A straightforward synthesis of natural oxygenatedent-kaurenoic acid derivatives

被引：1
|
作者：
Morarescu, Olga [1 ]
Grinco, Marina [1 ]
Kulcitki, Veaceslav [1 ]
Barba, Alic [1 ]
Garbuz, Olga [2 ,3 ]
Gudumac, Valentin [4 ]
Gulea, Aurelian [2 ]
Ungur, Nicon [1 ]
机构：
[1] Inst Chem MECR, Lab Chem Nat & Biol Act Cpds, 3 Acad Str, MD-2028 Kishinev, Moldova
[2] Moldova State Univ MECR, Dept Chem, Kishinev, Moldova
[3] Inst Zool MECR, Lab Mol Systemat & Phylogeny, Kishinev, Moldova
[4] Nicolae Testemitanu State Univ Med & Pharm, Lab Biochem, Kishinev, Moldova
来源：
SYNTHETIC COMMUNICATIONS | 2021年 / 51卷 / 01期
关键词：
Allylic isomerization; bioactivity; cell proliferation; dihydroxilation; epoxidation; ent-kaurane; ent-16 alpha-hydroxy-17-acetoxykauran-19-oic acid; ent-kaur-16-en-19-oic acid; ent-16 alpha 17-dihydroxylkauran-19-oic acid; ent-16; alpha; 17-diacetoxykauran-19-oic acid; ent-16 alpha 17-epoxykauran-19-oic acid; ent-17-oxo-16R-kauran-19-oic acid; ent-17-hydroxykaur-15-en-19-oic acid; natural diterpenoids; TERPENE DERIVATIVES; ENT-KAURANES; COPAIFERA-LANGSDORFFII; CONSTITUENTS; DITERPENOIDS; SUNFLOWER; BIOTRANSFORMATION; IDENTIFICATION; GROWTH;
D O I：
10.1080/00397911.2020.1821225
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The paper presents the synthesis of some natural diterpenoids ofent-kauranic structure, starting froment-kaur-16-en-19-oic acid, a natural diterpenoid readily available from the dried wastes of sunflower (Helianthus annuusL.). The reportedent-16 alpha,17-dihydroxykauran-19-oic,ent-16 alpha-hydroxy-17-acetoxykauran-19-oic andent-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 parentent-kaur-16-en-19-oic acid and two of its synthetic derivatives, which is in line with recent pioneering studies in this area. [GRAPHICS] .
引用
收藏
页码：123 / 133
页数：11
相关论文
共 50 条
  • [1] Straightforward synthesis of non-natural selenium containing amino acid derivatives and peptides
    Braga, AL
    Lüdtke, DS
    Paixao, MW
    Alberto, EE
    Stefani, HA
    Juliano, L
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (20) : 4260 - 4264
  • [2] Fluorination of kaurenoic acid derivatives by remote functionalization
    Anaya, J
    Grande, MC
    Grande, M
    Patino, AI
    Torres, P
    SYNLETT, 1999, (09) : 1429 - 1431
  • [3] Characterization of the antifungal activity on Botrytis cinerea of the natural diterpenoids kaurenoic acid and 3β-hydroxy-kaurenoic acid
    Cotoras, M
    Folch, C
    Mendoza, L
    JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2004, 52 (10) : 2821 - 2826
  • [4] Characterization of the bactericidal activity of the natural diterpene kaurenoic acid
    Wilkens, M
    Alarcón, C
    Urzúa, A
    Mendoza, L
    PLANTA MEDICA, 2002, 68 (05) : 452 - 454
  • [5] Novel derivatives of kaurenoic acid: Preparation and evaluation of their trypanocidal activity
    Vieira, HS
    Takahashi, JA
    de Oliveira, AB
    Chiari, E
    Boaventura, MAD
    JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2002, 13 (02) : 151 - 157
  • [6] Straightforward synthesis of substituted dibenzyl derivatives
    Mboyi, Cleve D.
    Gaillard, Sylvain
    Mabaye, Mbaye D.
    Pannetier, Nicolas
    Renaud, Jean-Luc
    TETRAHEDRON, 2013, 69 (24) : 4875 - 4882
  • [7] Straightforward synthesis of new tetrahydroquinoline derivatives
    Di Fabio, R
    Alvaro, G
    Bertani, B
    Giacobbe, S
    CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 2000, 78 (06): : 809 - 815
  • [8] Straightforward synthesis of novel spiroether derivatives
    Bobrovskaya, Olga V.
    Russkih, Aleksandr A.
    Yankin, Andrei N.
    Dmitriev, Maksim V.
    Bunev, Aleksandr S.
    Gein, Vladimir L.
    SYNTHETIC COMMUNICATIONS, 2021, 51 (11) : 1731 - 1741
  • [9] A straightforward synthesis of indole and benzofuran derivatives
    Fiandanese, Vito
    Bottalico, Daniela
    Marchese, Giuseppe
    Punzi, Angela
    TETRAHEDRON, 2008, 64 (01) : 53 - 60
  • [10] Evaluation of ent-Kaurenoic Acid Derivatives for their Anticariogenic Activity
    de Andrade, Bruna B.
    Moreira, Monique R.
    Ambrosio, Sergio R.
    Furtado, Niege A. J. C.
    Cunha, Wilson R.
    Heleno, Vladimir C. G.
    Silva, Aline N.
    Simao, Marilia R.
    da Rocha, Erilda M. P.
    Martins, Carlos H. G.
    Veneziani, Rodrigo C. S.
    NATURAL PRODUCT COMMUNICATIONS, 2011, 6 (06) : 777 - 780
12345