scholarly journals α-Glucosidase Inhibitory Activity of Cycloartane-Type Triterpenes Isolated from Indonesian Stingless Bee Propolis and Their Structure–Activity Relationship

2019 ◽  
Vol 12 (3) ◽  
pp. 102 ◽  
Author(s):  
Niken Pujirahayu ◽  
Debu Kumar Bhattacharjya ◽  
Toshisada Suzuki ◽  
Takeshi Katayama
Keyword(s):  
Inhibitory Activity ◽  
Antioxidant Activities ◽  
Stingless Bee ◽  
Structure Activity Relationships ◽  
Glucosidase Inhibitor ◽  
Structure Activity ◽  
Glucosidase Inhibitors ◽  
Ic50 Values ◽  
New Type ◽  
Treatment Of Diabetes

This study reports on the antioxidant activity and α-glucosidase inhibitory activity of five cycloartane-type triterpenes isolated from Indonesian stingless bee (Tetragonula sapiens Cockerell) propolis and their structure–activity relationships. The structure of the triterpenes was determined to include mangiferolic acid (1), Cycloartenol (2), ambonic acid (3), mangiferonic acid (4), and ambolic acid (5). The inhibitory test results of all isolated triterpenes against α-glucosidase showed a high potential for inhibitory activity with an IC50 range between 2.46 and 10.72 µM. Among the compounds tested, mangiferonic acid (4) was the strongest α-glucosidase inhibitor with IC50 2.46 µM compared to the standard (–)-epicatechin (1991.1 µM), and also had antioxidant activities with IC50 values of 37.74 ± 6.55 µM. The study on the structure–activity relationships among the compounds showed that the ketone group at C-3 and the double bonds at C-24 and C-25 are needed to increase the α-glucosidase inhibitory activity. The carboxylic group at C-26 is also more important for increasing the inhibitory activity compared with the methyl group. This study provides an approach to help consider the structural requirements of cycloartane-type triterpenes from propolis as α-glucosidase inhibitors. An understanding of these requirements is deemed necessary to find a new type of α-glucosidase inhibitor from the cycloartane-type triterpenes or to improve those inhibitors that are known to help in the treatment of diabetes.

Structure-Activity Relationships of Natural and Synthetic Indole-Derived Scaffolds as α-Glucosidase Inhibitors: A Mini-Review

2020 ◽  
Vol 20 (17) ◽  
pp. 1791-1818
Author(s):  
Jiangming Wang ◽  
Silei Lu ◽  
Ruilong Sheng ◽  
Junting Fan ◽  
Wenhui Wu ◽  
...  
Keyword(s):  
Side Effects ◽  
Oral Absorption ◽  
Positive Control ◽  
Structure Activity Relationships ◽  
Drug Candidates ◽  
Structure Activity ◽  
Glucosidase Inhibitors ◽  
Future Drug ◽  
Gastrointestinal Side Effects ◽  
Treatment Of Diabetes

α-Glucosidase plays an important role in carbohydrate metabolism and is an attractive drug target for the treatment of diabetes, obesity and other related complications. Currently, acarbose, miglitol and voglibose have been approved by the FDA for the treatment of diabetes by oral α-glucosidase inhibitors. With the development of anti-diabetic drugs, the emergence of novel drugs with various chemotypes has overshadowed α-glucosidase inhibitors. Since the 1990s, the FDA has not approved new chemical entities against α-glucosidase, which has resulted in restricted clinical medication. Nevertheless, this type of inhibitors possess several unparalleled advantages over other drugs, especially mild side effects (non-systemic gastrointestinal side effects and occasional allergic reactions). Additionally, α-glucosidase inhibitors for monotherapy or in combination with other drugs have been proved to be a feasible approach for the treatment of diabetes. In the last decade, the discovery of natural or synthetic indole derivatives possessing the inhibitory activity of α-glucosidase has received great attention. Herein, we have summarized indoles as inhibitors of α-glucosidase activity, their mechanism of action, synthetic methodologies and structure-activity relationships. Moreover, we have compared the inhibitory potencies of all compounds under their corresponding positive control as well as oral absorption in silico evaluated by tPSA. This review will provide a medium on which future drug design and development for the treatment of diabetes may be modeled as many drug candidates with present great potential as effective anti-diabetic chemotherapy.

