Chemistry Journal of Moldova

Natural product chemistry and synthesis

THE NATURAL PRODUCT CHEMISTRY OF TERPENOIDS - A TRIBUTE TO THE REMARKABLE LEGACY OF ACADEMICIAN PAVEL VLAD

Author(s):

Aculina Aricu


Field: Natural product chemistry and synthesis
Type: Invited paper
Issue: 2021 Volume 16, no.1
Pages: 8-29
Keywords: labdane diterpenoid, tetrahydrofuran, ozonolytic method, superacidic cyclisation, structure-ambra odour relationship.
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DOI: http://dx.doi.org/10.19261/cjm.2021.856
 
Abstract (PDF)
Graphical Abstract: The purpose of this paper is to put forward concisely some of the most valuable scientific contributions of academician Pavel Vlad and his disciples to the field of natural product chemistry of terpenoids. Under the guidance and with direct contribution of academician Pavel Vlad, new approaches to determining the absolute configuration of a series of labdanic diterpenoids and of converting them into bi-, tri- and tetra- cyclic compounds have been designed. Novel universal methods for synthesizing tetrahydrofurans from 1,4-glycols, olefins from tertiary alcoholic acetates, as well as dienones by means of photodehydrogenation of unsaturated cyclic ketons have been developed by academician Pavel Vlad.

Downloads: 131

COMPOSITION AND RADICAL SCAVENGING ACTIVITY OF THE EXTRACTS FROM DESCHAMPSIA ANTARCTICA É. DESV. PLANTS GROWN IN SITU AND IN VITRO

Author(s):

Roman Ivannikov, Iryna Laguta, Viktor Anishchenko, Iryna Skorochod, Pavlo Kuzema, Oksana Stavinskaya, Ivan Parnikoza, Oksana Poronnik, Ganna Myryuta, Viktor Kunakh


Field: Natural product chemistry and synthesis
Type: Research paper
Issue: 2021 Volume 16, no.1
Pages: 105-114
Keywords: phenolic acid, flavonoid, antiradical activity, plant extract, Deschampsia antarctica.
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DOI: http://dx.doi.org/10.19261/cjm.2021.841

Abstract (PDF) 
Graphical Abstract: The work was aimed at studying the phytochemicals available in D. antarctica plants from various sites on Antarctic Islands, introducing the plants into in vitro culture and comparing the extracts from the plants grown in situ and in vitro. All the extracts were found to contain high amount of phenols, with luteolin and hydroxybenzoic acids derivatives being the main phytochemicals in the extracts from the plants grown in situ and in vitro. Being diluted by 10 times, the extracts scavenged 50÷90% of DPPH• radicals, 20÷40% of NO• radicals and 40÷60% of OH• radicals. Despite the differences in composition, extracts from the plants grown in situ and in vitro showed similar radical scavenging activity.


 

Downloads: 117

(+)-LARIXOL AND LARIXYL ACETATE: SYNTHESES, PHYTOCHEMICAL STUDIES AND BIOLOGICAL ACTIVITY ASSESSMENTS

Author(s):

Alexandru Ciocarlan


Field: Natural product chemistry and synthesis
Type: Review
Issue: 2021 Volume 16, no.1
Pages: 30-45
Keywords: (+)-larixol, larixyl acetate, synthesis, chemical composition, biological activity.
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DOI: http://dx.doi.org/10.19261/cjm.2021.836
 
Abstract (PDF)
Graphical Abstract: (+)-Larixol is a well-known labdane-type diterpenoid widely used in organic synthesis. The present review covers the (+)-larixol based chemical transformations, the results of phytochemical analysis of new (+)-larixol containing species, as well as recent data on biological activity of (+)-larixol and practical applications where it is mentioned.


 

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ONE-STEP SELECTIVE SYNTHESIS OF 13-EPI-MANOYL OXIDE

Author(s):

Olga Morarescu, Marionela Traistari, Alic Barba, Gheorghe Duca, Nicon Ungur, Veaceslav Kulcițki


Field: Natural product chemistry and synthesis
Type: Research paper
Issue: 2021 Volume 16, no.1
Pages: 99-104
Keywords: sclareol, cyclization, superacid, ether, labdane.
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DOI: http://dx.doi.org/10.19261/cjm.2021.820

Abstract (PDF)
Supplementary Material (PDF)
Graphical Abstract: The selective one-step synthesis of 13-epi-manoyl oxide is reported based on a low-temperature superacidic cyclization of sclareol. The reaction conditions have been finely tuned in order to achieve a 9:1 ratio between epimeric oxides in favor of the desired 13-epi-oxide.


