Elecanacin, a Novel New Naphthoquinone from the Bulb of Eleutherine americana

Hara, H.; Maruyama, Naoki; Yamashita, Shinsuke; Hayashi, Yasuhisa; Lee, Kuo Hsiung̀; Bastow, Kenneth F.; Chairul,; Marumoto, Ryuji; Imakura, Yasuhiro

doi:10.1248/cpb.45.1714

Cited by 67 publications

(60 citation statements)

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“…As all sp 2 carbons were already allocated, the last insaturation must be due to a third ring based on the ether fragment deduced above. The connection of these fragments forms a 1,3-dihydro-naphtho(2,3-c) furan-4,9-dione ring system in which the quinonoid double bond between the methyne and the methylene of the furanoid ring could explain the long range coupling between them observed in the 1 H NMR and COSY experia b The spectral and physical properties of 2, 3, and 4 were identical to those published in the literature (Hara et al 1997).…”

Section: Methodssupporting

confidence: 69%

“…1). umn to afford four compounds. Three of them, 2, 3, and 4, were identified by comparison of their physical and spectral data with those published in the literature (Hara et al 1997). Compound 1 was found to be new and its structural elucidation is described bellow.…”

Section: Methodsmentioning

confidence: 94%

“…are used as haemostatic and antibacterial agents (Dam & Mai 1990) . Several compounds, including elecanicin, eleutherol, isoeleutherol, eleutherin, isoeleutherin (Hara et al 1997), hongconin (Zhengxiong et al 1984) as well as anthraquinones (Komura et al 1983) and their glycosides (Shibuya et al 1997) have already been isolated and identified from bulbs of plants belonging to this genus. Some compounds present in the genus display important biological activities.…”

mentioning

confidence: 99%

“…Some compounds present in the genus display important biological activities. Thus, Hara et al (1997) described eleutherin as forming a type of "noncleavable complex" with topoisomerase II with stereospecific and selective inhibitory activity. These authors also described the inhibitory activity of isoeleutherin and isoeleutherol against HIV replication in H9 lymphocytes.…”

mentioning

confidence: 99%

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Eleutherinone, a novel fungitoxic naphthoquinone from Eleutherine bulbosa (Iridaceae)

Alves

Kloos²,

Zani

2003

Mem. Inst. Oswaldo Cruz

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The dichloromethane extract prepared from the underground parts of Eleutherine bulbosa (Miller) Urban (Iridaceae) showed strong activity in the direct bioautography assay with the phytopathogenic fungus Cladosporium sphaerospermum. This assay was used to guide the fractionation of this extract and allowed the isolation of four compounds: the new naphthoquinone eleutherinone [8-methoxy-1-methyl-1,3-dihydro-naphtho(2,3-c) furan-4,9-dione] and the known compounds, previously isolated from this species, eleutherin [9-methoxy-1(R),3(S)-dimethyl-3,4-dihydro-1H-benzo(g)isochromene-5,10-dione], isoeleutherin [9-methoxy-1(R),3(R)-dimethyl-3,4-dihydro-1H-benzo(g)isochromene-5,10-dione], and eleutherol [4-hydroxy-5-methoxy-3(R)-methyl-3H-naphtho(2,3-c)

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Section: Methodssupporting

confidence: 69%

Section: Methodsmentioning

confidence: 94%

mentioning

confidence: 99%

mentioning

confidence: 99%

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Eleutherinone, a novel fungitoxic naphthoquinone from Eleutherine bulbosa (Iridaceae)

Alves

Kloos²,

Zani

2003

Mem. Inst. Oswaldo Cruz

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“…Spots were visualised by UV (254 nm) and reaction with sulphuric anisaldehyde heated at 100 C. Fractions 16-27 (635 mg), which exhibited the same chromatography profile by TLC, were purified by another column chromatography, furnishing 23 mg of pure eleutherine (1) and 25 mg of iso-eleutherine (2), already isolated from the bulbs of C. paludosa (Tessele et al 2011). Fractions 11-20 (83 mg) from the second column exhibited the same chromatography profile by TLC and were purified by flash chromatography, furnishing 14 mg of eleutherol (3), which was identified by spectroscopic data (NMR 1 H and 13 C) and comparison with of the literature (Hara et al 1997). …”

Section: Extraction and Isolationmentioning

confidence: 97%

Antiproliferative effect of extracts and pyranonaphthoquinones obtained from Cipura paludosa bulbs

Campos

Vendramini–Costa

Fiorito

et al. 2015

Pharmaceutical Biology

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Context: Cipura paludosa Aubl. (Iridaceae) is widely used in folk medicine to treat several ailments. Experimental studies have confirmed its anti-inflammatory, antinociceptive, and neuroprotective effects.Objective: This study evaluates the possible antiproliferative potential of the crude methanol extract and three isolated compounds from the bulbs of C. paludosa. Materials and methods: Phytochemical analysis was carried out by conventional chromatographic techniques, and the resulting compounds were identified by NMR 1 H and 13 C. The antiproliferative activity was analysed using the sulforhodamine B assay. Results: Crude methanol extract of C. paludosa bulbs showed GI 50 values of between 1.6 and 30.8 mg/mL. The naphthoquinone derivatives (eleutherine, isoeleutherine, and eleutherol) isolated from the bulbs of C. paludosa exhibited promising cytotoxicity against several human tumour cell lines, especially the two main compounds, eleutherine and isoeleutherine, against glioma and breast cancer cell lines, with TGI values of between 2.6 and 13.8 mg/mL. Conclusion: Cipura paludosa bulbs produce active principles with relevant antiproliferative potential, such as naphthoquinone derivatives, identified as eleutherine, isoeleutherine, and eleutherol. This is the first report indicating C. paludosa with antiproliferative potential. ARTICLE HISTORY

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New Wnt/β‐Catenin Signaling Inhibitors Isolated from Eleutherine palmifolia

Ohtsuki

Koyano³

et al. 2009

Chemistry An Asian Journal

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Aberrant Wnt/beta-catenin signaling has recently been implicated in tumorigenesis. On the basis of our screening program targeting inhibition of TCF/beta-catenin transcriptional activity, a plant extract of Eleutherine palmifolia was selected as a hit sample. Activity-guided fractionations led to the isolation of 15 naphthalene derivatives (1-15), including 4 new glucosides, eleutherinosides B-E (1-4), and 10 of the 15 compounds showed strong activities with high viability among 293T cells. Our data showed that 2 and 9 inhibited the transcription of TCF/beta-catenin in SW480 colon cancer cells in a dose-dependent manner. These two compounds also showed selective cytotoxicity against three colorectal cancer cell lines. In addition, treatment with 9 led to a significant decrease in the level of nuclear beta-catenin protein, suggesting this reduction to have resulted in the inhibitory effect of 9 on the transcription of TCF/beta-catenin.

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Elecanacin, a Novel New Naphthoquinone from the Bulb of Eleutherine americana

Cited by 67 publications

References 0 publications

Eleutherinone, a novel fungitoxic naphthoquinone from Eleutherine bulbosa (Iridaceae)

Eleutherinone, a novel fungitoxic naphthoquinone from Eleutherine bulbosa (Iridaceae)

Antiproliferative effect of extracts and pyranonaphthoquinones obtained from Cipura paludosa bulbs

New Wnt/β‐Catenin Signaling Inhibitors Isolated from Eleutherine palmifolia

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