Parguerenes Revisited: New Brominated Diterpenes From the Southern Australian Marine Red Alga Laurencia Filiformis

1996 ◽  
Vol 49 (1) ◽  
pp. 19 ◽  
Author(s):  
SJ Rochfort ◽  
RJ Capon
Keyword(s):  
Natural Product ◽  
Biosynthetic Pathway ◽  
Spectroscopic Analysis ◽  
Red Alga ◽  
Biosynthetic Precursor ◽  
Chemical Correlation ◽  
New Compounds

Five new pargueranes, 15-bromoparguer-9(11)-ene-2,7,16,19-tetrol 2,7,16-triacetate (20), 15-bromoparguer-9(11)-ene-2,7,16-triol 2,7-diacetate (21), 15-bromoparguer-9(11)-ene-2,16-diol 2-acetate (22), 15-bromoparguer-9(11)-en-16-ol (23) and 15-bromoisoparguer-9(11)-en-16-ol (24), together with a plausible biosynthetic precursor, preparguerene (25), two known parguerenes , 15-bromoparguer-9(11)-ene-2,7,16,19-tetrol tetraacetate (4) and 15-bromoparguer-9(11)-ene-2,7,16-triol 2,16 diacetate (7), and the known algal metabolites (-)- aromadendrene (17), austradiol acetate (18) and austradiol diacetate (19), have been isolated from a collection of the southern Australian marine red alga Laurencia filiformis. The known synthetic parguerane 15-bromoparguer-9(11)-ene-2,7-16-triol triacetate (5) was also found for thefirst time as a natural product. In addition to securing the structures of new compounds by chemical correlation and detailed spectroscopic analysis, a lausible biosynthetic pathway has been proposed linking preparguerene, parguerene, isoparguerene and secoparguerene carbon skeletons.

Trunculin-F and Contrunculin-A and -B: Novel Oxygenated Norterpenes From a Southern Australian Marine Sponge, Latrunculia conulosa

1993 ◽  
Vol 46 (9) ◽  
pp. 1363 ◽  
Author(s):  
MS Butler ◽  
RJ Capon
Keyword(s):  
Methyl Ester ◽  
Natural Product ◽  
Marine Sponge ◽  
Coastal Waters ◽  
Spectroscopic Analysis ◽  
Marine Natural Product ◽  
New Compounds ◽  
Absolute Stereochemistry

A specimen of Latrunculia conulosa from southern Australian coastal waters, previously observed to contain conulosin-A (6) and conulosin-B (7), has also been found to yield the known marine natural product trunculin-C methyl ester (14), along with three new norterpenes, trunculin-F (10), contrunculin-A (11) and contrunculin-B (12). Trunculin-F (10) was isolated, characterized and identified as its methyl ester (13), and its absolute stereochemistry determined by Horeau analysis. The structures for all new compounds were secured by detailed spectroscopic analysis.

A New Macrocyclic γ-Pyrone From a Southern Australian Marine Red Alga

1995 ◽  
Vol 48 (8) ◽  
pp. 1485 ◽  
Author(s):  
L Murray ◽  
G Currie ◽  
RJ Capon
Keyword(s):  
Spectroscopic Analysis ◽  
Red Alga ◽  
First Time

A new macrocyclic γ- pyrone (10) and two known γ- pyrones (2) and (6) have been isolated from a Victorian collection of Phacelocarpus peperocarpos. The Z geometry about ∆17,18 in (2) has been established for the first time. All structure elucidations were supported by detailed spectroscopic analysis.

Unsymmetrical phthalocyanines with cyclopalladated azo functions

2012 ◽  
Vol 16 (02) ◽  
pp. 192-199 ◽  
Author(s):  
H. Yasemin Yenilmez Akkurt ◽  
Ali ihsan Okur ◽  
Ahmet Gül
Keyword(s):  
Organic Solvents ◽  
Column Chromatography ◽  
Spectroscopic Analysis ◽  
Palladium Complex ◽  
Palladium Complexes ◽  
High Solubility ◽  
Synthetic Procedure ◽  
Different Types ◽  
New Compounds ◽  
Very High

