New Derivatives of Lupeol and Their Biological Activity

Molbank ◽  
10.3390/m1306 ◽  
2021 ◽  
Vol 2021 (4) ◽  
pp. M1306
Author(s):  
Hoang-Thuy-Tien Le ◽  
Quoc-Cuong Chau ◽  
Thuc-Huy Duong ◽  
Quyen-Thien-Phuc Tran ◽  
Nguyen-Kim-Tuyen Pham ◽  
...  
Keyword(s):  
Biological Activity ◽  
Natural Product ◽  
Starting Material ◽  
Chemical Structures ◽  
Spectroscopic Analyses ◽  
Ic50 Value ◽  
Derivatives Of

The natural product lupeol (1) was isolated from Bombax ceiba leaves, which were used as starting material in the semisynthetic approach. Three new derivatives (2a, 2b, and 3) were synthesized using oxidation and aldolization. Their chemical structures were elucidated by spectroscopic analyses (HRESIMS and NMR). Compounds 3 showed significant α-glucosidase inhibition with an IC50 value of 202 µM, whereas 2a and 2b were inactive.

scholarly journals Antimalarial Properties of Dunnione Derivatives as NQO2 Substrates

Molecules ◽  
2019 ◽  
Vol 24 (20) ◽  
pp. 3697 ◽  
Author(s):  
Monivan Chhour ◽  
Agnès Aubouy ◽  
Sandra Bourgeade-Delmas ◽  
Pierre Pério ◽  
Hélène Ternet-Fontebasso ◽  
...  
Keyword(s):  
Reactive Oxygen Species ◽  
Natural Product ◽  
Murine Model ◽  
Blood Cells ◽  
Oxygen Species ◽  
Ic50 Value ◽  
Quinone Reductases ◽  
Derivatives Of

Dunnione, a natural product isolated from the leaves of Streptocarpus dunnii (Gesneriaceae), acts as a substrate for quinone-reductases that may be associated with its antimalarial properties. Following our exploration of reactive oxygen species-producing compounds such as indolones, as possible new approaches for the research of new ways to treat this parasitosis, we explored derivatives of this natural product and their possible antiplasmodial and antimalarial properties, in vitro and in vivo, respectively. Apart from one compound, all the products tested had weak to moderate antiplasmodial activities, the best IC50 value being equal to 0.58 µM. In vivo activities in the murine model were moderate (at a dose of 50 mg/kg/mice, five times higher than the dose of chloroquine). These results encourage further pharmacomodulation steps to improve the targeting of the parasitized red blood cells and antimalarial activities.

Toward the Synthesis of Rimarikiamide A

2021 ◽  
Author(s):  
◽  
Ashton Nikylla Asbury
Keyword(s):  
Biological Activity ◽  
New Zealand ◽  
Natural Product ◽  
Therapeutic Agent ◽  
Starting Material ◽  
Marine Natural Product ◽  
Full Potential ◽  
Linear Product

<p>Rimarikiamide A is a linear diterpenoid marine natural product featuring an unusual taurine structural moiety. Rimarikiamide A was isolated from the sea sponge Latrunculia brevis found in the Rimariki Islands in northern New Zealand, and was shown to elicit low μM cytotoxicity against HL-60 cells. Unfortunately, only 400 μg of rimarikiamide A was isolated from 700 g of sea sponge, making the characterisation of the two chiral centres impossible by spectroscopic means. To explore the full potential of rimarikiamide A as a therapeutic agent, the molecule must be synthesised in a stereoselective manner or from a starting material of known stereochemistry, fully characterised, and tested for biological activity. A Barbier coupling of two terpene units is required early in the proposed synthesis of Rimarikiamide A, and previous attempts have failed to generate the desired linear product. In this work, the suitability of a titanium-mediated Barbier coupling was investigated, and proved successful for the generation of the desired linear product.</p>

scholarly journals Marine-Derived Natural Lead Compound Disulfide-Linked Dimer Psammaplin A: Biological Activity and Structural Modification