scholarly journals Intestinal α-Glucosidase Inhibitors in Achillea millefolium

2017 ◽  
Vol 12 (8) ◽  
pp. 1934578X1701200
Author(s):  
Kota Noda ◽  
Eisuke Kato ◽  
Jun Kawabata
Keyword(s):  
Enzyme Activity ◽  
Bioactive Compounds ◽  
Inhibitory Activity ◽  
Achillea Millefolium ◽  
Major Contributor ◽  
Caffeoylquinic Acids ◽  
Glucosidase Inhibitor ◽  
Glucosidase Inhibitors ◽  
Prevention And Treatment ◽  
Treatment Of Diabetes

Achillea millefolium is a plant used as a component of anti-diabetic preparation but the bioactive compounds responsible for its use are not known. Inhibition of intestinal α-glucosidase is a preferable effect for prevention and treatment of diabetes, and A. millefolium extract showed inhibitory activity against the enzyme. Activity-guided separation of the extract gave four mono- or di-caffeoylquinic acids as the isolate. Quantitation of these four caffeoylquinic acids and the activity of the isolates suggested that these are the major contributor for the α-glucosidase inhibitory activity in the extract. However also, the presence of unidentified, minor, but potent α-glucosidase inhibitor in the isolate was also suggested.

ChemInform Abstract: Structure-Activity Relationships of Biflavonoids for β-Secretase (BACE-1) Inhibitory Activity.

ChemInform ◽  
2013 ◽  
Vol 44 (11) ◽  
pp. no-no
Author(s):  
Hiroaki Sasaki ◽  
Yuki Kitoh ◽  
Kazuhiko Miki ◽  
Kaoru Kinoshita ◽  
Kiyotaka Koyama ◽  
...  
Keyword(s):  
Inhibitory Activity ◽  
Structure Activity Relationships ◽  
Structure Activity ◽  
Abstract Structure ◽  
Bace 1

Structure-activity relationships in the Hill inhibitory activity of substituted phenylureas

1987 ◽  
Vol 35 (4) ◽  
pp. 479-483 ◽  
Author(s):  
Patrick Camilleri ◽  
John R. Bowyer ◽  
Terence Gilkerson ◽  
Barbara Odell ◽  
Roger C. Weaver
Keyword(s):  
Inhibitory Activity ◽  
Structure Activity Relationships ◽  
Structure Activity ◽  
The Hill

scholarly journals Characterization of platinum(II) complexes exhibiting inhibitory activity against the 20S proteasome

2020 ◽  
Vol 7 (8) ◽  
pp. 200545
Author(s):  
Tatsuto Kiwada ◽  
Hiromu Katakasu ◽  
Serina Okumura ◽  
Akira Odani
Keyword(s):  
Inhibitory Activity ◽  
Chemical Structure ◽  
Competitive Inhibition ◽  
Proteasome Inhibitors ◽  
Platinum Complex ◽  
Platinum Complexes ◽  
Binding Mode ◽  
Structure Activity Relationships ◽  
Structure Activity

Proteasome inhibitors are useful for biochemical research and clinical treatment. In our previous study, we reported that the 4N-coordinated platinum complexes with anthracenyl ring and heterocycle exhibited proteasome-inhibitory activity. In the present study, the structure–activity relationships and characterization of these complexes were determined for the elucidation of the role of aromatic ligands. Lineweaver–Burk analysis revealed that the chemical structure of heterocycles affects the binding mode of platinum complexes. Platinum complexes with anthracenyl ring and pyridine showed competitive inhibition, although platinum complexes with anthracenyl ring and phenanthroline showed non-competitive inhibition. The structure–activity relationships demonstrated that anthracenyl moiety plays a crucial role in proteasome-inhibitory activity. The platinum complexes with naphthyl or phenyl rings exhibited lower inhibitory activities than the platinum complex with anthracenyl ring. The reactivity with N-acetylcysteine varied according to the chemical structure of complexes.

