• 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.

• 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 $100{\mu}g/mL$.

• 한국자원식물학회지
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• 제31권5호
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• pp.538-546
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• 2018

Inflorescence, stem, and leaf samples of lettuce grown in a greenhouse in spring and autumn seasons were assayed for sesquiterpene lactones (SLs) content by high performance liquid chromatography. The concentrations of SLs were significantly higher in the inflorescences followed by upper leaf and stem compared to the other plant parts in most of the samples. SLs content (sum of lactucin and lactucopicrin) in various tissues of lettuce cultivated in spring season varied from 5.7 to 22.5 fold ranging from $27.4{\mu}g/g$ dry weight (DW) in the upper stem (cultivar "PI 176588") as the lowest to as high as $2,292.0{\mu}g/g$ DW in the inflorescence (cultivar "709849-1"). During autumn cultivation, the concentration of SLs varied from 2.0 to 14.4 fold ranging from as low of $32.4{\mu}g/g$ DW in the lower stem (cultivar "PI176588") to as high of $838.0{\mu}g/g$ DW in the upper leaf (cultivar "Dambaesangchu"). Higher lactucin (1.2 to 5.6 fold) and lactucopicrin (1.1 to 3.9 fold) concentration was observed during spring compared to autumn cultivation in most of the samples. SLs content in various organs of lettuce increases from the basal plant part going upwards. As lactucin and lactucopicrin are the major SLs which affects the sensory property of lettuce, their quantitative variation in the lettuce cultivars is useful for breeding new varieties with better consumer acceptance.

• Applied Biological Chemistry
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• 제39권5호
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• pp.389-397
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• 1996

연속수증기증류장치를 이용하여 두릅으로부터 얻어진 휘발성농축물은 탄화수소구분 및 함산소구분으로 분리되었고, 함산소구분은 실리카겔 관 크로마토그래피에 의해서 9개의 계대구분으로 다시 분획하였다. 기체크로마토그래피와 기체크로마토그래피에 질량분석계를 연결시킨 장치는 휘발성성분을 동정하기 위하여 사용하였다. 동정된 167개의 휘발성성분은 72개의 탄화수소, 31개의 알콜, 23개의 알데히드, 16개의 에스테르, 10개의 산, 6개의 케톤, 3개의 푸론, 2개의 페놀, 1개의 인돌, 1개의 산화물, 1개의 설파이드 및 1개의 락톤이었다. Sesquiterpene 탄화수소인 ${\beta}-caryopyllene$은 두릅에서 동정된 휘발성 성분중에서 함량이 가장 높았으며, 19.53%를 차지하였다. 두릅정유는 관능검사용 기체크로마토그래피를 사용하여 각 구분에 함유된 개별 휘발성성분을 평가에 의해서 초목 모양의 향기를 함유하고 있음이 밝혀졌다.

• Applied Biological Chemistry
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• 제48권1호
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• pp.1-15
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• 2005

