76905-12-9Relevant academic research and scientific papers
Sesquiterpene dimers esterified with diverse small organic acids from the seeds of Sarcandra glabra
Wang, Peng,Luo, Jun,Zhang, Yang-Mei,Kong, Ling-Yi
, p. 5362 - 5370 (2015/07/15)
11 new sesquiterpene dimers, sarglabolides A-K (1-11), and five known ones were isolated from the seeds of Sarcandra glabra. Their structures were elucidated by spectroscopic data analysis and chemical evidence. Sarglabolide A (1) was verified to exclusively possess a seventeen-membered macrocyclic ester ring formed by the scaffold of the sesquiterpene dimer and small organic acids, different from the eighteen-membered rings of the other reported analogues. The chiral small organic acid moieties were assigned to l-malic acid, d-malic acid, and d-tartaric acid based on the combination of spectroscopy, chemical derivatization and HPLC analysis. Dimers 1, 12 and 13 can significantly inhibit NO production in LPS-induced macrophages with IC50 values at 3.04, 4.65 and 2.33 μmol/L, respectively.
Stereochemistry of the macrolactins
Rychnovsky, Scott D.,Skalitzky, Donald J.,Pathirana, Charles,Jensen, Paul R.,Fenical, William
, p. 671 - 677 (2007/10/02)
The macrolactins are a group of six 24-membered ring lactones isolated from a taxonomically-undefinable deep sea bacterium. Macrolactin A, the parent aglycone, shows a number of interesting biological activities, including the protection of T-lympboblast cells against human HIV viral replication. Herein we report the stereochemistries of macrolactin B and macrolactin F, which were determined by a combination of 13C-acetonide analysis using isotopically enriched acetone, oxidative degradation, and chemical correlation. Macrolactins B and F were found to have the same stereochemistry at each of the common stereogenic centers, and so we expect that macrolactin A, the aglycone of macrolactin B, has the stereochemistry 7S,13S,15R,23R.
