• Archives of Pharmacal Research
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• 제19권5호
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• pp.406-410
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• 1996

The flowers of Chrysanthemum boreale afforded handelin, a unique guaianolide dimer and a mixture of n-hydrocarbons and n-hydrocarbon alcohols in addition to b-sitosterol and b-sitosterol glucoside. Detailed analysis of the $^{1}H$- and $^{13}C$-NMR spectra of handelin was carried out by the application of two-dimensional $^{1}H-^{1}H$-COSY and $^{1}H$- $^{13}C$ multiple-bond, multiple-quantum spectroscopic correlation techniques. Handelin was inactive in the in vitro anti-tumor activity.

• 한국환경과학회지
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• 제26권11호
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• pp.1275-1284
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• 2017

Acyltransferase (AT) catalyzes the transfer of an acyl moiety from acyl-coenzyme A (acyl-CoA) to an acceptor. ATs play important roles in the maintenance of homeostasis in the human body and have been linked to various diseases; therefore, several ATs have been proposed as potential targets for the treatment or prevention of such diseases. The AT family includes acyl-CoA:cholesterol AT (ACAT), diacylglycerol AT, and monoacylglycerol AT for the metabolism of lipids. Furthermore, recent molecular biological studies revealed the existence of their isozymes with distinct functions in the body. ACAT plays a critical role in the formation of cholesteryl esters from cholesterol and fatty acids, and is a potential target for treating hypercholesterolemia. During an experiment designed to discover biologically active compounds from herbal medicines, we isolated two known guaianolide sesquiterpene lactones from Chrysanthemum boreale Makino (Compositae). The lactones were characterized from their spectroscopic data (NMR, IR, MASS). These compounds were subjected to ACAT inhibition assay. Here, we report the isolation and structural elucidation of the compounds 8-o-acetyl-2-methoxy-10-hydroxy-3,11(13)-guaiadiene-12,6-olide and 8-acetyl-3,10-hydroxy-4(15),11(13)-guaiadiene-12,6-olide. In the ACAT inhibition assay, compound 1 showed strong inhibitory activity, with an $IC_{50}$ value $45{\mu}g/mL$, whereas compound 2 did not exhibit significant inhibitory activity with an over $100{\mu}g/mL$.

• 대한약학회:학술대회논문집
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• 대한약학회 2002년도 Proceedings of the Convention of the Pharmaceutical Society of Korea Vol.1
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• pp.201.1-201.1
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• 2002

• 생약학회지
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• 제31권3호
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• pp.306-309
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• 2000

Two sesquiterpene lactones were isolated from methanol extracts of the whole plants of Youngia japonica (L.) DC. by the silica gel column chromatography and recrystallization. On the basis of spectrometric studies including $^1H-NMR,\;^{13}C-NMR,\;DEPT,\;^1H-^1H\;COSY,\;^{13}C-^1H\;COSY$, IR and MS, compounds 1 and 2 were identified as derivatives of 10(14)-guaien-12, 6-olide, isoamberboin and isolipidiol, respectively. This is the first report on the isolation of isoamberboin and isolipidiol from Youngia japonica (L.) DC.

• 약학회지
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• 제45권2호
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• pp.147-152
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• 2001

The phytochemical study of the aerial parts of Artemisia sylvatica (Asteraceae) led to the isolation of nine sesquiterpene lactones, l$\alpha$-hydroperoxy-rupicolin A acetate (1), rupicolin B acetate (2), rupicolin A acetate (3), l$\alpha$-hydroxy-4$\alpha$-hydroperoxy-bishopsolicepolide (4), 1$\alpha$-hydroperoxy-4$\beta$-hydroxy-8$\alpha$-acetoxy-guaia-2,9,11 (13)-triene-6$\alpha$,12-oxide (5), 1$\alpha$-hydroperoxy-4$\alpha$-hydroxybishopsolicepolide (6), l$\alpha$,4$\beta$-dihydroxy-8$\alpha$-acetoxy-guaia-2,9,11(13)-triene-6$\alpha$,12-olive (7), rupicolin A (8) and l$\alpha$,4$\alpha$-dihydroxy-bishopsolicepolide (9). Their structures were established by chemical and spectroscopic methods.

• Archives of Pharmacal Research
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• 제21권5호
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• pp.591-594
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• 1998

The structural analogues of cumambrin B(1, 2, 3, 4) were isolated from the flower of Chrysnathemum boreale Makino. The structures of compounds were determined by two-dimensional $^{1}H-^{1}H$ COSY and $^{13}C-^{1}H$ COSY spectra with the aid of homonuclear and heteronuclear double resonance experiment. The stereochemistry of compounds has been verified from single crystal X-ray diffraction of cumambrin A(2). the antimicrobial activities of these guaianolides have been studied.

