Vlasouliolides A-D, four rare C17/C15 sesquiterpene lactone dimers with potential anti-inflammatory activity from Vladimiria souliei

Abstract

Vlasouliolides A-D (1–4), four rare sesquiterpene lactone dimers, were isolated from Vladimiria souliei. The common structural characteristic of 1–4 is the C32 skeleton comprising two sesquiterpene lactone units linked by a C11-C13′ single bond with one acetyl connected to the C-13 position of one of the two sesquiterpene lactone units. The stereochemistries of 1–4 were assigned by a combination of NOESY correlations and Cu-Κα X-ray crystallographic analyses. Compounds 1–4 strongly inhibited the production of NO in LPS-stimulated RAW 264.7 cells. Furthermore, 1 and 2 inhibited the activation of NF-κB in LPS-induced 293T cells.

Synthesis of Vlasouliolides: A Pathway toward Guaiane–Eudesmane C17/C15 Dimers by Photochemical and Michael Additions

“…Similar changes were observed for the other vlasouliolides. The spectra of the synthesized vlasouliolides were identical to those reported for the natural products. , …”

“…HRMS (ESI) m / z : [M – H] − calcd for C 32 H 39 O 5 505.2959; found 505.2592. NMR data obtained for 13 matches the one reported in the bibliography . NMR data is available in the SI.…”

Plastome Evolution in Dolomiaea (Asteraceae, Cardueae) Using Phylogenomic and Comparative Analyses

“…Dolomiaea is commonly known as "Chuan Mu Xiang" in traditional Chinese medicine (Wei et al, 2014;Huang et al, 2019). Species of Dolomiaea are used medicinally for their significant bioactivities such as antioxidant , anti-inflammatory (Chen et al, 2017;Shi et al, 2017) and antimicrobial (Chen et al, 2015) properties, and are also rich resources of multiple chemical components such as sesquiterpenes (Chen et al, 2015), triterpenes , and phenylpropanoids (Wei et al, 2014). Despite significant medicinal value, genomic resources of Dolomiaea are lacking.…”

A comprehensive chemical and pharmacological review of three confusable Chinese herbal medicine—Aucklandiae radix, Vladimiriae radix, and Inulae radix

“…Chen reported that vlasouliolides A‐D isolated from Vladimiria souliei , inhibited the production of NO in LPS‐stimulated RAW 264.7 cells. Furthermore, 1–10 μM vlasouliolides A and B inhibited the activation of NF‐κB in LPS‐induced 293 T cells (L. Chen et al, 2017). Shi et al found that 50 and 100 μM alismol reduced NO and PGE 2 levels and suppressed the expression of iNOS and COX‐2 in LPS‐stimulated primary and cultured microglia.…”

“…Zhou et al have separated, purified and determined 9‐oxonerolidol ( V36 ), vaernopolyanthone ( V37 ), 15‐acetoxy‐11 α H‐germacra‐1(10) E ,4 E ‐diene‐12,6 α ‐olide ( V38 ), 15‐acetoxy‐11 β H‐germacra‐1(10) E ,4 E ‐diene‐12,6 α ‐olide ( V39 ), 12‐hydroxy‐5 α (H),7 α (H)‐eudesm‐4(14),11(13)‐diene‐9‐one ( V40 ), oplodiol ( V41 ), dihydroestafiatone ( V42 ), 10‐oxodihydroxy‐11 β ,13‐dihydrodehydrocostuslactone ( V43 ), (11 S )‐13‐hydroxylguaia‐4(15),10(14)‐diene‐12,6 α ‐olide ( V44 ) from Vladimiria souliei in 2017 (Zhou, Chen, Li, Zhang, & Wang, 2017). Vlasouliolide A ( V45 ), vlasouliolide B ( V46 ), vlasouliolide C ( V47 ), and vlasouliolide D ( V48 ) were also discovered in 2017 (L. Chen et al, 2017). 25‐Hydroxy‐uvaol ( V49 ) was found in 2019 (Lan et al, 2019; Y.…”