강남콩 미숙종자 내생 식물 호르몬 Brassinosteroids의 구조와 활성과의 상관관계

김성기 中央大學校 遺傳工學硏究所 1992 遺傳工學硏究論集 Vol.5 No.1

Phaselus vulgaris 미숙종자로부터 새롭게 구조결정된 brassinosteroids의 생리활성을 조사한 결과, 구조와 활성과의 상관관계면에서 다음과 같은 사실이 밝혀졌다. 1. A ring 구조중 C-2, C-3위의 수산기는 C-2α, C-3α: C-2α, C-3β: C-2β,C-3α: C-2β, C-3β의 순서로 활성이 감소하며, C-2α수산기의 도입이 활성에 매우 중요하다. 2. Side chain의 alkyation은 활성을 증가시키며, 특히 C-25위의 methyl기의 도입은 활성을 약 10배정도 높인다. 3. C-23위의 glucosylation은 활성을 저하시켰으며, 그 활성은 검정 유식물내에서의 가수분해에 의한 것으로 사료된다. Biological activity of brassinosteroids identified from immature seeds of Phaselus vulgaris were examined by rice lamina inclination assay. Based on the activity of these brassinosteroids, the following characterisics of structure-activity relationship of brassinosteriods were established. 1.Decreasing order of activity C-2α, C-3α> C-2α, C-3β> C-2β,C-3α> C-2β, C-3α suggests that α-oriented hydroxyl at C-2 is essential for strong biological activity. 2.The introduction of methyl at C-25 enhances the activity ca. 10 fold. 3.Glucosylation of C-23 hydroxyl reduces the activity. The biological activity observed might be due to hydrolysis in the test-plant tissue.

Structure-Activity Relationship and Functional Evaluation of Cannabinoid Type-1 Receptor

( Shujie Wang ),( Xinru Tian ),( Suresh Paudel ),( Sungho Ghil ),( Choon-gon Jang ),( Kyeong-man Kim ) 한국응용약물학회 2024 Biomolecules & Therapeutics(구 응용약물학회지) Vol.32 No.4

The type-1 cannabinoid receptor (CB1R) is a potential therapeutic target in several pathological conditions, including neuropsychological disorders and neurodegenerative diseases. Owing to their structural diversity, it is not easy to derive general structure-activity relationships (SARs) for CB₁R ligands. In this study, CB₁R ligands were classified into six structural families, and the corresponding SAR was determined for their affinities for CB1R. In addition, we determined their functional activities for the activation of extracellular signal-regulated kinases (ERKs). Among derivatives of indol-3-yl-methanone, the highest ligand affinity was observed when a pentyl and a naphthalenyl group were attached to the N1 position of the indole ring and the carbon site of the methanone moiety, respectively. In the case of adamantane indazole-3-carboxamide derivatives, the presence of fluorine in the pentyl group, the substituent at the N1 position of the indazole ring, strongly increased the affinity for CB₁R. For (naphthalen-1-yl) methanone derivatives, the presence of 4-alkoxynaphthalene in the methanone moiety was more beneficial for the affinity to CB₁R than that of a heterocyclic ring. The functional activities of the tested compounds, evaluated through ERK assay, were correlated with their affinity for CB₁R, suggesting their agonistic nature. In conclusion, this study provides valuable insight for designing novel ligands for CB₁R, which can be used to control psychiatric disorders and drug abuse.

Structure-antioxidant Activity Relationships of Isoflavonoids

Young Ki Park,Don Ha Choi,Hak Ju Lee,Sung Suk Lee,Wi Young Lee,Jin Kwon Ahn 한국목재공학회 2004 목재공학 Vol.32 No.3

Pharmacological Activities of Flavonoids (III) Structure-Activity Relationships of Flavonoids in Immunosuppression

Kim, Chang-Johng,Cho, Seung-Kil The Pharmaceutical Society of Korea 1991 Archives of Pharmacal Research Vol.14 No.2

Effects of twenty-one different flavonoids and their related compounds on the phagocytosis of colloidal carbon by macrophages in liver and spleen humoral immune responses against bacterial $\alpha$-amylase and cellular immune responses against oxazolone and dinitrofluorobenzene were studied in vivo and in vitro. It was shown that most of the flavonoids accelerated significantly the phagocytosis, and they suppressed significantly not only humoral and cellular immune responses but also the development of immunological memory after the antigenic stimulation. Especially, malvin was the most active in phagocysis, and disodium cromoglycate and morin were the most active in humoral and cellular immunosuppression, respectively. Daidzuin had the most potent inhibitory activity in the development of memory cells. The structure-activity relationships of the flavonoids in immunosuppression became apparant from these results: 1. The presence of $C_{2-3}$ double bond and $C_4$ Ketone group in C-ring was important for their immunosuppressive activity. 2. Flavonoids with benzene ring at 2 or 3 position in C-ring showed the almost same activities. 3. The opening of C-ring did not affect their immunosuppressive activity. 4. The glycosylated flavonoids at 3 position in C-ring were less less potent than their aglycones. 5. Di-or tri-hydroxylated flavonoids in B-ring were more potent than mono-hydroxylated. 6. Chromanochromanone also had the immunosuppressive activity.

