New neolignans and lignans from the aril of Myristica fragrans

Hada, Sumitra; Hattori, Masao; Tezuka, Yasuhiro; Kikuchi, Tohru; Namba, Tsuneo

doi:10.1016/0031-9422(88)83142-x

Cited by 82 publications

(63 citation statements)

References 13 publications

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“…These characteristics suggested that compound 1 has the 8-O-4Ј neolignan skeleton. [13][14][15] By comparing the spectral data with reference, structure of 1 was similar to that…”

Section: Resultsmentioning

confidence: 84%

“…These characteristics suggested that compound 1 has the 8-O-4Ј neolignan skeleton. [13][14][15] By comparing the spectral data with reference, structure of 1 was similar to that15) The coupling constant between protons H-7 and H-8 of the erythro compound was 4.0 Hz while that of 1 was much larger (Jϭ7.8 Hz) confirming that 1 was threo enantiomer.16) The Mosher's method 13) experiments were carried out to determine the absolute configuration at C-7. In the 1 H-NMR spectrum of (S)-MTPA ester (1a), proton signals assigned to H-8, H-9 were observed in higher field than those of the (R)-MTPA ester (1b), while signals due to H-3, H-5 in 1a were shifted to slightly lower field than those of 1b.…”

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confidence: 74%

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New Inhibitor against Nuclear Factor of Activated T Cells Transcription from Ribes fasciculatum var. chinense

Dat

Cai

Shen

et al. 2005

CHEMICAL & PHARMACEUTICAL BULLETIN

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Transcription factor called "nuclear factor of activated T cells" (NFAT) is a cytoplasmic protein and activated by stimulation of cell surface receptors coupled to Ca 2ϩ mobilization. The Ca 2ϩ activated phosphatase, calcineurin, dephosphorylates this NFAT proteins, thereby promoting their translocation into the nucleus and subsequent activation. 1)However, excessive activation of NFAT provokes immunopathological reactions including autoimmunity, transplant rejection and inflammation.2) Therefore, modulation of NFAT transcription factor should be useful in the therapy of immune diseases.Ribes fasciculatum var. chinense MAX. (Saxifragaceae) grows widely in Korea, Japan, China and other countries, but its chemical constituents and biological activities have not been studied previously. In the biological pre-screening program, the MeOH extract of R. fasciculatum var. chinense showed significantly inhibitory activity for the NFAT transcription factor. Because of this property, the plant was investigated on the chemical components with NFAT transcription inhibitory activity. The work produced two new compounds (1, 2) as well as nine known compounds:5) sarmentosin (6), 6) quercitrin (7), 7) glucosyl p-coumarate ester (8), 8) octadecanyl 3-(4-hydroxy-3-methoxy-phenyl)-acrylate ester (9), 9,10) 1,2-dimethoxy-4-(1-cis-propenyl)-benzene (10) 11) and lupenyl acetate (11). 12) Results and DiscussionCompound 1 was obtained as yellow oil and the positive FAB-MS showed the [MϩH] ϩ peak at m/z 285. The HR-FAB-MS revealed the molecular formula C 18 H 21 O 3 base on the peak at m/z 285.1387. The 13 C-NMR spectrum of 1 revealed totally eighteen carbon atoms structure with two parasubstituted benzene rings. Two tertiary carbon signals appeared at d 79.5 and 78.1 indicating that each one bore an oxygen atom. In the 1 H-NMR spectrum, the aromatic proton produced the broad peaks at d 7.31 (2H, dd, Jϭ2.1, 6.6 Hz, H-2, 6), 7.27 (2H, dd, Jϭ2.1, 6.6 Hz, H-2Ј, 6Ј), 6.90 (2H, dd, Jϭ2.1, 6.6 Hz, H-3, 5) and 6.83 (2H, dd, Jϭ2.1, 6.6 Hz, H-3Ј, 5Ј). The 1-(E)-propenyl moiety was observed with the large coupling constant (Jϭ15.6 Hz) between double bond protons. These characteristics suggested that compound 1 has the 8-O-4Ј neolignan skeleton. [13][14][15] By comparing the spectral data with reference, structure of 1 was similar to that15) The coupling constant between protons H-7 and H-8 of the erythro compound was 4.0 Hz while that of 1 was much larger (Jϭ7.8 Hz) confirming that 1 was threo enantiomer.16) The Mosher's method 13) experiments were carried out to determine the absolute configuration at C-7. In the 1 H-NMR spectrum of (S)-MTPA ester (1a), proton signals assigned to H-8, H-9 were observed in higher field than those of the (R)-MTPA ester (1b), while signals due to H-3, H-5 in 1a were shifted to slightly lower field than those of 1b. Therefore, the absolute configuration at C-7 was concluded to be 7S. The nuclear Overhauser effect correlations were observed between protons H-3, 5 and H-8, and not between protons H-7 and H-8 in the N...

