Dianthiamides A-E, Proline-Containing Orbitides from Dianthus chinensis
Jin Woo Lee1, Jun Gu Kim1, Jae Sang Han1
1College of Pharmacy, Chungbuk National University, Cheongju 28160, Korea.
Molecules (Basel, Switzerland)
|December 10, 2021
Summary
Researchers discovered five new plant-derived cyclic peptides, dianthiamides A-E, from Dianthus chinensis. Dianthiamide A showed weak cytotoxic activity against A549 lung cancer cells.
Area of Science:
- Natural Product Chemistry
- Medicinal Chemistry
- Pharmacognosy
Background:
- Orbitides are plant-derived cyclic peptides known for diverse biological activities.
- Dianthus chinensis is a potential source for novel bioactive compounds.
Purpose of the Study:
- To isolate and characterize new bioactive orbitides from Dianthus chinensis.
- To evaluate the cytotoxic potential of isolated compounds.
Main Methods:
- Phytochemical investigation using spectroscopic methods (NMR, MS/MS).
- Structure elucidation of isolated compounds.
- Determination of absolute configurations via Marfey's method.
- Cytotoxicity assays against A549 cell line.
Main Results:
- Five new proline-containing orbitides, dianthiamides A-E (1-5), were isolated.
- Structures were confirmed using extensive NMR and mass spectrometry data.
- Dianthiamide A (1) demonstrated weak cytotoxic activity (IC50 = 47.9 μM) against A549 cells.
Conclusions:
- Dianthus chinensis yielded novel cyclic peptides with potential bioactivity.
- Dianthiamide A represents a lead compound for further investigation in cancer research.
Related Concept Videos
01:19Diazonium Group Substitution: –OH and –H
2.9K
Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
2.9K
03:35Hybridization of Atomic Orbitals II
35.1K
sp3d and sp3d 2 Hybridization
35.1K
01:13Five-Membered Heterocyclic Aromatic Compounds: Overview
4.5K
Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom,...
4.5K
01:11ortho–para-Directing Activators: –CH3, –OH, –NH2, –OCH3
6.6K
All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
6.6K
01:18π Molecular Orbitals of the Allyl Cation and Anion
4.7K
An allyl group is a three-carbon conjugated system where the sp³-hybridized allylic carbon is bonded to a CH=CH2 group via a single bond. Allyl anions can be obtained by treating propene with a strong base that can deprotonate methyl groups. Allyl cations are formed as intermediates during substitution reactions involving allylic halides. In both cases, the hybridization of the allylic carbon changes from sp3 to sp2, giving rise to a carbon chain with three sp2-hybridized carbons, each with...
4.7K
01:22Indirect-Acting Cholinergic Agonists: Pharmacokinetics
1.2K
Indirect-acting cholinergic agonists, or anticholinesterases, enhance the body's cholinergic activity by inhibiting acetylcholine's breakdown. They are categorized as reversible or irreversible agents based on their mechanism of action. They are further classified into short-acting, intermediate-acting, and long-acting agents based on their duration of action.
Reversible agents containing quaternary amines, such as neostigmine and edrophonium, are not easily absorbed orally because they...
Reversible agents containing quaternary amines, such as neostigmine and edrophonium, are not easily absorbed orally because they...
1.2K