Natural product chemistry and synthesis

SYNTHESIS OF CYCLE B FUNCTIONALIZED DERIVATIVES OF (+)-LARIXOL

Author(s):

Alexandru Ciocarlan, Lidia Lungu, Svetlana Blaja, Sergiu Shova, Aculina Aricu

Field: Natural product chemistry and synthesis
Type: Research paper
Issue: 2024 Volume 19, no.1
Pages: 69-75

Keywords: (+)-larixol, enolacetylation, dye-sensitized photooxidation, reduction, X-ray analysis.
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https://doi.org/10.19261/cjm.2024.1156

Abstract (PDF)
Supplementary Material (PDF)
Graphical Abstract: The main purpose of this research was the synthesis of highly functionalized derivatives of (+)-larixol by combination of classical and nonconventional method, like dye-sensitized photooxidation with preservation of outside chain. As a result, a series of four new cycle B derivatives of (+)-larixol were obtained. The structure of all synthesized compounds was fully confirmed by spectral method (IR, ¹H and ¹³C NMR) and for compound containing endoperoxide functional group, additionally by single crystal X-ray diffraction analysis.

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CHEMICAL COMPOSITION AND ANTIOXIDANT ACTIVITY OF LIPIDS FROM FICUS CARICA L. FRUITS

Author(s):

Hadjira Naoui, Mohamed Benalia, Soumaya Hachani, Amar Djeridane, Ziyad Ben Ahmed, Veronique Seidel, Mohamed Yousfi

Field: Natural product chemistry and synthesis
Type: Research paper
Issue: 2023 Volume 18, no.1
Pages: 92-101

Keywords: oil extract, fatty acid, tocopherol, sterol, antioxidant activity.
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https://doi.org/10.19261/cjm.2022.1029

Abstract (PDF)
Graphical Abstract: Samples of oils from seven types of Ficus carica L. fruits from Algeria were investigatedwith the aim to assess the chemical characteristics, quantifying sterols and tocopherols, and to analyse the fatty acids profiles using gas chromatography, and evaluation of antioxidant activity by 1,1-diphenyl-2-picrylhydrazyl method and total antioxidant activity using phosphomolybdenum methods. The results showed that the major unsaturated fatty acids of different lipid classes were linoleic (11.70-34.74%) and linolenic (1.15-35.27%), the main saturated fatty acids was palmitic. Aditionally, it was demonstrated for the first time that the studied figs oils possessed good antioxidant activity which may be associated with their alleged health benefits.

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SYNTHESIS AND EVALUATION OF ANTIMICROBIAL ACTIVITY OF TETRANORLABDANE COMPOUNDS BEARING 1,3,4-THIADIAZOLE UNITS

Author(s):

Svetlana Blaja, Lidia Lungu, Alexandru Ciocarlan, Nicoleta Vornicu, Aculina Aricu

Field: Natural product chemistry and synthesis
Type: Research paper
Issue: 2023 Volume 18, no.1
Pages: 86-91

Keywords: (+)-sclareolide, tetranorlabdane compound, 1,3,4-thiadiazole, thiosemicarbazone, antimicrobial activity.
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https://doi.org/10.19261/cjm.2022.1026

Abstract (PDF)
Graphical Abstract: The study describes the synthesis of novel tetranorlabdane compounds bearing 1,3,4-thiadiazole units and intermediary tetranorlabdane compounds with thiosemicarbazone fragment. The structures of the synthesized compounds were confirmed using IR and ¹H, ¹³C, and ¹⁵N NMR spectroscopy. The in vitro antifungal and antibacterial activities of the tetranorlabdane compounds with thiosemicarbazone and 1,3,4-thiadiazole units have been evaluated. One of the tested compounds has an excellent activity against five strains of fungi and two species of bacteria at minimum inhibitory concentration values of 0.125 and 2.5 µg/mL, respectively.

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FROM (-)-SCLAREOL TO NORLABDANE HETEROCYCLIC HYBRID COMPOUNDS

Author(s):

Alexandru Ciocarlan

Field: Natural product chemistry and synthesis
Type: Review
Issue: 2022 Volume 17, no.2
Pages: 19-34

Keywords: (-)-sclareol, norlabdane-heterocyclic compound, antimicrobial activity, biological activity.
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https://doi.org/10.19261/cjm.2022.958

Abstract (PDF)

Graphical Abstract: This review relates to chemistry of the well-known biologically active natural labdane diterpenoid (-)-sclareol easily available from Clary sage (Salvia sclarea L.). It is mainly used in industry, especially for synthesis of fragrance compounds and natural analogs. The paper covers achievements on the synthesis, structure determination and biological activity of molecular hybrid compounds bearing hydrazide and thiosemicarbazone fragments or diazine, 1,2,4-triazole, carbazole, 1,3-thiazole, 1,3,4-oxadiazole, 1,3,4-thiadiazole units prepared based on it.

