Structure and Absolute Configuration of Abietane Diterpenoids from Salvia clinopodioides: Antioxidant, Antiprotozoal, and Antipropulsive Activities

被引:33
作者
Bustos-Brito, Celia [1 ]
Joseph-Nathan, Pedro [2 ]
Burgueno-Tapia, Eleuterio [3 ]
Martinez-Otero, Diego [4 ]
Nieto-Camacho, Antonio [1 ]
Calzada, Fernando [5 ]
Yepez-Mulia, Lilian [6 ]
Esquivel, Baldomero [1 ]
Quijano, Leovigildo [1 ]
机构
[1] Univ Nacl Autonoma Mexico, Inst Quim, Ciudad Univ, Mexico City 04510, DF, Mexico
[2] Inst Politecn Nacl, Ctr Invest & Estudios Avanzados, Dept Quim, Apartado 14-740, Mexico City 07000, DF, Mexico
[3] Inst Politecn Nacl, Escuela Nacl Ciencias Biol, Dept Quim Orgn, Mexico City 11340, DF, Mexico
[4] UNAM, UAEM, Ctr Conjunto Invest Quim Sustentable, Carretera Toluca Atlacomulco,Km 14-5, Toluca 50200, Mexico
[5] Ctr Med Nacl Siglo XXI, UMAE, IMSS, Unidad Invest Med Farmacol,Hosp Especialidades, Ave Cuauhtemoc 330, Mexico City 06725, DF, Mexico
[6] Ctr Med Nacl Siglo XXI, UMAE, Unidad Invest Med Enfermedades Infecciosas & Para, IMSS,Hosp Especialidades, Ave Cuauhtemoc 330, Mexico City 06725, DF, Mexico
来源
JOURNAL OF NATURAL PRODUCTS | 2019年 / 82卷 / 05期
关键词
LIPID-PEROXIDATION; LAMIACEAE; PRODUCTS; MEXICO;
D O I
10.1021/acs.jnatprod.8b00952
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
The aerial parts of Salvia clinopodioides afforded abietanes 1a, 2a, and 3 (clinopodiolides A-C), two of which possess an unusual lactol moiety at C-19-C-20, together with an icetexane named clinopodiolide D (4a). Their structures were established by spectroscopic means, mainly H-1 and C-13 NMR, including 1D and 2D homo- and heteronuclear experiments. The antioxidant, antiprotozoal, and antidiarrheal effects of the isolates were evaluated. Compounds 2a and 3 showed better effects than a-tocopherol in the inhibition of lipid peroxidation with IC50 (mu M) = 5.9 +/- 0.1 and 2.7 +/- 0.2, respectively, and moderate activity in the DPPH assay. All tested compounds showed moderate antiamoebic and antigiardial activity, as well as a good antipropulsive effect.
引用
收藏
页码:1207 / 1216
页数:10
相关论文
共 36 条
[1]  
[Anonymous], 2014, APEX 2 VER 2014 11 0
[2]  
Bentham G., 1876, GENERA PLANTARUM, V2, P1160
[3]  
Burgueño-Tapia E, 2015, NAT PROD COMMUN, V10, P1785
[4]   Antiprotozoal Constituents from Annona cherimola Miller, a Plant Used in Mexican Traditional Medicine for the Treatment of Diarrhea and Dysentery [J].
Calzada, Fernando ;
Correa-Basurto, Jose ;
Barbosa, Elizabeth ;
Mendez-Luna, David ;
Yepez-Mulia, Lilian .
PHARMACOGNOSY MAGAZINE, 2017, 13 (49) :148-152
[5]   Effect of plants used in Mexico to treat gastrointestinal disorders on charcoal-gum acacia-induced hyperperistalsis in rats [J].
Calzada, Fernando ;
Arista, Ramon ;
Perez, Halley .
JOURNAL OF ETHNOPHARMACOLOGY, 2010, 128 (01) :49-51
[6]   A Confidence Level Algorithm for the Determination of Absolute Configuration Using Vibrational Circular Dichroism or Raman Optical Activity [J].
Debie, Elke ;
De Gussem, Ewoud ;
Dukor, Rina K. ;
Herrebout, Wouter ;
Nafie, Laurence A. ;
Bultinck, Patrick .
CHEMPHYSCHEM, 2011, 12 (08) :1542-1549
[7]   Antioxidant activities of extracts from Barkleyanthus salicifolius (Asteraceae) and Penstemon gentianoides (Scrophularlaceae) [J].
Dominguez, M ;
Nieto, A ;
Marin, JC ;
Keck, AS ;
Jeffery, E ;
Céspedes, CL .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2005, 53 (15) :5889-5895
[8]  
Epling C, 1940, REPERTORIUM SPECIERU, V110
[9]   Antioxidant capacity of abietanes from Sphacele salviae [J].
Escuder, B ;
Torres, R ;
Lissi, E ;
Labbé, C ;
Faini, F .
NATURAL PRODUCT LETTERS, 2002, 16 (04) :277-281
[10]  
Esquivel B, 2000, PHYTOCHEMICALS AND PHYTOPHARMACEUTICALS, P371