Alexandru Gh. Ciocarlan

Moldova State University. Institute of Chemistry

n terms of synthetic potential, (+)-larixol 1 outperform other labdanic diterpenoids due to the hydroxyl group at the C6 position. Over the years, various chemical transformations have been performed on the basis of this compound, selectively or on both hydroxyl groups, or by modifying of the side chain [1-4]. Unlike the syntheses mentioned above,...

The known phenothiazine derivatives exhibit a wide spectrum of biological activities, including such as antiparasitic, antioxidant, anticancer, antiproliferative, antineoplastic, antimicrobial, etc. [1]. For this reason, terpeno-phenothiazine molecular hybrids represent one of the priority strategies of organic synthesis in the design of new bioact...

Industrially produced Lavender (Lavandula angustifolia L.) and Clary sage (Salvia sclarea Mill.) essential oils are frequently used as ingredients in aromatherapy, traditional medicine, perfumery and cosmetics [1]. The chemical composition of both fresh volatile oils is mainly determined by unsaturated sesquiterpenic hydrocarbons and their oxygenat...

New, original, and ecologically pure methods for the synthesis of compounds with hybrid terpene and heteroatomic functional groups or fragments have been developed, starting from accessible (+)-sclareolide, obtained from (-)-sclareol, well-known labdane diterpenoid diol extracted from the waste of Clary sage (Salvia sclarea L.) remaining after extr...

Synthesis of novel tetranorlabdane compounds bearing 1,3,4-thiadiazole units and intermediary tetranorlabdane compounds with thiosemicarbazone fragment has been reported. The structures of the new synthesized compounds were confirmed using IR and 1H, 13C, and 15N NMR spectroscopy. The in vitro antifungal and antibacterial activities of the mentione...

Herein we report a feasible study concerning the synthesis and the in vitro antimicrobial activity of some new homodrimane sesquiterpenoids with a benzimidazole unit. Based on some homodrimane carboxylic acids, on their acyl chlorides and intermediate monoamides, a series of seven N-homodrimenoyl-2-amino-1,3-benzimidazoles and 2-homodrimenyl-1,3-be...

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 biologic...

Based on some homodrimane carboxylic acids and their acyl chlorides, a series of fourteen 2-homodrimenyl-1,3-benzothiazoles, N-homodrimenoyl-2-amino-1,3-benzothiazoles, 4′-methyl-homodrimenoyl anilides and 4′-methyl-homodrimenthioyl anilides were synthesized and their biological activities were evaluated on five species of fungi (Aspergillus niger,...

Teucrium L. is a widely distributed genus often used for the treatment of digestive disorders and respiratory problems. The aim of the present study was to determine the chemical composition of essential oils and elemental content of the plant species Teucrium polium, Teucrium hircanicum, Teucrium botrys, Teucrium chamaedrys, Teucrium flavum, Teucr...

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 assessm...

The producers of essential oils from the Republic of Moldova care about the quality of their products and at the same time, try to capitalize on the waste from processing. The purpose of the present study was to analyze the chemical composition of lavender (Lavanda angustifolia L.) essential oil and some by-products derived from its production (res...

The vic-dioximes are compounds with various industrial uses and scientific applications. Many coordination compounds have been synthesized based on vic-dioximes. This study presents the synthesis and full characterization of two vic-dioximes based on dichloroglyoxime, p-aminobenzoic acid, and p-aminotoluene. Their structures were proved by IR, ¹H,...

(+)-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.

The mineral contents of roots, leaves, stalks, and inflorescences of the aromatic plant species Anethum graveolens L., Coriandrum sativum L., Lavandula angustifolia Mill., Levisticum officinale W.D.J. Koch, and Salvia sclarea L. were studied by means of neutron activation analysis. The contents of 36 major and trace elements were determined and bio...

Apple (Malus domestica Borkh.), a popular and widely cultivated fruit world-wide, contains bioactive compounds responsible for their health benefits. Here we report the amounts of some bioactive compounds: two major triterpenes (oleanolic and ursolic acids) and polyphenols (phenolic acids, flavan-3-ols, flavonoids and t-resveratrol), together with...

New di-, tri-, tetra-, and pentanorlabdane compounds with thiosemicarbazone and 1,3-thiazole fragments were synthesized. Their antifungal and antibacterial activities were studied. The main advantages of this research were the available starting material, i.e., the natural labdane diterpenoid (–)-sclareol, which was isolated from renewable resource...