scholarly journals UFLC-MS-IT-TOF and Bioassay Guided Isolation of Flavonoids as Xanthine Oxidase Inhibitors from Diospyros dumetorum

2017 ◽  
Vol 12 (11) ◽  
pp. 1934578X1701201
Author(s):  
Zhen-Tao Deng ◽  
Tong-Hua Yang ◽  
Xiao-Yan Huang ◽  
Xing-Long Chen ◽  
Jian-Gang Zhang ◽  
...  
Keyword(s):  
Xanthine Oxidase ◽  
Inhibitory Activity ◽  
Folk Medicine ◽  
Hydroxyl Groups ◽  
Active Constituents ◽  
Structure Activity Relationships ◽  
Structure Activity ◽  
Pulmonary Abscess ◽  
Xanthine Oxidase Inhibitors

Diospyros dumetorum is an important folk medicine for treating pulmonary abscess and inflammation. The leaves of D. dumetorum revealed xanthine oxidase (XOD) inhibitory activity. With the guidance of UFLC-MS-IT-TOF analyses combined with bioassay in vitro, 15 flavonoids were isolated from the active parts of D. dumetorum. Except for 11 (IC50 > 200μM), all compounds showed obvious XOD inhibitory activity with IC50 values of 32.5 ± 0.7 ~ 145.0 ± 3.3 μM. The preliminary structure-activity relationships study suggested that glycosylation on C-3 was unfavorable for XOD inhibitory activity; hydroxyl groups on ring B were essential for maintaining activity; the activity was closely related with the position of galloylation. This is the first recognition of the XOD inhibitory activity and active constituents of D. dumetorum, and will provide valuable information for this plant as a new resource for treating hyperuricemia and gout.

Phloroglucinol Derivatives as Potent Photosystem II Inhibitors

1990 ◽  
Vol 45 (5) ◽  
pp. 317-321 ◽  
Author(s):  
Koichi Yoneyama ◽  
Makoto Konnai ◽  
Ichiro Honda ◽  
Shigeo Yoshida ◽  
Nobutaka Takahashi ◽  
...  
Keyword(s):  
Photosystem Ii ◽  
Eucalyptus Grandis ◽  
Binding Domain ◽  
Side Chains ◽  
Ps Ii ◽  
Structure Activity Relationships ◽  
Structure Activity ◽  
Phloroglucinol Derivatives ◽  
New Type

Studies on structure/activity relationships of phloroglucinol derivatives that had been designed based on the structures of grandinol and homograndinol. potent photosystem II (PS II) inhibitors in Eucalyptus grandis, revealed that two electron-withdrawing groups which differ by their electron-withdrawing power on a phloroglucinol nucleus were essential for activity. A larger difference in the electron-withdrawing power between the two groups enhanced the activity, and 3-nitro-phloroglucinecarboxamides and the corresponding thioamides were the most active ones when they had proper lipophilic side chains. Their binding domain seems to overlap with those of DCMU and atrazine, whereas they may approach to the site in a similar manner to that of phenol type inhibitors. Accordingly, the phloroglucinol derivatives represent a new type of PS II inhibitors.

A new type of ketolide bearing an N-aryl-alkyl acetamide moiety at the C-9 iminoether: Synthesis and structure–activity relationships (2)

2006 ◽  
Vol 14 (11) ◽  
pp. 3697-3711 ◽  
Author(s):  
Takashi Nomura ◽  
Tsutomu Iwaki ◽  
Yukitoshi Narukawa ◽  
Koichi Uotani ◽  
Toshihiko Hori ◽  
...  
Keyword(s):  
Structure Activity Relationships ◽  
Structure Activity ◽  
New Type
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