Previously, Lin et al. reported the isolation and structural determination of two triterpenoids, garcinielliptin oxide (GO) and garcinielliptone E (GE). Their unusual structural features, which remained unparalleled in subsequent decades despite the intervening discovery of hundreds of other polycyclic polyprenylated acylphloroglucinols (PPAPs), caused us to question the originally assigned structures, so GO was reisolated from , and its NMR spectra were reacquired. In this Note, we revise the structures of GO and the related GE via NMR analysis, biosynthetic considerations, and chemical conversion. Garcinielliptone T, a new PPAP, was also isolated and characterized. GO exhibited weak inhibitory activity against acetylcholinesterase with an IC value of 20.7 μM.
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http://dx.doi.org/10.1021/acs.jnatprod.0c00306 | DOI Listing |
Molecules
April 2021
School of Life Sciences, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan.
Cytotoxicity and apoptosis-inducing properties of compounds isolated from leaves were investigated. The hexane-soluble portion of MeOH extracts of leaves that showed cytotoxic activity was separated to yield seven compounds -. Chemical structure analysis using NMR spectroscopy and mass spectrometry confirmed that compound was canophyllol, and compounds - were garcinielliptones N, O, J, G, F, and garcinielliptin oxide, respectively.
View Article and Find Full Text PDFJ Nat Prod
June 2020
State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People's Republic of China.
Previously, Lin et al. reported the isolation and structural determination of two triterpenoids, garcinielliptin oxide (GO) and garcinielliptone E (GE). Their unusual structural features, which remained unparalleled in subsequent decades despite the intervening discovery of hundreds of other polycyclic polyprenylated acylphloroglucinols (PPAPs), caused us to question the originally assigned structures, so GO was reisolated from , and its NMR spectra were reacquired.
View Article and Find Full Text PDFChemistry
May 2003
School of Pharmacy, Kaohsiung Medical University Kaohsiung, Taiwan 807, Republic of China.
Four novel phloroglucinol derivatives, garcinielliptones A (1), B (2), C (3), D (4), a novel triterpenoid, garcinielliptone E (5), and three known compounds were isolated from the seeds of Garcinia subelliptica. The structures, including relative configurations, were elucidated by means of spectroscopic data. Known compounds garsubellin A (6) and garcinielliptin oxide (7) showed potent inhibitory effects on the release of beta-glucuronidase, and beta-glucuronidase and histamine, respectively, from peritoneal mast cells stimulated with compound 48/80 in a concentration-dependent manner with IC(50) values of 15.
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