• 약학회지
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• 제51권2호
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• pp.145-149
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• 2007

Saussurea Radix, the dried roots of Saussurea lappa Clark (Compositae), has been used in oriental traditional medicine for aromatic stomachic. Present study was carried out for the anticancer effect of Saussurea Radix. Bioassay-directed fractionation of Saussurea Radix led to the isolation of two sesquiterpenes, dehydrocostuslactone (1) and costunolide (2). The structures of 1 and 2 were elucidated by spectral methods (MS, IR, $^1$H and $^{13}$C NMR). These compounds showed a potent cell proliferation activity against human breast cancer cell MCF-7 and MDA-MB-453.

• 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.67.1-67.1
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• 2003

Three new guaianolide type of sesquiterpene lactones, 8${\alpha}$-angeloyloxy-1${\alpha}$-hydroxy-3${\alpha}$,4${\alpha}$-epoxy-5${\alpha}$, 7${\alpha}$H-10(14), 11(13)-guaiadien-12,6${\alpha}$-olide (1), 8${\alpha}$-methylbutyryloxy-1${\alpha}$-hydroxy-3${\alpha}$, 4${\alpha}$-epoxy-5${\alpha}$, 7${\alpha}$H-10(14),11(13)-guaiadien-12,6${\alpha}$-olide (2), and 8${\alpha}$-isovaleryloxy-1${\alpha}$-hydroxy-3${\alpha}$, 4${\alpha}$-epoxy-5${\alpha}$, 7${\alpha}$H-10(14),11 (13)- guaiadien-12,6${\alpha}$-olide (3), together with six known sesquiterpenes, artemisolide (4), 3-methoxytanapartholide (5), deacetyllaurenobiolide (6), moxartenolide (7), arteminolide B (8), and arteminolide D (9) were isolated by bioassay-guided fractionation using the NF-kB mediated reporter gene assay system. (omitted)

• BMB Reports
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• 제54권2호
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• pp.106-111
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• 2021

Hemistepsin A (HsA) is a guaianolide sesquiterpene lactone that inhibits hepatitis and liver fibrosis. We evaluated the effects of HsA on liver X receptor (LXR)-mediated hepatic lipogenesis in vitro and in vivo. Up to 10 μM, HsA did not affect the viability of HepG2 and Huh7 cells. Pretreatment with 5-10 μM HsA significantly decreased the luciferase activity of the LXR response element, which was transactivated by T0901317, GW 3965, and LXRα/retinoid X receptor α overexpression. In addition, it significantly inhibited the mRNA expression of LXRα in HepG2 and Huh7 cells. It also suppressed the expression of sterol regulatory element-binding protein-1c and lipogenic genes and reduced the triglyceride accumulation triggered by T0901317. Intraperitoneal injection of HsA (5 and 10 mg/kg) in mice significantly alleviated the T0901317-mediated increases in hepatocyte diameter and the percentage of regions in hepatic parenchyma occupied by lipid droplets. Furthermore, HsA significantly attenuated hepatic triglyceride accumulation by restoring the impaired expression of LXRα-dependent lipogenic genes caused by T0901317. Therefore, based on its inhibition of the LXRα-dependent signaling pathway, HsA has prophylactic potential for steatosis.

• Applied Biological Chemistry
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• 제47권2호
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• pp.251-257
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• 2004

식용식물자원으로부터 활성소재를 찾기 위하여 흰씀바귀 뿌리를 80% MeOH로 추출하고, 얻어진 추출물을 EtOAc, n-BuOH및 $H_2O$로 용매 분획하였다. EtOAc와 n-BuOH 분획에 대하여 column chromatography를 반복하여 4종의 화합물을 분리하였다. 각각에 대하여 2D-NMR을 포함한 스펙트럼 데이터의 해석과 문헌 자료를 조사하여 zaluzanin C (1), $9{\alpha}-hydroxyguaian-4(l5),10(14),11(13)-triene-6,12-olide$ (2), $3{\beta}-O-{\beta}-D-glucopyranosyl-8{\beta}-hydroxyguaian-4(15),\;10(14 )-diene-6,12-olide$ (3), $3-O-{\beta}- D-glucopyranosyl-8{\beta}hydroxyguaian-10(14)-ene-6,12-olide$ (4)로 구조를 결정하였다. 이들 화합물에 대하여 ACAT(Acyl-CoA: cholesterol acyltransferase), DGAT (diacylglycerol acyltransferase) 및 FPTase(farnesyl-protein transferase)의 활성에 미치는 억제효과를 측정하였다. Compound 1과 Compound 2는 DGAT에 대한 활성억제효과에 있어서 $IC_{50}$ 값이 각각 0.13 mM, 0.10 mM로 나타났고, FPTase에 대하여는 각각 0.15 mM, 0.18 mM로 나타났으며, ACAT에 대하여는 약한 억제 활성을 나타냈다. 따라서 흰씀바귀는 항암 및 항고혈압의 소재 개발에 있어서 유용한 자원으로 활용될 수 있을 것이다.