 

Downloads: 56

LC-MS ANALYSIS AND ANTIOXIDANT ACTIVITY OF THE HYDRO-ALCOHOLIC EXTRACT OF MELISSA OFFICINALIS L. FROM ALGERIA

Author(s):

Brahim Ben Aicha, Rachid Rouabhi, Salim Gasmi, Chawki Bensouici, Hichem Mohammedi, Imad Mennai


Field: Natural product chemistry and synthesis
Type: Research paper
Issue: 2020 Volume 15, no.2
Pages: 78-87
Keywords: hydro-methanolic extract, Melissa officinalis L., LC-MS analysis, antioxidant activity.
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DOI: http://dx.doi.org/10.19261/cjm.2020.778

Abstract (PDF)
Supplementary Material (PDF)
Graphical Abstract: The present work focuses on evaluation of the chemical composition and antioxidant activity of the hydro-methanolic extract of Melissa officinalis from Algeria. The liquid chromatography-mass spectrometry analysis allowed the identification of six compounds: caffeic acid, caftaric acid, hydroxyjasmonic acid glucoside, caftaric acid glucoside, rosmarinic acid and sagerinic acid. The in-vitro antioxidant activity of the hydro-methanolic extract was evaluated by using four different methods including: radical scavenging assay (DPPH), scavenging activity (ABTS), cupric reducing antioxidant capacity, and ferric reducing power assay.  The extract exhibited a relatively strong antioxidant activity compared to the synthetic antioxidants. The highest radical scavenging activity was registered using DPPH and ABTS methods,  IC50= 20.53±2.64 μg/mL and 22.50±0.67 μg/mL, respectively. These results suggest that Melissa officinalis L. could be considered a potential source of natural antioxidants with potential interest in the agrochemical and pharmaceutical industries.


 


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THE USE OF SOME NON-CONVENTIONAL METHODS IN CHEMISTRY OF BICYCLOHOMOFARNESENIC METHYL ESTERS

Author(s):

Alexandru Ciocarlan, Lidia Lungu, Svetlana Blaja, Ion Dragalin, Aculina Aricu


Field: Natural product chemistry and synthesis
Type: Research paper
Issue: 2020 Volume 15, no.2
Pages: 69-77
Keywords: bicyclohomofarnesenic methyl ester, microwave irradiation, anodic electrooxidation, dye-sensitized photooxidation.
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DOI: http://dx.doi.org/10.19261/cjm.2020.791

Abstract (PDF)
Graphical Abstract: The present paper reports the results of microwave irradiation assisted method for the preparation of bicyclohomofarnesenic methyl esters versus classical Stoll and Hinder method. Moreover, the chemical transformations of bicyclohomofarnesenic methyl esters via anodic electrooxidation and dye-sensitized photooxidation were performed. A new method for the preparation of methyl 7-oxo-13,14,15,16-tetranorlabd-6,8(8)-dien-12-oate and the mechanism of electrochemical products formation are presented. The structure of all synthesized compounds was fully confirmed by spectral methods.


 

Downloads: 100

THE EFFECT OF SOLVENTS AND EXTRACTION PROCEDURE ON THE RECOVERY OF PHENOLIC COMPOUNDS AND THE ANTIOXIDANT CAPACITY OF ALGERIAN BASSIA MURICATA L. EXTRACTS

Author(s):

Hichem Mohammedi, Samira Idjeri-Mecherara, Fouad Menaceur, Aicha Hassani


Field: Natural product chemistry and synthesis
Type: Research paper
Issue: 2019 Volume 14, no.2
Pages: 79-89
Keywords: polyphenol, flavonoid, condensed tannin, antioxidant, Bassia muricata.
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DOI: http://dx.doi.org/10.19261/cjm.2019.637   
 
Abstract (PDF)
Graphical Abstract: This paper focuses on the study of the effect of extraction solvent choice on phenolic compounds contents and antioxidant activity of Bassia muricata. In this study, five different solvents namely: water, acetone, ethanol, methanol and hexane, and three extraction techniques were used to extract phenolic compounds: microwave-assisted extraction, Soxhlet and maceration. Total phenolics, total flavonoids and condensed tannins contents were determined. The results showed that different solvents with different polarity had a major effect on polyphenolic contents and antioxidant activity. Microwave-assisted extraction was the best suited for the extraction of antioxidant molecules when compared to Soxhlet and maceration.


