The structure of macelignan from Myristica fragrans

Woo, Won Sick; Shin, Kuk Hyun; Wagner, Hildebert; Lotter, H.

doi:10.1016/s0031-9422(00)81858-0

Cited by 52 publications

(25 citation statements)

References 3 publications

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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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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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“…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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“…In this regard and as part of our program to search for new AMPK activators with chemopreventive activity from plants, 12 we found that diarylbutane-type lignans from M. fragrans exhibited potential AMPK activation effects and strong growth inhibition activities against MCF-7 breast cancer cells. As major active principles, two diarylbutane-type lignans, macelignan (1) 13 and MDGA (2)…”

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confidence: 99%

Diarylbutane-type Lignans fromMyristica fragrans(Nutmeg) show the Cytotoxicity against Breast Cancer Cells through Activation of AMP-activated Protein Kinase

Nguyen

Choi

et al. 2017

Nat Prod Sci

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-In our program to search for new AMP-activated protein kinase (AMPK) activators from plants that exert potential anticancer property, we found that an EtOAc extract of Myristica fragrans (nutmeg) activated AMPK enzyme in human breast cancer MCF-7 cells. Two major diarylbutane-type lignans, macelignan and meso-dihydroguaiaretic acid (MDGA), were isolated as active principles from this extract. Treatment of breast cancer cells with two compounds induced cellular apoptosis, evidenced by cleavage of poly-(ADP-ribose) polymerase (PARP) and Ser 15 phosphorylation of p53. Moreover, macelignan and MDGA significantly inhibited the colony formation of MCF-7 breast cancer cells on soft agar. Intraperitoneal injection of macelignan and MDGA (20 mg/kg) suppressed the tumor growth of 4T1 mammary cancer cells. These results indicate that the chemopreventive effects of two major diarylbutane-type lignans from Myristica fragrans (nutmeg) may be associated with induction of apoptosis presumably through AMPK activation.

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The structure of macelignan from Myristica fragrans

Cited by 52 publications

References 3 publications

Isolation of some compounds from nutmeg and their antioxidant activities

Isolation of some compounds from nutmeg and their antioxidant activities

Resorcinol Compounds Isolated form the Bark of Myristica fatua Houtt.

Diarylbutane-type Lignans fromMyristica fragrans(Nutmeg) show the Cytotoxicity against Breast Cancer Cells through Activation of AMP-activated Protein Kinase

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