농작물이 병해충 및 잡초 등에 의하여 피해를 받게 되면 농업생산성은 상당히 저하된다. 따라서 농업생산성을 높이기 위하여 합성농약을 과용해 왔고, 이로 인하여 토양의 질과 농업환경이 파괴되는 결과를 초래하고 있어서 지속적인 농업이 점차 어려워지고 있다. 오늘날의 농업은 농업환경의 파괴를 최소화하고 농산물의 안전성을 확보함과 동시에 생산성을 증대해야하는 복합적인 문제에 직면해 있다. 한편, 식물은 일반적으로 생존하기 위하며 외부의 침입으로부터 자신을 보호하거나 자신의 영역을 확보하기 위하며 다양한 종류의 2차대사물질을 생산하고 방출한다. 병원균이 침입했을 때 식물이 생산하는 항생물질인 phytoalexin으로는 화본과 식물의 경우 flavonoid계와 diterpenoid계의 물질을 생성하고, 쌍자엽 식물은 감염된 병원균의 종류에 상관없이 Leguminosae과는 flavonoids계, Cruciferae과는 indole 유도체, Solanaceae과는 sesquiterpenoid계, Umbelliferae과는 coumarin계 물질들을 생성하여 병원균에 저항성을 가진다. 곤충의 생리작용을 저해하거나 섭생을 싫어하게 하는 기능의 물질로는 terpene계의 pyrethrin, azadirachtin, limonin, cedrelanoid, toosendanin, fraxinellone/dictamnine 등이 있으며, alkaloid계로서는 terpenoid와 alkaloid가 결합된 sesquiterpene pyridine 및 norditerpenoids alkaloids와 azepine계, amide계, loline계, stemofoline계, pyrrolizidine계 alkaloids 등이 있다. 식물은 또한 자신의 영역을 확보하기 위하여 다른 식물의 생장을 저해하는 물질을 생성하는데 여기에는 terpene계의 essential oil 및 sesquiterpene lactone과 이외에 benzoxazinoids, glucosinolate, quassinoid, cyanogenic glycoside, saponin, sorgolennone, juglone 등 다수의 2차 대사물질들이 있다. 이와 같은 기능의 2차 대사물질을 병해충 및 잡초 방제에 직, 간접으로 이용하는 것은 친환경농업의 한 가지 방법일 수 있다. 그러나 천연물질들은 자연계에서 쉽게 분해되어 효율이 떨어지는 경우가 많고 식물을 통하여 생산하는데도 한계가 있다. 따라서 보다 안전성과 효율성이 뛰어난 2차 대사물질을 찾아내는 연구와 아울러 방제기능이 있는 물질의 생합성경로를 구명하고 대사공학적으로 이용하므로 병해충에 저항성이 있고 잡초 방제효과를 갖는 형질전환 식물을 육성하는 연구가 지속적으로 이루어져야 할 것이다.

• 한국자원식물학회지
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• 제29권6호
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• pp.679-689
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• 2016

Lettuce is an important annual leafy vegetable and bitterness is its potent flavor character. Lettuce germplasm differ their phenotypic characters and sesquiterpene lactones (SLs) contents which are important for consumer's acceptance. This study was carried out to evaluate the phenotypic characters and SLs contents in one hundred lettuce germplasm in Jeonju, Korea. Twenty-three agro-morphological (16 qualitative and 7 quantitative) traits and two SLs (lactucin and lactucopicrin) contents were studied in these germplasm. Germplasm exhibited the variation in qualitative and quantitative characters. Average plant weight was 423.9 g with a range from 116.0 to 905.0 g. Lactucin content was varied from 19.7 (IT 294226) to $194.4{\mu}g/g$ (IT 294298) with an average concentration of $84.7{\mu}g/g$. Lactucopicrin ranged from 82.5 (IT 300134) to $2228.6{\mu}g/g$ (IT 294210) with an average concentration of $586.3{\mu}g/g$. Total SLs content was ranged from 120.1 (IT 300134) to 2286.6 (IT 294210)${\mu}g/g$ with the average concentration of $671.0{\mu}g/g$. Significant ($p{\leq}0.05$) differences were found between crisp head and butter head germplasm for lactucin, lactucopicrin and total SLs content. Crisp head germplasm revealed the highest average lactucin ($112.9{\mu}g/g$), lactucopicrin ($734.8{\mu}g/g$) and total SLs content ($847.7{\mu}g/g$). Crisp head and leafy type germplasm exhibited more total SLs content (847.7 and $744.7{\mu}g/g$, respectively) than cos ($524.9{\mu}g/g$) and butter head type ($519.4{\mu}g/g$). Principal component analyses of the quantitative traits indicated that the first principal component axis accounted more than 91% of the total variation. This study revealed the ample genetic variation in the agro-morphological traits and SLs contents to support the selection for improved lettuce varieties.

