육두구의 리그난 성분

김갑준,한용남 대한약학회 2002 약학회지 Vol.46 No.2

The phytochemical study of nutmeg, the seeds of Myristica fragrans Houttuyn (Myristicaceae) led to the isolation of three lignans, safrole (I), macelignan (III), and a 3,4 : 3',4'-bis(methylenedioxy)lignan (II). The compound II was identified by a mixture (1:1) of (8S, 8'R)- and (8S, 8'S)-forms of bis(3, 4-methylenedioxy)-8, 8'-neolignan by $^1$H-, $^{13}$ C-NMR and $^1$H-$^1$H COSY spectral data. The compound II was isolated for the first time from Myristica fragrans.

Compounds from the Seeds of Myristica fragrans and Their Cytotoxic Activity

TODAO CUONG,Chae Jin Lim,Tran Thi Thu Trang,Yoon Ho Bae,NGUYENVAN THU,Nguyen The Tung,Tran Manh Hung,우미희,최재수,민병선 한국생약학회 2012 Natural Product Sciences Vol.18 No.2

Six lignan compounds, 1-(17,21-dihydroxyphenyl)-9-(12,13-dihydroxyphenyl)-1-nonanone (malabaricone C) (1), 7'-(3',4'-methylenedioxyphenyl)-8,8'-dimethyl-7-(3,4-dihydroxyphenyl)-butane (2), 7'-(3',4'-dimethoxyphenyl)-8,8'-dimethyl-7-(3-methoxy-4-hydroxyphenyl)-butane (3), 7-(4-hydroxy-3-methoxyphenyl)-7′-(3′,4′-methylenedioxyphenyl)-8,8′-lignan-7-methyl ether (4), (+)-erythro-(7S,8R)-Δ8′-7-hydroxy-3,4,3′,5′-tetramethoxy-8-O-4′-neolignan (5), and (+)-erythro-(7S,8R)-Δ8′-7-acetoxy-3,4,3′,5′-tetramethoxy-8-O-4′-neolignan (6), were isolated from the seeds of Myristica fragrans. The chemical structures of these compounds were determined on the basis of spectroscopic analyses including 2D NMR. Compounds 1 - 6 were evaluated for their cytotoxic activity against the HL-60, MCF-7, and A549 cancer cell lines in in vitro.

Sialidase inhibitory activity of diarylnonanoid and neolignan compounds extracted from the seeds of <i>Myristica fragrans</i>

Park, Ji-Young,Hwan Lim, Su,Ram Kim, Bo,Jae Jeong, Hyung,Kwon, Hyung-Jun,Song, Gyu-Yong,Bae Ryu, Young,Song Lee, Woo Elsevier 2017 Bioorganic & medicinal chemistry letters Vol.27 No.14

<P><B>Abstract</B></P> <P>Sialidases are key virulence factors that remove sialic acid from host cell surface glycans, thus unmasking receptors to facilitate bacterial adherence and colonization. In this study, we report the isolation and characterization of novel inhibitors of the <I>Streptococcus pneumoniae</I> sialidases NanA, NanB, and NanC from <I>Myristica fragrans</I> seeds. Of the isolated compounds (<B>1</B>–<B>12</B>), malabaricone C showed the most pneumococcal sialidases inhibition (IC<SUB>50</SUB> of 0.3μM for NanA, 3.6μM for NanB, and 2.9μM for NanC). These results suggested that malabaricone C and neolignans could be potential agents for combating <I>S. pneumoniae</I> infection agents.</P> <P><B>Highlights</B></P> <P> <UL> <LI> Twelve compounds with sialidase inhibitory potency were extracted from <I>M. fragrans.</I> </LI> <LI> Malabaricone C showed the maximal inhibitory activity against NanA, NanB, and NanC. </LI> <LI> Natural diarylnonanoids and lignans are useful against bacterial infection. </LI> </UL> </P> <P><B>Graphical abstract</B></P> <P>[DISPLAY OMISSION]</P>

