• Advances in Traditional Medicine
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• v.10 no.4
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• pp.319-321
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• 2010

Plant saponins are widely distributed amongst plants and have a wide range of biological properties. Icosahydropicenic acid, $C_{51}H_{80}O_{19}$ ((4S,6bS)-8a-((4,5-dihydroxy-6-methyl-3-((3R)-3,4,5-trihydroxy-6-methyl-tetrahydro-2H-pyran-2-yloxy)-tetrahydro-2H-pyran-2-yloxy)carbonyl)-2-hydroxy-4, 6a, 6b, 11, 14b-pentamethyl-11-(2-methylprop-1-enyl)-3-(3,4,5-trihydroxy-6-(hydroxymethyl) - tetrahydro-2Hpyran-2-yloxy)-1, 2, 3, 4, 4a, 5, 6, 6a, 6b, 7, 8, 8a, 9, 10, 11, 12, 12a, 14, 14a, 14b-icosahydropicene-4-carboxylic acid), a new saponin was first time isolated from the roots of Clerodendrum Serratum (L) Moon (Verbenaceae). The structure elucidation of the compound was carried out by $^1H$ NMR and DART-MS studies.

• Natural Product Sciences
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• v.18 no.2
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• pp.97-101
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• 2012

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)-${\Delta}^{8^'}$-7-hydroxy-3,4,3',5'-tetramethoxy-8-O-4'-neolignan (5), and (+)-erythro-(7S,8R)-${\Delta}^{8^'}$-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.

• YAKHAK HOEJI
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• v.44 no.2
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• pp.128-134
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• 2000

The synthesis of new 6-exomethylene penams with triazole ring was described. The 6,6-dibromopenam 5 was treated with $CH_3$MgBr and carbaldehyde 4 to afford the 6-bromo-6-(1-hydroxy-1-methyl)penicillanate 6, which was reacted with acetic anhydride to give acetoxy compound 7. The deacetobromination of 7 with zinc and acetic acid gave 6-exomethylenpenams, Z-isomer 8 and E-isomer 9, which were oxidized to sulfones 10 and 11 by m-CPBA. The p-methoxybenzyl compounds 6~11 were deprotected by AlCl$_3$ and neutralized to give the sodium salts 12~17.

• Korean Journal of Pharmacognosy
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• v.30 no.3
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• pp.340-344
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• 1999

To evaluate antimicrobial activity of Moutan cortex the compounds isolated from $CHCl_3$ and EtOAc fractions of Moutan cortex were subjected to eight pathogenic strains. Benzoic acid, witch was identified from the $CHCl_3$ fraction, had MICs with $625{\sim}1,250\;{\mu}g/ml$ against all of the strains tested. Methyl gallate, p-hydroxy benzoic acid, gallic acid and $1,2,3,4,6-penta-O-gallyol-{\beta}-D-glucose$, which were identified from the EtOAc fraction, showed the antimicrobial activity, and the methyl gallate had the widest antimicrobial activity with MICs of $625{\sim}5,000\;{\mu}g/ml$ against all strains tested. p-Hydroxy benzoic acid showed MICs of $1,250{\sim}2,500\;{\mu}g/ml$ against all of the strains tested except C.albicans. Gallic acid had the best antimicrobial activities with MICs against the Shigella dysenteriae and Streptococcus mutans-strains of 78.1 and $312.5\;{\mu}g/ml$, respectively, but not against the C. albicans. And $1,2,3,4,6-penta-O-gallyol-{\beta}-D-glucose$ had the best antimicrobial activitie with MICs against the B. cereus, Staph. epidermidis and C. albicans strains of 39.1, 39.1 and $156.3\;{\mu}g/ml$, respectively, but not against the E. coli and Shig. Dysenteriae.

• Applied Biological Chemistry
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• v.40 no.6
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• pp.501-507
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• 1997

Chloroplasts isolated from Stevia rebaudiana Bertoni leaves contained an enzyme activity which catalyzed hydroxylation of ent-kaurenoic acid (ent-kaur-16-en-19-oic acid; ent-KA) to steviol (ent-13-hydroxy kaur-16-en-19-oic acid), the diterpenoid carboxylic alcohol which is the aglycone of sweet stevioside-related glycosides. $[^(14)C]-methylated$ ent-KA was used to localize ent-KA hydroxylase. $[^(14)C]-methyl-KA$ was most actively was transformed into methyl-steviol in chloroplast. The enzymatic activity was found in stroma fraction but not in thylakoid membrane in Stevia rebaudiana Bertoni. However, ent-KA 13-hydroxylase activity was not detected in stroma fraction of either Spinacia oleracea and Solidago altissima. The reaction products using $[^(14)C]-methyl-KA$ were purified and identified on TLC autoradiogram. The hydroxylation of ent-KA from stromal protein to form steviol required NADPH and oxygen. FAD and riboflavin stimulated the enzyme activity 1.5-and 1.7-fold, respectively. It also turned out that the activity of this enzyme using methyl-KA as a substrate was 16.7% that of ent-KA. The purified ent-KA 13-hydroxylase did not act on t-cinnamic acid, 4-hydroxyphenyl acetic acid, choline and resorcinol, known as monooxygenase and hydroxylase substrates.

