DataSheet1_Grandiflolines A–F, new anti-inflammatory diterpenoid alkaloids isolated from Delphinium grandiflorum.pdf

Delphinium grandiflorum L. (family Ranunculaceae), one of the most important and widely distributed Delphinium species, has received considerable interest due to its extremely high medicinal value. The discovery of novel metabolites from D. grandiflorum supported and broadened its application as an herbal medicine. In this study, the whole herb of D. grandiflorum was phytochemically investigated to obtain fourteen C19-lycaconitine-type diterpenoid alkaloids (1–14), including six undescribed alkaloids, grandiflolines A–F (1–6). The structural elucidation of them was accomplished by detailed spectroscopic analyses, mainly including HR-MS, 1D and 2D NMR (1H–1H COSY, NOESY, HMBC and HSQC), and IR spectra. New alkaloids 1–3 and 5 possess a characteristic △2,3 functional group in the A ring, while compounds 5 and 6 feature a rare OH-16 substituent. In addition, known compounds 7–12 were isolated from D. grandiflorum for the first time. Moreover, according to its medicinal use, new alkaloids 1–6 were estimated for their potential in vitro anti-inflammatory effects, and some of them exhibited inhibitory effects on NO production in LPS-activated RAW 264.7 macrophages. Our work enriched the chemical diversity of D. grandiflorum and the genus Delphinium and presented beneficial information for further investigations.</p

Changes in Every Hundred Meters Elevation of Highly Suitable Habitat for <i>P</i>. <i>tenuifolia</i> in China.

<p>The blue columns indicate the future highly suitable habitat area increased relative to the current in the corresponding altitudinal interval, and the red decreased. The following numbers were the magnitude of changes.</p

Altitudinal Pattern of High Suitable Habitat and Medium Suitable Habitat for Potential Distribution of <i>P</i>. <i>Tenuifolia</i> in the Current Scenario.

The cells indicate the proportion of each hundred altitude to the whole.</p

Results of the Jackknife Test of Environmental Variables’ Contribution in Modeling <i>P</i>. <i>tenuifolia</i>’s Potential Habitat Distribution.

<p>The graph shows the result of the Jackknife test of variable importance using regularized training gain, test gain and AUC on test data respectively. The red bars indicate the gain using solo environmental variable, the hollow bars indicate the gain excluding the single variable from the full model, and the blue bars indicate the gain considering all variables.</p

Response Curves of the Three Most Important Environmental Variables in Modeling Habitat Distribution for <i>P</i>. <i>tenuifolia</i>.

(a) Precipitation in the Warmest Quarter, (b) Annual Mean Temperature and (c) Altitude.</p

Shift in the <i>P</i>. <i>tenuifolia</i> Potential Distribution under the Four RCPs (RCP2.6, RCP4.5, RCP6.0 and RCP8.5) in the Two Periods (2050 and 2070), Compared with the Current Potential Distribution.

<p>Shift in the <i>P</i>. <i>tenuifolia</i> Potential Distribution under the Four RCPs (RCP2.6, RCP4.5, RCP6.0 and RCP8.5) in the Two Periods (2050 and 2070), Compared with the Current Potential Distribution.</p

Relative Contributions of 20 Environmental Variables in Habitat Distribution Model of P. tenuifolia from Four Different RCP Scenarios (RCPs 2.6, 4.5, 6.0 and 8.5) in Current and Two future Periods (2050 and 2070).

<p>The abbreviations of variables could be looked up from <a href="http://www.plosone.org/article/info:doi/10.1371/journal.pone.0163718#pone.0163718.s001" target="_blank">S1 Table</a>.</p

AUC Values of Modeling <i>P</i>. <i>tenuifolia</i>’s Habitat Distribution from Four Different RCP Scenarios (RCPs 2.6, 4.5, 6.0 and 8.5) in Current and Two future Periods (2050 and 2070).

<p>AUC Values of Modeling <i>P</i>. <i>tenuifolia</i>’s Habitat Distribution from Four Different RCP Scenarios (RCPs 2.6, 4.5, 6.0 and 8.5) in Current and Two future Periods (2050 and 2070).</p

Mean Altitude of the Highly Suitable Regions for <i>P</i>. <i>tenuifolia</i> in China.

<p>Bars indicate means ± sd (n = 10 circle), and significant differences at P < 0.01 within each group are indicated by different letters (a, b and c).</p

Potential Distribution Modeled by Maxent for <i>P</i>. <i>tenuifolia</i> in China under the Current Climate.

<p>Blue to red colors show the increase of presence probability. 0 indicates completely unsuitable and 1 indicates optimal.</p