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Molecules 2014, 19(4), 4326-4337; doi:10.3390/molecules19044326
Article

Germacranes and m-Menthane from Illicium lanceolatum

1,2,* , 3
, 4,* , 4
, 5
, 1,2
, 1,2
, 1,2,6
 and 1,2
1 Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, Chicago, IL 60612, USA 2 WHO Collaborative Center for Traditional Medicine, College of Pharmacy, University of Illinois at Chicago, Chicago, IL 60612, USA 3 Department of Pharmacology, College of Medicine, University of Illinois at Chicago, Chicago, IL 60612, USA 4 State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Science and Peking Union Medical College, Beijing 100050, China 5 Jiangsu Key Laboratory for TCM Formulae Research, Nanjing University of Traditional Chinese Medicine, Nanjing 210046, China 6 Department of Natural Medicinal Chemistry, China Pharmaceutical University, Nanjing 210009, China
* Authors to whom correspondence should be addressed.
Received: 15 March 2014 / Revised: 27 March 2014 / Accepted: 28 March 2014 / Published: 4 April 2014
(This article belongs to the Section Metabolites)
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Abstract

Three new germacrane sesquiterpenes and a new m-menthane monoterpene were isolated together with four known compounds from the pericarp of Illicium lanceolatum, an adulterant to star anise (Illicium verum). All compounds were isolated from Illicium plants for the first time. The absolute stereochemistry of all germacranes and m-menthane was established by a combination of NMR and the modified Mosher’s ester method. The biological activity was evaluated on SH-SY5Y neuroblastoma cell line. (1S,5R,7R)-1,5-Dihydroxygermacra-4(15),10(14),11(12)-triene (at 62.5 µM) and (1R,5R,7R)-1,5-dihydroxygermacra-4(15),10(14),11(12)-triene (at 15.6 µM) promoted the proliferation of SH-SY5Y by 36.2% and 45.8%, respectively, after 48 h incubation, indicating potential neurotrophic activity.
Keywords: Illicium lanceolatum; Illiciaceae; germacrane sesquiterpenes; m-menthane monoterpene; absolute stereochemistry; proliferative promotion; SH-SY5Y Illicium lanceolatum; Illiciaceae; germacrane sesquiterpenes; m-menthane monoterpene; absolute stereochemistry; proliferative promotion; SH-SY5Y
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Zhao, M.; Zhang, X.; Wang, Y.; Huang, M.; Duan, J.-A.; Gödecke, T.; Szymulanska-Ramamurthy, K.M.; Yin, Z.; Che, C.-T. Germacranes and m-Menthane from Illicium lanceolatum. Molecules 2014, 19, 4326-4337.

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