Stizolophus balsamita subsp. leaves, (Lam.) K. Koch (Lam.) K. Koch

Nawrot, Joanna, Budzianowski, Jaromir & Nowak, Gerard, 2019, Phytochemical profiles of the leaves of Stizolophus balsamita and Psephellus sibiricus and their chemotaxonomic implications, Phytochemistry 159, pp. 172-178 : 176-177

3.3. Extraction and isolation of compounds from S. balsamita leaves

The dried leaves of S. balsamita (630 g) were crushed and soaked in MeOH. The MeOH extract was evapd, and the residue was dissolved in H 2 O. The aq. soln was re-extracted with CH 2 Cl 2 and then with AcOEt. The CH 2 Cl 2 extract which was dried with Na 2 SO 4, filtrated and evapd gave a residue (15.5 g). The AcOEt extract evapd and gave a residue 4.6 g.

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The CH 2 Cl 2 extract was chromatographed on silica gel with a mixtures of CH 2 Cl 2 and ( CH 3) 2 CO (ratio 15:1) as eluent. The polarity was gradually increased with added ( CH 3) 2 CO. Some collected fractions needed purifying and were rechromatographed on silica gel with mixture of n-hexane and ( CH 3) 2 CO (ratio1:3 or 1:8) or n-hexane and AcOEt (ratio1:3). The result was the isolation of the following compounds: balsamin (1) (35.6 mg, m.p. 225–228 °C), izospiciformin (2) (98.9 mg, m.p. 192–195 °C), stizolin (3) (176 mg, m.p. 183–188 °C), 9α-hydroxyparthenolide (4) (15.3 mg, m.p. 140–142 °C), 8α- E- (4′-hydroxy)-senecioyloxy-9α-hydroxyparthenolide (5) (24.1 mg, m.p. 188–190 °C), 11βH,13-dihydrostizolicin (6) (5.3 mg, amorphous solid) and stizolicin (7) (342 mg, m.p. 143–144 °C). NMR data in Tables 2–4

The purified AcOEt extract (4.6 g) was chromatographed on silica gel. A mixture of CH 2 Cl 2 and ( CH 3) 2 CO (ratio 4:1) was used as eluent, and the polarity was gradually increased with added ( CH 3) 2 CO. The collected fractions with the dominating compound needed purifying, so it was rechromatographed on silica gel with a mixture of CH 2 Cl 2 and CH 3 OH (ratio 25:1 then 20:1 and 15:1). The result was a white amorphous solid (40.4 mg) identified as 3-(3,4-dihydroxyphenyl)propyl senecioate 3- O -β-glucopyranoside = [(3-(3,4- dihydroxyphenyl)propyl-3-methylbut-2-enoate- 3- O -β-glucopyranoside)] (8). 1 H and 13 C NMR data in Table 6 . HR-ESI-MS (positive mode): m/z 435.1631 [M+Na] + (calcd for C 20 H 28 O 9 +Na, 435.1625), 413.1812 [M+H] + (calcd for C 20 H 28 O 9 +H, 413.1806); LR-ESI-MS (negative mode): m/z 411 [M-H] -, 249 [M-H-162] ¯; LR-EI-MS (70 eV) m/z 250.2 [M-163 + H] +, 168.0, 150.0, 83.0.