• Proceedings of the Korean Society of Postharvest Science and Technology of Agricultural Products Conference
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• 1993.12a
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• pp.10-11
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• 1993

기저상태의 산소분자는 비교적 안정하지만 생체ㅇ내외에서 물리적, 화학적으로 활성화 되어 $O_{2}$, $^{1}O_{2}$, OH, $H_{2}O_{2}$ 등의 활성산소종을 생성하며, 생체의 지질, 단백질, 핵산 당등의 분자에 산화적 상해를 초래하여 노화, 암, 순환기, 호흡기 게통의 질환과 식품의 품질열화에 관여하는 것으로 알려져 있다. 따라서 본인은 식품의 맛, 향기, 색 등을 부여하는 고유의 기능 외에도 방부제, 한방약으로 널리 이용되고 오고 있는 51종의 향신료를 대상으로 활성산소포촉활성을 조사하고 나아가 활성물질을 분리, 정제 및 동정함으로 향신료의 새로운 기능을 밝히고 신약 개발의 기초적 자료를 제시하고저 한다. Fenton 반응을 이용하여 2-deozyribose 산화법과 sodium benzoic acid 수산화법으로 51종의 향신료의 OH 포촉활성을 검색한 결과, Cruciferae과의 nustard 류, Labiatae과의 thyme, saga, savory, oregano, Myrtaceae과의 clove, allspice 가 1ug/ml 농도에서 50%이상의 포촉활성을 나타내었으며 그중 mustard 류는 같은 농도에서 거의 90%이상의 활성을 나타내었다. 활성물질의 분리 및 정제는 Amberlite XAD-2 갈럼과 preparative-HPLC를 이용 하였으며, EI, FAB-MS, IR, $^{1}H$, $^{13}C-NMR$, Cosy-NMR로 그 화학적 구조를 동정하였다. Brown mustard에서 동정된 4-hydroxy-3,5-dimethoxy cinnamic acid Methyl ester는 0.42$\mu$ mol 농도에서 90% 이상의 OH 포촉활성을 나타내어 이를 diazomethane 반응으로 조제하였으며 white mistard에서는 4-hydroxy-3,5-dimethoxy cinnamoyl choline을 동정하였다.

• Archives of Pharmacal Research
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• v.26 no.5
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• pp.367-374
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• 2003

In the course of screening neuraminidase inhibitors from herbal medicines, Reynoutria elliptica exhibited high inhibitory activity. Four active compounds were isolated from the ethyl acetate soluble fraction by consecutive purification using sillica gel, Sephadex LH-20 chromatography, and recrystallization. The chemical structures of these compounds were identified as 1,3,8-trihydroxy-6-methylanthraquinone (emodin) 1,8-dihydroxy-3-methoxy-6-methylanthraquinone (emodin 3-methyl ether; physcion), 1,3,8-trihydroxy-6-hydoxymethylanthraquinone ($\omega$-hydroxyemodin), and 3,5,4 -trihydroxystilbene (trans-resvertrol) by spectral data including MS, $^1 H-, and ^{13}C-NMR. The IC_{50}$ values of emodin, emodin 3-methyl ether, $\omega$-hydroxyemodin, and trans-resvertrol were 2.81, 74.07, 10.49, and 8.77 $\mu$M, respectively. They did not inhibit other glycosidase such as glucosidase, mannosidase, and galactosidase, indicating that they were relatively specific inhibitors of neuraminidase.

