Confirmation of the Absolute (3R,3′S,6′R)‐Configuration of (all‐E)‐3′‐Epilutein

Molnár, Péter; Deli, József; Ősz, Erzsébet; Zsila, Ferenc; Simonyi, Miklós; Tóth, Gyula

doi:10.1002/hlca.200490195

Cited by 18 publications

(15 citation statements)

References 20 publications

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“…From the above data, compound 1 was identified as a carotenoid, lutein. These spectroscopic data were consistent with those reported [27,28]. The analyzed data of compound 1 are shown below.…”

Section: Structure Determination Of Compoundsupporting

confidence: 86%

Purified Canola Lutein Selectively Inhibits Specific Isoforms of Mammalian DNA Polymerases and Reduces Inflammatory Response

Horie

Okuda

Yamashita³

et al. 2010

Lipids

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In the screening of DNA polymerase (pol) inhibitor, we isolated lutein, a carotenoid, from the crude (unrefined) pressed oil of canola (low erucic acid rapeseed, Brassica napus L.). Commercially prepared carotenoids such as lutein (1), zeaxanthin (2), b-cryptoxanthin (3), astaxanthin (4), canthaxanthin (5), b-carotene (6), lycopene (7), capsanthin (8), fucoxanthin (9) and fucoxanthinol (10), were investigated for the inhibitory activities of pols. Compounds 1, 2 and 8 exhibited strong inhibition of the activities of mammalian pols b and k, which are DNA repair-and/or recombination-related pols. On the other hand, all carotenoids tested had no influence on the activity of a mammalian pol a, which is a DNA replicative pol.Lutein (1) was the strongest pol inhibitor of mammalian pols b and k in the prepared ten carotenoids tested, but did not influence of the activities of mammalian pols a, c, d and e. The tendency for pols b and k inhibition by these carotenoids showed a positive correlation with the suppression of TPA (12-O-tetradecanoylphorbol-13-acetate)-induced inflammation. These results suggest that cold pressed unrefined canola/rapeseed oil, or other oils with high levels of lutein and other carotenoids, may be useful for their anti-inflammatory properties.

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Section: Structure Determination Of Compoundsupporting

confidence: 86%

Purified Canola Lutein Selectively Inhibits Specific Isoforms of Mammalian DNA Polymerases and Reduces Inflammatory Response

Horie

Okuda

Yamashita³

et al. 2010

Lipids

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“…This formula matched to the known carotenoid lutein. The 1 H and 13 C NMR spectroscopic data of 1 (Table 1) also corresponded closely to those reported for lutein [6,7]. Further, the specific rotation of compound 1 ( showed a [M+H] + at m/z 583.4564, which corresponded to the molecular formula of C 41 H 58 O 2 (calculated for 583.4515).…”

supporting

confidence: 80%

“…Lutein is the main xanthophyll found in the major light-harvesting pigment-protein complex of higher plants, and is involved in energy-transfer mechanisms during photosynthesis. In the fatty acid ester form, it is widely distributed in fruits, flowers, and yellow autumn leaves [6]. However, lutein 3′methyl ether has never been isolated from plants and has only been prepared synthetically [7][8].…”

mentioning

confidence: 99%

The Isolation of Lutein and Lutein 3′-methyl ether from Peristrophe lanceolaria

Prapalert

Santiarworn

Liawruangrath

et al. 2016

Natural Product Communications

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Two carotenoids, lutein (1) and lutein 3′-methyl ether (2), have been isolated from the EtOAc fraction of the MeOH extract of Peristrophe lanceolaria, growing in Thailand. The structures of these compounds were elucidated from their 1D and 2D NMR spectroscopic data and from comparisons made with the literature data. This is the first report of the isolation of lutein-3′-methyl ether as a natural product.