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“…These characteristics suggested that compound 1 has the 8-O-4Ј neolignan skeleton. [13][14][15] By comparing the spectral data with reference, structure of 1 was similar to that…”

Section: Resultsmentioning

confidence: 84%

mentioning

confidence: 74%

New Inhibitor against Nuclear Factor of Activated T Cells Transcription from Ribes fasciculatum var. chinense

Dat

Cai

Shen

et al. 2005

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Compound 4 possesses o-dihydroxyl groups in the benzene ring, which explains its high antioxidant activity. Previous studies reported other nonvolatile constituents of nutmeg and mace (Woo et al 1987;Hada et al 1988;Leela 2008). Most of these constituents are phenolic compounds with more methoxyl groups and fewer hydroxyl groups, which have a lower antioxidant activity than the compounds possessing ortho-dihydroxyl groups.…”

Section: • Scavenging Methodsmentioning

confidence: 99%

Isolation of some compounds from nutmeg and their antioxidant activities

Hou¹,

Wang²,

Weng³

2012

Czech J. Food Sci.

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Hou J.P., Wu H., Wang Y., Weng X.C. (2012): Isolation of some compounds from nutmeg and their antioxidant activities. Czech J. Food Sci., 30: 164-170.Six compounds, licarin-B (1), dehydrodiisoeugenol (2), malabaricone B (3), malabaricone C (4), β-sitosterol (5), and daucosterol (6) were isolated from the seed (nutmeg) of Myristica fragrans Houtt and identified. Among them, malabaricone B was identified for the first time in nutmeg. Antioxidant activities of the isolated compounds were studied using oil stability index (OSI), reducing power, ABTS•+ scavenging, and DPPH • scavenging methods. The resultsshowed that Malabaricone C is an efficient antioxidant agent which exhibits a stronger antioxidant activity than the commonly used synthetic antioxidants in all studied methods. This compound may have a potential to be used as a natural antioxidant in food.

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“…Lignans and acylphenols are the secondary metabolites major compound produced by this family (Nemethy, 1986;Woo, 1987;Cooray, 1987;Kumar, 1988;Hada, 1988;Nakatani, 1988;Herath, 1996;Herath, 1997;Pham, 2000& 2002Talukdar, 2000;Calliste, 2010;Cuong, 2011;Chong, 2011;Manjunatha, 2011;Ragasa, 2013;Cao, 2013;Cao, 2015;Acuna, 2016;Wahab, 2016;Pandey, 2016;. In addition to their activities of antioxidant, antibacterial, antimicrobial, nematocide, and cytotoxic (Pham, 2000;Talukdar, 2000;Pham, 2002), antiinflammatory (Cuong, 2011;Cao, 2013;Cao, 2015), anxiogenic (Sonavane, 2002),antihelmintic (Lopez, 2015), cholinesterase inhibitor (Wahab, 2016), terapeutic (Jangid, 2014), acylphenols also been known to have alpha-glucosidase inhibitor activity .…”

Section: Myristicamentioning

confidence: 99%

Resorcinol Compounds Isolated form the Bark of Myristica fatua Houtt.

Megawati¹,

Darmawan²

2017

Indonesian J. Pharm.

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Myristica fatua Houtt. is one of the endemic plants growth in Wallace region. Isolation of the secondary metabolite compounds from the ethyl acetate fraction of the bark of Myristica fatua Houtt. has been done using some chromatography techniques afforded two resorcinol compounds, malabaricone C (1), and malabaricone B (2). The structures of 1-2 were determined using spectroscopic techniques, including mass spectrometry, 1D-NMR and 2D-NMR. Both compounds showed in vitro cytotoxic activity against the breast carcinoma cancer cell lines MCF-7 using alamar blue assay method, with IC 50 of 2.38 and 0.71 μg/mL, respectively.

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New neolignans and lignans from the aril of Myristica fragrans

Cited by 82 publications

References 13 publications

New Inhibitor against Nuclear Factor of Activated T Cells Transcription from Ribes fasciculatum var. chinense

New Inhibitor against Nuclear Factor of Activated T Cells Transcription from Ribes fasciculatum var. chinense

Isolation of some compounds from nutmeg and their antioxidant activities

Resorcinol Compounds Isolated form the Bark of Myristica fatua Houtt.

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