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 f...

Synthesis of novel (+)-sclareolide-based homodrimane sesquiterpenoids bearing 1,3,4-oxadiazole or 1,3,4-thiadiazole units has been reported. These terpeno-heterocyclic compounds demonstrate promising antifungal and antibacterial activities toward fungal species Aspergillus niger, Fusarium solani, Penicillium chrysogenum, Penicillium frequentans, an...

The elemental composition of 45 species of medicinal plants of Lamiaceae family growing in the Republic of Moldova was determined by neutron activation analysis. The following elements were determined in analysed samples: Al, As, Ba, Br, Ca, Ce, Cl, Co, Cr, Cs, Fe, Hf, K, La, Mg, Mo, Mn, Na, Rb, Sb, Sc, Sr, Sm, Th, U and Zn. The essential, rare ear...

The non-conventional methods of synthesis belong to green chemistry and offer many advantages. The microwave and ultrasound irradiation, as well as electrochemical and photochemical transformations often lead to desired results through nonspecific mechanisms, reduces the cost, increase yields and exclude the use of reagents, or the formation of tox...

Synthesis of novel (+)-sclareolide-based homodrimane sesquiterpenoids bearing hydrazinecarbothioamide or N-substituted 1,2,4-triazole unit has been reported. These heterocyclic compounds demonstrate promising in vitro antifungal and antibacterial activities toward fungal species Aspergillus niger, Fusarium solani, Penicillium chrysogenum, Penicilli...

For the first time the elemental composition of Tanacetum corymbosum (L.) Sch. Bip. of Moldavian origin was determined by means of neutron activation analysis. The content of 21 major and trace elements Al, As, Br, Ca, Cl, Co,Cs, Fe, K, La, Mg, Mn, Mo, Na, Rb, Sb, Sc, Sm, Sr, Th, and Zn were determined. The content of As in analysed plants was lowe...

The phenylethanoids rostkovianoside, 6′-O-acetylcrassifolioside and the flavonoid rutin 3‴-acetate, were isolated from the methanolic extract of the aerial parts of Euphrasia rostkoviana Hayne. The structures of these previously undescribed compounds were elucidated by interpretation of spectroscopic data. The acetylation of rutin was also carried...

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....

The study describes the synthesis of 11-homodrim-6,8-dien-12-oic acid N-substituted amides containing diazine, 1,2,4-triazole and carbazole rings based on commercially available sclareolide. The mentioned compounds were prepared for the first time by interaction of the generated in situ acyl chloride with some heterocyclic amines: 2- and 4-aminopyr...

The present paper describes biochemical (fatty oil) composition of Silybummarianum (L.) Gaertn. of Moldovan origin. The oil content of the seeds was approximately 25%. Linoleic acid (C18:2), an essential polyunsaturated fatty acid, is the most abundant (48.88%), followed by monounsaturated oleic acid (C18:1, 31.94%) and saturated palmitic acid (C16...

The traditional use of extracts of Euphrasia rostkoviana to relieve ocular inflammation or infections is well documented and supported by clinical studies. Various classes of chemical compounds such as iridoids, phenylethanoids, flavonoids and hydroxycinnamic acids have been reported. The present work aims to assess the chemical diversity among sev...

For the first time the results of GC-MS analysis of Satureja subspicata L. oil of Moldovan origin are reported. The chemical profile includes forty-four constituents and consists mostly (97.86%) of phenolic monoterpenes, monoterpene hydrocarbons, bicyclic sesquiterpenes and their oxygenated derivatives. A substantial quantitative and qualitative ch...

Synthesis of novel tetranorlabdane derivatives including hybride with terpeno-(1,2)-diazine units and dimers with an unprecedented carbon skeleton, was performed based on methyl 7-oxo-13,14,15,16-tetranorlabd-8-en-12-oate intermediate. The structures of the synthesized compounds have been fully confirmed, including by X-ray diffraction, and their a...

In order to find new biologically active compounds and in continuation of our work on the synthesis of the novel compounds containing both terpenic and heterocyclic fragments, herein we report the synthesis and assessment of the in vitro antifungal and antibacterial activities of some new drimane sesquiterpenoids with azaheterocyclic fragments. The...

Topic applications of Calendula officinalis L. lipophilic extracts are used in phytotherapy to relieve skin inflammatory conditions whereas infusions are used as a remedy for gastric complaints. Such a different usage might be explained by some cytotoxicity of lipophilic extracts at gastric level but little is known about this. Therefore, we screen...

