Structure-Activity Relationship of Acetylenes from Galls of Hedera rhombea as Plant Growth Inhibitors

2006 ◽  
Vol 61 (7-8) ◽  
pp. 536-540 ◽  
Author(s):  
Sayumi Yamazoe ◽  
Koji Hasegawa ◽  
Hideyuki Shigemori
Keyword(s):  
Structure Activity Relationship ◽  
Activity Relationship ◽  
Aliphatic Chain ◽  
Structure Activity ◽  
Growth Inhibitory ◽  
Growth Inhibitory Activity ◽  
Almost All ◽  
Relationship Of ◽  
Methylene Group ◽  
Hedera Rhombea

The structure-activity relationship of 12 isolated acetylenes from galls of Hedera rhombea (Araliaceae) induced by Asphondylia sp. (Cecidomyiidae) and their derivatives has been studied for the inhibition of the shoot and root growth of rice, perennial ryegrass, cockscomb, lettuce, and cress. Almost all acetylenes generally showed growth inhibitory activity. The diacetylenes exhibited higher activity than the monoacetylenes, suggesting that a conjugated diyne segment is essential for the activity. On the other hand, the acetylenes with a nonoxidated methylene group at C-8 showed stronger activity comparing with those possessing hydroxy and acetoxy groups at C-8. Furthermore, it has been demonstrated that the acetylenes bearing a terminal olefinic group at C-16,C-17 enhanced the activity. It is thus clarified that important sites for the activity of the acetylenes from galls of H. rhombea are a conjugated diyne and a terminal olefinic group connecting to the aliphatic chain and that less oxidated compounds show more activity.

Structure-activity relationship of a novel pentapeptide with cancer cell growth-inhibitory activity

2010 ◽  
Vol 16 (5) ◽  
pp. 242-248 ◽  
Author(s):  
Masakatsu Kamiya ◽  
Keisuke Oyauchi ◽  
Yoshinori Sato ◽  
Takuya Yokoyama ◽  
Mofei Wang ◽  
...  
Keyword(s):  
Cell Growth ◽  
Cancer Cell ◽  
Inhibitory Activity ◽  
Structure Activity Relationship ◽  
Activity Relationship ◽  
Cancer Cell Growth ◽  
Structure Activity ◽  
Growth Inhibitory ◽  
Growth Inhibitory Activity ◽  
Relationship Of

scholarly journals Inhibition of Aminoglycoside 6’-N-Acetyltransferase Type Ib [Aac(6′)-Ib]: Structure-Activity Relationship of Substituted Pyrrolidine Pentamine Derivatives as Inhibitors

2021 ◽  
Author(s):  
Kenneth Rocha ◽  
Jesus Magallon ◽  
Craig Reeves ◽  
Kimberly Phan ◽  
Peter Vu ◽  
...  
Keyword(s):  
Combinatorial Libraries ◽  
Phenyl Group ◽  
Carbon Chain ◽  
Structure Activity Relationship ◽  
Activity Relationship ◽  
Aliphatic Chain ◽  
Structure Activity ◽  
Binding Cavity ◽  
Sar Analysis ◽  
Relationship Of

The aminoglycoside 6′-N-acetyltransferase type Ib [AAC(6′)-Ib] is a common cause of resistance to amikacin and other aminoglycosides in Gram-negatives. Utilization of mixture-based combinatorial libraries and application of the positional scanning strategy identified an inhibitor of AAC(6′)-Ib. This inhibitor’s chemical structure consists of a pyrrolidine pentamine scaffold substituted at four locations (R1, R3, R4, and R5). The substituents are two S-phenyl (R1 and R4), an S-hydroxymethyl (R3), and a 3-phenylbutyl (R5) groups. Another location, R2, does not have a substitution, but it is named because its stereochemistry was modified in some compounds utilized in this study. Structure-activity relationship (SAR) analysis using derivatives with different functionalities, modified stereochemistry, and truncations were carried out by assessing the effect of the addition of each compound at 8 µM to 16 µg/ml amikacin-containing media and performing checkerboard assays varying the concentrations of the inhibitor analogs and the antibiotic. The results showed that: 1) the aromatic functionalities at R1 and R4 are essential, but the stereochemistry is essential only at R4, 2) the stereochemical conformation at R2 is critical, 3) the hydroxyl moiety at R3 as well as stereoconformation are required for full inhibitory activity, 4) the phenyl functionality at R5 is not essential and can be replaced by aliphatic groups, 5) the location of the phenyl group on the butyl carbon chain at R5 is not essential, 6) the length of the aliphatic chain at R5 is not critical, 7) all truncations of the scaffold resulted in inactive compounds. Molecular docking revealed that all compounds preferentially bind to the kanamycin C binding cavity, and binding affinity correlates with the experimental data for most of the compounds evaluated. The SAR results in this study will serve as the basis for the design of new analogs in an effort to improve their ability to induce phenotypic conversion to susceptibility in amikacin-resistant pathogens.

