Isolation of Sesquiterpenoids and Steroids from the Soft Coral Sinularia brassica and Determination of Their Absolute Configuration

被引:9
|
作者
Pham, Giang Nam [1 ]
Kang, Da Yeun [1 ]
Kim, Min Ju [2 ]
Han, Se Jong [2 ,3 ]
Lee, Jun Hyuck [3 ,4 ]
Na, MinKyun [1 ]
机构
[1] Chungnam Natl Univ, Coll Pharm, Daejeon 34134, South Korea
[2] Korea Polar Res Inst, Div Life Sci, Incheon 21990, South Korea
[3] Univ Sci & Technol, Dept Polar Sci, Incheon 21990, South Korea
[4] Korea Polar Res Inst, Res Unit Cryogen Novel Mat, Incheon 21990, South Korea
关键词
Sinularia brassica; sesquiterpenoids; steroids; antileishmanial activity; antimicrobial activity; RED-SEA; CONSTITUENTS; METABOLITES;
D O I
10.3390/md19090523
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Two undescribed rearranged cadinane-type sesquiterpenoids (1-2), named sinulaketol A-B, together with one new chlorinated steroid (3), one new gorgosterol (4), one known sesquiterpene (5), one known dibromoditerpene (6) and two known polyhydroxylated steroids (7-8) were isolated from the soft coral Sinularia brassica. The structures of these compounds were established by extensive spectroscopic analysis, including HRESIMS, 1D, and 2D NMR spectroscopy. Their absolute configurations were also determined by the ECD calculations and DP4+ probability analysis. Antileishmanial activity of compounds 1-8 was evaluated in vitro against the amastigote forms of Leishmania donovani, in which compounds 3, 6, and 7 inhibited the growth of L. donovani by 58.7, 74.3, 54.7%, respectively, at a concentration of 50 mu M. Antimicrobial effect of the isolated compounds were also evaluated against Candida albicans, Staphylococcus aureus, and Escherichia coli. Compound 6, a brominated diterpene, exhibited antimicrobial effect against S. aureus.
引用
收藏
页数:12
相关论文
共 50 条
  • [41] Sesquiterpenoids and artificial 19-oxygenated steroids from the Formosan soft coral Nephthea erecta
    Cheng, Shi-Yie
    Dai, Chang-Feng
    Duh, Chang-Yih
    JOURNAL OF NATURAL PRODUCTS, 2007, 70 (09): : 1449 - 1453
  • [42] Secondary Metabolites from the Soft Coral Sinularia nanolobata
    Duh, C. Y.
    Hsu, F. Y.
    Wang, S. K.
    PLANTA MEDICA, 2013, 79 (10) : 845 - 846
  • [43] Secondary Metabolites from the Soft Coral Sinularia arborea
    Chen, Kuan-Hua
    Dai, Chang-Feng
    Lu, Mei-Chin
    Li, Jan-Jung
    Chen, Jih-Jung
    Chang, Yu-Chia
    Su, Yin-Di
    Wang, Wei-Hsien
    Sung, Ping-Jyun
    MARINE DRUGS, 2013, 11 (09): : 3372 - 3380
  • [44] Oxygenated Cembranoids from the Soft Coral Sinularia flexibilis
    Su, Ching-Chyuan
    Wong, Bing-Sang
    Chin, Chuen
    Wu, Yu-Jen
    Su, Jui-Hsin
    INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 2013, 14 (02): : 4317 - 4325
  • [45] A new cembranolide from the soft coral Sinularia capillosa
    Su, JY
    Yang, RL
    Kuang, YY
    Zeng, LM
    JOURNAL OF NATURAL PRODUCTS, 2000, 63 (11): : 1543 - 1545
  • [46] Cembranoids from the Cultured Soft Coral Sinularia gibberosa
    Lin, Hsiu-Fen
    Su, Huey-Jen
    Lee, Nai-Lun
    Su, Jui-Hsin
    NATURAL PRODUCT COMMUNICATIONS, 2013, 8 (10) : 1363 - 1364
  • [47] Bioactive norditerpenoids from the soft coral Sinularia gyrosa
    Cheng, Shi-Yie
    Chuang, Cheng-Ta
    Wen, Zhi-Hong
    Wang, Shang-Kwei
    Chiou, Shu-Fen
    Hsu, Chi-Hsin
    Dai, Chang-Feng
    Duh, Chang-Yih
    BIOORGANIC & MEDICINAL CHEMISTRY, 2010, 18 (10) : 3379 - 3386
  • [48] New sesquiterpenoid from the soft coral Sinularia dissecta
    Ramesh, P
    Ravikanth, V
    Venkateswarlu, Y
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2001, 40 (09): : 867 - 868
  • [49] New norcembranoids from the soft coral Sinularia lochmodes
    Tseng, Yen-Ju
    Ahmed, Atallah F.
    Hsu, Chi-Hsin
    Su, Jui-Hsin
    Dai, Chang-Feng
    Sheu, Jyh-Horng
    JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2007, 54 (04) : 1041 - 1044
  • [50] Steroid Constituents from the Soft Coral Sinularia nanolobata
    Ninh Thi Ngoc
    Pham Thi Mai Huong
    Nguyen Van Thanh
    Nguyen Xuan Cuong
    Nguyen Hoai Nam
    Do Cong Thung
    Phan Van Kiem
    Chau Van Minh
    CHEMICAL & PHARMACEUTICAL BULLETIN, 2016, 64 (09) : 1417 - 1419