Structural and Stereochemical Studies of Laurokamurols A-C, Uncommon Bis-sesquiterpenoids from the Chinese Red Alga Laurencia okamurai Yamada.
Three novel heterodimeric laurane-type sesquiterpenoids, laurokamurols A-C (1-3), along with eight known related monomeric ones (4-11) were isolated from the East China Sea red alga Laurencia okamurai Yamada. The absolute configurations of the new bis-sesquitepenoids, especially their axial chirality, were determined by extensive spectroscopic analyses and TDDFT-ECD method. All of the new compounds showed promising PTP1B inhibitory activities with IC50values comparable to the positive control, indicating them as potential food additives or pharmaceutical drug leads toward obesity or diabetes.
State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences , No. 555 Zu Chong Zhi Road, Zhangjiang Hi-Tech Park, Shanghai 201203, China.|University of Chinese Academy of Sciences , No. 19A Yuquan Road, Beijing 100049, China.
Xiao-Lu
XL
Li
Department of Organic Chemistry, University of Debrecen , Egyetemtér 1, P.O. Box 400, 4002 Debrecen, Hungary.
Tibor
T
Kurtán
State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences , No. 555 Zu Chong Zhi Road, Zhangjiang Hi-Tech Park, Shanghai 201203, China.|University of Chinese Academy of Sciences , No. 19A Yuquan Road, Beijing 100049, China.
Jun-Chi
JC
Hu
Department of Organic Chemistry, University of Debrecen , Egyetemtér 1, P.O. Box 400, 4002 Debrecen, Hungary.
Attila
A
Mándi
State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences , No. 555 Zu Chong Zhi Road, Zhangjiang Hi-Tech Park, Shanghai 201203, China.
Jia
J
Li
State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences , No. 555 Zu Chong Zhi Road, Zhangjiang Hi-Tech Park, Shanghai 201203, China.
Xu-Wen
XW
Li
State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences , No. 555 Zu Chong Zhi Road, Zhangjiang Hi-Tech Park, Shanghai 201203, China.
Yue-Wei
http://orcid.org/0000-0003-0413-2070
YW
Guo
D002681:China; D004791:Enzyme Inhibitors / Q000737:chemistry* / Q000302:isolation & purification; D006801:Humans; D044722:Laurencia / Q000737:chemistry*; D019906:Nuclear Magnetic Resonance, Biomolecular; D010936:Plant Extracts / Q000737:chemistry* / Q000302:isolation & purification; D054562:Protein Tyrosine Phosphatase, Non-Receptor Type 1 / Q000037:antagonists & inhibitors / Q000737:chemistry; D012717:Sesquiterpenes / Q000737:chemistry* / Q000302:isolation & purification
D004791:Enzyme Inhibitors; D010936:Plant Extracts; D012717:Sesquiterpenes; C516607:PTPN1 protein, human; D054562:Protein Tyrosine Phosphatase, Non-Receptor Type 1
PTP1B; axial chirality; laurane; red alga; sesquiterpenoid