Structure–activity relationship of human GLO I inhibitory natural flavonoids and their growth inhibitory effects

2008 ◽  
Vol 16 (7) ◽  
pp. 3969-3975 ◽  
Author(s):  
Ryoko Takasawa ◽  
Saki Takahashi ◽  
Kazunori Saeki ◽  
Satoshi Sunaga ◽  
Atsushi Yoshimori ◽  
...  
Keyword(s):  
Structure Activity Relationship ◽  
Activity Relationship ◽  
Inhibitory Effects ◽  
Structure Activity ◽  
Growth Inhibitory ◽  
Relationship Of

scholarly journals Inhibition of Aminoglycoside 6′-N-acetyltransferase Type Ib (AAC(6′)-Ib): Structure–Activity Relationship of Substituted Pyrrolidine Pentamine Derivatives as Inhibitors

Biomedicines ◽  
2021 ◽  
Vol 9 (9) ◽  
pp. 1218
Author(s):  
Kenneth Rocha ◽  
Jesus Magallon ◽  
Craig Reeves ◽  
Kimberly Phan ◽  
Peter Vu ◽  
...  
Keyword(s):  
Combinatorial Libraries ◽  
Phenyl Group ◽  
Carbon Chain ◽  
Structure Activity Relationship ◽  
Activity Relationship ◽  
Aliphatic Chain ◽  
Hydroxymethyl Group ◽  
Structure Activity ◽  
Binding Cavity ◽  
Relationship Of

The aminoglycoside 6′-N-acetyltransferase type Ib (AAC(6′)-Ib) is a common cause of resistance to amikacin and other aminoglycosides in Gram-negatives. Utilization of mixture-based combinatorial libraries and application of the positional scanning strategy identified an inhibitor of AAC(6′)-Ib. This inhibitor’s chemical structure consists of a pyrrolidine pentamine scaffold substituted at four locations (R1, R3, R4, and R5). The substituents are two S-phenyl groups (R1 and R4), an S-hydroxymethyl group (R3), and a 3-phenylbutyl group (R5). Another location, R2, does not have a substitution, but it is named because its stereochemistry was modified in some compounds utilized in this study. Structure–activity relationship (SAR) analysis using derivatives with different functionalities, modified stereochemistry, and truncations was carried out by assessing the effect of the addition of each compound at 8 µM to 16 µg/mL amikacin-containing media and performing checkerboard assays varying the concentrations of the inhibitor analogs and the antibiotic. The results show that: (1) the aromatic functionalities at R1 and R4 are essential, but the stereochemistry is essential only at R4; (2) the stereochemical conformation at R2 is critical; (3) the hydroxyl moiety at R3 as well as stereoconformation are required for full inhibitory activity; (4) the phenyl functionality at R5 is not essential and can be replaced by aliphatic groups; (5) the location of the phenyl group on the butyl carbon chain at R5 is not essential; (6) the length of the aliphatic chain at R5 is not critical; and (7) all truncations of the scaffold resulted in inactive compounds. Molecular docking revealed that all compounds preferentially bind to the kanamycin C binding cavity, and binding affinity correlates with the experimental data for most of the compounds evaluated. The SAR results in this study will serve as the basis for the design of new analogs in an effort to improve their ability to induce phenotypic conversion to susceptibility in amikacin-resistant pathogens.

Structure-activity relationship of (-) mammea A/BB derivatives against Leishmania amazonensis

Planta Medica ◽  
2008 ◽  
Vol 74 (09) ◽  
Author(s):  
MA Brenzan ◽  
CV Nakamura ◽  
BPD Filho ◽  
T Ueda-Nakamura ◽  
MCM Young ◽  
...  
Keyword(s):  
Structure Activity Relationship ◽  
Leishmania Amazonensis ◽  
Activity Relationship ◽  
Structure Activity ◽  
Relationship Of

Antineoplastic Activity, Structural Modification, Synthesis and Structure-activity Relationship of Dammarane-type Ginsenosides: An Overview

2019 ◽  
Vol 23 (5) ◽  
pp. 503-516 ◽  
Author(s):  
Qiang Zhang ◽  
Xude Wang ◽  
Liyan Lv ◽  
Guangyue Su ◽  
Yuqing Zhao
Keyword(s):  
Structural Modification ◽  
Gastrointestinal Disease ◽  
Structure Activity Relationship ◽  
Cerebrovascular Diseases ◽  
Activity Relationship ◽  
Cycle Arrest ◽  
Structure Activity ◽  
Wide Range ◽  
Structural Association ◽  
Relationship Of

Dammarane-type ginsenosides are a class of tetracyclic triterpenoids with the same dammarane skeleton. These compounds have a wide range of pharmaceutical applications for neoplasms, diabetes mellitus and other metabolic syndromes, hyperlipidemia, cardiovascular and cerebrovascular diseases, aging, neurodegenerative disease, bone disease, liver disease, kidney disease, gastrointestinal disease and other conditions. In order to develop new antineoplastic drugs, it is necessary to improve the bioactivity, solubility and bioavailability, and illuminate the mechanism of action of these compounds. A large number of ginsenosides and their derivatives have been separated from certain herbs or synthesized, and tested in various experiments, such as anti-proliferation, induction of apoptosis, cell cycle arrest and cancer-involved signaling pathways. In this review, we have summarized the progress in structural modification, shed light on the structure-activity relationship (SAR), and offered insights into biosynthesis-structural association. This review is expected to provide a preliminary guide for the modification and synthesis of ginsenosides.

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