Inhibitory Effects of Macelignan Isolated from <i>Myristica fragrans</i> H<small>OUTT.</small> on Melanin Biosynthesis

Cho, Yumi,Kim, Kyu-Hoi,Shim, Jae-Seok,Hwang, Jae-Kwan Pharmaceutical Society of Japan 2008 Biological & pharmaceutical bulletin Vol.31 No.5

<P>The aim of this study was to investigate the <I>in vitro</I> inhibitory effects of macelignan isolated from <I>Myristica fragrans</I> H<SMALL>OUTT.</SMALL> on melanogenesis and its related enzymes such as tyrosinase, tyrosinase-related protein-1 (TRP-1), and tyrosinase-related protein-2 (TRP-2) in melan-a murine melanocytes. The IC<SUB>50</SUB> values of macelignan for melanogenesis and tyrosinase were 13 μ<SMALL>M</SMALL> and 30 μ<SMALL>M</SMALL>, respectively, while those of arbutin as a positive control were 990 μ<SMALL>M</SMALL> and 660 μ<SMALL>M</SMALL>, respectively. In Western blot analysis, macelignan also significantly decreased tyrosinase, TRP-1, and TRP-2 protein expression. These results indicate that macelignan effectively inhibits melanin biosynthesis and thus could be employed as a new skin-whitening agent.</P>

육두구의 形態 鑑別에 관한 硏究

韓孝尙,吉基正,李暎鍾 대한본초학회 2005 大韓本草學會誌 Vol.20 No.1

Objectives : Myristicae Semen is the seed of Myristica fragrans Houttuyn. Recently, the seed of Myristica argentea Warburg is also sold as a fake of Myristicae Semen. Thus, in order to distinguish Myristica fragrans Houttuyn and Myristica argentea Warburg, their external, internal, and flour states were observed via microscopic examination. Method : The slice of the tested material made by paraffin section technique was colored with Safranine Malachite Green contrast methods, and the flour of it was mounted by the liquid made by the same ratio of each of glycerin, acetic acid, and water, and then observed and photographed by olymphus-BHT. Result 1. The seed of Myristica fragrans Houttuyn is oval with a length of 2~3cm and diameter of 1.5~2.5 cm, while the seed of Myristica argentea Warburg is of a longer oval shape with a length of 2.5?3.5cm and diameter of 1.5cm. 2. There was no difference between the internal parts of the cross-sections of Myristica fragrans Houttuyn and Myristica argentea Warburg. 3. There was no difference between the flour states of Myristica fragrans Houttuyn and Myristica argentea Warburg. Conclusion : There was a distinctive difference between the external forms of Myristica fragrans Houttuyn and Myristica argentea Warburg, while there was no significant difference in their internal and flour states. This makes it difficult to distinguish them via microscopic examination, when cut by cross-sections or grounded into flour states. Therefore, they should be distinguished through TLC, or some research on the characterising compound is needed.

육두구(Myristica fragrans Houttuyn) 내의 myristicin의 분리 및HPLC를 이용한 함량분석 방법 밸리데이션

김수환,이동호,권수한,임병호,이상훈,민범찬 한국생약학회 2007 생약학회지 Vol.38 No.1

fragrans has been used for the treatment of stomachache in East Asia. It is very important to deter-mine the amount of myristicin in Myristica fragrans, because excess myristicin causes side effects. In this study, wedeveloped and validated the method for determination contents of myristicin in Myristica fragrans which was purchasedfrom various regions of Korea. The average content of myristicin in Myristica fragrans was 2.10% with the validatedHPLC analysis method. Key wordsMyristicin, Myristica fragrans, quantitative analysis, validation

