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

Conţinutul numărului revistei

Articolul precedent

Articolul urmator

687

SM ISO690:2012

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, 2021, nr. 1(51), pp. 123-133. ISSN 0039-7911. DOI: https://doi.org/10.1080/00397911.2020.1821225

EXPORT metadate:
Google Scholar
Crossref
CERIF

DataCite
Dublin Core

Synthetic Communications

Numărul 1(51) / 2021 / ISSN 0039-7911 /ISSNe 1532-2432

A straightforward synthesis of natural oxygenated ent-kaurenoic acid derivatives

DOI:https://doi.org/10.1080/00397911.2020.1821225

Pag. 123-133

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

Disponibil în IBN: 6 aprilie 2021

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, ent-16, ent-16α-hydroxy-17-acetoxykauran-19-oic acid, ent-16α17-dihydroxylkauran-19-oic acid, ent-16α17-epoxykauran-19-oic acid, ent-17-hydroxykaur-15-en-19-oic acid, ent-17-oxo-16R-kauran-19-oic acident-kaur-16-en-19-oic acid, ent-kaurane, epoxidation, natural diterpenoids, α17-diacetoxykauran-19-oic acid

Dublin Core Export

<?xml version='1.0' encoding='utf-8'?>
<oai_dc:dc xmlns:dc='http://purl.org/dc/elements/1.1/' xmlns:oai_dc='http://www.openarchives.org/OAI/2.0/oai_dc/' xmlns:xsi='http://www.w3.org/2001/XMLSchema-instance' xsi:schemaLocation='http://www.openarchives.org/OAI/2.0/oai_dc/ http://www.openarchives.org/OAI/2.0/oai_dc.xsd'>
<dc:creator>Morărescu (Chetraru), O.</dc:creator>
<dc:creator>Grinco, M.C.</dc:creator>
<dc:creator>Kulciţki, V.N.</dc:creator>
<dc:creator>Barbă, A.N.</dc:creator>
<dc:creator>Garbuz, O.S.</dc:creator>
<dc:creator>Gudumac, V.S.</dc:creator>
<dc:creator>Gulea, A.P.</dc:creator>
<dc:creator>Ungur, N.D.</dc:creator>
<dc:date>2021-01-14</dc:date>
<dc:description xml:lang='en'><p>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-16&alpha;,17-dihydroxykauran-19-oic, ent-16&alpha;-hydroxy-17-acetoxykauran-19-oic and ent-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 ent-kaur-16-en-19-oic acid and two of its synthetic derivatives, which is in line with recent pioneering studies in this area.</p></dc:description>
<dc:identifier>10.1080/00397911.2020.1821225</dc:identifier>
<dc:source>Synthetic Communications 51 (1) 123-133</dc:source>
<dc:subject>Allylic isomerization</dc:subject>
<dc:subject>bioactivity</dc:subject>
<dc:subject>cell proliferation</dc:subject>
<dc:subject>dihydroxilation</dc:subject>
<dc:subject>ent-16</dc:subject>
<dc:subject>ent-16α-hydroxy-17-acetoxykauran-19-oic acid</dc:subject>
<dc:subject>ent-16α17-dihydroxylkauran-19-oic acid</dc:subject>
<dc:subject>ent-16α17-epoxykauran-19-oic acid</dc:subject>
<dc:subject>ent-17-hydroxykaur-15-en-19-oic acid</dc:subject>
<dc:subject>ent-17-oxo-16R-kauran-19-oic acident-kaur-16-en-19-oic acid</dc:subject>
<dc:subject>ent-kaurane</dc:subject>
<dc:subject>epoxidation</dc:subject>
<dc:subject>natural diterpenoids</dc:subject>
<dc:subject>α17-diacetoxykauran-19-oic acid</dc:subject>
<dc:title>A straightforward synthesis of natural oxygenated ent-kaurenoic acid derivatives</dc:title>
<dc:type>info:eu-repo/semantics/article</dc:type>
</oai_dc:dc>