ent-Labdane Diterpenoids from Dodonaea viscosa

被引:12
|
作者
Olivier, Wesley J. [1 ]
Kilah, Nathan L. [1 ]
Horne, James [2 ]
Bissember, Alex C. [1 ]
Smith, Jason A. [1 ]
机构
[1] Univ Tasmania, Sch Phys Sci Chem, Hobart, Tas, Australia
[2] Univ Tasmania, Cent Sci Lab, Hobart, Tas, Australia
来源
JOURNAL OF NATURAL PRODUCTS | 2016年 / 79卷 / 12期
基金
澳大利亚研究理事会;
关键词
OCCURRING TERPENE DERIVATIVES; CLERODANE DITERPENOIDS; SECONDARY METABOLITES; PRACTICAL ISOLATION; ACID; FLAVONOIDS; CHEMISTRY; CONSTITUENTS; EXTRACTION; PLANTS;
D O I
10.1021/acs.jnatprod.6b00858
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
Seven new and two known ent-labdane diterpenoids have been isolated from a single plant specimen of Dodonaea viscosa ssp. spatulata, found in Tasmania, Australia. Prior to this study, only seven different labdane diterpenoids had been isolated from D. viscosa. The structures of the natural products were assigned via 1D and 2D NMR spectroscopy and other standard spectroscopic methods. The absolute configuration of three ent-labdane diterpenoids was determined by single-crystal X-ray crystallography of synthetic derivatives. Significantly, the results of this study suggest that the absolute configuration of some known labdane diterpenoids may have been misassigned.
引用
收藏
页码:3117 / 3126
页数:10
相关论文
共 50 条
  • [1] ent-labdane diterpenoids from Andrographis paniculata
    Shen, YH
    Li, RT
    Xiao, WL
    Gang-Xu
    Lin, ZW
    Zhao, QS
    Sun, HD
    JOURNAL OF NATURAL PRODUCTS, 2006, 69 (03): : 319 - 322
  • [2] Diastereoisomeric ent-Labdane Diterpenoids from Andrographis paniculata
    Hu, Yong-Mei
    Wang, Guo-Cai
    Wang, Ying
    Sung, Herman H. -Y.
    Williams, Ian D.
    Ye, Wen-Cai
    HELVETICA CHIMICA ACTA, 2012, 95 (01) : 120 - 126
  • [3] Two ent-labdane diterpenoids from Andrographis paniculata
    Issac, M.
    Carmeli, S.
    PLANTA MEDICA, 2012, 78 (11) : 1203 - 1203
  • [4] Ent-abietane and ent-labdane diterpenoids from Isodon parvifolius
    Li, -Mei Li
    Huang, Sheng-Xiong
    Peng, Li-Yan
    Li, Guo-You
    Xiao, Wei-Lie
    Zhou, Yan
    Han, Quan-Bin
    Ding, Li-Sheng
    Sun, Han-Dong
    CHEMICAL & PHARMACEUTICAL BULLETIN, 2006, 54 (07) : 1050 - 1052
  • [5] Isolation of three new ent-labdane diterpenes from Dodonaea viscosa Jacquin (Sapindaceae): Preliminary evaluation of antiherpes activity
    de Oliveira, Simone Quintana
    Rojo de Almeida, Maria Tereza
    Maraslis, Flora
    Silva, Izabella Thais
    Marques Sincero, Thais Cristine
    Palermo, Jorge Alejandro
    Cabrera, Gabriela Myriam
    Balparda Caro, Miguel Soriano
    Oliveira Simoes, Claudia Maria
    Schenkel, Eloir Paulo
    PHYTOCHEMISTRY LETTERS, 2012, 5 (03) : 500 - 505
  • [6] ent-Labdane Diterpenoids from the Aerial Parts of Eupatorium obtusissmum
    Castillo, Quirico A.
    Triana, Jorge
    Eiroa, Jose L.
    Calcul, Laurent
    Rivera, Edwin
    Wojtas, Lukasz
    Padron, Jose M.
    Boberieth, Lise
    Keramane, Mehdi
    Abel-Santos, Ernesto
    Baez, Luis A.
    Germosen, Evelyn A.
    JOURNAL OF NATURAL PRODUCTS, 2016, 79 (04): : 907 - 913
  • [7] Ent-3,4-seco-labdane and ent-labdane diterpenoids from Croton stipuliformis (Euphorbiaceae)
    Ramos, Freddy
    Takaishi, Yoshihisa
    Kashiwada, Yoshiki
    Osorio, Coralia
    Duque, Carmenza
    Acuna, Ricardo
    Fujimoto, Yoshinori
    PHYTOCHEMISTRY, 2008, 69 (12) : 2406 - 2410
  • [8] Anticomplement ent-labdane diterpenoids from the aerial parts of Andrographis paniculata
    Wen, Quan
    Jin, Xin
    Lu, Yan
    Chen, Dao-Feng
    FITOTERAPIA, 2020, 142
  • [9] Synthetic studies towards the ent-labdane diterpenoids:: Rearrangement of ent-halimanes
    Marcos, Isidro S.
    Sexmero, Maria J.
    Hernandez, Felix A.
    Corrales, Marta
    Basabe, Pilar
    Diez, David
    Urones, Julio G.
    MOLECULES, 2006, 11 (10) : 792 - 807
  • [10] ent-Labdane and ent-kaurane diterpenoids from Chelonopsis odontochila with α-glucosidase inhibitory activity
    Deng, Zhen-Tao
    Chen, Ji-Jun
    Geng, Chang-An
    BIOORGANIC CHEMISTRY, 2020, 95