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Tyrosinase Inhibitory Activities of Meso-dihydroguaiaretic Acid from Machilus thunbergii
Hyun Sook Kwon(권현숙),Kyung Dong Lee(이경동),Su Cheol Kim(김수철),Soo Jeong Cho(조수정) 한국생명과학회 2015 생명과학회지 Vol.25 No.11
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-, <SUP>13</SUP>C-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(Ki 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. Machilus thunbergii (Lauraceae) is an evergreen tree cultivated in Korea and Japan. M. thunbergii has long been used as a traditional medicine in Korea, China, and Japan to treat various diseases, including edema, abdominal pain, and abdominal distension. In this study, dried stem bark of M. thunbergii extracted in methanol and extract was partitioned into n-hexane, CHCl₃, and BuOH. The CHCl₃-soluble extracts chromatographed on silica gel column using a CHCl₃/acetone and n-hexane/EtOAc mixture to afford Compound 1 and 2. Two dibenzylbutane lignans, macelignan (1) and meso-dihydroguaiaretic acid (2), were isolated from the CHCl₃-soluble extract of M. thunbergii stem bark. The structures of 1 and 2 were determined by <SUP>1</SUP>H- and <SUP>13</SUP>C-NMR spectroscopic data analyses and a comparison with literature data. The tyrosinase inhibitory activity of the isolated compounds was evaluated. Among these compounds, Compound 2 strongly inhibited the monophenolase (IC50=10.2 μM) activity of tyrosinase. A kinetic analysis showed that Compound 2 was a competitive inhibitor. The apparent inhibition constant (Ki) for Compound 2 binding to free enzyme was 4.8 μM. Based on these results, it can be concluded that meso-dihydroguaiaretic acid (2) is a potential candidate for the treatment of melanin biosynthesis-related skin diseases.
( Ji Won Song ),( Chang Seob Seo ),( Eun Sang Cho ),( Tae In Kim ),( Young Suk Won ),( Hyo Jung Kwon ),( Jong Keun Son ),( Hwa Young Son ) 영남대학교 약품개발연구소 2016 영남대학교 약품개발연구소 연구업적집 Vol.26 No.-
meso-Dihydroguaiaretic acid (MDGA), which is a dibenzylbutane lignin isolated from the ethyl acetate fraction of Saururus chinensis, has various biological activities, including anti-oxidative, anti-inflammatory, anti-bacterial, and neuroprotective effects. However, no report has examined the potential anti-asthmatic activity of MDGA. In this study, we evaluated the protective effects of MDGA on asthmatic responses, particularly airway inflammation and mucus hypersecretion in an ovalbumin (OVA)-induced murine model of asthma. lntragastric adminis-tration of MDGA significantly lowered the productions of interleukin (IL)-4, IL-5, IL-13, tumor necrosis-IT (TNF- α), eotaxin, monocyte chemoattractant protein-1 (MCP-1), vascular cell adhesion molecule-1 (VCAM-1), and im-munoglobulin (lg)E in bronchoalveolar lavage fluid (BALF), plasma, or lung tissues. Histological studies showed that MDGA inhibited OVA-induced inflammatory cell infiltration and mucus production in the respiratory tract. Moreover, MDGA markedly attenuated the OVA-induced activations of nuclear factor kappa B (NF-KB), extracellular-signal-regulated kinases 1/2 (ERK1/2), and p38 mitogen-activated protein kinase (p38 MAPK). To-gether, these results suggest that MDGA effectively inhibits airway inflammation and mucus hypersecretion by downregulating the levels of T helper 2 (Th2) cyrokines, chemokines, and adhesion molecules, and inhibiting the activations of NF-KB and MAPKs.
Song, M.C.,Kim, E.C.,Kim, W.J.,Kim, T.J. North-Holland ; Elsevier Science Ltd 2014 european journal of pharmacology Vol.744 No.-
Abnormal proliferation of vascular smooth muscle cells (VSMCs) plays an essential functional role in the pathogenesis of vascular disorders, such as atherosclerosis, restenosis, and neointimal hyperplasia. In this study, we examined the effects of meso-dihydroguaiaretic acid (MDGA) on platelet-derived growth factor (PDGF)-BB-induced proliferation and the molecular basis of its underlying mechanism of action in rat aortic VSMCs. Incubation of resting VSMCs with MDGA for 24h significantly diminished PDGF-BB-induced DNA synthesis in a dose-dependent manner. We also examined the effects of MDGA on PDGF-BB signal transduction. Pre-treatment of VSMCs with MDGA inhibited PDGF-BB-induced phosphorylation of extracellular signal-regulated kinases ½ (ERK½), p38, and C-Jun N-terminal kinase (JNK). MDGA also effectively inhibited phosphorylation of Akt, phospholipase C gamma 1 (PLCγ1), and PDGF receptor beta (PDGFRβ). These results indicate that MDGA may inhibit proliferation of VSMCs by suppressing autophosphorylation of PDGFRβ, and may be useful in the treatment of VSMC-associated vascular disease such as atherosclerosis, restenosis, and neointimal hyperplasia after angioplasty.
Anti-inflammatory Properties of Meso-dihydroguaiaretic Acid in Lipopolysaccharide-induced Macrophage
Yong-Jae Kim,Yeo-Jin Kang,Tack-Joong Kim(김택중) 대한의생명과학회 2010 Biomedical Science Letters Vol.16 No.2
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 μM) inhibited 100 ng/㎖ 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-1β (IL-1β) as well as tumor necrosis factor-α (TNF-α). 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.
