Eremane, viscidane and isozizaene diterpenoids from the leaves of Eremophila rigida and their absolute configurations
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Eremane, viscidane and isozizaene diterpenoids from the leaves of Eremophila rigida and their absolute configurations. / Liang, Chao; Ndi, Chi; Semple, Susan; Buirchell, Bevan; Coriani, Sonia; Møller, Birger Lindberg; Stærk, Dan.
I: Phytochemistry, Bind 219, 113972, 2024.Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt
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TY - JOUR
T1 - Eremane, viscidane and isozizaene diterpenoids from the leaves of Eremophila rigida and their absolute configurations
AU - Liang, Chao
AU - Ndi, Chi
AU - Semple, Susan
AU - Buirchell, Bevan
AU - Coriani, Sonia
AU - Møller, Birger Lindberg
AU - Stærk, Dan
PY - 2024
Y1 - 2024
N2 - Previously undescribed eremane, viscidane, and isozizaene diterpenoids, eremorigidanes A-F, along with six known O-methylated flavonoids and three known triterpenoids were isolated and identified from the leaves of Eremophila rigida Chinnock by combined use of high-resolution PTP1B inhibition profiling, semipreparative- and analytical-scale HPLC separations, HPLC-PDA-HRMS analysis, and NMR spectroscopy. The absolute configuration of the unreported diterpenoids were determined by comparison of their experimental and calculated ECD spectra as well as by biosynthetic arguments. All isolates were evaluated for their PTP1B inhibitory activities, which revealed the flavonoid penduletin (3) to show inhibition with an IC50 value of 18.3 μM, and the triterpenoids 3,4-seco-olean-12-ene-3,28-dioic acid (15), oleanolic acid (16), and 3-oxo-oleanolic acid (17) to show inhibitionwith IC50 values of 55.7, 9.9, and 6.3 μM, respectively. The preliminary structure-activity relationship (SAR) of isolated flavonoids and triterpenoids is discussed. Plausible biosynthetic steps involved in eremane and isozizaene metabolism are presented and discussed.
AB - Previously undescribed eremane, viscidane, and isozizaene diterpenoids, eremorigidanes A-F, along with six known O-methylated flavonoids and three known triterpenoids were isolated and identified from the leaves of Eremophila rigida Chinnock by combined use of high-resolution PTP1B inhibition profiling, semipreparative- and analytical-scale HPLC separations, HPLC-PDA-HRMS analysis, and NMR spectroscopy. The absolute configuration of the unreported diterpenoids were determined by comparison of their experimental and calculated ECD spectra as well as by biosynthetic arguments. All isolates were evaluated for their PTP1B inhibitory activities, which revealed the flavonoid penduletin (3) to show inhibition with an IC50 value of 18.3 μM, and the triterpenoids 3,4-seco-olean-12-ene-3,28-dioic acid (15), oleanolic acid (16), and 3-oxo-oleanolic acid (17) to show inhibitionwith IC50 values of 55.7, 9.9, and 6.3 μM, respectively. The preliminary structure-activity relationship (SAR) of isolated flavonoids and triterpenoids is discussed. Plausible biosynthetic steps involved in eremane and isozizaene metabolism are presented and discussed.
U2 - 10.1016/j.phytochem.2024.113972
DO - 10.1016/j.phytochem.2024.113972
M3 - Journal article
C2 - 38211848
VL - 219
JO - Phytochemistry
JF - Phytochemistry
SN - 0031-9422
M1 - 113972
ER -
ID: 379659837