星毛米仔兰茎中的环戊并[b]苯并呋喃和次生达玛烷衍生物。
Cyclopenta[b]benzofuran and Secodammarane Derivatives from the Stems of Aglaia stellatopilosa.
作者信息
Othman Nuraqilah, Pan Li, Mejin Michele, Voong Julian C L, Chai Hee-byung, Pannell Caroline M, Kinghorn A Douglas, Yeo Tiong C
机构信息
Sarawak Biodiversity Centre , KM20, Jalan Borneo Heights, Semengoh, Locked Bag No. 3032, Kuching 93990, Sarawak Malaysia.
Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University , Columbus, Ohio 43210, United States.
出版信息
J Nat Prod. 2016 Apr 22;79(4):784-91. doi: 10.1021/acs.jnatprod.5b00810. Epub 2016 Mar 14.
Abstract
Four new 2,3-secodammarane triterpenoids, stellatonins A-D (3-6), together with a new 3,4-secodammarane triterpenoid, stellatonin E (7), and the known silvestrol (1), 5‴-episilvestrol (2), and β-sitosterol, were isolated from a methanol extract of the stems of Aglaia stellatopilosa through bioassay-guided fractionation. The structures of the new compounds were elucidated using spectroscopic and chemical methods. The compounds were evaluated for their cytotoxic activity against three human cancer cell lines and for their antimicrobial activity using a microtiter plate assay against a panel of Gram-positive and Gram-negative bacteria and fungi.
摘要
通过生物活性导向分离，从毛瓣米仔兰茎的甲醇提取物中分离得到了4个新的2,3-裂达玛烷三萜类化合物，即米仔兰酮A-D（3-6），以及1个新的3,4-裂达玛烷三萜类化合物，米仔兰酮E（7），还有已知的silvestrol（1）、5‴-表silvestrol（2）和β-谷甾醇。采用光谱和化学方法阐明了这些新化合物的结构。利用微量滴定板法，针对3种人类癌细胞系评估了这些化合物的细胞毒性活性，并针对一组革兰氏阳性菌、革兰氏阴性菌和真菌评估了它们的抗菌活性。
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本文引用的文献
1
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Oncotarget. 2015 Feb 20;6(5):2693-708. doi: 10.18632/oncotarget.2098.
2
Complete (1)H-NMR and (13)C-NMR spectral analysis of the pairs of 20(S) and 20(R) ginsenosides.完成对 20(S)和 20(R)人参皂苷对映异构体的 1H-NMR 和 13C-NMR 光谱分析。
J Ginseng Res. 2014 Jul;38(3):194-202. doi: 10.1016/j.jgr.2014.05.002. Epub 2014 May 27.
3
Rocaglamide, silvestrol and structurally related bioactive compounds from Aglaia species.从山桂花属植物中分离得到的罗卡酰胺、西维因醇和结构相关的生物活性化合物。
Nat Prod Rep. 2014 Jul;31(7):924-39. doi: 10.1039/c4np00006d. Epub 2014 May 2.
4
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J Hematol Oncol. 2013 Mar 16;6:21. doi: 10.1186/1756-8722-6-21.
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Clin Cancer Res. 2012 Sep 1;18(17):4600-11. doi: 10.1158/1078-0432.CCR-12-0839. Epub 2012 Jul 12.
9
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Bioorg Med Chem. 2012 Mar 15;20(6):1857-64. doi: 10.1016/j.bmc.2011.10.048. Epub 2011 Oct 20.
10
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Prog Chem Org Nat Prod. 2011;94:1-58. doi: 10.1007/978-3-7091-0748-5_1.
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