Structure Activity Relationship of Antioxidative Property of Flavonoids and Inhibitory Effect on Matrix Metalloproteinase Activity in UVA-Irradiated Human Dermal Fibroblast

심관섭,이범천,조호성,이재웅,김진화,이동환,김진희,표형배,문동철,오기완,윤여표,홍진태 대한약학회 2007 Archives of Pharmacal Research Vol.30 No.3

Collagenase, a matrix metalloproteinases (MMPs), is a key regulator in the photoaging process of skin due to the reactive oxygen species generated after exposure to ultraviolet A (UVA). Flavonoid compounds have been demonstrated to possess antioxidant properties, and could be useful in the prevention of photoaging. In this study, to investigate the structure-activity relationship of flavonoid compounds on their antioxidant property and inhibitory effects against the MMP activity, the effects of several flavonoids; myricetin, quercetin, kaempferol, luteolin, apigenin and chrysin, on the reactive oxygen species scavengering activity and inhibitory effect against the MMP activity were examined in vitro and in human dermal fibroblasts induced by UVA. The relative order of antioxidative efficacy, as determined using the 1, 1- diphenyl-2-picrylhydrazyl (DPPH) method and the xanthine/xanthine oxidase system, was as follows; flavones: luteolin > apigenin > chrysin, flavonols: myricetin > quercetin > kaempferol, and correlated with the respective number of OH group on their B-ring. In good correlation with the antioxidant properties, the flavonoids inhibited the collagenase activities, in a dose-dependent manner, and the MMP expression. These results suggested the UVA induced antioxidative activity and inhibitory effects of flavonoids on the collagenase in human dermal fibroblasts depends on the number of OH group in the flavonoid structure, and those with a higher number of OH group may be more useful in the prevention of UV stressed skin aging.

Structure-antimicrobial activity relationship between pleurocidin and its enantiomer

Juneyoung Lee,이동건 생화학분자생물학회 2008 Experimental and molecular medicine Vol.40 No.4

To develop novel antibiotic peptides useful as therapeutic drugs, the enantiomeric analogue of pleurocidin (Ple), which is a well known 25-mer antimicrobial peptide, was designed for proteolytic resistance by D-amino acids substitution. The proteolytic resistance was confirmed by using HPLC after the digestion with various proteases. To investigate the antibiotic effect of L- and D-Ple, the antibacterial activity and hemolytic effect were tested against human erythrocytes. The D-Ple showed a decreased antibacterial activity and a dramatically decreased hemolytic activity compared with L-Ple. The hemolytic effect of analogue was further confirmed by using calcein leakage measurement with liposome. To elucidate these results, the secondary structure of the peptides was investigated by using circular dichroism spectroscopy. The results revealed that D-Ple, as well as L-Ple, had typical α-helical structures which were mirror images, with a different helicity. These results suggested that the discrepancy of the structure between the two peptides made their antibacterial activity distinct.

Structure Activity Relationship of Antioxidative Property of Flavonoids and Inhibitory Effect on Matrix Metalloproteinase Activity in UVA-Irradiated Human Dermal Fibroblast

Sim, Gwan-Sub,Lee, Bum-Chun,Chol, Ho-Seung,Lee, Jae-Woong,Kim, Jin-Hwa,Lee, Dong-Hwan,Kim, Jin-Hui,Pyo, Hyeong-Bae,Moon, Dong-Cheul,Oh, Ki-Wan,Hong, Jin-Tae 대한약학회 2007 Archives of Pharmacal Research Vol.30 No.3