• Archives of Pharmacal Research
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• v.13 no.4
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• pp.319-324
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• 1990

Synthesis of $\alpha$-piperidino and $\alpha$-morphelino styryl quinoxalinone 2f, 2g respectively by facile one step method is reported. The Michael adducts (3a-d) obtained by the interaction of 2-styryl-2 (1H) quinoxalinone (2) and ethylacetoacetate have been treated with resorcino and hydroxylamine separately. With resorcinol the chromones (4) are obtained whereas with ydroxylamine isoxazoles (6) are the products. Michael addition of acetylacetone to 2 leads to 3-[1'-aryl-2'-(2'-hydroxy-3'-quinoxalinyl)ethyl]-2, 4-pentanediones (5) which undergo cyclisation with hydroxylamine to give isoxazoles (7). Addition of thiopenol and thioglycolic acid to 2 gives 3-$\alpha$[$\beta$-(phenyl)-$\beta$-(plenylthio)]ethyl-2(1H)-quinoxalinone (8) and 3-$\alpha$-[$\beta$-phenyl)-$\beta$-(hydroxycarbonylmethylithio)]-ethyl-2(1H)-qui noxalinone (9) respectively. 2-Bromomethyl-2(1H)-quinoxalinone (1b) reacts with thioglycolic acid to gives S-[2 (1H)-oxoquionoxaline-3-yl-methyl] mercaptoacetic acid (10) which on cyclisation with acetic anhydride/pyridine affords 1, 2, 5, 6-tetrahydro [1, 4]thiazino[4, 3-a] quinoxaline-1, 6-dione (11).

• Biomedical Science Letters
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• v.26 no.2
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• pp.101-108
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• 2020

There has been a lot of interest in medicinal effects for hyperlipidemia from the natural product since the therapy of atherosclerosis has emerged as social concern. Rats were acclimated to the feeding environment for one week and induced to obesity with high fat diet during 4 weeks until their body weight were more than 30% of normal range. To evaluate the effect of hyperlipidemia of mulberry leaf of Morus alba and yacon tuber of Smallanthus sonchifolia extracts (MLYT), 1%, 3%, 5% of MLYT were treated to Sprague-Dawley rats. Aspartate transaminase (AST) was significantly increased 26.2% in high fat diet group (G2) compared to normal diet group (G1) (P<0.05). But AST were significantly decreased in high fat diet with 0.5% hydroxycitric acid diet group (G3) and all the MLYT treated groups compared to G2. Total cholesterol, low-density lipoprotein (LDL), triglycerides and phospholipids were observed significant improvements in the MLYT-treated groups (P<0.05). These improvements in liver and feces were further supported by the lipid content. MLYT remarkably suppressed the level of lipid peroxidation caused by high-fat diet in rats. The level of 3-hydroxy-3-methyl-glutaryl-coenzyme A (HMG-CoA) reductase activity. As a result, the proper combination of mulberry leaves and yacon tuber extract will have a synergistic effect on hyperlipidemia. These results indicate that MLYT could be a candidate for the improvement of hyperlipidemia.

• Natural Product Sciences
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• v.22 no.2
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• pp.111-116
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• 2016

Phytochemical investigation of the stems of Pueraria lobata (Wild) Ohwi (Leguminosae), led to the isolation of eighteen known compounds: ${\beta}$-amyrone (1), (+)-pinoresinol (2), (+)-syringaresinol (3) $(+)-syringaresinol-O-{\beta}-{\small{D}}-glucoside$ (4), (+)-lariciresinol (5), (-)-tuberosin (6), naringenin (7), liquiritigenin (8), isoliquiritigenin (9) genistein (10), daidzein (11) daidzin (12) daidzein 4',7-diglucoside (13) 2,4,4'-trihydroxy deoxybenzoin (14), S-(+)-1-hydroxy-3-(4-hydroxyphenyl)-1-(4-hydroxy-2-methoxy-phenyl)propan-2-one (15), methyl $2-O-{\beta}-{\small{D}}-glucopyranosylbenzoate$ (16), pyromeconic acid $3-O-{\beta}-{\small{D}}-glucopyranoside$ 6'- (O-4''-hydroxy-3-methoxybenzoate) (17), and allantion (18). The chemical structures of these compounds were elucidated from spectroscopic data and by comparison of those data with previously published results. The effects of isolated compounds on mushroom tyrosinase enzymatic activity were screened. The results indicated that, chloroform extract of P. lobata stems turned out to be having tyrosinase inhibitory effect, and only compounds 5, 8, 9, and 11 showed enzyme inhibitory activity, with $IC_{50}$ values of $21.49{\pm}4.44$, $25.24{\pm}6.79$, $4.85{\pm}2.29$, and $17.50{\pm}1.29{\mu}M$, respectively, in comparison with these of positive control, kojic acid ($IC_{50}\;12.28{\pm}2.72{\mu}M$). The results suggest that P. lobata stems extract as well as its chemical components may represent as potential candidates for tyrosinase inhibitors.