Marine Drugs ◽  
2019 ◽  
Vol 17 (7) ◽  
pp. 384 ◽  
Author(s):  
Qinxue Jing ◽  
Xu Hu ◽  
Yanzi Ma ◽  
Jiahui Mu ◽  
Weiwei Liu ◽  
...  
Keyword(s):  
Natural Products ◽  
Biological Activity ◽  
Total Synthesis ◽  
Marine Natural Products ◽  
Structural Modification ◽  
Research Focus ◽  
Chemical Structures ◽  
Therapeutic Drugs ◽  
Psammaplin A ◽  
Derivatives Of

Marine natural products are considered to be valuable resources that are furnished with diverse chemical structures and various bioactivities. To date, there are seven compounds derived from marine natural products which have been approved as therapeutic drugs by the U.S. Food and Drug Administration. Numerous bromotyrosine derivatives have been isolated as a type of marine natural products. Among them, psammaplin A, including the oxime groups and carbon–sulfur bonds, was the first identified symmetrical bromotyrosine-derived disulfide dimer. It has been found to have a broad bioactive spectrum, especially in terms of antimicrobial and antiproliferative activities. The highest potential indole-derived psammaplin A derivative, UVI5008, is used as an epigenetic modulator with multiple enzyme inhibitory activities. Inspired by these reasons, psammaplin A has gradually become a research focus for pharmacologists and chemists. To the best of our knowledge, there is no systematic review about the biological activity and structural modification of psammaplin A. In this review, the pharmacological effects, total synthesis, and synthesized derivatives of psammaplin A are summarized.

Synthesis and Biological Activity of Novel Deoxynojirimycin Derivatives as Potent α-Glucosidase Inhibitors

2013 ◽  
Vol 68 (4) ◽  
pp. 383-390 ◽  
Keyword(s):  
Biological Activity ◽  
Kinetic Parameters ◽  
Competitive Inhibitor ◽  
Skeletal Structures ◽  
Glucosidase Inhibitors ◽  
Ic50 Value ◽  
Inhibitory Activities ◽  
Derivatives Of

Thirteen 1-deoxynojirimycin (DNJ) derivatives of five different skeletal structures were designed and synthesized. The newly synthesized compounds were evaluated using an in vitro a- glucosidase assay, and kinetic parameters (Ki, IC50) were measured. Some DNJ derivatives showed weak a-glucosidase inhibitory activities, and the compounds 1-(3-benzyloxy-2-hydroxypropyl)- 2-hydroxymethyl-piperidine-3,4,5-triol (2a) and 1-{3-[1-(4-fluorophenyl)-1H-[1,2,3]triazol-4-ylmethoxy]- 2-hydroxypropyl}-2-hydroxymethyl-piperidine-3,4,5-triol (13d) showed activities comparable to that of DNJ. While 2a was found to be a reversible, non-competitive inhibitor of a-glucosidase with a Ki value of 1.56X10-4 M and an IC50 value of 3.07X10x4 M, 13d was a reversible, competitive inhibitor of a-glucosidase with a Ki value of 2.08X10-4 M and an IC50 value of 3.31X10-4 M.

Toward the Synthesis of Rimarikiamide A

2021 ◽  
Author(s):  
◽  
Ashton Nikylla Asbury
Keyword(s):  
Biological Activity ◽  
New Zealand ◽  
Natural Product ◽  
Therapeutic Agent ◽  
Starting Material ◽  
Marine Natural Product ◽  
Full Potential ◽  
Linear Product

<p>Rimarikiamide A is a linear diterpenoid marine natural product featuring an unusual taurine structural moiety. Rimarikiamide A was isolated from the sea sponge Latrunculia brevis found in the Rimariki Islands in northern New Zealand, and was shown to elicit low μM cytotoxicity against HL-60 cells. Unfortunately, only 400 μg of rimarikiamide A was isolated from 700 g of sea sponge, making the characterisation of the two chiral centres impossible by spectroscopic means. To explore the full potential of rimarikiamide A as a therapeutic agent, the molecule must be synthesised in a stereoselective manner or from a starting material of known stereochemistry, fully characterised, and tested for biological activity. A Barbier coupling of two terpene units is required early in the proposed synthesis of Rimarikiamide A, and previous attempts have failed to generate the desired linear product. In this work, the suitability of a titanium-mediated Barbier coupling was investigated, and proved successful for the generation of the desired linear product.</p>

scholarly journals Isolation of Two New Compounds and Other Constituents from Leaves of Piper crocatum and Study of Their Soluble Epoxide Hydrolase Activities

