Sesquiterpenes from Artemisia argyi: Absolute Configurations and Biological Activities

Abstract

Nine guaiane‐type sesquiterpenes and one eudesmane‐type one – namely argyinolides A–J (1–10) – as well as nine known analogues were isolated from the leaves of Artemisia argyi Levl. et Vant. Their structures were determined by interpretation of spectroscopic data (MS, 1D and 2D NMR). A combination of X‐ray crystal diffraction, specific optical rotations, CD spectroscopy, ECD calculation, and Mosher ester methods was employed to resolve the absolute configurations of the isolated compounds. Biological investigations into their cytotoxicities and anti‐inflammatory effects showed that 1, 13, 16, and 18 were remarkably cytotoxic against Bel‐742 and/or A549 cells, with IC50 values of 3.3–6.0 μM, whereas 7, 11–13, 16, and 18 exhibited sound inhibitory activity on LPS‐stimulated NO production in BV‐2 microglial cells, with IC50 values ranging from 3.2 to 8.6 μM. In addition, a brief discussion on the applicability of Geissman's rule for the sesquiterpene lactones, the probable reason for the presence of chlorine‐containing sesquiterpenes, and preliminary structure–activity relationships (SARs) are included.

Anti-Apoptotic and Antioxidant Effects of 3-Epi-Iso-Seco-Tanapartholide Isolated from Artemisia argyi against Iodixanol-Induced Kidney Epithelial Cell Death

“…TH5-23-5 (113.0 mg) was subjected to silica gel CC gradient elution with n-hexane-EtOAc (1:0 to 0:1), resulting in the preparation of fractions TH5-27-1 to -6. Fraction TH5-27-4 was argyinolide G (4, 8.7 mg) [21], and fraction TH5-27-3 (9.0 mg) was purified by preparative HPLC (40-60% MeOH in H 2 O) to yield deacetylmatricarin (5, 5.2 mg) [22]. TH5-23-7 (133.2 mg) was applied to silica gel CC gradient elution with n-hexane-EtOAc (1:0 to 0:1), leading to the isolation of rupicolin A (6, 4.2 mg) [23].…”

“…The purity of the isolates (>95%) was determined by NMR. The chemical structures of compounds 1-9 were identified as moxartenolide (compound 1) [18], dehydromatricarin A (compound 2) [19], tuberiferin (compound 3) [20], argyinolide G (compound 4) [21], deacetylmatricarin (compound 5) [22], rupicolin A (compound 6) [23], acrifolide (compound 7) [24], 3-epi-iso-seco-tanapartholide (compound 8) [25], iso-seco-tanapartholide (compound 9) [25], by 1D and 2D NMR spectroscopic data and by comparison with published values (Figure 1). Figure 1.…”

Dysifragilones A–C, Unusual Sesquiterpene Aminoquinones and Inhibitors of NO Production from the South China Sea Sponge Dysidea fragilis

“…Of the three compounds, 1 exhibited the most potent inhibitory activity, with an IC 50 value of 6.61 μm. [27,28] [27,28] …”

Structural, spectroscopic, and computational characterization of the cleavage product of dimolybdenum(II) core under aerobic conditions

“…[10][11][12][13][14][15] This method excels for both threo and erythro diols, as well as for diols of varying mobility or variable steric hindrance, 16,17 and is becoming widely used in many laboratories thanks to its simplicity, ease, and confidence of the assignment of the absolute configuration. [18][19][20][21][22][23] For the purpose of this method the dimolybdenum(II) tetraacetate remains the most frequently used stock complex. However, other carboxylates such as dimolybdenum tetrakis(l-pivalate) or tetrakis(lisovalerate) are an effective alternative.…”