Twelve formyl phloroglucinol meroterpenoids from the leaves of Eucalyptus robusta

被引:26
|
作者
Shang, Zhi-Chun [1 ,2 ]
Han, Chao [1 ,2 ]
Xu, Jia-Li [1 ,2 ]
Liu, Rui-Huan [1 ,2 ]
Yin, Yong [1 ,2 ]
Wang, Xiao-Bing [1 ,2 ]
Yang, Ming-Hua [1 ,2 ]
Kong, Ling-Yi [1 ,2 ]
机构
[1] China Pharmaceut Univ, Sch Tradit Chinese Pharm, Jiangsu Key Lab Bioact Nat Prod Res, 24 Tong Jia Xiang, Nanjing 210009, Jiangsu, Peoples R China
[2] China Pharmaceut Univ, Sch Tradit Chinese Pharm, State Key Lab Nat Med, 24 Tong Jia Xiang, Nanjing 210009, Jiangsu, Peoples R China
基金
中国国家自然科学基金;
关键词
Eucalyptus robusta Smith; Myrtaceae; Phloroglucinol meroterpenoids; Antifungal; CIRCULAR-DICHROISM; FRUITS; SESQUITERPENOIDS;
D O I
10.1016/j.phytochem.2019.04.008
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Twelve formyl phloroglucinol meroterpenoids (FPMs) were isolated from the leaves of Eucalyptus robusta Smith. Their structures were elucidated via spectroscopic data analysis, the circular dichroism (CD) exciton chirality method, Rh-2(OCOCF3)(4)-induced CD experiments, and application of the Snatzke chirality rules. Eucalrobusones Q, S, and X are the first FPMs that have been identified in which the C-7' of phloroglucinol is linked to the C-15 of cadinane, the C-4 of cubebane, and the C-8 of menthane, respectively. (+)-Eucalrobusone X exhibited the most potent antifungal ability against Candida albicans with a MIC50 value of 10.78 mu g/mL, and eucalrobusone U exhibited the greatest anti-C. glabrata activity with MIC50 value of 1.53 mu g/mL.
引用
收藏
页码:111 / 117
页数:7
相关论文
共 50 条
  • [31] New phloroglucinol derivative isolated from Eucalyptus globulus
    Hasegawa, Tatsuya
    Takata, Takanobu
    Takano, Fumihide
    Ohta, Tomihisa
    YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 2007, 127 : 135 - 136
  • [32] Diverse benzyl phloroglucinol-based meroterpenoids from the fruits of Melaleuca leucadendron
    Wu, Lin
    Xie, Xin
    Wang, Xiao-Bing
    Yang, Ming-Hua
    Luo, Jun
    Kong, Ling-Yi
    TETRAHEDRON, 2020, 76 (28-29)
  • [33] Phloroglucinol derivatives from leaves of Bosistoa pentacocca
    Auzi, AA
    Forster, PI
    Hartley, TG
    Waigh, RD
    Waterman, PG
    PHYTOCHEMISTRY, 1997, 45 (08) : 1673 - 1678
  • [34] Atropisomeric meroterpenoids with rare triketone-phloroglucinol-terpene hybrids from Baeckea frutescens
    Hou J.-Q.
    Wang B.-L.
    Han C.
    Xu J.
    Wang Z.
    He Q.-W.
    Zhang P.-L.
    Zhao S.-M.
    Pei X.
    Wang H.
    Wang, Hao (wanghao@cpu.edu.cn), 2018, Royal Society of Chemistry (16): : 8513 - 8524
  • [35] New formylated phloroglucinol compounds from Eucalyptus globulus foliage
    Chenavas, Sophie
    Fiorini-Puybaret, Christel
    Joulia, Philippe
    Larrouquet, Camille
    Waton, Hugues
    Martinez, Agathe
    Casabianca, Herve
    Fabre, Bernard
    PHYTOCHEMISTRY LETTERS, 2015, 11 : 69 - 73
  • [36] Unusual Meroterpenoids from Leaves of Psidium guajava']java
    Liu, Jian
    Jiang, Li-Rong
    Liu, Mei-Feng
    CHEMISTRY OF NATURAL COMPOUNDS, 2016, 52 (01) : 67 - 70
  • [37] Atropisomeric meroterpenoids with rare triketone-phloroglucinol-terpene hybrids from Baeckea frutescens
    Hou, Ji-Qin
    Wang, Bao-Lin
    Han, Chao
    Xu, Jian
    Wang, Zhe
    He, Qi-Wei
    Zhang, Pei-Lin
    Zhao, Shu-Min
    Pei, Xin
    Wang, Hao
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (44) : 8513 - 8524
  • [38] Phloroglucinol Derivatives from the Fruits of Eucalyptus globulus and Their Cytotoxic Activities
    Thi-Anh Pham
    Mohammad, Imran Shair
    Van-Tuan Vu
    Hu, Xiao-Long
    Birendra, Chaurasiya
    Ulah, Aftab
    Guo, Cui
    Lu, Xian-Yu
    Ye, Wen-Cai
    Wang, Hao
    CHEMISTRY & BIODIVERSITY, 2018, 15 (06)
  • [39] Five phloroglucinol-monoterpene adducts from Eucalyptus grandis
    Umehara, K
    Singh, IP
    Etoh, H
    Takasaki, M
    Konoshima, T
    PHYTOCHEMISTRY, 1998, 49 (06) : 1699 - 1704
  • [40] Structural Diversity of Complex Phloroglucinol Derivatives from Eucalyptus Species
    Faezeh Taghizadeh, Seyedeh
    Panahi, Ali
    Esmaeilzadeh Kashi, Marziyeh
    Kretschmer, Nadine
    Asili, Javad
    Ahmad Emami, Seyed
    Azizi, Majid
    Shakeri, Abolfazl
    CHEMISTRY & BIODIVERSITY, 2022, 19 (06)