A straightforward synthesis of natural oxygenated ent-kaurenoic acid derivatives

Morărescu (Chetraru) Olga; Grinco Marina; Kulciţki Veaceslav; Barba Alic; Garbuz Olga; Gudumak V.; Gulya Aurelian; Ungur Nikon

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MORĂRESCU (CHETRARU), Olga, GRINCO, Marina, KULCIŢKI, Veaceslav, BARBA, Alic, GARBUZ, Olga, GUDUMAK, V., GULYA, Aurelian, UNGUR, Nikon. A straightforward synthesis of natural oxygenated ent-kaurenoic acid derivatives. In: Synthetic Communications, 2020, nr. 9(17), pp. 1-11. ISSN 0039-7911.

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Synthetic Communications

Numărul 9(17) / 2020 / ISSN 0039-7911 /ISSNe 1532-2432

A straightforward synthesis of natural oxygenated ent-kaurenoic acid derivatives

Pag. 1-11

Morărescu (Chetraru) Olga¹, Grinco Marina¹, Kulciţki Veaceslav¹, Barba Alic¹, Garbuz Olga²³, Gudumak V.⁴, Gulya Aurelian², Ungur Nikon¹

¹ Institute of Chemistry,
² Moldova State University,
³ Institute of Zoology,
⁴ ”Nicolae Testemițanu” State University of Medicine and Pharmacy

Proiecte:

Menționat în lucrare: 20.80009.8007.03 Noi substanțe cu potențial preventiv și terapeutic în baza compușilor naturali de origine vegetală și a matodelor moderne de sinteză organică

Disponibil în IBN: 20 decembrie 2020

Rezumat

The paper presents the synthesis of some natural diterpenoids of ent-kauranic structure, starting from ent-kaur-16-en-19-oic acid, a natural diterpenoid readily available from the dried wastes of sunflower (Helianthus annuus L.). The reported ent-16α,17-dihydroxykauran-19-oic, ent-16α-hydroxy-17-acetoxykauran-19-oic and ent-16α,17-diacetoxykauran-19-oic acids have been previously isolated from different plant sources and showed diverse biological activities, including anti-HIV, anti-cancer and anti-Alzheimer properties. Their chemical synthesis has not been disclosed so far. Additional cytotoxicity studies of the obtained compounds revealed a remarkable cell proliferative effect of parent ent-kaur-16-en-19-oic acid and two of its synthetic derivatives, which is in line with recent pioneering studies in this area.

Cuvinte-cheie
Allylic isomerization, bioactivity, cell proliferation, dihydroxilation, epoxidation, ent-kaurane, ent-16α-hydroxy-17-acetoxykauran-19-oic acid, ent-kaur-16-en-19-oic acid, ent-16α17-dihydroxylkauran-19-oic acid, ent-16α, 17-diacetoxykauran-19-oic acid, ent-16α17-epoxykauran-19-oic acid, ent-17-oxo-16R-kauran-19-oic acid, ent-17-hydroxykaur-15-en-19-oic acid. natural diterpenoids

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<creatorName>Ungur, N.D.</creatorName>
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<titles>
<title xml:lang='en'>A straightforward synthesis of natural oxygenated ent-kaurenoic acid derivatives</title>
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<publisher>Instrumentul Bibliometric National</publisher>
<publicationYear>2020</publicationYear>
<relatedIdentifier relatedIdentifierType='ISSN' relationType='IsPartOf'>0039-7911</relatedIdentifier>
<subjects>
<subject>Allylic isomerization</subject>
<subject>bioactivity</subject>
<subject>cell proliferation</subject>
<subject>dihydroxilation</subject>
<subject>epoxidation</subject>
<subject>ent-kaurane</subject>
<subject>ent-16α-hydroxy-17-acetoxykauran-19-oic acid</subject>
<subject>ent-kaur-16-en-19-oic acid</subject>
<subject>ent-16α17-dihydroxylkauran-19-oic acid</subject>
<subject>ent-16α</subject>
<subject>17-diacetoxykauran-19-oic acid</subject>
<subject>ent-16α17-epoxykauran-19-oic acid</subject>
<subject>ent-17-oxo-16R-kauran-19-oic acid</subject>
<subject>ent-17-hydroxykaur-15-en-19-oic acid. natural diterpenoids</subject>
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<date dateType='Issued'>2020-09-21</date>
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<description xml:lang='en' descriptionType='Abstract'><p>The paper presents the synthesis of some natural diterpenoids of&nbsp;<em>ent</em>-kauranic structure, starting from&nbsp;<em>ent</em>-kaur-16-en-19-oic acid, a natural diterpenoid readily available from the dried wastes of sunflower (<em>Helianthus annuus</em>&nbsp;L.). The reported&nbsp;<em>ent-</em>16&alpha;,17-dihydroxykauran-19-oic,&nbsp;<em>ent-</em>16&alpha;-hydroxy-17-acetoxykauran-19-oic and&nbsp;<em>ent-</em>16&alpha;,17-diacetoxykauran-19-oic acids have been previously isolated from different plant sources and showed diverse biological activities, including anti-HIV, anti-cancer and anti-Alzheimer properties. Their chemical synthesis has not been disclosed so far. Additional cytotoxicity studies of the obtained compounds revealed a remarkable cell proliferative effect of parent&nbsp;<em>ent</em>-kaur-16-en-19-oic acid and two of its synthetic derivatives, which is in line with recent pioneering studies in this area.</p></description>
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