• 생명과학회지
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• 제31권4호
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• pp.430-441
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• 2021

세스퀴테르펜 락톤(Sesquiterpene lactones; STL) 화합물은 테르페노이드의 일종으로 주로 국화과에서 발견이 되고 강한 세포 독성을 나타내는 생리학적 특성을 지니고 있다. 이러한 세스퀴테르펜 락톤은 강한 세포 독성으로 인해 연구가 미미하였으나, 최근 화학적 변형을 통해 독성이 적은 형태로 합성하여 새로운 의약품 개발로서의 연구가 활발히 진행되고 있다. 세스퀴테르펜 락톤 화합물인 artemisinin 및 mipsagargin 화합물은 현재 말라리아 및 종양성장에 대한 약물로 사용되고 있다. 또한 항산화, 간보호, 항바이러스, 항균, 항종양 및 항노화 등의 생리활성 효능이 보고되어 있으며, 종양세포에서 자멸사를 유도하여 항암제로서의 연구가 진행되고 있다. 본 연구에서는 세스퀴테르펜 락톤 화합물인 artemisinin, costunolide, thapsigargin, arglabin, parthenolide, alantolactone, cynaropicrin, helenalin, 및 santonin의 생리활성 효능에 대한 연구 동향을 검토하고자 한다.

• Toxicological Research
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• 제17권
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• pp.271-280
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• 2001

We report on the applicability oj a method recently developed in our laboratory for measuring the antioxidant potential of isolated chemicals and extracts derived from natural products. Peroxyl radicals generated by thermal homolysis of 2,2'-azobis-amidinopropane (ABAP) oxidize $\alpha$-keto-${\gamma}$-methiolbutyric acid (KMBA) to ethylene, which is monitored by gas chromatography. Inhibition of ethylene formation in the presence of antioxidants that compete with KMBA for peroxyl radicals is the basis of the Total Oxyradical Scavenging Capacity Assay (TOSCA; Winston et al., 1998). Antioxidative activities of water-soluble extracts of American green tea, the anti-hepatotoxic flavonolignan from milk thistle (Silybum marianum) silybin, Ginkgo biloba extract EGb 761, and a series of naturally occuring sesquiterpene lactones (all ger-macranolides found in in fungi, liverworts, and plants) were studied. The specific TOSC value per $\mu$M silybin was 5.2, which is essentially comparable to that of Trolo $x^{ⓡ}$, a water-soluble vitamine E analog. Tea and Ginkgo extracts exhibited potent peroxyl radical scavenging capacity with values, respectively of =1700 and 1000 $\mu$mols Trolo $x^{ⓡ}$ equivalent per gram dry matter. The known anti-inflammatory activity of some germacranolides prompted study of their antioxidant capacity. None of the lactones exhibited antioxidant capacity toward peroxyl radicals comparable to Trolo $x^{ⓡ}$; costunilide, the most lipophilic, had a TOSC value = to glutathione. The potential role of peroxyl radicals in lipidperoxidation, other cellular damage, and var-ious disease states suggest a possible preventive role for silybin, green tea and Ginkgo biloba in oxidative stress caused by these free radical species.ecies.

• 생약학회지
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• 제30권1호
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• pp.74-78
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• 1999

Nine sesquiterpene lactones, which were isolated from Hemisteptia lyrata Bunge, Chrysanthemum zawadskii Herbich var. latilobum Kitamura and Chrysanthemum boreale Makino were evaluated for the inhibition upon the nitric oxide release from the Raw cell and for the ACAT (acyl Co A: cholesterol acyltransferase) inhibitory assay. In the nitric oxide release inhibitory experiment, hemistepsin B $(IC_{50}\;=\;0.05\;{\mu}g/ml,\;0.15\;{\mu}M),$ cumambrin B, tulipinolide and costunolide exhibited strong inhibition with $IC_{50}$ values $0.05\;{\mu}g/ml\;(0.15\;{\mu}M),\;0.1\;{\mu}g/ml\;(0.38\;{\mu}M),\;0.2\;{\mu}g/ml\;(0.69\;{\mu}M)$ and $0.2\;{\mu}g/ml(0.86\;{\mu}M),$ respectively. In the ACAT inhibitory assay, angeloylcumambrin B, tigloylcumambrin B, tulipinolide and costunolide exhibited strong inhibition with $IC_{50}$ values $33\;{\mu}g/ml\;(95.4\;{\mu}M),\;22\;{\mu}g/ml\;(63.6\;{\mu}M),\;38\;{\mu}g/ml\;(151\;{\mu}M)$ and $17\;{\mu}g/ml(73.3\;{\mu}M),$ respectively, whereas other compounds did not exhibit significant activity against ACAT above $100\; {\mu}g/ml.$.