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ISOMERIZATION OF LIMONENE ON ZEOLITE-CONTAINING CATALYSTS BASED ON KAOLIN

Author(s):

Lyubov Patrylak, Stepan Zubenko, Serhyi Konovalov, Anzhela Yakovenko, Volodymyr Povazhnyi, Oleksandra Pertko, Yulia Voloshyna, Oleksandr Melnychuk, Mykhailo Filonenko

Field: Natural product chemistry and synthesis
Type: Research paper
Issue: 2022 Volume 17, no.2
Pages: 84-93

Keywords: kaolin, zeolite, limonene isomerization, terpinolene yield.
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https://doi.org/10.19261/cjm.2022.980

Abstract (PDF)
Graphical Abstract: The aim of the work was to study the isomerization of limonene on zeolite-containing biporous acid catalysts based on kaolin (from Ukraine). Results of this study show that at 160°C, the maximum isomer yield was 60–65% with an 80–90% conversion. The studied samples do not have a significant accumulation of carbonaceous deposits because limonene has high solubility, which helps to remove intermediate products of transformation from the surface of the samples.

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CHEMICAL COMPOSITION OF THE ESSENTIAL OIL AND ANTIMICROBIAL PROPERTIES OF CRUDE EXTRACT FROM TANACETUM CORYMBOSUM (L.) SHI. BIP.

Author(s):

Alexandru Ciocarlan, Lucian Lupascu, Aculina Aricu, Ion Dragalin, Nina Ciocarlan, Inga Zinicovscaia, Valerina Slanina, Nikita Yushin

Field: Natural product chemistry and synthesis
Type: Research paper
Issue: 2021 Volume 16, no.2
Pages: 83-90

Keywords: chemical composition, essential oil, ethanolic extract, antimicrobial activity, Corymbflower tansy.
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DOI: https://doi.org/10.19261/cjm.2021.877

Abstract (PDF)
Graphical Abstract: The GC-MS analysis of the essential oil from Tanacetum corymbosum revealed the presence of 38 compounds, including terpenes - germacrene D, (Z)-β-farnesene, g-elemene, β-caryophyllene, aliphatic - palmitic and linoleic fatty acids, fatty alcohol n-octadecanol, higher alkane n-heneicosane as the major constituents. The in vitro antimicrobial assessment of the ethanolic extract showed promising antibacterial/antifungal activities against five Gram-(+), Gram-(-) and phytopathogenic bacteria species and two fungi strains. The data obtained in this study may be useful both for researchers and for producers interested in new or less studied species of medicinal plants in healthcare and their biological activities.

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β-D-GALACTOPYRANOSIDE SECO-PHYTOPORPHYRIN FROM ATROPA BELLADONNA AND SOLANUM TUBEROSUM YELLOW LEAVES DETERMINED BY NUCLEAR MAGNETIC RESONANCE

Author(s):

Nina Djapic

Field: Natural product chemistry and synthesis
Type: Research paper
Issue: 2021 Volume 16, no.2
Pages: 76-82

Keywords: chlorophyll catabolite, structure, nuclear magnetic resonance, Atropa belladonna, Solanum tuberosum.
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DOI: https://doi.org/10.19261/cjm.2021.861

Abstract (PDF)
Supplementary Material (PDF)

Graphical Abstract: The study described the isolation of β-D-galactopyranoside seco-phytoporphyrin from Atropa belladonna and Solanum tuberosum yellow leaves. Column chromatography was applied for its isolation. The UV-Vis, mass spectrometry and NMR spectroscopy were used for the structure confirmation. The results demonstrate that the two plants that the same chlorophyll catabolite structure.

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CHEMICAL COMPOSITION AND LIPOXYGENASE INHIBITORY ACTIVITY OF THE ESSENTIAL OIL OF ALSTONIA ANGUSTILOBA

Author(s):

Wan Mohd Nuzul Hakimi Wan Salleh, Muhammad Helmi Nadri, Shamsul Khamis

Field: Natural product chemistry and synthesis
Type: Short communication
Issue: 2021 Volume 16, no.2
Pages: 112-116

Keywords: essential oil, hydrodistillation, lipoxygenase, Alstonia angustiloba, Apocynaceae.
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DOI: https://doi.org/10.19261/cjm.2021.848

Abstract (PDF)
Graphical Abstract: This study was aimed to investigate the chemica l compositions and lipoxygenase inhibitory activity of the essential oil from Alstonia angustiloba growing in Malaysia. The essential oils were obtained by hydrodistillation and fully characterized by gas chromatography and gas chromatography-mass spectrometry. Analysis of the A. angustiloba essential oil resulted in the identification of twenty-five chemical components, attributed 90.8% of the total oil. The most abundant components of A. angustiloba oil were linalool (21.2%), 1,8-cineole (16.8%), α-terpineol (9.5%), terpinene-4-ol (8.5%), β-caryophyllene (6.2%), and caryophyllene oxide (5.2%). The essential oil displayed moderate activity towards lipoxygenase activity with IC₅₀ value of 45.8 μg/mL.

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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: https://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.

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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: https://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.

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