New pentacyclic triterpene saponins with strong anti-leishmanial activity from the leaves of Maesa balansae

被引:37
|
作者
Germonprez, N
Van Puyvelde, L
Maes, L
Van Tri, M
De Kimpe, N
机构
[1] State Univ Ghent, Dept Organ Chem, Fac Agr & Appl Biol Sci, B-9000 Ghent, Belgium
[2] Natl Ctr Nat Sci & Technol, Inst Chem, Hanoi, Vietnam
[3] Tibotec Virco, B-2800 Mechelen, Belgium
关键词
Maesa balansae; Myrsinaceae; leaves; isolation; structure elucidation; triterpene saponins; anti-leishmanial activity;
D O I
10.1016/j.tet.2003.09.042
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Six new triterpene saponins bearing an oxygen bridge between C-13 and C-28 and with pronounced anti-leishmanial activity were isolated from the methanolic extract of leaves of the Vietnamese medicinal plant Maesa balansae. The structure was established on the basis of detailed NMR (COSY, NOESY, HMQC, HMBC, TOCSY and DEPT) and FAB-MS studies along with chemical degradation. All saponins identified contained the same pentaglycosidic side chain, but a different esterification pattern on the triterpenoid part. Biological evaluation of the individual compounds against visceral leishmaniasis (Leishmania infantum amastigotes) revealed a much better activity in vitro compared to the reference compound Pentostam(R), which is currently used as first-line treatment for leishmaniasis. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:219 / 228
页数:10
相关论文
共 50 条
  • [1] In vitro and in vivo anti-leishmanial activity of triterpenoid saponins isolated from Maesa balansae and some chemical derivatives
    Germonprez, N
    Maes, L
    Van Puyvelde, L
    Van Tri, M
    Tuan, DA
    De Kimpe, N
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (01) : 32 - 37
  • [2] Concise synthesis of a pentasaccharide related to the anti-leishmanial triterpenoid saponin isolated from Maesa balansae
    Rajput, Vishal Kumar
    Mukhopadhyay, Balaram
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (17): : 6924 - 6927
  • [3] Two New Pentacyclic Triterpene Saponins from the Leaves of Akebia trifoliata
    Xu, Qiao-Lin
    Wang, Jing
    Dong, Li-Mei
    Zhang, Qiang
    Luo, Bi
    Jia, Yong-Xia
    Wang, Hong-Feng
    Tan, Jian-Wen
    [J]. MOLECULES, 2016, 21 (07)
  • [4] Anti-leishmanial and Anti-cancer Activities of a Pentacyclic Triterpenoid Isolated from the Leaves of Terminalia arjuna Combretaceae
    Moulisha, Biswas
    Kumar, Ghosh Ashok
    Kanti, Haldar Pallab
    [J]. TROPICAL JOURNAL OF PHARMACEUTICAL RESEARCH, 2010, 9 (02) : 135 - 140
  • [5] New iminodibenzyl derivatives with anti-leishmanial activity
    Arndt, Anderson
    Liria, Cleber Wanderlei
    Yokoyama-Yasunaka, Jenicer K. U.
    Teresa Machini, M.
    Bortolin Uhana, Silvia Reni
    Esposito, Breno Pannia
    [J]. JOURNAL OF INORGANIC BIOCHEMISTRY, 2017, 172 : 9 - 15
  • [6] Anti-leishmanial activity of a new formulation of amphotericin B
    Dea-Ayuela, MA
    Rama-Iñiguez, S
    Sánchez-Brunete, JA
    Torrado, JJ
    Alunda, JM
    Bolás-Fernández, F
    [J]. TROPICAL MEDICINE & INTERNATIONAL HEALTH, 2004, 9 (09) : 981 - 990
  • [7] Anti-leishmanial activity of alkaloidal extract from Aspidosperma ramiflorum
    Ferreira, LCP
    Lonardoni, MVC
    Machado, GMC
    Leon, LL
    Gobbi, L
    Pinto, LHB
    de Oliveira, AJB
    [J]. MEMORIAS DO INSTITUTO OSWALDO CRUZ, 2004, 99 (03): : 325 - 327
  • [8] Potential Anti-leishmanial Activity of a Semi-purified Fraction Isolated from the Leaves of Parthenium hysterophorus
    Joydip Ghosh
    Sondipon Chakraborty
    Somaditya Dey
    Debarati Mukherjee
    Biswajyoti Sarkar
    Suvadip Mallick
    Aritri Dutta
    Tanmoy Dutta
    Soumen Bhattacharjee
    Narayan Ghorai
    Chiranjib Pal
    [J]. Acta Parasitologica, 2021, 66 : 1480 - 1489
  • [9] Potential Anti-leishmanial Activity of a Semi-purified Fraction Isolated from the Leaves of Parthenium hysterophorus
    Ghosh, Joydip
    Chakraborty, Sondipon
    Dey, Somaditya
    Mukherjee, Debarati
    Sarkar, Biswajyoti
    Mallick, Suvadip
    Dutta, Aritri
    Dutta, Tanmoy
    Bhattacharjee, Soumen
    Ghorai, Narayan
    Pal, Chiranjib
    [J]. ACTA PARASITOLOGICA, 2021, 66 (04) : 1480 - 1489
  • [10] New flavonoid and pentacyclic triterpene from Sesamum indicum leaves
    Nguyen Tien Dat
    Nguyen Hai Dang
    Le Nguyen Thanh
    [J]. NATURAL PRODUCT RESEARCH, 2016, 30 (03) : 311 - 315