Garsubellin A (1), a novel polyprenylated phloroglucin derivative, has been isolated from the wood of Garcinia subelliptica and its structure has been elucidated by spectroscopic analyses. Compound 1 could increase the ChAT activity at 10 microM in P10 rat septal neuron cultures.
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Evolution of a Synthetic Strategy for Garsubellin A.
Chemistry
December 2022
Department of Chemistry, Seoul National University, Seoul, 08826, Republic of Korea.
Garsubellin A is a thirty-carbon meroterpenoid capable of enhancing the enzyme choline acetyltransferase whose decreased level is associated with the symptoms of Alzheimer's disease. Due to the potentially useful biological activity along with the novel molecular architecture, this plant metabolite has remained a popular synthetic target. Herein we report a full account of our synthetic investigations that have led to the enantioselective total synthesis of garsubellin A, establishing its absolute stereostructure.
View Article and Find Full Text PDFEnantioselective Total Synthesis of (+)-Garsubellin A.
Angew Chem Int Ed Engl
October 2021
Department of Chemistry, Seoul National University, Seoul, 08826, Republic of Korea.
Garsubellin A is a meroterpene capable of enhancing the enzyme choline acetyltransferase whose decreased level is believed to play a central role in the symptoms of Alzheimer's disease. Due to the potentially useful biological activity together with the novel bridged and fused cyclic molecular architecture, garsubellin A has garnered substantial synthetic interest, but its absolute stereostructure has been undetermined. We report here the first enantioselective total synthesis of (+)-garsubellin A.
View Article and Find Full Text PDFNovel and anti-inflammatory constituents of Garcinia subelliptica.
Chemistry
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.
View Article and Find Full Text PDFGarsubellin A, a novel polyprenylated phloroglucin derivative, increasing choline acetyltransferase (ChAT) activity in postnatal rat septal neuron cultures.
Chem Pharm Bull (Tokyo)
May 1997
Institute of Pharmacognosy, Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Japan.
Garsubellin A (1), a novel polyprenylated phloroglucin derivative, has been isolated from the wood of Garcinia subelliptica and its structure has been elucidated by spectroscopic analyses. Compound 1 could increase the ChAT activity at 10 microM in P10 rat septal neuron cultures.
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