In this study, a synthetic procedure for unsymmetrical metallophthalocyanines of the form M[Pc(AB3)], where A and B refer to two different types of peripheral functionality, has been developed and the new compounds have been converted to monomeric and dimeric palladium complexes. Asymmetrically substituted phthalocyanines were synthesized with the well-known statistical condensation method, by using two differently substituted precursors, namely 4-(2-ethoxyethoxy)-1-2-dicyanobenzene (1) and 4-{4-[Z/E]-phenylazo]-1-naphthyl}oxy-1,2-dicyanobenzene (2). Consequently, electron-donating 2-ethoxyethoxy groups and electron-withdrawing palladium complex are present in the same structure. Cyclopalladation was performed with [Pd(PhCN)2Cl2] to yield the bis-μ-chloro-bridged dimers and subsequently, the corresponding monomers were obtained by refluxing with three equivalents of potassium acetylacetonate. The resulting products were purified by column chromatography and characterized by several chemical and spectroscopic analysis methods. All compounds have very high solubility in organic solvents due to the presence of 2-ethoxyethoxy moiety.

scholarly journals The Tripod for Bacterial Natural Product Discovery: Genome Mining, Silent Pathway Induction, and Mass Spectrometry-Based Molecular Networking

mSystems ◽  
2018 ◽  
Vol 3 (2) ◽  
Author(s):  
Daniela B. B. Trivella ◽  
Rafael de Felicio
Keyword(s):  
Mass Spectrometry ◽  
Natural Products ◽  
Natural Product ◽  
Biosynthetic Pathway ◽  
Genome Mining ◽  
Chemical Compounds ◽  
Gene Clusters ◽  
Tandem Mass ◽  
Molecular Networking ◽  
Natural Product Discovery

ABSTRACT Natural products are the richest source of chemical compounds for drug discovery. Particularly, bacterial secondary metabolites are in the spotlight due to advances in genome sequencing and mining, as well as for the potential of biosynthetic pathway manipulation to awake silent (cryptic) gene clusters under laboratory cultivation. Further progress in compound detection, such as the development of the tandem mass spectrometry (MS/MS) molecular networking approach, has contributed to the discovery of novel bacterial natural products. The latter can be applied directly to bacterial crude extracts for identifying and dereplicating known compounds, therefore assisting the prioritization of extracts containing novel natural products, for example. In our opinion, these three approaches—genome mining, silent pathway induction, and MS-based molecular networking—compose the tripod for modern bacterial natural product discovery and will be discussed in this perspective.

scholarly journals Quantum Mechanics-Based Structure Analysis of Cyclic Monoterpene Glycosides from Rhodiola Rosea

2020 ◽  
Author(s):  
Yu Tang ◽  
J. Brent Friesen ◽  
David C. Lankin ◽  
James McAlpine ◽  
Dejan Nikolić ◽  
...  
Keyword(s):  
Quantum Mechanics ◽  
Spectroscopic Analysis ◽  
Spatial Arrangement ◽  
Spin Coupling ◽  
Rhodiola Rosea ◽  
Analysis Software ◽  
Nmr Data ◽  
Biological Studies ◽  
Spin Analysis ◽  
New Compounds

NMR- and MS-guided metabolomic mining for new phytoconstituents from a widely used dietary supplement, <i>Rhodiola rosea</i>, yielded two new (+)-myrtenol glycosides, <b>1</b> and <b>2</b>, and two new cuminol glycosides (<b>3</b> and <b>4</b>), along with three known analogues (<b>5</b>–<b>7</b>). The structures of the new compounds were determined by extensive spectroscopic analysis. Quantum Mechanics-driven <sup>1</sup>H iterative Full Spin Analysis (QM-HiFSA) decoded the spatial arrangement of the methyl groups in <b>1</b> and <b>2</b>, as well as other features not recognizable by conventional methods, including higher order spin-coupling effects. The application of QM-HiFSA will provide a definitive reference point for future phytochemical and biological studies of <i>R. rosea</i> as a resilience botanical. Application of a new NMR data analysis software package, CT, for QM-based iteration of NMR spectra is also discussed.

scholarly journals A Systematic Review of Recently Reported Marine Derived Natural Product Kinase Inhibitors

Marine Drugs ◽  
2019 ◽  
Vol 17 (9) ◽  
pp. 493 ◽  
Author(s):  
Li ◽  
Wang ◽  
Zhang ◽  
Zhang ◽  
Sajeevan ◽  
...  
Keyword(s):  
Small Molecules ◽  
Natural Product ◽  
Drug Targets ◽  
Kinase Inhibitors ◽  
Protein Kinase Inhibitors ◽  
Disease States ◽  
Clinical Drugs ◽  
Kinase Inhibitory Activity ◽  
New Compounds ◽  
Further Development

