Structures and absolute stereochemistry of guaiane sesquiterpenoids from the gorgonian Menella woodin

被引:16
|
作者
Chau Ngoc Diep [1 ]
Lyakhova, Ekaterina G. [2 ]
Berdyshev, Dmitrii V. [2 ]
Kalinovsky, Anatoly I. [2 ]
Vu Anh Tu [1 ]
Nguyen Xuan Cuong [1 ]
Nguyen Hoai Nam [1 ]
Chau Van Minh [1 ]
Stonik, Valentin A. [2 ,3 ]
机构
[1] Vietnam Acad Sci & Technol, Inst Marine Biochem, Hanoi, Vietnam
[2] Russian Acad Sci, Far Eastern Branch, GB Elyakov Pacific Inst Bioorgan Chem, Vladivostok 690022, Russia
[3] Far Eastern Fed Univ, Vladivostok 690950, Russia
关键词
Menella woodin; Gorgonian coral; Guaianolides; Quantum chemical modelling; Absolute stereochemistry; LACTONES;
D O I
10.1016/j.tetlet.2015.10.102
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Guaiane sesquiterpenoids (1, 2) were isolated from the gorgonian Menello woodin and their structures elucidated by extensive spectroscopic analysis. A complex approach was used to determine the configurations of the asymmetric centres in these natural products, based on the application of Mosher's method, and the calculation of stable conformations of the rings along with a comparison of experimental ECD, NMR spectra, and specific optical rotations with those theoretically calculated by quantum-chemical methods. (C) 2015 Elsevier Ltd. All rights reserved.
引用
收藏
页码:7001 / 7004
页数:4
相关论文
共 50 条
  • [1] Guaiane Sesquiterpenoids from the Gorgonian Menella woodin
    Lyakhova, Ekaterina G.
    Chau Ngoc Diep
    Berdyshev, Dmitrii V.
    Kolesnikova, Sophia A.
    Kalinovsky, Anatoly I.
    Dmitrenok, Pavel S.
    Vu Anh Tu
    Nguyen Xuan Cuong
    Nguyen Van Thanh
    Nguyen Hoai Nam
    Phan Van Kiem
    Stonik, Valentin A.
    Chau Van Minh
    NATURAL PRODUCT COMMUNICATIONS, 2016, 11 (07) : 913 - 916
  • [2] Discovery of novel sesquiterpenoids from a gorgonian Menella sp.
    Kao, Shih-Yao
    Su, Jui-Hsin
    Hwang, Tsong-Long
    Sheu, Jyh-Horng
    Su, Yin-Di
    Lin, Chan-Shing
    Chang, Yu-Chia
    Wang, Wei-Hsien
    Fang, Lee-Shing
    Sung, Ping-Jyun
    TETRAHEDRON, 2011, 67 (38) : 7311 - 7315
  • [3] Polyoxygenated steroids from the gorgonian Menella woodin with capabilities to modulate ROS levels in macrophages at response to LPS
    Tu, Vu A.
    Lyakhova, Ekaterina G.
    Diep, Chau N.
    Kalinovsky, Anatoly I.
    Dmitrenok, Pavel S.
    Cuong, Nguyen X.
    Thanh, Nguyen V.
    Menchinskaya, Ekaterina S.
    Pislyagin, Evgeny A.
    Nam, Nguyen H.
    Kiem, Phan V.
    Stonik, Valentin A.
    Minh, Chau V.
    STEROIDS, 2015, 104 : 246 - 251
  • [4] Menelloides C and D, New Sesquiterpenoids from the Gorgonian Coral Menella sp.
    Kao, Shih-Yao
    Su, Jui-Hsin
    Hwang, Tsong-Long
    Sheu, Jyh-Horng
    Wen, Zhi-Hong
    Wu, Yang-Chang
    Sung, Ping-Jyun
    MARINE DRUGS, 2011, 9 (09): : 1534 - 1542
  • [5] Further highly oxygenated guaiane lactones from the South China Sea gorgonian Menella sp.
    Li, Liang
    Wang, Chang-Yun
    Huang, Hui
    Mollo, Ernesto
    Cimino, Guido
    Guo, Yue-Wei
    HELVETICA CHIMICA ACTA, 2008, 91 (01) : 111 - 117
  • [6] Menverins A-D, new highly oxygenated guaiane lactones from Hainan gorgonian Menella verrucosa (Brundin)
    Zhang, W
    Guo, YW
    Mollo, E
    Cimino, G
    HELVETICA CHIMICA ACTA, 2004, 87 (11) : 2919 - 2925
  • [7] Menverins H-L, New Highly Oxygenated Guaiane Lactones from the Gorgonian Coral Menella kanisa
    Yu, Lian
    Lin, Lin
    Long, Bin
    Chen, Yinning
    Lei, Fu
    Wen, Liangjuan
    Sun, Haiyan
    Gao, Chenghai
    Huang, Riming
    HELVETICA CHIMICA ACTA, 2015, 98 (05) : 710 - 718
  • [8] Absolute Configurations and Bioactivities of Guaiane-Type Sesquiterpenoids Isolated from Pogostemon cablin
    Zhou, Qin-Mei
    Chen, Ming-Hua
    Li, Xiao-Hong
    Peng, Cheng
    Lin, Da-Sheng
    Li, Xiao-Nian
    He, Yang
    Xiong, Liang
    JOURNAL OF NATURAL PRODUCTS, 2018, 81 (09): : 1919 - 1927
  • [9] Guaiane sesquiterpenoids from Haplopappus foliosus
    Labbé, C
    Faini, F
    Coll, J
    Carbonell, P
    PHYTOCHEMISTRY, 1998, 49 (03) : 793 - 795
  • [10] Guaiane Sesquiterpenoids from Jatropha curcas
    Wang, Xia-Chang
    Ma, Shi-Ping
    Liu, Jing-Han
    Hu, Li-Hong
    NATURAL PRODUCT COMMUNICATIONS, 2008, 3 (10) : 1649 - 1652