Linderaggrenolides A–N, Oxygen-Conjugated Sesquiterpenoid Dimers from the Roots of Lindera aggregata

Abstract

Linderaggrenolides A–N (1–14), 14 new lindenane sesquiterpenoid dimers with oxygen bridges were isolated from the roots of Lindera aggregata. Their structures were elucidated on the basis of comprehensive spectroscopic data analysis, with the absolute configurations established by empirical approaches, electronic circular dichroism calculations, and X-ray crystallography. Compounds 8 and 9 were found to exhibit significant transforming growth factor-β inhibitory activity, with IC50 values of 25.91 and 21.52 μM, respectively.

Atrachinenynes A–D, four diacetylenic derivatives with unprecedented skeletons from the rhizomes of Atractylodes chinensis

“…The proton chemical shift of H-14′ ( δ H 0.76) was close to that of the eudesmane-type sesquiterpene lactones with the α-orientation of the C-8 substituent group, 34 further suggesting the relative configuration of C-8′ and C-12′. To distinguish these overlapping signals between H-8 and H-9 measured in CDCl 3 , the NMR experiment of 3 was measured in CD 3 OD again (see Table S1, ESI†).…”

“…3) between H-12 0 and H-14 0 (d H 0.76) (spatial distance as 4.3 Å) disclosed that both these protons are b-oriented according to those of atractylon in the natural occurrence. 30,31 The proton chemical shift of H-14 0 (d H 0.76) was close to that of the eudesmane-type sesquiterpene lactones with the a-orientation of the C-8 substituent group, 34 further suggesting the relative configuration of C-8 0 and C-12 0 . To distinguish these overlapping signals between H-8 and H-9 measured in CDCl 3 , the NMR experiment of 3 was measured in CD 3 OD again (see Table S1, ESI †).…”

Synthesis of γ-hydroxy-γ-perfluoroalkyl butenolides and exocyclic double bond butanolides via regioselective allylic alkylations of MBH carbonates with 2-perfluoroalkyl-oxazol-5(2H)-ones

“…When ethanol was changed to methanol, the corresponding product 5aa was obtained in 71% yield within 9 h (Table 1, entry 2). Saturated aqueous solutions of other bases, such as Na 2 CO 3 , NaOH and K 2 CO 3 , was investigated and the yields were also not improved (Table 1, entries [3][4][5]. When a saturated aqueous solution of CH 3 ONa was used, the reaction did not occur (Table 1, entry 6).…”

“…2 Strchnistenolide A ( II ) was obtained from the root of Lindera strychnifolia , which has an inhibitory effect on nitric oxide production in RAW 264.7 cells. 3 Compound ( III ) with antifungal activity was produced by Pseudomonas aureofaciens strain 63–28. 4 Coronarin D ( IV ) as a diterpene compound was isolated from the rhizome extract of Hedychium coronarium , which has several potential biological activities.…”

A review on the chemical constituents and pharmacological efficacies of Lindera aggregata (Sims) Kosterm

“…Sesquiterpene dimers are a characteristic class of constituents with C 30 cores in L. aggregata , which are plausibly biosynthesized via the coupling of two identical or different sesquiterpenoid molecules ( 32 ). Forty-three dimers have been reported, among which lindenane-type sesquiterpenoid dimers are the most representative structures, such as linderaggrenolides A–N (88–101) and linderanoids H–O (109–116), where linderaggrenolides A–N have an oxygen bridge ( 32 , 33 ).…”