Collagenase, a matrix metalloproteirases (MMPs), is a key regulator in the photoaging process of skin due to the reactive oxygen species generated after exposure to ultraviolet A(UVA). Flavonoid compounds have been demonstrated to possess antioxidant properties, and could be useful in the prevention of photoaging. In this study, to investigate the structure-activity relationship of flavonoid compounds on their antioxidant property and inhibitory effects against the MMP activity, the effects of several flavonoids; myricetin, quercetin, kaempferol, luteolin, apigenin and chrysin, on the reactive oxygen species scavengering activity and inhibit of effect against the MMP activity were examined in vitro and in human dermal fibroblasts induced by UVA. The relative order of antioxidative efficacy, as determined using the 1, 1-diphenyl-2-picrylhydrazyl (DPPH) method and the xanthine/xranthine oxidase system, was as follows; flavones: luteolin > apigenin > chrysin, flavonols: myricetin > quercetin > kaempferol, and correlated with the respective number of OH group on their B-ring. In good correlation with the antioxidant properties, the flavonoids inhibited the collagenase activities, in a dose-dependent manner, and the MMP expression. These results suggested the UVA induced antioxidative activity and inhibitory effects of flavonoids on the collagenase in human dermal fibroblasts depends on the number of OH group in the flavonoid structure, and those with a higher number of OH group may be more useful in the prevention of UV stressed skin aging.

Acaricidal activity and structure-activity relationships of Spiro- Butyrolactone derivatives against Tetranychus cinnabarinus

Shaoyong Ke,Ting Ke,Zhigang Zhang,Liqiao Shi,Daye Huang,Kaimei Wang,Ziwen Yang,Nina Yang 한국응용곤충학회 2018 Journal of Asia-Pacific Entomology Vol.21 No.3

The phytophagous mite is highly polyphagous and widespread in warmer regions and greenhouses around the world, and so the focus of novel acaricides is shifting towards more effective, ecofriendly new chemical entity with unique modes of action. In this study, eighteen spirobutyrolactones derived from natural tetronic acid have been synthesized and their acaricidal activities against Tetranychus cinnabarinus were investigated by slide-dip method. The results of preliminary bioassay indicate that some of these compounds exhibited promising acaricidal activities, especially, compounds 6 and 18 show significant activities against T. cinnabarinus than the commercial spirodiclofen 1 (27.37% mortality), and which present 58.55% and 82.24% mortality at tested dose, respectively. The relationship between structure and acaricidal activity was also discussed based on the experimental data, and which indicate that the compounds (16, 17 and 18) with non-substituted phenyl ring (R1=H) show obviously better activities. Especially, we also can find that substituted benzoyl unit will help to increase the activity than substituted phenylacetyl group.

Antioxidant activities of coumarins from Korean medicinal plants and their structure–activity relationships

Thuong, Phuong Thien,Hung, Tran Manh,Ngoc, Tran Minh,Ha, Do Thi,Min, Byung Sun,Kwack, Seung Jun,Kang, Tae Suk,Choi, Jae Sue,Bae, KiHwan John Wiley Sons, Ltd. 2010 Phytotherapy research Vol.24 No.1

<P>The aim of this work was to study the structure–activity relationships of the antioxidant activity of natural coumarins isolated from four Korean medicinal plants (1–17) and four purchased coumarins (18–21). The free radical scavenging and lipid peroxidation assays revealed that five phenolic coumarins, scopoletin (1), aesculetin (2), fraxetin (3), umbelliferone (18) and daphnetin (19), possessed considerable antioxidant activities. The coumarins having a catechol group, 2, 3 and 19, showed significant free radical scavenging activity and inhibitory effects on lipid peroxidation, indicating that the catechol group significantly contributed to the antioxidant activities of coumarins. In contrast, the sugar moiety markedly reduced the activities of coumarin glycosides. The results also demonstrate that the α-pyrone ring of coumarins significantly enhanced the capacity of inhibiting oxidative reactions of coumarins. Copyright © 2009 John Wiley & Sons, Ltd.</P>

Ginsentology II : Chemical Structure-Biological Activity Relationship of Ginsenoside

Byung-Hwan Lee,Seung-Yeol Nah 고려인삼학회 2007 Journal of Ginseng Research Vol.31 No.2

Since chemical structures of ginsenoside as active ingredient of Panax ginseng are known, accumulating evidences have shown that ginsenoside is one of bio-active ligands through the diverse physiological and pharmacological evaluations. Chemical structure of ginsenoside could be divided into three parts depending on diol or triol ginsenoside: Steroid- or cholesterol-like backbone structure, carbohydrate portions, which are attached at the carbon-3, -6 or -20, and aliphatic side chain coupled to the backbone structure at the carbon-20. Ginsenosides also exist as stereoisomer at the carbon-20. Bioactive ligands usually exhibit the their structure-function relationships. In ginsenosides, there is little known about the relationship of chemical structure and biological activity. Recent reports have shown that ginsenoside Rg₃, one of active ginsenosides, exhibits its differential physiological or pharmacological actions depending on its chemical structure. This review will show how ginsenoside Rg₃, as a model compound, is functionally coupled to voltage-gated ion channel or ligand-gated ion channel regulations in related with its chemical structure.