• 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.

• 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.

• Natural Product Sciences
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• 제16권3호
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• pp.143-147
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• 2010

The chromatographic separation of a methanol extract of Artemisia princes led to the isolation of two sesquiterpene lactones, artecanin (1) and canin (2), together with a flavonoid, eupatilin (3). Their structures were determined by 1D, 2D-NMR and MS data analysis. All of the isolates were evaluated for their potential to inhibit the LPS-induced production of nitric oxide in murine macrophage RAW 264.7 cells. Compounds 1 - 3 inhibited nitric oxide production with $IC_{50}$ values of 19.5, 20.4 and 25.1 ${\mu}M$, respectively.

• Archives of Pharmacal Research
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• 제27권10호
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• pp.1029-1033
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• 2004

From the methanol extract of the whole plants of Carpesium macrocephalum $F_R$. et $S_{AV}$., five sesquiterpene lactones (1: carabron, 2: tomentosin, 3: ivalin, 4: 4H-tomentosin, 5: carabrol) and three terpenoids (6: loliolide, 7: vomifoliol, 8: citrusin C) were isolated. The structures and stereochemistry of compounds 1-8 were established on the basis of chemical analysis as well as 1D- and 2D-NMR spectroscopy. Among them, compounds 2, 4, and 6-8 were isolated for the first time from Carpesium species.

• Advances in Traditional Medicine
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• 제9권2호
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• pp.192-199
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• 2009

Bioactivity-directed isolation has led to the isolation of (-)-ent-costunolide (1) as the major active compound from Hepatostolonophora paucistipula. This compound (1) was determined by spectroscopic data interpretation. This sesquiterpene lactone (1) inhibited the growth of the dermatophytic fungus Trichophyton mentagrophytes ATCC 28185, (4 mm inhibition zone at $15{\mu}g$/disc), cytotoxic activity to murine leukaemia cell lines ATCC CCL 46 P 388D1 ($IC_{50}$ 687 ng/ml, at $0.075{\mu}g$/disk), BSC monkey kidney cell lines (100% of well at $15{\mu}g$/disk) and antiviral activity to Herpes simplex virus (0.25 mg/ml, 100% of well at $7.5{\mu}g$/disk) and Polio virus (0.125 mg/ml, 100% of well at $3.75{\mu}g$/disk). These results suggest that (-)-ent-costunolide (1) has potential antimicrobial and cytotoxic agents.

• 한국약용작물학회지
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• 제9권4호
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• pp.269-274
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• 2001

쑥갓(Chrysanthemum coronarium L.) 꽃으로부터 암 예방활성 성분을 가진 2종의 화합물을 분리하여 다양한 spectral data를 종합한 결과, sesquiterpene lactone계인 eudesmanolide의 일종으로 밝혀졌으며 , compound 1과 2는 각각 douglanine과 reynosin인 것으로 동정되었다. 이 화합물들은 쓱갓에서는 처음으로 분리 보고되는 화합물이며, 세포독성을 측정한 결과, 두 화합물 모두 3종의 인체암 세포주에 대하여 비교적 강한 활성을 나타내었다.

• Natural Product Sciences
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• 제4권1호
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• pp.42-44
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• 1998

Aromatic esters named benzyl-2,6-dimethoxy and benzyl-2,3,5,6-tetramethoxybenzoates along with previously reported compounds were isolated from aerial parts of Blainvillea latifolia.