Unusual cytotoxic sulfated cadinene-type sesquiterpene glycosides from cottonseed (Gossypium hirsutum)

被引：6
|
作者：
Piccinelli, Anna Lisa [1 ]
Lotti, Cinzia [1 ]
Severino, Lorella [2 ]
Luongo, Diomira [2 ]
Rastrelli, Luca [1 ]
机构：
[1] Univ Salerno, Dipartimento Sci Farmaceut, I-84084 Fisciano, SA, Italy
[2] Univ Naples Federico II, Dipartimento Patol & Sanita Anim, Sez Tossicol, Naples, Italy
来源：
TETRAHEDRON | 2008年 / 64卷 / 23期
关键词：
cotton; whole cottonseed; Gossypium hirsutum; sesquiterpenes; desoxyhemigossypol; sulfate; cytotoxic; Jurkat cells;
D O I：
10.1016/j.tet.2008.04.013
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Two new sulfated cadinene-type sesquiterpene glycosides, 13-hydroxy-7-O-(6'-O-sulfate-beta-D-glucopyranosyl)-desoxyhemigossypol (1) and 13,15-dihydroxy-7-O-(6'-O-sulfate-beta-D-glucopyranosyl)-desoxyhemigossypol (2), have been isolated from whole cottonseed (Gossypium hirsutum). Their structures, which possess an unusual 6-O-sulfate-glucopyranosyl moiety, were determined through the interpretation of 2D NMR spectral data and H/D exchange ESI-MS experiments. Compounds 1 and 2 were screened for their toxicity on Jurkat cells. Both compounds inhibited cellular proliferation with IC50 values of 8.1 and 4.2 mu g, respectively. (C) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码：5449 / 5453
页数：5
相关论文
共 50 条
  • [41] Eudesmane-type sesquiterpene glycosides: sonneratiosides A–E and eudesmol β-d-glucopyranoside from the leaves of Sonneratia alba
    Kazuma Katsutani
    Sachiko Sugimoto
    Yoshi Yamano
    Hideaki Otsuka
    Katsuyoshi Matsunami
    Tsutomu Mizuta
    Journal of Natural Medicines, 2020, 74 : 119 - 126
  • [42] Three new muurolane-type sesquiterpene glycosides from the whole plants of Balanophora fungosa subsp. indica
    Bui Huu Tai
    Ngu Yen Xuan Nhiem
    Pham Hai Yen
    Tran Hong Quang
    Nguyen Thi Cuc
    Do Thi Trang
    Vu Van Doan
    Dan Thi Thuy Hang
    Chau Van Minh
    Phan Van Kiem
    NATURAL PRODUCT RESEARCH, 2020, 34 (20) : 2964 - 2970
  • [43] Five New Cucurbitane-Type Triterpenoid Glycosides from the Rhizomes of Hemsleya penxianensis with Cytotoxic Activities
    Chen, De-Li
    Xu, Xu-Dong
    Li, Rong-Tao
    Wang, Bo-Wen
    Yu, Meng
    Liu, Yang-Yang
    Ma, Guo-Xu
    MOLECULES, 2019, 24 (16):
  • [44] Proteomic analysis of anthers from wild-type and photosensitive genetic male sterile mutant cotton (Gossypium hirsutum L.)
    Liu, Ji
    Pang, Chaoyou
    Wei, Hengling
    Song, Meizhen
    Meng, Yanyan
    Fan, Shuli
    Yu, Shuxun
    BMC PLANT BIOLOGY, 2014, 14
  • [45] Data for proteomic profiling of Anthers from a photosensitive male sterile mutant and wild-type cotton (Gossypium hirsutum L.)
    Liu, Ji
    Pang, Chaoyou
    Wei, Hengling
    Song, Meizhen
    Meng, Yanyan
    Ma, Jianhui
    Fan, Shuli
    Yu, Shuxun
    DATA IN BRIEF, 2015, 4 : 500 - 509
  • [46] Proteomic analysis of anthers from wild-type and photosensitive genetic male sterile mutant cotton (Gossypium hirsutum L.)
    Ji Liu
    Chaoyou Pang
    Hengling Wei
    Meizhen Song
    Yanyan Meng
    Shuli Fan
    Shuxun Yu
    BMC Plant Biology, 14
  • [47] Eudesmane-type sesquiterpene glycosides: sonneratiosides A-E and eudesmol β-d-glucopyranoside from the leaves of Sonneratia alba
    Katsutani, Kazuma
    Sugimoto, Sachiko
    Yamano, Yoshi
    Otsuka, Hideaki
    Matsunami, Katsuyoshi
    Mizuta, Tsutomu
    JOURNAL OF NATURAL MEDICINES, 2020, 74 (01) : 119 - 126
  • [48] Two New Eudesmane-Type Sesquiterpene from Clonostachys sp. Y6-1and Their Cytotoxic Activity
    Wang, Mengru
    Yang, Run
    Chen, Yuansi
    Ni, Dongxuan
    Bi, Dewen
    Li, Qi
    Huang, Jiabi
    Wang, Hairong
    Wang, Weiguang
    Li, Hongliang
    Xiao, Weilie
    CHEMISTRY & BIODIVERSITY, 2023, 20 (09)
  • [49] iTRAQ-facilitated proteomic profiling of anthers from a photosensitive male sterile mutant and wild-type cotton (Gossypium hirsutum L.)
    Liu, Ji
    Pang, Chaoyou
    Wei, Hengling
    Song, Meizhen
    Meng, Yanyan
    Ma, Jianhui
    Fan, Shuli
    Yu, Shuxun
    JOURNAL OF PROTEOMICS, 2015, 126 : 68 - 81
  • [50] The crystal structure of annexin Gh1 from Gossypium hirsutum reveals an unusual S3 cluster -: Implications for cellulose synthase complex formation and oxidative stress response
    Hofmann, A
    Delmer, DP
    Wlodawer, A
    EUROPEAN JOURNAL OF BIOCHEMISTRY, 2003, 270 (12): : 2557 - 2564
12345