Protein kinases are validated drug targets for a number of therapeutic areas, as kinase deregulation is known to play an essential role in many disease states. Many investigated protein kinase inhibitors are natural product small molecules or their derivatives. Many marine-derived natural products from various marine sources, such as bacteria and cyanobacteria, fungi, animals, algae, soft corals, sponges, etc. have been found to have potent kinase inhibitory activity, or desirable pharmacophores for further development. This review covers the new compounds reported from the beginning of 2014 through the middle of 2019 as having been isolated from marine organisms and having potential therapeutic applications due to kinase inhibitory and associated bioactivities. Moreover, some existing clinical drugs based on marine-derived natural product scaffolds are also discussed.

scholarly journals New Holostan-type Triterpene Glycosides from the Sea Cucumber Apostichopus Japonicus

2012 ◽  
Vol 7 (11) ◽  
pp. 1934578X1200701 ◽  
Author(s):  
Zenglei Wang ◽  
Wei Gong ◽  
Guoquan Sun ◽  
Hua Tang ◽  
Baoshu Liu ◽  
...  
Keyword(s):  
Antifungal Activity ◽  
Sea Cucumber ◽  
Spectroscopic Analysis ◽  
Apostichopus Japonicus ◽  
Triterpene Glycosides ◽  
New Compounds

Two new holostan-type glycosides, holotoxin D1 (1) and 25,26-dihydroxy-holotoxin A1 (2), together with two known analogues, stichlorosides C1 (3) and bivittoside D (4), were isolated from the sea cucumber Apostichopus japonicus Selenka. The structures of the new compounds were elucidated on the basis of detailed spectroscopic analysis. Glycosides 1 and 3 exhibited potent antifungal activity.

scholarly journals Dechdigliotoxins A–C, Three Novel Disulfide-Bridged Gliotoxin Dimers from Deep-Sea Sediment Derived Fungus Dichotomomyces cejpii

Marine Drugs ◽  
2019 ◽  
Vol 17 (11) ◽  
pp. 596 ◽  
Author(s):  
Zhaoming Liu ◽  
Zhen Fan ◽  
Zhanghua Sun ◽  
Hongxin Liu ◽  
Weimin Zhang
Keyword(s):  
Tumor Cell ◽  
Quantum Chemical Calculations ◽  
Cell Lines ◽  
Deep Sea ◽  
Quantum Chemical ◽  
Biosynthetic Pathway ◽  
Spectroscopic Analysis ◽  
Tumor Cell Lines ◽  
Disulfide Linkage ◽  
Deep Sea Sediment

Dechdigliotoxins A–C (1–3), which represented the first examples of gliotoxin dimers with an unprecedented exocyclic disulfide linkage, were obtained from a deep-sea derived fungus Dichotomomyces cejpii FS110. The structures of these compounds were elucidated on the basis of spectroscopic analysis and the absolute configurations were unambiguously determined through quantum chemical calculations, as well as DP4+ probability simulations. The proposed biosynthetic pathway suggested 1–3 were generated from unusual L-Phe and D-Ser. All the isolates were evaluated for their cytotoxicity against four tumor cell lines.

scholarly journals New Cyclopentyl Fatty Acid and Cyanohydrin Glycosides from Fruits of Hydnocarpus hainanensis

2017 ◽  
Vol 12 (2) ◽  
pp. 1934578X1701200
Author(s):  
Thanh Tra Nguyen ◽  
Bich Ngan Truong ◽  
Huong Doan Thi Mai ◽  
Marc Litaudon ◽  
Van Hung Nguyen ◽  
...  
Keyword(s):  
Fatty Acid ◽  
Cytotoxic Activity ◽  
Cell Line ◽  
Spectroscopic Analysis ◽  
2D Nmr ◽  
New Compounds ◽  
Line Compound

Three new compounds, hydnohainanic acid (1), and hydnohainanin A (2) and B (3) were isolated from the fruits of Hydnocarpus hainanensis (Achariaceae). Their structures were determined by spectroscopic analysis, including 2D NMR, and MS. Compounds 1-3 were evaluated for their cytotoxic activity against the KB cell line. Compound 1 had a moderate cytotoxicity with an IC50 value of 32.5 μg/mL, while the two remaining compounds did not exhibit inhibition, even at a concentration of 128 μg/mL.

scholarly journals A Biosynthetic Pathway for BE-7585A, a 2-Thiosugar-Containing Angucycline-Type Natural Product

2010 ◽  
Vol 132 (21) ◽  
pp. 7405-7417 ◽  
Author(s):  
Eita Sasaki ◽  
Yasushi Ogasawara ◽  
Hung-wen Liu
Keyword(s):  
Natural Product ◽  
Biosynthetic Pathway
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