10.1021/acs.jnatprod.5b00969.s002
Jinyu Zhang
Jinyu
Zhang
Ling Liu
Ling
Liu
Bo Wang
Bo
Wang
Yang Zhang
Yang
Zhang
Lili Wang
Lili
Wang
Xingzhong Liu
Xingzhong
Liu
Yongsheng Che
Yongsheng
Che
Phomanolides A and B from the Fungus <i>Phoma</i> sp.:
Meroterpenoids Derived from a Putative Tropolonic Sesquiterpene
via Hetero-Diels–Alder Reactions
American Chemical Society
2015
culture
Compound 4
NMR spectroscopic data
eupenifeldin
crystallography
dichroism calculations
phomanoxide
Derived
ReactionsPhomanolide
biosynthetic precursor
antiproliferative effects
IC 50 values
compounds 1
Putative Tropolonic Sesquiterpene
monotropolonic sesquiterpene
fungus
Biogenetically
pentacyclic
Phomanolide
substrate
Meroterpenoid
tetracyclic skeletons
Phoma
Fungu
meroterpenoid
glioma cell lines
2015-12-24 00:00:00
Dataset
https://acs.figshare.com/articles/dataset/Phomanolides_A_and_B_from_the_Fungus_i_Phoma_i_sp_Meroterpenoids_Derived_from_a_Putative_Tropolonic_Sesquiterpene_via_Hetero_Diels_Alder_Reactions/2095045
Phomanolides A (<b>1</b>) and
B (<b>2</b>), unique
meroterpenoids with new pentacyclic and tetracyclic skeletons, respectively,
and phomanoxide (<b>3</b>), the double-epoxidation product of
a putative biosynthetic precursor of <b>1</b> and <b>2</b>, were isolated from the solid substrate fermentation cultures of
the fungus <i>Phoma</i> sp., along with the known compound
eupenifeldin (<b>4</b>). The structures of <b>1</b>–<b>3</b> were elucidated based on NMR spectroscopic data and electronic
circular dichroism calculations and further secured by X-ray crystallography.
Biogenetically, compounds <b>1</b> and <b>2</b> could
be derived from a hypothetical monotropolonic sesquiterpene intermediate
via hetero-Diels–Alder reactions. Compound <b>4</b> showed
potent antiproliferative effects against three human glioma cell lines,
with IC<sub>50</sub> values of 0.08–0.13 μM.