Myristicae Semen Extract Protects Excitotoxicity in Cultured Neuronal Cells

김지예,반주연,방경환,성낙술,송경식,배기환,성연희 한국약용작물학회 2004 韓國藥用作物學會誌 Vol.12 No.5

Myristica fragrans seed from Myristica fragrans Houtt (Myristicaceae) has various pharmacological activities peripherally and centrally. The present study aims to investigate the effect of the methanol extract of Myristica fragrans seed (MF) on kainic acid (KA)-induced neurotoxicity in primary cultured rat cerebellar granule neuron. MF, over a concentration range of 0.05 to 5 ㎍/㎖ , inhibited KA (500 μM)-induced neuronal cell death, which was measured by trypan blue exclusion test and 3-[4,5-dimethylthiazol-2-yl]-2,5- diphenyl-tetrazolium bromide (MTT) assay. MF (0.5 μg/㎖) inhibited glutamate release into medium induced by KA (500 μM, which was measured by HPLC. Pretreatment of MF (0.5 μg/㎖) inhibited KA (500 μM)-induced elevation of cytosolic calcium concentration ([Ca 2+]c), which was measured by a fluorescent dye, Fura 2-AM, and generation of reactive oxygen species (ROS). These results suggest that MF prevents KA-induced neuronal cell damage in vitro.

Phytochemical and pharmacological properties of Myristica fragrans Houtt.: an updated review

HAMANH TUAN,Ngoc Khanh Vu,Thu Huong Tran,Jeong Ah Kim,Mi Hee Woo,Byung Sun Min 대한약학회 2020 Archives of Pharmacal Research Vol.43 No.11

Myristica fragrans Houtt. (Myristicaceae), anaromatic evergreen tree, is well known as a commercialsource of mace (aril) and nutmeg (seed), which have longbeen widely used as spices in the culinary field. In addition,various parts of M. fragrans have been used in folk medicinefor treating several diseases. Since its extensive uses inthe culinary sector and folk medicine, M. fragrans has longattracted a great deal of attention from pharmacologists andchemists. Numerous studies have indicated that M. fragranscontains diverse phytochemicals such as lignans, neolignans,diphenylalkanes, phenylpropanoids, and terpenoids, whichexhibit many of pharmacological activities. Among them,macelignan (1), meso-dihydroguaiaretic acid (2), myristicin(111), and malabaricone C (Mal C, 104) are the most activecompounds. The aim of this review is to comprehensivelysummarize the phytochemical and pharmacological propertiesof M. fragrans that have reported to date.

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

Thi Van Thu Le,Phi Hung Nguyen,최홍석,양준이,강금욱,안상건,오원근 한국생약학회 2017 Natural Product Sciences Vol.23 No.1

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.

Myristicae Semen Extract Protects Excitotoxicity in Cultured Neuronal Cells

Kim, Ji-Ye,Ban, Ju-Yeon,Bang, Kyong-Hwan,Seong, Nak-Sul,Song, Kyung-Sik,Bae, Ki-Whan,Seong, Yeon-Hee The Korean Society of Medicinal Crop Science 2004 韓國藥用作物學會誌 Vol.12 No.5

Myristica fragrans seed from Myristica fragrans Houtt (Myristicaceae) has various pharmacological activities peripherally and centrally. The present study aims to investigate the effect of the methanol extract of Myristica fragrans seed (MF) on kainic acid (KA)-induced neurotoxicity in primary cultured rat cerebellar granule neuron. MF, over a concentration range of 0.05 to $5\;{\mu}g/ml$ inhibited KA $(500\;{\mu}M)-induced$ neuronal cell death, which was measured by trypan blue exclusion test and 3-[4,5-dimethylthiazol-2-yl]-2,5-diphenyl-tetrazolium bromide (MTT) assay. MF $(0.5\;{mu}g/ml)$ inhibited glutamate release into medium induced by KA $(500\;{\mu}M)$, which was measured by HPLC. Pretreatment of MF $(0.5\;{mu}g/ml)$ inhibited KA $(500\;{\mu}M)-induced$ elevation of cytosolic calcium concentration $([Ca^{2+}]_c)$, which was measured by a fluorescent dye, Fura 2-AM, and generation of reactive oxygen species (ROS). These results suggest that MF prevents KA-induced neuronal cell damage in vitro.