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“…7) In addition, other five known compounds were identified by comparison of their spectroscopic data (NMR, UV, IR, MS, CD and optical rotation) with reported values. These compounds were lutein (4), 8) (ϩ)-(1R,2S,5R,6S)-2,6-di-(4Ј-hydroxyphenyl)-3,7-dioxabicyclo(3,3,0)octane (5), 9,10) indole-3-aldehyde (6), 11) indole-3-carboxylic acid (7), 12) and adenosine (8), 13) respectively.…”

Section: Resultsmentioning

confidence: 99%

Two New Megastigmanes from the Leaves of Cucumis sativus

2007

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Cucumis sativus L., which belongs to the Cucurbitaceae family, is cultivated worldwide as a vegetable crop. The fruit of C. sativus (cucumber) is used not only as food, but also in folk medicines and folk cosmetics. The leaves, stems and roots of C. sativus are reportedly used in Chinese folk medicine as antidiarrheal, detoxicant and antigonorrheal agents. 1)However, these are not major uses, so after harvest of the cucumber fruits, almost all the remaining plant material is waste. There have been few chemical studies regarding the constituents of this material. The only reports are by Enslin et al., who isolated the triterpenoid cucurbitacin C, 2) and McNally et al., who isolated C-glycosyl flavonoid.3) Thus, in the present study, we attempted to identify useful components of cucumber plant material to support its development as a medicinal resource.As part of our ongoing search for medicinal materials in cucumber plant material, chromatographic separation and purification led to the identification of two new megastigmanes, one known megastigmane, one known carotenoid, one known lignan and three other known compounds. In the present paper, we report the isolation and structural elucidation of the new megastigmanes. Results and DiscussionAir-dried leaves of C. sativus were extracted using methanol (MeOH). The MeOH extract was partitioned into an ethyl acetate (EtOAc)-water mixture to furnish EtOAcsoluble and water-soluble parts. The EtOAc-soluble part was subjected to normal-and reversed-phase column chromatography and HPLC to yield compounds 1, 3, 4, 5, 6 and 7 (Fig. 1). The water-soluble part was again extracted with EtOAc, then with n-butanol (BuOH), using an automatic extractor. The n-BuOH-soluble part was subjected to normal-and reversed-phase column chromatography and HPLC to yield compounds 2 and 8 (Fig. 1).Compound 1 C heteronuclear multiple bond coherence (HMBC) study for 1, long-range correlations were observed between the following protons and carbons: H-4 and C-2; H-2a, 2b and C-3; H-13 and C-4; H-2a, 2b, 4, 7, 8, 13 and C-6; H-7, 8 and C-9; and H-10a, 10b and C-8 (Fig. 2). Furthermore, acetylation of 1 with acetic anhydride in dry pyridine yielded di-O-acetate (1a), whose 13 C-NMR spectrum showed an acetylation shift around the 9 and 10 position of 1a. These findings and comparisons of the 1 H-and 13 C-NMR spectra of 1 and 1a with those of a known megastigmane led us to formulate the 3-oxo-6,9,10-trihydroxy-ionone structure of 1 (Fig. 1). The absolute configuration of C-6 of 1 was determined by application of the circular dichroism (CD) helicity rule 4) with known (ϩ)-dehydrovomifoliol (3). The CD spectrum of 3 showed a positive Cotton effect (De ϩ27.00) at 243.2 nm, and the 6-position was determined to have an S configuration by the CD helicity rule.4) On the basis of this evidence, the CD spectrum of 1 exhibited a positive Cotton effect (De ϩ15.79) at 240.8 nm, and the 6-position was shown to have an S configuration. In order to clarify the absolute stereostructure of the 9-position of 1, a...

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Confirmation of the Absolute (3R,3′S,6′R)‐Configuration of (all‐E)‐3′‐Epilutein

Cited by 18 publications

References 20 publications

Purified Canola Lutein Selectively Inhibits Specific Isoforms of Mammalian DNA Polymerases and Reduces Inflammatory Response

Purified Canola Lutein Selectively Inhibits Specific Isoforms of Mammalian DNA Polymerases and Reduces Inflammatory Response

The Isolation of Lutein and Lutein 3′-methyl ether from Peristrophe lanceolaria

Two New Megastigmanes from the Leaves of Cucumis sativus

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