants belonging to the family Celastraceae have used worldwide as medicines and have been the subject of many investigations for their biologically active components.1) In a previous study on the chemical constituents of Celastraceae, we have recently reported on the isolation and structural elucidation of several new sesquiterpene polyesters with b-dihydroagarofuran skeletons 2,3) and triterpenes. 4,5) Some of these novel isolates exhibited antitumor activities. Continuing studies on the seeds of E. nanoides have provided two additional new: 1S,13-diacetyloxy-4S-hydroxy-6R-(3-)furancarbonyloxy-9S-cinnamoyloxy-b-dihydroagarofuran (1), 1S,6R-di(2-) methylbutanoyloxy-4S-hydroxy-8S-benzoyloxy-9R-(3-)furancarbonyloxy-13-acetyloxy-b-dihydroagarofuran (2) and one known 1S-diacetyloxy-4S,6R-dihydroxy-9S-benzoyloxy-13-cinnamoyloxy-b-dihydroagarofuran (3). The pure compounds were tested on a panel of three human and one mouse cancer cell lines. Details of the isolation and structure determination of 1 and 2 are presented here. Results and DiscussionSilica gel column chromatography and vacuum liquid chromatography (VLC) of the acetone extract of the seeds of E. nanoides afforded 20 fractions. Further separation of these fractions using thin layer chromatography (TLC) and reversed phase column chromatography (RP-18) yielded compounds 1-3. The known compound 3 was identified by comparison of their physical and spectral data with those reported in the literature. 69.4, 89.7, 50.9, 83.7). These data were in good agreement with the spectral values assigned to the 5-substituted b-dihydroagarofuran parent skeleton. 7,8) Moreover, the molecular composition suggested the presence of one free hydroxyl group. One free hydroxyl group and the four esters mentioned above locates at C-1, C-4, C-6, C-9 and C-13 of b-dihydroagarofuran.The carbonyl signal at d 161.8 and 165.8 were correlated with the proton signals at H-6 and H-9 respectively, revealing that the (3-)furancarboxylate ester was located at C-6 and cinnamate ester was located at C-9. Also, two acetate esters were positioned at C-1 and C-13 respectively, because the carbonyl signals at d 169.7 and 170.5 were correlated with the proton signals H-1 and H-13, respectively.The relative stereochemistry of 1 was determined on the Two new b b-dihydroagarofuran sesquiterpene polyesters, 1S,13-diacetyloxy-4S-hydroxy-6R-(3-)furancarbonyloxy-9S-cinnamoyloxy-b b-dihydroagarofuran (1) and 1S,6R-di(2-)methylbutanoyloxy-4S-hydroxy-8S-benzoyloxy-9R-(3-)furancarbonyloxy-13-acetyloxy-b b-dihydroagarofuran (2), together with one known compound (3) were isolated from the seeds of Euonymus nanoides LOES. Their structures were elucidated by spectroscopic data interpretation. Compound 2 showed moderate antitumor activity against BEL-7402, P-388, HL-60 and A-549.

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“…In skeleton of β-dihydroagarofuran sesquiterpene, H-1 and H-6 have axial stereochemistry. 5,6 From the results of the NOESY spectrum of 1, the correlation between H-6 and H-9 indicated the presence of H-9eq (Fig. 1).…”

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A New Antitumor β-Dihydroagarofuran Sesquiterpene Polyol Ester from the Euonymus Nanoides

Wang¹,

Tian²,

Pan³

2003

Bulletin of the Korean Chemical Society

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The Celastraceae family is a rich source of β-dihydroagarofuran sesquiterpene skeleton with cytotoxic, antitumorpromoting, immunosuppressive, insecticidal and insectantifeedant activities.1 In a previous study of the chemical constituents of genus Euonymus (Celastraceae), we reported on the isolation of several β-dihydroagarofuran sesquiterpenes.2,3 Recently, we examined sesquiterpene constituents of Euonymus nanoides Loes. (Celastraceae) and isolated a new (1) β-dihydroagarofuran sesquiterpene polyol ester. We report here the structure elucidation of new compound by a combination of 1D-and 2D-NMR techniques and antitumor activity of 1. and 5.33 t (H-9) were assigned to three protons attached to carbon atoms bearing secondary ester groups, while signals at δ 4.85 d (J = 12.8 Hz, H-13a) and δ 4.51 d (J = 12.8 Hz, H-13b) were assigned to the two protons attached to carbon atoms bearing primary ester groups. The 13 C NMR (DEPT) spectrum of the parent skeleton of 1 showed three methyls at δ 16.8, 24.8 and 29.1, three methylene at δ 31.0, 31.8 and 33.5, one methylene attached to an oxygen function at δ 66.3, two methine at δ 32.2 and 43.4, three methines attached to an oxygen function at δ 68.3, 68.8 and 69.4, one quaternary carbon at δ 51.2, and two quaternary carbons attached to an oxygen function at δ 83.8 and 89.8, whose chemical shifts were very similar to those of reported β-dihydroagarofurans. 4 It was determined that compound 1

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Five New Insecticidal Sesquiterpenoids from Celastrus angulatus

Cited by 77 publications

References 8 publications

A New Dihydroagarofuranoid Sesquiterpene from Microtropis fokienensis with Antituberculosis Activity

A New Dihydroagarofuranoid Sesquiterpene from Microtropis fokienensis with Antituberculosis Activity

Two New Sesquiterpene Polyesters from the Seeds of Euonymus nanoides LOES.

A New Antitumor β-Dihydroagarofuran Sesquiterpene Polyol Ester from the Euonymus Nanoides

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