New Megastigmane and Tetraketide from the Leaves of Euscaphis japonica.

Takeda, Yoshio; Okada, Yoshihiro; Masuda, Toshiya; Hirata, Eiji; Shinzato, Takakazu; Takushi, Anki; Qian, Yu; Otsuka, Hideaki

doi:10.1248/cpb.48.752

Cited by 52 publications

(37 citation statements)

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“…Comparison of the DEPT results and molecular formula indicated the presence of one exchangeable proton. These data, together with the signals corresponding to two carboxyl groups (δ 170.5 and 176.2) observed in the 13 C NMR data, indicated that compound 1 must be a bicyclic compound possessing a free hydroxy group to account the molecular formula. The COSY (Table 1) (Table 1), and connectivities among the subunits in 1 were deduced from HMBC correlations ( Table 1).…”

Section: Resultsmentioning

confidence: 82%

“…Protulactone A (1) has the molecular formula C 10 H 14 O 6 , as deduced from 13 C NMR and HRESIMS data. This formula indicated four degrees of unsaturation.…”

Section: Resultsmentioning

confidence: 97%

“…Protulactone B (2) has the molecular formula C10H14O6, as deduced from 13 C NMR and HRESIMS data (four degrees of unsaturation). Although protulactone B (2) was suggested to be related to protulacton A (1) by comparing the 1 H and 13 C NMR data, the gross structure of 2 was determined to be somewhat different on the basis of detailed analysis of 2D NMR data.…”

Section: Resultsmentioning

confidence: 99%

“…Although protulactone B (2) was suggested to be related to protulacton A (1) by comparing the 1 H and 13 C NMR data, the gross structure of 2 was determined to be somewhat different on the basis of detailed analysis of 2D NMR data. As is the case with 1, COSY ( Table 2) experiments only defined the partial proton spin systems in 2 corresponding to C-2 -C-3 and C-4 -C-8 due to some signal overlapping.…”

Section: Resultsmentioning

confidence: 99%

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Protulactones A and B: Two New Polyketides from the Marine-derived Fungus Aspergillus sp. SF-5044

Sohn¹,

Oh²

2010

Bulletin of the Korean Chemical Society

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Protulactones A (1) and B (2), two new polyketide-derived fungal metabolites, have been isolated from an EtOAc extract of the marine-derived fungus Aspergillus sp. SF-5044 by various chromatographic methods. The structures of 1 and 2 were mainly determined by analysis of the NMR spectroscopic data and MS data, along with chemical methods such as Mosher method. Protulactones A (1) and B (2) are new members of polyketide-derived secondary metabolites, possessing unique ring systems among the fungal metabolites produced by the genus Aspergillus.

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Section: Resultsmentioning

confidence: 82%

“…Protulactone A (1) has the molecular formula C 10 H 14 O 6 , as deduced from 13 C NMR and HRESIMS data. This formula indicated four degrees of unsaturation.…”

Section: Resultsmentioning

confidence: 97%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

See 2 more Smart Citations

Protulactones A and B: Two New Polyketides from the Marine-derived Fungus Aspergillus sp. SF-5044

Sohn¹,

Oh²

2010

Bulletin of the Korean Chemical Society

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“…The 13 C NMR data (Table 1) showed three methyl, three methylene, four methine (including two olefinic ones), and three quaternary carbons, suggesting 2 to be a megastigmane-type norsesquiterpenoid and the planar structure resembling the aglycone of kowiionoside. 11 The only difference was that C-10 of 2 was oxygenated which resulted in a downfield shift of C-10 at δ 67.7. The relative stereochemistry of 2 was determined by ROESY observations (Figure 2).…”

Section: Resultsmentioning

confidence: 99%

New Compounds from Euphorbia helioscopia and Absolute Configuration Determination by Computational Methods

He¹,

Zhu²,

Luo³

et al. 2010

Bulletin of the Korean Chemical Society

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The whole plant of Euphorbia helioscopia is an important traditional Chinese medicine. Fom its BuOH soluble extract, one new lactam (1), three new terpenoids (2-4) including a new naturally occurring compound, and three known compounds were isolated. Their structures were identified by spectroscopic evidences. In particular, the absolute configurations of side chain of compounds 1 and 2 were determined using computational methods.

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Chemical Constituents of the Rare Cliff Plant Oresitrophe rupifraga and Their Antineuroinflammatory Activity

Xiong

Liu

et al. 2016

Chemistry & Biodiversity

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Four new (1 - 4) and thirteen known (5 - 17) compounds were isolated from a rare cliff plant, Oresitrophe rupifraga. Based on spectroscopic evidence, the new structures were established to be [(2S,3R,4R)-4-(4-methoxybenzyl)-2-(4-methoxyphenyl)-tetrahydrofuran-3-yl]methanol (1), (3α)-23-(acetyloxy)-3-hydroxyolean-12-en-29-oic acid (2), 3α,23-(isopropylidenedioxy)olean-12-en-29-oic acid (3, artifact of isolation), and (3β,15β)-3-hydroxycholest-5-en-15-yl β-d-glucopyranoside (4), respectively. Among the isolates, compounds 1, 4, epieudesmin (7), and 1-O-(9Z,12Z,15Z-octadecatrienoyl)glycerol (17) were found to show significant antineuroinflammatory effects by inhibiting the NO production in lipopolysaccharide (LPS)-stimulated murine BV-2 microglial cells, with IC50 values of 7.21, 9.39, 4.96, and 8.51 μm, respectively.

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New Megastigmane and Tetraketide from the Leaves of Euscaphis japonica.

Cited by 52 publications

References 0 publications

Protulactones A and B: Two New Polyketides from the Marine-derived Fungus Aspergillus sp. SF-5044

Protulactones A and B: Two New Polyketides from the Marine-derived Fungus Aspergillus sp. SF-5044

New Compounds from Euphorbia helioscopia and Absolute Configuration Determination by Computational Methods

Chemical Constituents of the Rare Cliff Plant Oresitrophe rupifraga and Their Antineuroinflammatory Activity

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