Germacranes and m-menthane from Illicium lanceolatum.
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.
Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, Chicago, IL 60612, USA. mingz@uic.edu.
Ming
M
Zhao
Department of Pharmacology, College of Medicine, University of Illinois at Chicago, Chicago, IL 60612, USA. zhangxm1973@gmail.com.
Xianming
X
Zhang
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. wangyan@imm.ac.cn.
Yan
Y
Wang
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. Huangmin@imm.ac.cn.
Min
M
Huang
Jiangsu Key Laboratory for TCM Formulae Research, Nanjing University of Traditional Chinese Medicine, Nanjing 210046, China. Duanja@163.com.
Jin-Ao
JA
Duan
Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, Chicago, IL 60612, USA. tan13ja@gmail.com.
Tanja
T
Gödecke
Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, Chicago, IL 60612, USA. kszymu2@uic.edu.
Karina M
KM
Szymulanska-Ramamurthy
Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, Chicago, IL 60612, USA. chyzq2005@126.com.
Zhiqi
Z
Yin
Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, Chicago, IL 60612, USA. chect@uic.edu.
Chun-Tao
CT
Che
D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D005638:Fruit / Q000737:chemistry*; D006801:Humans; D029523:Illicium / Q000737:chemistry*; D039821:Monoterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D009474:Neurons / Q000166:cytology / Q000187:drug effects; D018696:Neuroprotective Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D010936:Plant Extracts / Q000737:chemistry; D045788:Sesquiterpenes, Germacrane / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology
D039821:Monoterpenes; D018696:Neuroprotective Agents; D010936:Plant Extracts; D045788:Sesquiterpenes, Germacrane