 

Downloads: 170

SYNTHESIS OF NEW DI- AND TRINORLABDANE COMPOUNDS WITH 2-AMINO-1,3-THIAZOLE UNITS

Author(s):

Svetlana Blaja


Field: Natural product chemistry and synthesis
Type: Research paper
Issue: 2019 Volume 14, no.2
Pages: 72-78
Keywords: synthesis, di-norlabdane, tri-norlabdane, 2-amino-1,3-thiazole, cyclization reaction.
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DOI: http://dx.doi.org/10.19261/cjm.2019.609   
 
Abstract (PDF)
Graphical Abstract: TThe present paper reports the synthesis of new hybrid terpeno-heterocyclic compounds belonging to di- and tri-norlabdane series. Starting from natural labdane diterpenoide (-)-sclareol, via its intermediates 8α-hydroxy-15,16-dinorlabd-13-one and sclareolide, two di-norlabdane and three tri-norlabdane, previously unreported compounds possessing 2-amino-1,3-thiazole structural units were obtained in three and four steps, respectively, with acceptable to good overall yields. The structures of newly obtained compounds were confirmed by means of spectral IR, 1H and 13C NMR analyses.


 

Downloads: 115

NATURAL PRODUCTS FROM MARINE HETEROBRANCHS: AN OVERVIEW OF RECENT RESULTS

Author(s):

Margherita Gavagnin, Marianna Carbone, Maria Letizia Ciavatta, Ernesto Mollo


Field: Natural product chemistry and synthesis
Type: Invited paper
Issue: 2019 Volume 14, no.2
Pages: 9-31
Keywords: marine mollusk, natural product, chemical ecology, bioprospecting.
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DOI: http://dx.doi.org/10.19261/cjm.2019.617   
 
Abstract (PDF)
Graphical Abstract: Heterobranchs are a fascinating group of marine mollusks that are recognized as an important source of bioactive natural products. Often, these molecules, which are either selected from the diet or de novo biosynthesized by the mollusks, play a fundamental role for their survival being utilized as defensive chemicals against predators. A summary of the studies carried out, in the last decade, on heterobranchs is presented here. A number of new compounds exhibiting different molecular architectures were chemically characterized. 


 

Downloads: 79

CHEMICAL COMPOSITION AND ANTIMICROBIAL ACTIVITY OF THE LEVISTICUM OFFICINALE W.D.J. KOCH ESSENTIAL OIL

Author(s):

Alexandru Ciocarlan, Ion Dragalin, Aculina Aricu, Lucian Lupascu, Nina Ciocarlan, Violeta Popescu


Field: Natural product chemistry and synthesis
Type: Research paper
Issue: 2018 Volume 13, no.2
Pages: 63-68
Keywords: Levisticum officinale, essential oil, GC-MS analysis, antibacterial activity, antifungal activity.
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DOI: http://dx.doi.org/10.19261/cjm.2018.514 

Abstract (PDF)
Graphical Abstract: The chemical composition of industrially obtained Levisticum officinale W.D.J. Koch (lovage) essential oil of Moldovan origin was analysed by means of chromatographic (GC-MS) and spectral (IR, 1H and 13C NMR) methods. The obtained results show that the main components of L. officinale essential oil are monoterpenic hydrocarbons which make up to 53.50% of the total number of components. L. officinale essential oil is also characterized by a high content of oxygenated monoterpenes (alcohols, cetones and esters), which reaches up to 33.60%. For the first time the presence of 6-butyl-cyclohepta-1,4-diene (0.56%) and 7-formyl-4-methyl-cumarine (0.15%) in lovage essential oil is reported. Antibacterial and antifungal activities of mentioned oil were evaluated in vitro on five strains of microorganisms. It was found that lovage volatile oil (L .officinale) exhibits high antibacterial and antifungal properties in the range of concentrations 0.015-0.030%.


 

Downloads: 189