Carapanins A-C: new limonoids from andiroba (Carapa guianensis) fruit oil

被引:0
|
作者
Kikuchi, Takashi [1 ]
Akita, Keiko [1 ]
Koike, Hiroki [1 ]
In, Yasuko [1 ]
Yamada, Takeshi [1 ]
Tanaka, Reiko [1 ]
机构
[1] Osaka Univ Pharmaceut Sci, 4-20-1 Nasahara, Takatsuki, Osaka 5691094, Japan
关键词
GUIANOFRUITS;
D O I
10.1039/d0ob01872d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Carapanins A-C (1-3) were isolated from the fruit oil of Carapa guianensis. Compounds 1 and 2 are limonoids with unique structures. Namely, compound 1 is an andirobin-type limonoid with a C-15/C-30 gamma-lactone instead of the delta-lactone of the D-ring, and compound 2 is a mexicanolide-type limonoid with a C-16/C-30 delta-lactone ring. The absolute structures of 1 and 2 were determined using X-ray crystallography, whereas the structure of 3 was established mainly via NMR and mass spectroscopy. The inhibitory effects of 1-3 on nitric oxide production were evaluated, and it was revealed that 2 and 3 were potent nitric oxide inhibitors.
引用
收藏
页码:9268 / 9274
页数:7
相关论文
共 50 条
  • [11] The use of the andiroba oil (Carapa guianensis) on cutaneous wounds in Wistar rats
    Marten Fernandesi, Ciciane Pereira
    de Lima, Charles Silva
    Lopes, Thiago Vaz
    Felix, Samuel Rodrigues
    Schons, Sandro de Vargas
    Fernandes, Cristina Gevehr
    Nobre, Marcia de Oliveira
    BRAZILIAN JOURNAL OF HYGIENE AND ANIMAL SANITY, 2014, 8 (03): : 147 - 159
  • [12] Andirolides W-Y from the flower oil of andiroba (Carapa guianensis, Meliaceae)
    Sakamoto, Asami
    Tanaka, Yuji
    Yamada, Takeshi
    Kikuchi, Takashi
    Muraoka, Osamu
    Ninomiya, Kiyofumi
    Morikawa, Toshio
    Tanaka, Reiko
    FITOTERAPIA, 2015, 100 : 81 - 87
  • [13] In vitro efficacy of oil from the seed of Carapa guianensis (andiroba) in the control of Felicola subrostratus
    de Barros, Fabiola N.
    Farias, Marcia P. O.
    Tavares, Juliana P. C.
    Alves, Leucio C.
    Faustino, Maria A. da G.
    REVISTA BRASILEIRA DE FARMACOGNOSIA-BRAZILIAN JOURNAL OF PHARMACOGNOSY, 2012, 22 (05): : 1130 - 1133
  • [14] Viscosimetric Study of Andiroba Oil-based Polyols (Carapa Guianensis Aubl)
    Cavalcante, G. H. R.
    Cavalcante, K. S. B.
    Martiniano, L. C.
    Marques, A. L. B.
    Marques, E. P.
    REVISTA VIRTUAL DE QUIMICA, 2016, 8 (03) : 926 - 944
  • [15] Larvicidal effect of andiroba oil, Carapa guianensis (Meliaceae), against Aedes aegypti
    Silva, Onilda S.
    Prophiro, Josiane S.
    Nogared, Juliana C.
    Kanis, Luiz
    Emerick, Sheila
    Blazius, Rene D.
    Romao, Pedro R. T.
    JOURNAL OF THE AMERICAN MOSQUITO CONTROL ASSOCIATION, 2006, 22 (04) : 699 - 701
  • [16] Guianolides A and B, New Carbon Skeletal Limonoids from the Seeds of Carapa guianensis
    Inoue, Takanobu
    Matsui, Yuuki
    Kikuchi, Takashi
    In, Yasuko
    Yamada, Takeshi
    Muraoka, Osamu
    Matsunaga, Shunyo
    Tanaka, Reiko
    ORGANIC LETTERS, 2013, 15 (12) : 3018 - 3021
  • [17] Carapanolides T-X from Carapa guianensis (Andiroba) Seeds
    Miyake, Teppei
    Ishimoto, Sari
    Ishimatsu, Naoko
    Higuchi, Keiichiro
    Minoura, Katsuhiko
    Kikuchi, Takashi
    Yamada, Takeshi
    Muraoka, Osamu
    Tanaka, Reiko
    MOLECULES, 2015, 20 (11): : 20955 - 20966
  • [18] Typification and quality control of the Andiroba (Carapa guianensis) oil via mass spectrometry fingerprinting
    Cabral, Elaine C.
    da Cruz, Georgiana F.
    Simas, Rosineide C.
    Sanvido, Gustavo B.
    Goncalves, Lenise de V.
    Leal, Rodrigo V. P.
    da Silva, Regina C. F.
    da Silva, Julio C. T.
    Barata, Lauro E. S.
    da Cunha, Valnei S.
    de Franca, Luiz F.
    Daroda, Romeu J.
    de Sa, Gilberto F.
    Eberlin, Marcos N.
    ANALYTICAL METHODS, 2013, 5 (06) : 1385 - 1391
  • [19] Bioactive limonoids from Carapa guianensis seeds oil and the sustainable use of its by-products
    da Silva, Vagner Pereira
    Brito, Lavinia de Carvalho
    Marques, Andre Mesquita
    Camillo, Flavia da Cunha
    Figueiredo, Maria Raquel
    CURRENT RESEARCH IN TOXICOLOGY, 2023, 4
  • [20] LIMONOIDS ISOLATED FROM FRUITS OF Carapa guianensis Aublet (Meliaceae)
    Silva, Sunia Gomes
    Saraiva Nunomura, Rita de Cassia
    Nunomura, Sergio Massayoshi
    QUIMICA NOVA, 2012, 35 (10): : 1936 - U90