Mollebenzylanols A and B, Highly Modified and Functionalized
Diterpenoids with a 9‑Benzyl-8,10-dioxatricyclo[5.2.1.01,5]decane Core from Rhododendron molle
Posted on 2018-03-13 - 11:36
Two
highly modified and functionalized diterpenoids, mollebenzylanols
A (1) and B (2), and a known grayanane diterpenoid
rhodojaponin III (3) were isolated from Rhododendron
molle. Their structures were determined by spectroscopic
data analysis, an electronic circular dichroism (ECD) exciton chirality
method, ECD calculations, and X-ray diffraction analysis of the p-bromobenzoate ester of 1 (1a). Compounds 1 and 2 possess an unprecedented
diterpene carbon skeleton featuring a unique 9-benzyl-8,10-dioxatricyclo[5.2.1.01,5]decane core, and their plausible biosynthetic pathways
are proposed. Their PTP1B inhibitory activity and modes of action
were investigated.
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Zhou, Junfei; Liu, Junjun; Dang, Ting; Zhou, Haofeng; Zhang, Hanqi; Yao, Guangmin (2018). Mollebenzylanols A and B, Highly Modified and Functionalized
Diterpenoids with a 9‑Benzyl-8,10-dioxatricyclo[5.2.1.01,5]decane Core from Rhododendron molle. ACS Publications. Collection. https://doi.org/10.1021/acs.orglett.8b00606
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AUTHORS (6)
JZ
Junfei Zhou
JL
Junjun Liu
TD
Ting Dang
HZ
Haofeng Zhou
HZ
Hanqi Zhang
GY
Guangmin Yao
KEYWORDS
spectroscopic data analysismollebenzylanolfunctionalizedcalculation1BbromobenzoateCoreDiterpenoidECDRhododendron molleX-ray diffraction analysisgrayanane diterpenoid rhodojaponin IIIdichroismBenzylCompoundesterdecanePTPcore9-Modifiedbiosyntheticditerpene carbon skeletonbenzylexciton chirality methodMollebenzylanolFunctionalizedpathwaymode