• 생명과학회지
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• 제25권11호
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• pp.1298-1303
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• 2015

후박나무(녹나무과)는 한국과 일본 등지에 서식하는 상록 교목으로 한국, 중국, 일본에서 부종, 복통, 복부 팽만 등의 질병 치료를 위해 오랫동안 사용되어오고 있다. 본 연구에서는 후박나무 껍질을 메탄올에 추출하고 메탄올 추출물을 헥산, 클로로포름, 부탄올에 순차적으로 분획하였다. 클로로포름 분획물로부터 2종의 화합물을 분리하였으며 분리된 화합물1과 2의 구조는 ¹H-, ¹³C-NMR과 참고 문헌 데이터에 의해 dibenzylbutane lignin 화합물인 macelignan (1)과 meso-dihydroguaiaretic acid (2)로 동정되었다. 분리된 화합물들의 tyrosinase 저해 활성을 측정한 결과, 화합물 2는 tyrosinase 저해 활성 중 monophenolase (IC₅₀ = 10.2 μM)에 대해 높은 저해활성을 나타내는 경쟁적 저해제였으며 효소에 결합하는 화합물 2의 저해 상수(K_i 값)는 4.8 μM였다. 따라서 meso-dihydroguaiaretic acid (2)는 멜라닌 생합성과 관련된 피부 질환 치료를 위한 잠재적 후보가 될 수 있을 것으로 판단된다.

• 대한의생명과학회지
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• 제16권2호
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• pp.91-95
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• 2010

Meso-dihydroguaiaretic acid (MDGA) is a medicinal herbal product isolated from the bark of Machilus thunbergii Sieb. et Zucc. (Lauraceae). It exhibits a neuroprotective effect and also exerts cytotoxicity to certain cancer cells. In the present study, we investigated whether or not MDGA inhibits inflammatory reaction through the inhibition of nitric oxide (NO) generation. The results showed that MDGA (5~$25 {\mu}M$) inhibited 100 ng/ml lipopolysaccharide (LPS)- induced NO generation in macrophage Raw 264.7 cells in a concentration-dependent manner. We also measured the cytotoxic effects of MDGA on Raw 264.7 cells and found no evidence of cytotoxicity. The inhibition of NO generation by MDGA was consistent with the inhibitory effect on the expression of inducible nitric oxide synthase (iNOS). In addition, MDGA inhibited the LPS-induced gene expression of $interleukin-1{\beta}$ $(IL-1{\beta})$ as well as tumor necrosis $factor-{\alpha}$ $(TNF-{\alpha})$. The present results may provide that MDGA has anti-inflammatory properties through inhibition of the toll-like receptors (TLRs) pathway, and suggest that MDGA can be used as an anti-inflammatory agent.

• 대한약학회:학술대회논문집
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• 대한약학회 2003년도 Proceedings of the Convention of the Pharmaceutical Society of Korea Vol.2-2
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• pp.195.2-195.2
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• 2003

The CH$_2$Cl$_2$ fraction of the bark of Machilus thunbergii Sieb. et Zucc. (Lauraceae) significantly protected primary cultures of rat cortical cells exposed to the excitotoxic amino acid, L-glutamate. Several lignans including (-)-isoguaiacin, meso- dihydroguaiaretic acid, machilin A, (+)-galbelgin, licarin A, (-)-sesamin, and (+)-guaiacin were isolated from the CH$_2$Cl$_2$ fraction using by bioactivity-guided isolation techniques. Among these lignans, (-)-isoguaiacin, meso-dihydroguaiaretic acid, licarin A and (+)-guaiacin had significant neuroprotective activities against glutamate-induced toxicity in primary cultures of rat cortical cells at concentration ranging from 0.1 ${\mu}$M to 10.0 ${\mu}$M. (omitted)

• 생약학회지
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• 제21권4호
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• pp.270-273
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• 1990

Antioxidant activity of diarylbutane type lignans was evaluated in TBA-reactant assay to elucidate the structure-activity relationship. The antioxidant potency of lignans increased with increasing the number of hydroxyl groups, with the exception of macelignan(I), which showed a more potent activity than demethyl meso-dihydroguaiaretic acid(III).

• Bulletin of the Korean Chemical Society
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• 제31권6호
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• pp.1751-1752
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• 2010

• Applied Biological Chemistry
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• 제47권3호
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• pp.366-369
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• 2004

Myristica fragrans Houtt were extracted in 80% aq. MeOH and solvent fractionated sing $CHCl_3$, EtOAc, n-BuOH and water, successively. The n-BuOH fraction gave three phenylpropanoids through application of silica gel column chromatographies. The chemical structures of the phenylpropanoids were determined by the interpretation of several spectral data, including NMR and MS as meso-dihydroguaiaretic acid (1), nectandrin B (2) and syringin methyl ether (3). Compound 1, which was first isolated from this plant by authors, showed inhibitory activities with $60.0{\pm}2.1%\;(100\;{\mu}g/ml),\;42.6{\pm}0.9%\;(140\;{\mu}g/ml)\;and\;12.2{\pm}0.2%\;(200\;{\mu}g/ml)$ on ACAT(acyl-CoA:Cholesterol Acyltransferase), chitin synthase III and HMG-CoA reductase (3-hydroxy-3-methylglutaryl coenzyme A reductase), respectively. Compound 3 showed inhibitory activities with $27.2{\pm}0.9%\;(100\;{\mu}g/ml),\;45.5{\pm}0.8%\;(200\;{\mu}g/ml)$ on ACAT and chitin synthase III.

• Natural Product Sciences
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• 제18권4호
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• pp.227-232
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• 2012

Ten known compounds, 7-hydroxysauchinone (1), sauchinone (2), di-O-methyltetrahydrofuriguaiacin B (3), henricine (4), saucerneol K (5), meso-dihydroguaiaretic acid (6), (-)-guaiacin (7), (3R,4S)-4-(4-hydroxy-3-methoxyphenyl)-4-methoxy-3-methylbutan-2-one (8), (E)-7-(4-hydroxy-3-methoxyphenyl)-7-methylbut-8-en-9-one (9), and licarin A (10), were isolated from aerial part of Sarurus chinensis. The chemical structures of these compounds were determined on the basis of spectroscopic analyses including 2D NMR. Compounds 1 - 10 were evaluated for their cytotoxic activity against the HL-60, MCF-7, and A549 cancer cell lines in in vitro.

• Natural Product Sciences
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• 제23권1호
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• pp.21-28
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• 2017

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.