Moon, Tae-Chul,Seo, Chang-Seob,Haa, Kyung-Mi,Kim, Jin-Cheul,Hwang, Nam-Kyung,Hong, Tae-Gyun,Kim, Jee-Hyeun,Kim, Do-Hun,Son, Jong-Keun,Chang, Hyeun-Wook 대한약학회 2008 Archives of Pharmacal Research Vol.31 No.5
Meso-dihydroguaiaretic acid (MDGA) is a medicinal herbal product isolated from the aerial parts of Saururus chinensis that inhibits the cyclooxygenase-2 (COX-2)-dependent phase of prostaglandin $D_2\;(PGD_2)$ generation in bone marrow-derived mast cells (BMMC) ($IC_{50}\;9.8\;{\mu}M$). However, this compound did not inhibit COX-2 protein expression in BMMC at concentrations up to $30\;{\mu}M$, indicating that MDGA directly inhibits COX-2 activity. In addition, this compound consistently inhibited the production of leukotriene $C_4\;(IC_{50}\;1.3\;{\mu}M)$. These results demonstrate that MDGA inhibits both COX-2 and 5-lipoxygenase. Furthermore, this compound strongly inhibited the degranulation reaction in BMMC ($IC_{50}\;11.4\;{\mu}M)$. Therefore, this compound might provide a basis for novel anti-inflammatory drug development.
Tae Chul Moon,Chang Seob Seo,Kyungmi Haa,Jin Cheul Kim,Nam Kyung Hwang,Tae Gyun Hong,Jee Hyeun Kim,Do Hun Kim1,손종근,장현욱 대한약학회 2008 Archives of Pharmacal Research Vol.31 No.5
Meso-dihydroguaiaretic acid (MDGA) is a medicinal herbal product isolated from the aerial parts of Saururus chinensis that inhibits the cyclooxygenase-2 (COX-2)-dependent phase of prostaglandin D2 (PGD2) generation in bone marrow-derived mast cells (BMMC) (IC50 9.8 μM). However, this compound did not inhibit COX-2 protein expression in BMMC at concentrations up to 30 μM, indicating that MDGA directly inhibits COX-2 activity. In addition, this compound consistently inhibited the production of leukotriene C4 (IC50 1.3 μM). These results demonstrate that MDGA inhibits both COX-2 and 5-lipoxygenase. Furthermore, this compound strongly inhibited the degranulation reaction in BMMC (IC50 11.4 μM). Therefore, this compound might provide a basis for novel anti-inflammatory drug development.
Thuong, Phuong Thien,Hung, Tran Manh,Khoi, Nguyen Minh,Nhung, Hoang Thi My,Chinh, Nguyen Thi,Quy, Nguyen Thi,Jang, Tae Su,Na, MinKyun 대한약학회 2014 Archives of Pharmacal Research Vol.37 No.3
Four lignans, meso-dihydroguaiaretic acid (DHGA), macelignan, fragransin $A_2$ and nectandrin B, were isolated from the seeds of Myristica fragrans (Vietnamese nutmeg) and investigated for their cytotoxic activity against eight cancer cell lines. Of these, DHGA exhibited potent cytotoxicity against H358 with $IC_{50}$ value of $10.1{\mu}M$. In addition, DHGA showed antitumor activity in allogeneic tumor-bearing mice model.
Phuong Thien Thuong,Tran Manh Hung,Nguyen Minh Khoi,Hoang Thi My Nhung,Nguyen Thi Chinh,Nguyen Thi Quy,장태수,나민균 대한약학회 2014 Archives of Pharmacal Research Vol.37 No.3
Four lignans, meso-dihydroguaiaretic acid(DHGA), macelignan, fragransin A2 and nectandrin B,were isolated from the seeds of Myristica fragrans (Vietnamesenutmeg) and investigated for their cytotoxicactivity against eight cancer cell lines. Of these, DHGAexhibited potent cytotoxicity against H358 with IC50 valueof 10.1 lM. In addition, DHGA showed antitumor activityin allogeneic tumor-bearing mice model.
Cho, Jun Young,Choi, Gyung Ja,Son, Seung Wan,Jang, Kyoung Soo,Lim, He Kyoung,Lee, Sun Og,Sung, Nack Do,Cho, Kwang Yun,Kim, Jin-Cheol John Wiley Sons, Ltd. 2007 PEST MANAGEMENT SCIENCE Vol.63 No.9
<P>BACKGROUND: In a search for plant extracts with potent in vivo antifungal activity against various plant diseases, we found that treatment with a methanol extract of Myristica fragrans Houttyn (nutmeg) seeds reduced the development of various plant diseases. The objectives of the present study were to isolate and determine antifungal substances from My. fragrans and to evaluate their antifungal activities.</P> <P>RESULTS: Three antifungal lignans were isolated from the methanol extract of My. fragrans seeds and identified as erythro-austrobailignan-6 (EA6), meso-dihydroguaiaretic acid (MDA) and nectandrin-B (NB). In vitro antimicrobial activity of the three lignans varied according to compound and target species. Alternaria alternata, Colletotrichum coccodes, C. gloeosporioides, Magnaporthe grisea, Agrobacterium tumefaciens, Acidovorax konjaci and Burkholderia glumae were relatively sensitive to the three lignans. In vivo, all three compounds effectively suppressed the development of rice blast and wheat leaf rust. In addition, EA6 and NB were highly active against the development of barley powdery mildew and tomato late blight, respectively. Both MDA and NB also moderately inhibited the development of rice sheath blight.</P> <P>CONCLUSION: This is the first study to demonstrate the in vitro and in vivo antifungal activities of the three lignans from My. fragrans against plant pathogenic fungi. Copyright © 2007 Society of Chemical Industry</P>