Cucurbalsaminones A-C, Rearranged Triterpenoids with a 5/6/3/6/5-Fused Pentacyclic Carbon Skeleton from Momordica balsamina, as Multidrug Resistance Reversers

被引:7
|
作者
Monico, Andreia [1 ]
Ramalhete, Catia [1 ,2 ]
Andre, Vania [3 ]
Spengler, Gabriella [4 ]
Mulhovo, Silva [5 ]
Duarte, M. Teresa [3 ]
Ferreira, Maria-Jose U. [1 ]
机构
[1] Univ Lisbon, Fac Pharm, Res Inst Med iMed ULisboa, Ave Prof Gama Pinto, P-1649003 Lisbon, Portugal
[2] ATLANTICA Escola Univ Ciencias Empresariais Saude, Fabr Polvora Barcarena, P-2730036 Oeiras, Portugal
[3] Univ Lisbon, Ctr Quim Estrutural, Inst Super Tecn, Ave Rovisco Pais, P-1049001 Lisbon, Portugal
[4] Univ Szeged, Fac Med, Dept Med Microbiol & Immunobiol, Dom Ter 10, H-6720 Szeged, Hungary
[5] Univ Pedagag, Fac Ciencias & Matemat, Ctr Estudos Mocambicanos & Etnociencias, Maputo 21402161, Mozambique
来源
JOURNAL OF NATURAL PRODUCTS | 2019年 / 82卷 / 08期
关键词
ALPHA; BETA-UNSATURATED DELTA-DIKETONE; P-GLYCOPROTEIN; PHOTOCHEMICAL-REACTIONS; MEMBRANE;
D O I
10.1021/acs.jnatprod.9b00019
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
Three new triterpenoids, cucurbalsaminones A-C (1-3), featuring a unique 5/6/3/6/5-fused pentacyclic carbon skeleton, named cucurbalsaminane, were isolated from a methanol extract of Momordica balsamina. Their structures were elucidated by spectroscopic methods and corroborated, for 1, by structure solution using single-crystal X-ray diffraction analysis. A hypothetical biogenetic pathway for these compounds is proposed. Compounds 1-3 were evaluated for their P-glycoprotein (P-gp/ABCB1) modulation ability, using a mouse T-lymphoma MDR1-transfected cell model by the rhodamine-123 accumulation assay, and displayed potent multidrug resistance (MDR)-reversing activity.
引用
收藏
页码:2138 / 2143
页数:6
相关论文
共 34 条
  • [1] Two Terpenoid Derivatives with Different 3/5/6/6/5-Fused Pentacyclic Skeletons from Hedyosmum orientale
    Fan, Yao-Yue
    Zheng, Cheng-Yu
    Zhou, Bin
    Zimbres, Flavia M. M.
    Cassera, Maria B. B.
    Yue, Jian-Min
    CHINESE JOURNAL OF CHEMISTRY, 2023, 41 (04) : 392 - 398
  • [2] A Synthetic Approach for Constructing the 3/6/6/5-Fused Tetracyclic Skeleton of Tenuipesine A
    Tian, Jin-Miao
    Zhao, Xiong
    Tu, Yong-Qiang
    Gong, Wei
    Zhang, Fu-Min
    Zhang, Shu-Yu
    Wang, Shao-Hua
    CHEMISTRY-AN ASIAN JOURNAL, 2014, 9 (03) : 724 - 727
  • [3] Kadcoccitones A and B, Two New 6/6/5/5-Fused Tetracyclic Triterpenoids from Kadsura coccinea
    Liang, Cheng-Qin
    Shi, Yi-Ming
    Luo, Rong-Hua
    Li, Xing-Yao
    Gao, Zhong-Hua
    Li, Xiao-Nian
    Yang, Liu-Meng
    Shang, Shan-Zhai
    Li, Yan
    Zheng, Yong-Tang
    Zhang, Hong-Bin
    Xiao, Wei-Lie
    Sun, Han-Dong
    ORGANIC LETTERS, 2012, 14 (24) : 6362 - 6365
  • [4] Ganolearic Acid A, a Hexanorlanostane Triterpenoid with a 3/5/6/5-Fused Tetracyclic Skeleton from Ganoderma cochlear
    Peng, Xing-Rong
    Huang, Yan-Jie
    Lu, Shuang-Yang
    Yang, Jing
    Qiu, Ming-Hua
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (21): : 13178 - 13183
  • [5] Peniroquesines A-C: Sesterterpenoids Possessing a 5-6-5-6-5-Fused Pentacyclic Ring System from Penicillium roqueforti YJ-14
    Wang, Jia-Peng
    Yu, Jing
    Shu, Yan
    Shi, Ya-Xian
    Luo, Ping
    Cai, Le
    Ding, Zhong-Tao
    ORGANIC LETTERS, 2018, 20 (18) : 5853 - 5856
  • [6] Euphnerins A and B, Diterpenoids with a 5/6/6 Rearranged Spirocyclic Carbon Skeleton from the Stems of Euphorbia neriifolia
    Du, Min
    An, Lijun
    Xu, Jing
    Guo, Yuanqiang
    JOURNAL OF NATURAL PRODUCTS, 2020, 83 (09): : 2592 - 2596
  • [7] Ganoapplins A and B with an unprecedented 6/6/6/5/6-fused pentacyclic skeleton from Ganoderma inhibit Tau pathology through activating autophagy
    Peng, Xingrong
    Luo, Rongcan
    Ran, Xiaoqian
    Guo, Yarong
    Yao, Yong-Gang
    Qiu, Minghua
    BIOORGANIC CHEMISTRY, 2023, 132
  • [8] Phlegmadines B and C, two Lycopodium alkaloids with 6/5/5/5/7 pentacyclic skeleton from Phlegmariurus phlegmaria
    Zhang, Zhi-Jun
    Zhu, Qin-Feng
    Wu, Xing-De
    Zhao, Qin-Shi
    TETRAHEDRON LETTERS, 2020, 61 (02)
  • [9] Spongenolactones A-C, Bioactive 5,5,6,6,5-Pentacyclic Spongian Diterpenes from the Red Sea Sponge Spongia sp.
    Tai, Chi-Jen
    Ahmed, Atallah F.
    Chao, Chih-Hua
    Yen, Chia-Hung
    Hwang, Tsong-Long
    Chang, Fang-Rong
    Huang, Yusheng M.
    Sheu, Jyh-Horng
    MARINE DRUGS, 2022, 20 (08)
  • [10] Nototronesides A-C, Three Triterpene Saponins with a 6/6/9 Fused Tricyclic Tetranordammarane Carbon Skeleton from the Leaves of Panax notoginseng
    Liu, Xin-Yi
    Li, Chuang-Jun
    Chen, Fang-You
    Ma, Jie
    Wang, Shuo
    Yuan, Yu-He
    Li, Li
    Zhang, Dong-Ming
    ORGANIC LETTERS, 2018, 20 (15) : 4549 - 4553