Molecules ◽  
2019 ◽  
Vol 24 (3) ◽  
pp. 489 ◽  
Author(s):  
Hong Li ◽  
Seo Yang ◽  
Young Kim ◽  
Wei Li
Keyword(s):  
Inhibitory Activity ◽  
Epoxide Hydrolase ◽  
2D Nmr ◽  
Soluble Epoxide Hydrolase ◽  
Chemical Structures ◽  
Phenolic Glucosides ◽  
Spectroscopic Analyses ◽  
Ic50 Value ◽  
Reported Data ◽  
New Compounds

Two new phenolic glucosides, pipercroside A and B (1 and 2), along with 10 known compounds were isolated from the leaves of Piper crocatum Ruiz & Pav. Their chemical structures were elucidated through extensive spectroscopic analyses, including 1D and 2D NMR experiments and HR-ESI-MS analysis and comparison with previously reported data. All the isolated compounds were assessed for soluble epoxide hydrolase (sEH) inhibitory activity. Among them, erigeside II (5) showed inhibitory activity with an IC50 value of 58.5 µM.

Synthetic derivatives of pulchrol: An antiparasitic natural product

Planta Medica ◽  
2016 ◽  
Vol 81 (S 01) ◽  
pp. S1-S381
Author(s):  
P Terrazas ◽  
O Sterner
Keyword(s):  
Natural Product ◽  
Synthetic Derivatives ◽  
Derivatives Of

Unzipping Natural Products: Improved Natural Product Structure Predictions by Ensemble Modeling and Fingerprint Matching

2018 ◽  
Author(s):  
William A. Shirley ◽  
Brian P. Kelley ◽  
Yohann Potier ◽  
John H. Koschwanez ◽  
Robert Bruccoleri ◽  
...  
Keyword(s):  
Natural Products ◽  
Open Source ◽  
Natural Product ◽  
Gene Cluster ◽  
Public Domain ◽  
Product Structure ◽  
Fingerprint Matching ◽  
Ensemble Modeling ◽  
Chemical Structures ◽  
Source Gene

This pre-print explores ensemble modeling of natural product targets to match chemical structures to precursors found in large open-source gene cluster repository antiSMASH. Commentary on method, effectiveness, and limitations are enclosed. All structures are public domain molecules and have been reviewed for release.

Synthesis and Biological Activity of Embelin and its Derivatives: An Overview

2020 ◽  
Vol 20 (5) ◽  
pp. 396-407 ◽  
Author(s):  
Zhaojun Sheng ◽  
Siyuan Ge ◽  
Min Gao ◽  
Rongchao Jian ◽  
Xiaole Chen ◽  
...  
Keyword(s):  
Biological Activity ◽  
Biological Effects ◽  
New Drugs ◽  
Hydroxyl Groups ◽  
Carbonyl Groups ◽  
Cellular Mechanisms ◽  
Embelia Ribes ◽  
Naturally Occurring ◽  
Ic50 Value ◽  
Apoptosis Protein

Embelin is a naturally occurring para-benzoquinone isolated from Embelia ribes (Burm. f.) of the Myrsinaceae family, and contains two carbonyl groups, a methine group and two hydroxyl groups. With embelin as the lead compound, more than one hundred derivatives have been reported. Embelin is well known for its ability to antagonize the X-linked inhibitor of apoptosis protein (XIAP) with an IC50 value of 4.1 μM. The potential of embelin and its derivatives in the treatment of various cancers has been extensively studied. In addition, these compounds display a variety of other biological effects: antimicrobial, antioxidant, analgesic, anti-inflammatory, anxiolytic and antifertility activity. This paper reviews the recent progress in the synthesis and biological activity of embelin and its derivatives. Their cellular mechanisms of action and prospects in the research and development of new drugs are also discussed.

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