• Natural Product Sciences
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• 제14권1호
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• pp.56-61
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• 2008

Bioactivity guided phytochemical study of the petroleum ether and butanol extracts of Clematis hirsuta resulted in the isolation of 12 compounds. Rat paw edema as a model of acute inflammation was used to evaluate the anti-inflammatory activity of the extracts and the chromatographic fractions. Five known sterols and triterpenes namely: ${\beta}-amyrin$ (1), lupeol (2), ${\beta}-sitosterol$ (3), oleanolic acid (4) and stigmasterol glycoside (5) were isolated from the petroleum ether extract. The n-butanol extract afforded two compounds reported for the first time from natural source: (S)-(+)-dihydro-5-(hydroxymethyl)-2(3H)-furanone (7) and (s)-(-)-5-hydroxymethyl-2(5H)-furanone (8). In addition, anemonin (6), dihydro-4-hydroxy-5-(hydroxymethyl)-2(3H)-furanone (2-deoxy-D-ribono-1,4-lactone) (9), biophenol (cimidahurin) (10), glucose (11) and sucrose (12) were also identified. The structures were determined from spectroscopic data including 1D- and 2D-NMR experiments.

• Archives of Pharmacal Research
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• 제22권6호
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• pp.575-578
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• 1999

Derivatives of elema-1,3-diene were synthesized in several steps as polar analogs of $\beta$-elemene, antitumor agent under clinical phase. The lactone ring of compound 1 was opened by LiAlH4 to give diol 2 which was selectively protected by TBDPSCI. After acetylation of the secondary alcohol, the acetylated product was ozonolyzed and reduced to give elemene derivative 4 which was converted to diolefin 8 via selenides subsequent deprotection by tetrabutylammonium fluoride gave two compounds 9, 10.

• Journal of Microbiology and Biotechnology
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• 제1권3호
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• pp.188-196
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• 1991

The ${\beta}-glucosidase$ was purified to homogeneity from the culture filtrate of P. verruculosum by column chromatography. The enzyme was a glycoprotein with a relative size of approximately 220 kDa with an isoelectric point of 4.8, which was composed of dimeric protein of 105 kDa. The enzyme was stable up to $60^{\circ}C$ and the presence of glycerol significantly increased its thermostability. The enzyme was found to hydrolyze both ${\beta}-aryl$ and ${\beta}-alkyl-glucosides$ in addition to ${\beta}-glucosyl$ glucose and catalyzed glucosyl transfer to cellobiose. The enzyme attacked laminarin in an exotype-like fashion. The apparent Km's of the enzyme toward cellobiose, laminaribiose, laminarin were 0.53 mM, 0.35 mM and 1.11 mM, respectively. Glucose and glucono-${\delta}-lactone$ were competitive inhibitors for the enzyme. Copper ($Cu^{2+}$), mercury ($Hg^{2+}$) and p-chloromercuribenzoate were strong inhibitors of the enzyme. The immunoblotting result revealed that one form of ${\beta}-glucosidase$ was biosynthesized, irrespective of carbon sources used. Polyacrylamide gel electrophoresis analysis of the in vitro translated product of total RNA from avicel grown mycelium established that the P. verruculosum ${\beta}-glucosidase$ precursor was approximately 95 kDa in size. The amino acid composition and N-terminal amino acid sequence are given.

• Natural Product Sciences
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• 제23권4호
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• pp.291-298
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• 2017

Six dammarane-type triterpenoids, dammar-24-en-$3{\beta}$-ol (1), $3{\beta}$-epicabraleahydroxy lactone (2), (E)-25-hydroperoxydammar-23-en-$3{\beta}$,20-diol (3), dammar-24-en-$3{\beta}$,20-diol (4), $3{\beta}$-acetyl-20S,24S-epoxy-25-hydroxydammarane (5), and $3{\beta}$-epiocotillol (6) were isolated from the methanolic extract of the bark of Aglaia elliptica. The chemical structure were identified on the basis of spectroscopic evidence and by comparison with those spectra previously reported. Compounds 1 - 6 were isolated first time from this plant. Compounds 1 - 6, along with a known synthetic analog, cabraleone (7) were evaluated their cytotoxic activity against P-388 murine leukimia cells in vitro. Among those compounds $3{\beta}$-acetyl-20S,24S-epoxy-25-hydroxydammarane (5) showed strongest cytotoxic activity with $IC_{50}$ value of $8.02{\pm}0.06{\mu}M$.

• Journal of Microbiology and Biotechnology
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• 제21권5호
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• pp.503-508
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• 2011

A ${\beta}$-glucosidase from Phoma sp. KCTC11825BP isolated from rotten mandarin peel was purified 8.5-fold with a specific activity of 84.5 U/mg protein. The purified enzyme had a molecular mass of 440 kDa with a subunit of 110 kDa. The partial amino acid sequence of the purified ${\beta}$-glucosidase evidenced high homology with the fungal ${\beta}$- glucosidases belonging to glycosyl hydrolase family 3. Its optimal activity was detected at pH 4.5 and $60^{\circ}C$, and the enzyme had a half-life of 53 h at $60^{\circ}C$. The $K_m$ values for p-nitrophenyl-${\beta}$-D-glucopyranoside and cellobiose were 0.3 mM and 3.2 mM, respectively. The enzyme was competitively inhibited by both glucose ($K_i$=1.7 mM) and glucono-${\delta}$-lactone ($K_i$=0.1 mM) when pNPG was used as the substrate. Its activity was inhibited by 41% by 10 mM $Cu^{2+}$ and stimulated by 20% by 10 mM $Mg^{2+}$.

