Nuphar alkaloids with immediately apoptosis-inducing activity from Nuphar pumilum and their structural requirements for the activity

被引：48
|
作者：
Matsuda, H [1 ]
Yoshida, K [1 ]
Miyagawa, K [1 ]
Nemoto, Y [1 ]
Asao, Y [1 ]
Yoshikawa, M [1 ]
机构：
[1] Kyoto Pharmaceut Univ, Yamashima Ku, Kyoto 6078412, Japan
来源：
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2006年 / 16卷 / 06期
关键词：
Nuphar alkaloids; 6-hydroxythiobinupharidine; apoptosis-inducing activity; cytotoxic effect; caspases; U937; B16F10; HT1080;
D O I：
10.1016/j.bmcl.2005.12.032
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
The methanolic extract and its alkaloid fraction from the rhizomes of Nuphar pumilum showed cytotoxic effects on human leukemia cell (U937), mouse melanoma cell (B16F10), and human fibroblast (HT 1080). Dimeric sesquiterpene thioalkaloids with the 6-hydroxyl group (6-hydroxythiobinupharidine, 6,6'-dihydroxythiobinupharidine, 6-hydroxythionuphlutine B) showed substantial cytotoxic activity at a concentration of 10 mu M, but dimeric sesquiterpene thioalkaloids lacking the 6-hydroxyl group (thiobinupharidine, thionuphlutine B, 6'-hydroxythionuphlutine B, neothiobinupharidine, thionuphlutine B beta-sulfoxide, and neothiobinupharidine beta-sulfoxide) and monomeric sesquiterpene alkaloids (nupharidine, 7-epideoxynupharidine, and nupharolutine) showed weak activity. Next, apoptosis-inducing activity of a principal active constituent, 6-hydroxythiobinupharidine, on U937 was examined using morphological observation and DNA fragmentation assay (TUNEL method). Apoptosis of U937 was immediately observed within 1 h after treatment of 6-hydroxythiobinupharidine at 2.5-10 mu M. (C) 2006 Published by Elsevier Ltd.
引用
收藏
页码：1567 / 1573
页数：7
相关论文
共 50 条
  • [21] Copper, but not iron, enhances apoptosis-inducing activity of antioxidants
    Satoh, K
    Kadofuku, T
    Sakagami, H
    ANTICANCER RESEARCH, 1997, 17 (4A) : 2487 - 2490
  • [22] Crude drugs from aquatic plants .6. On the alkaloid constituents of Chinese Nupharis Rhizoma, the dried rhizoma of Nuphar pumilum (TIMM.) DC. (Nymphaceae): Structures and rearragement reaction of thiohemiaminal type nuphar alkaloids
    Yoshikawa, M
    Murakami, T
    Wakao, S
    Ishikado, A
    Murakami, N
    Yamahara, J
    Matsuda, H
    HETEROCYCLES, 1997, 45 (09) : 1815 - 1824
  • [23] Composition and Biological Activity of Furanoquinolizidine Alkaloids from Yellow Water-Lily (Nuphar Lutea L. Smith) Rhizomes
    V. I. Sheichenko
    O. N. Tolkachev
    V. I. Osipov
    O. P. Sheichenko
    V. V. Anufrieva
    V. A. Timoshina
    T. V. Fateeva
    V. V. Bortnikova
    V. A. Bykov
    Pharmaceutical Chemistry Journal, 2019, 53 : 553 - 558
  • [24] COMPOSITION AND BIOLOGICAL ACTIVITY OF FURANOQUINOLIZIDINE ALKALOIDS FROM YELLOW WATER-LILY (NUPHAR LUTEA L. SMITH) RHIZOMES
    Sheichenko, V. I.
    Tolkachev, O. N.
    Osipov, V. I.
    Sheichenko, O. P.
    Anufrieva, V. V.
    Timoshina, V. A.
    Fateeva, T. V.
    Bortnikova, V. V.
    Bykov, V. A.
    PHARMACEUTICAL CHEMISTRY JOURNAL, 2019, 53 (06) : 553 - 558
  • [25] Crude drugs from aquatic plants. VII. Four new thiaspirane sulfoxide type nuphar alkaloids, nupharpumilamines A, B, C, and D, from Chinese Nupharis rhizoma, the rhizoma of Nuphar pumilum (Timm.) DC. (Nymphaceae)
    Yoshikawa, M
    Murakami, T
    Ishikado, A
    Wakao, S
    Murakami, N
    Yamahara, J
    Matsuda, H
    HETEROCYCLES, 1997, 46 : 301 - 308
  • [26] Semisynthesis of Mallotus B from Rottlerin: Evaluation of Cytotoxicity and Apoptosis-Inducing Activity
    Jain, Shreyans K.
    Pathania, Anup S.
    Meena, Samdarshi
    Sharma, Rajni
    Sharma, Ashok
    Singh, Baljinder
    Gupta, Bishan D.
    Bhushan, Shashi
    Bharate, Sandip B.
    Vishwakarma, Ram A.
    JOURNAL OF NATURAL PRODUCTS, 2013, 76 (09): : 1724 - 1730
  • [27] Structural Basis for the Tumor Cell Apoptosis-Inducing Activity of an Antitumor Lectin from the Edible Mushroom Agrocybe aegerita
    Yang, Na
    Li, De-Feng
    Feng, Lei
    Xiang, Ye
    Liu, Wei
    Sun, Hui
    Wang, Da-Cheng
    JOURNAL OF MOLECULAR BIOLOGY, 2009, 387 (03) : 694 - 705
  • [28] Tumor-specific cytotoxicity and apoptosis-inducing activity of berberines
    Inoue, K
    Kulsum, U
    Chowdhury, SA
    Fujisawa, S
    Ishihara, M
    Yokoe, I
    Sakagami, H
    ANTICANCER RESEARCH, 2005, 25 (6B) : 4053 - 4059
  • [29] Relationship between ascorbyl radical intensity and apoptosis-inducing activity
    Sakagami, H
    Satoh, K
    Ohata, H
    Takahashi, H
    Yoshida, H
    Iida, M
    Kuribayashi, N
    Sakagami, T
    Momose, K
    Takeda, M
    ANTICANCER RESEARCH, 1996, 16 (5A) : 2635 - 2644
  • [30] Synthesis of Oxovanadium Complexes and Their Apoptosis-Inducing Activity in Leukemia Cells
    Yamaguchi, Tomoko
    Watanabe, Shinya
    Matsumura, Yuriko
    Tokuoka, Yoshikazu
    Yokoyama, Akihiro
    CHEMICAL & PHARMACEUTICAL BULLETIN, 2012, 60 (04) : 508 - 512
12345