• 대한의생명과학회지
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• 제16권1호
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• pp.39-45
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• 2010

Toll-like receptors (TLRs), which are pattern recognition receptors (PRRs), recognize pathogen-associated molecular patterns (PAMPs) and regulate the activation of innate immunity. All TLR signaling pathways culminate in the activation of NF-${\kappa}B$, leading to the induction of inflammatory gene products such as cyclooxygenase-2 (COX-2) and inducible nitric oxide synthase (iNOS). Parthenolide, a sesquiterpene lactone isolated from the herb feverfew (Tanacetum parthenium), has been used as folk remedies to treat many chronic diseases for many years. In the present report, we present biochemical evidence that parthenolide inhibits the NF-${\kappa}B$ activation induced by TLR agonists and the overexpression of downstream signaling components of TLRs, MyD88, $IKK{\beta}$, and p65. Parthenolide also inhibits TLR agonists-induced COX-2 and iNOS expression. These results suggest that parthenolide can modulate the immune responses regulated by TLR signaling pathways.

• 대한수의학회지
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• 제35권1호
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• pp.123-130
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• 1995

Artemisinin, a sesquiterpene lactone, is isolated from the leafy portion of the Artemisia annua and has been known to be effective against Plasmodium species. Since the genera of Plasmodium and Eimeria(E) tenella are included the same order, Eucoccidiidae, it is presumed that artemisinin may also be effective against E tenella. In order to study the anticoccididal effects of artemisinin, the chickens inoculated with E tenella were treated with artemisinin at different concentrations as feed additive and the results were compared to those of non-medicated, infected control(NIC) and non-medicated, non-infected control(NNC) group. Artemisinin demonstrated anticoccidial effects by showing, compared to NIC group, improved results in all parameters, such as bloody diarrhea, lesion scores, the numbers of excreted oocystis in feces, body weight gain and feed conversion rate. Anticoccidial index(ACI) of artemisinin treated group (5ppm~50ppm) was higher than that of NIC group. Improvements were greatest in the group treated with artemisinin 50ppm with an ACI of 147.6. These results indicate that artemisinin has anticoccidial effects on the Eimeria tenella.

• 동의생리병리학회지
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• 제18권4호
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• pp.1186-1191
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• 2004

The root of Saussurea lappa includes sesquiterpene lactones such as costunolide and dehydrocostus lactone, and has been shown to be anti-tumorigenic with being used in traditional medicinal therapy in the Eastern Asia. However, the molecular basis of the effects of Saussurea lappa on fate of gastric carcinoma, which incur very frequently in the area, has not been well identified. In this study, the cytostatic effects of Saussurea lappa were examined using gastric AGS cancer cells. Cell viability was dramatically reduced by Saussurea lappa, in a dose-dependent manner. As time passed after its treatment, apoptotic population was increased and clearly showed G2-arrest. Being consistent, its treatment resulted in maintaining of G1 and S-phase cyclins D1, E, and A even until a significant apoptotic population was observed, for example, at 24h after treatment. However, G2/M phase cyclin B1 was reduced even at 12 h after treatment. In addition, its treatment increased expression of p53, p21/sup Wafl / cyclin dependent kinase inhibitor (CKI), and Bax, resulted in cleavages of procaspase 3 and poly ADP-ribose polymerase(PARP), indicating that such G2 arrest- and apoptosis-related molecules are involved. Therefore, these suggest that extracts of Saussurea lappa root may be a safer and effective reagent to deal with gastric cancers either by traditional herbal therapy or combinational therapy with conventional chemotherapy.

• 동의생리병리학회지
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• 제27권3호
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• pp.306-312
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• 2013

Costunolide ($C_{15}H_{20}O_2$) is a sesquiterpene lactone that was isolated from many herbal medicines and it has diverse effects (anti-viral, anti-fungal, and anti-inflammatory) according to previous reports. However, the anti-cancer effects of Costunolide and its mechanism of actions are not well known in estrogen receptor positive breast cancer. In this study, we observed that costunolide suppresses cell growth in estrogen receptor positive MCF-7 breast cancer cells as shown by MTT assay and soft agar colony formation assay. To examine the mechanism by which costunolide inhibits MCF-7 cell growth, we performed FACS analysis. We found that costunolide induced G2/M and S cell cycle arrest, and regulated cycle-related protein expression. In addition, costunolide inhibited ERK signaling pathway and induced autophagy. Therefore, costunolide might be a good and useful chemotherapy agent for estrogen receptor positive breast cancer patients.