• 생명과학회지
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• 제15권1호
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• pp.147-151
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• 2005

양귀비의 성분중 하나인 $(-)-\alpha-narcotine$은 ethyl chloroformate와 가온반응시 diastereomeric chloro-carbamate 혼한물과 Z/E-enol lactone혼합물을 생성하였는데 이 중에서 Z/E-isomer의 생성비를 HPLC로 측정한 결과 Z:E=1:1.12로 나타나 열역학적으로 불안정한 E-isomer가 다소 많이 생성되었다. 그러나 이 isomer 혼합물을 chromatography로 각각 분리 한 결과, 그 생성 비는 Z:E=7:1로 나타나 분리도중에 column 내 에서 E-isomer가 보다 안정한 Z-isomer로 대부분 변하였음을 알 수 있었다. Z/E-isomer의 생성비가 유사한 구조의 화합물에서 어떻게 변하는지를 관찰하기 위하여 $\beta-narcotine$, deuterated $\beta-narcotine$ 및 $\beta-hydrastine$을 대상으로 동일한 조건하에 반응시킨 결과, 이들의 isomer 생성비율이 구조에 따라 크게 차이가 있음을 알 수 있었으며 그 이유를 설명하였다. 한편, 일반적인 보고와는 달리, narcotine에서 생성된 안정한 Z-isomer는 광화학반응에 의해 불안정한 E-isomer로 쉽게 변한다는 사실도 확인하였다.

• Archives of Pharmacal Research
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• 제29권11호
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• pp.937-941
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• 2006

Ixeris dentata forma albiflora was extracted with 80% aqueous MeOH, and the concentrated extract was partitioned with EtOAc, n-BuOH and $H_{2}O$. Eight sesquiterpenes were isolated through repeated silica gel and octadecyl silica gel ($C_{18},\;ODS$) column chromatography of the EtOAc and n-BuOH fractions. Physicochemical analysis using NMR, MS and IR revealed the chemical structures of the sesquiterpenes, which were zaluzanin (1), 9a-hydroxyguaian-4(15), 10(14), 11 (13)-triene-6, 12-olide(2), $3{\beta}-O-{\beta}-D-glucopyranosyl-8{\beta}-hydroxyguaian$-4(15), 10(14)-diene-6, 12-olide (3), $3-O-{\beta}-D-glucopyranosyl-8{\beta}-hydroxyguauan$-10(14)-ene-6, 12-olide (4), ixerin M (5), glucozaluzanin C (6), crepiside I (7), and ixerin D (8). This is the first time that these sesquiterpene lactones have been isolated from this plant. Compounds 1, 2 and 7 revealed relatively high cytotoxicities on human colon carcinoma cell and lung adeno-carcinoma cell, while compounds 5 and 7 showed acyl-CoA: cholesterol acyltransferase (ACAT) inhibitory activity.

• 한국응용약물학회:학술대회논문집
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• 한국응용약물학회 2004년도 Annual Meeting of KSAP : New Drug Development from Natural Products
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• pp.21-35
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• 2004

Heme oxygenase (HO)-l catabolizes heme into three products: carbon monoxide, bilirubin, and free iron. HO-l serves as a protective gene by virtue of the anti-inflammatory, anti-apoptotic and anti-proliferative actions of one or more of these three products. HO-l can be regarded as a potential therapeutic target in a variety of oxidant-mediated and inflammatory diseases. In this respect, it would be valuable to develop potent and selective inducers of HO-1 for therapeutic use. Here, we have shown that 1,2,3,4,6-penta-O-galloyl-beta-D-glucose, catalposide and dehydrocostus lactone are potent inducers of HO-1 and exert cytoprotective and anti-inflammatory activities via HO-1-ependent machanism.

• 생약학회지
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• 제27권3호
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• pp.207-211
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• 1996

Cumambrin A has been isolated from the dried flowers of Chrysanthemum boreale Makino. The complete $^1H$ and $^{13}C$ NMR assignment of cumambrin A was achieved from two-dimensional $^1H$-$^1H$ COSY and $^{13}C$-$^1H$ COSY spectra with the aid of homonuclear and heteronuclear double resonance experiments. The its structure has been verified by single crystal X-ray diffraction.

• Archives of Pharmacal Research
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• 제28권10호
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• pp.1142-1146
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• 2005

Seven sesquiterpene lactones were isolated by the chromatographic separation of the MeOH extract of the aerial parts of Saussurea calcicola (Compositae). Their structures were determined spectroscopically to be cynaropicrin (1), arguerin B (2), cebellin F (3), 8${\alpha}$-hydroxy-11${\alpha}$, 13-dihydrozaluzanin C (4), desacylcynaropicrin (5), 3${\beta}$-hydroxy-8${\alpha}$-epoxymethylacriloiloxy-4(15), 10(14), 11(13)-trien-guaian-6, 12-olide (6), and kandavanolide (7). Compounds 1 and 2 showed significant cytotoxicity against five cultured human tumor cell lines with $ED_{50}$ values ranging from $0.23{\~}1.72\;{\mu}g/mL$.