Calendula officinalis L. has been largely known for its topical anti-inflammatory properties; however, there are no experimental evidences about its antiphlogistic effect at the gastric level. To investigate whether marigold might exert an activity against gastric inflammation, a CH2Cl2 extract obtained from C. officinalis flowers was evaluated in...

The paper describes a new pathway for an efficient synthesis of natural and bioactive drimanic compounds ( - )-pereniporin B (1) and ( - )-cinnamosmolide (2) from ketodiol 7, an intermediate obtained before from accessible labdane diterpenoid (+)-larixol (3). The key step involves allylic bromination of acetate 8 with N-bromosuccinimide. The in vit...

A series of 15 new polyfunctional drimanic compounds have been obtained by synthesis via dye-sensitized photooxygenation, bromination with N-bromosuccinimide, and electrochemical transformation of drim-7,9(11)-diene 1 and drim-8-en-7-one 2. Three alternative syntheses of 12-acetoxy-drim-7,9(11)-diene 8 and two of 11-bromo-drim-8(9)-en-7-one 10 have...

Starting from (+)-larixol and (−)-sclareol, new syntheses of (+)-6-ketoeuryfuran, (+)-6-ketowinterin, and (−)-7-ketoeuryfuran have been elaborated in high yields. (+)-6-Ketowinterin was synthesized for the first time. Both euryfurans are excellent starting materials for the synthesis of important polyfunctional biologically active drimanic compound...

A novel synthesis of natural drimanic compounds, (-)-albrassitriol (2) and (-)-6-epi-albrassitriol (3), has been carried out starting from an easily available labdane diterpenoid, (+)-larixol (1). In a two-step procedure, (+)-larixol (1) was converted into 14,15-bisnorlab-7-ene-6,13-dione (9), which was then submitted to a Norrish type II photochem...

The current communication represents an extended abstract of the presentation delivered on the joint Moldo-Italian seminar “New frontiers in natural product chemistry”, held in the Institute of Chemistry, Academy of Sciences of Moldova on 30 September. An overview of the synthetic methods oriented to the synthesis of C6 and C7 functionalized euryfu...

БАЕВ, О.М.; ШЕПЕЛЬ, Ф.Г.; ШЕПЕЛЬ, Д.Ф.; ЧОКЫРЛАН, А.А.; МАКАЕВ, Ф.З. Способы высушивания виноградной выжимки при утилизации отходов виноделия. Материалы Всероссийской научно-практической конференции с международным участием: Новые материалы, химические технологии и реагенты для промышленности, медицины и сельского хозяйства на основе нефтехимическо...

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

This article describes a new efficient synthesis of drim-7,9(11)-diene and its hydroxylated derivates from drim-8-en-7-one. Reduction of this ketone with NaBO4 in the presence of CeCl3 · 7H2O afforded regio- and stereoselectively drim-8-en-7-ol in a high yield. Its dehydration with H2SO4 under mild conditions led to drim-7,9(11)-diene. Noncatalyti...

A mixture of 7α- and 17-bromonorambreinolides was obtained on treatment of the mixture of isomeric methyl bicyclohomofarnesenoates, the norambreinolide transesterification product, with NBS and H2O2. The structure of 7α- and 17-bromonorambreinolides was elucidated on the basis of spectral data. The structure of 17-bromonorambreinolide was confirmed...

An efficient two-step procedure for photooxidative dehydrogenation of drimane and 11-homodrimane compounds containing an 8-en-7-one structural unit into α,α′-dienones was elaborated. The method is based on the transformation of ketones into the respective enol acetates followed by photosensitized oxygenation. Methyl 7-oxo-11-homodrima-5,8-dien-12-o...

Valuable chiral drimanic dienic synthons have been prepared by a photolytic Norrish type II degradation of the corresponding 14,15-bisnorlabdene-13-ones. Minor by-products with unexpected bi- and tricyclic structures were formed and some of them were isolated and identified

An efficient two-step procedure for photooxidative dehydrogenation of drimane and 11-homodrimane compounds containing an 8-en-7-one structural unit into α,α′-dienones was elaborated. The method is based on the transformation of ketones into the respective enol acetates followed by photosensitized oxygenation. Methyl 7-oxo-11-homodrima-5,8-dien-12-o...