Jain Sandeep, Laphookhieo Surat, Shi Zhi, Fu Li-Wu, Akiyama Shin-Ichi, Chen Zhe-Sheng, Youssef Diaa T A, van Soest Rob W M, El Sayed Khalid A
Department of Basic Pharmaceutical Sciences, College of Pharmacy, University of Louisiana at Monroe, Monroe, Louisiana 71209, USA.
J Nat Prod. 2007 Jun;70(6):928-31. doi: 10.1021/np0605889. Epub 2007 May 9.
Nineteen triterpenoids, possessing four different skeletons, have been reported so far from the Red Sea sponge Siphonochalina siphonella. However, no biological activity of these compounds was ever reported. This study describes the isolation of two new triterpenoids, siphonellinol C (3) and sipholenol I (4), along with several known sipholane triterpenoids from the Red Sea sponge Callyspongia (=Siphonochalina) siphonella. Allylic oxidation of the major sipholane triterpenoids, sipholenol A (1) and sipholenone A (2), by selenium dioxide afforded four C-28-oxidized derivatives. Sipholane triterpenoids along with their semisynthetic derivatives were evaluated for their cytotoxicity and effect on reversing P-glycoprotein-mediated MDR to colchicine. Sipholenol A was found to be the most potent, and it increased the sensitivity of resistant KB-C2 cells by 16 times toward colchicine. This is the first report related to reversal of cancer chemotherapy resistance using these triterpenoids.
迄今为止，已从红海海绵动物管杯海绵中报道了19种具有四种不同骨架的三萜类化合物。然而，这些化合物的生物活性从未被报道过。本研究描述了从红海海绵动物管杯海绵中分离出两种新的三萜类化合物，管杯海绵醇C（3）和管杯海绵烯醇I（4），以及几种已知的海绵烷三萜类化合物。主要的海绵烷三萜类化合物，管杯海绵烯醇A（1）和管杯海绵烯酮A（2），通过二氧化硒进行烯丙基氧化，得到了四种C-28氧化衍生物。对海绵烷三萜类化合物及其半合成衍生物进行了细胞毒性评估以及对逆转P-糖蛋白介导的对秋水仙碱的多药耐药性的作用评估。发现管杯海绵烯醇A最具活性，它使耐药的KB-C2细胞对秋水仙碱的敏感性提高了16倍。这是关于使用这些三萜类化合物逆转癌症化疗耐药性的首次报道。
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