Eremane, viscidane and isozizaene diterpenoids from the leaves of Eremophila rigida and their absolute configurations

Chao Liang; Chi Ndi; Susan Semple; Bevan Buirchell; Sonia Coriani; Birger Lindberg Møller; Dan Stærk

doi:10.1016/j.phytochem.2024.113972

Eremane, viscidane and isozizaene diterpenoids from the leaves of Eremophila rigida and their absolute configurations

Chao Liang, Chi Ndi, Susan Semple, Bevan Buirchell, Sonia Coriani, Birger Lindberg Møller, Dan Stærk^*

^*Corresponding author for this work

Research output: Contribution to journal › Journal article › Research › peer-review

19 Downloads (Pure)

Abstract

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 inhibition
with 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.

Original language	English
Article number	113972
Journal	Phytochemistry
Volume	219
Number of pages	16
ISSN	0031-9422
DOIs	https://doi.org/10.1016/j.phytochem.2024.113972
Publication status	Published - 2024

Access to Document

10.1016/j.phytochem.2024.113972Licence: CC BY

FulltextFinal published version, 6.83 MBLicence: CC BY

Cite this

@article{6287da905ebd468599ec1dde9dc50c05,

title = "Eremane, viscidane and isozizaene diterpenoids from the leaves of Eremophila rigida and their absolute configurations",

abstract = "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.",

author = "Chao Liang and Chi Ndi and Susan Semple and Bevan Buirchell and Sonia Coriani and M{\o}ller, {Birger Lindberg} and Dan St{\ae}rk",

year = "2024",

doi = "10.1016/j.phytochem.2024.113972",

language = "English",

volume = "219",

journal = "Phytochemistry",

issn = "0031-9422",

publisher = "Pergamon Press",

}

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 -