Cytotoxic gelsedine-type indole alkaloids from Gelsemium elegans

Abstract The ethanol extract of the leaves and branches of Gelsemium elegans afforded three new gelsedine-type indole alkaloids, 11-methoxy-14,15-dihydroxyhumantenmine (1), 11-methoxy-14,15-dihydroxy-19-oxogelsenicine (2), and 11-methoxy-14-hydroxygelsedilam (3), along with one known alkaloid 11-methoxy-14-hydroxyhumantenmine (4). The structures of isolated compounds were established based on 1D and 2D (1H-1H COSY, HMQC, and HMBC) NMR spectroscopy, in addition to high-resolution mass spectrometry. The isolated alkaloids were tested in vitro for cytotoxic potential against four laryngeal tumor cell lines including Hep-2, LSC-1, TR-LCC-1, and FD-LSC-1. As a result, compounds 1 and 4 exhibited some cytotoxic activities against all tested tumor cell lines with IC50 values of 10.9–12.1 μM and 9.2–10.8 μM, respectively.

[1]  Qing-Jie Zhao,et al.  Limonoids isolated from Toona sinensis and their radical scavenging, anti-inflammatory and cytotoxic activities , 2015, Journal of Functional Foods.

[2]  Jie Zhao,et al.  New oxindole alkaloids from Gelsemium elegans , 2015 .

[3]  Lin Yang,et al.  Koumine, Humantenine, and Yohimbane Alkaloids from Gelsemium elegans. , 2015, Journal of natural products.

[4]  Jiang Hu,et al.  Alkaloids from Toddalia asiatica and their cytotoxic, antimicrobial and antifungal activities. , 2014, Food chemistry.

[5]  Ming Liu,et al.  Medicinal plants of the genus Gelsemium (Gelsemiaceae, Gentianales)--a review of their phytochemistry, pharmacology, toxicology and traditional use. , 2014, Journal of ethnopharmacology.

[6]  X. Bao,et al.  Bisindole alkaloids with neural anti-inflammatory activity from Gelsemium elegans. , 2013, Journal of natural products.

[7]  Xiao Lin,et al.  Gelsochalotine, a novel indole ring-degraded monoterpenoid indole alkaloid from Gelsemium elegans , 2013 .

[8]  Hong-ping He,et al.  Three novel β-carboline alkaloids from Gelsemium elegans. , 2012, Fitoterapia.

[9]  Qing-Wen Zhang,et al.  Six new monoterpenoid indole alkaloids from the aerial part of Gelsemium elegans , 2011 .

[10]  H. Takayama,et al.  Seven new monoterpenoid indole alkaloids from Gelsemium elegans. , 2011, Chemistry, an Asian journal.

[11]  Li‐jun Wu,et al.  Two new alkaloids from Gelsemium elegans , 2010, Journal of Asian natural products research.

[12]  M. Kitajima.  Chemical studies on monoterpenoid indole alkaloids from medicinal plant resources Gelsemium and Ophiorrhiza , 2006, Journal of Natural Medicines.

[13]  H. Takayama,et al.  Four novel gelsenicine-related oxindole alkaloids from the leaves of Gelsemium elegans benth. , 2006, Organic letters.

[14]  H. Takayama,et al.  Isolation of gelsedine-type indole alkaloids from Gelsemium elegans and evaluation of the cytotoxic activity of gelsemium alkaloids for A431 epidermoid carcinoma cells. , 2006, Journal of natural products.

[15]  H. Takayama,et al.  New oxindole alkaloids and iridoid from Carolina jasmine (Gelsemium sempervirens Ait. f.). , 2003, Chemical & pharmaceutical bulletin.

[16]  H. Takayama,et al.  Structure reinvestigation of gelsemoxonine, a constituent of Gelsemium elegans, reveals a novel, azetidine-containing indole alkaloid. , 2003, Organic letters.

[17]  H. M. Karakaş,et al.  152 ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? , 2005 .