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Structure of the compounds isolated from L.viridiflorum Deoxyshikonin (1): dark red powder; mp: 93-94°C, 1 H NMR (400 MHz, CDCl 3 , δ) 12.62 (s, 1H,-OH), 12.46 (s, 1H,-OH), 7.19(d, J = 1.3 Hz, 2H), 6.85 (d, J = 1.3 Hz, 1H), 5.19 (t, J = 7.1 Hz, 1H), 2.65 (t, J = 7.6 Hz, 2H), 2.31 (q, J = 7.6 Hz, 2H), 1.69 (s, 3H), 1.58 (s, 3H); 13 C NMR (100 MHz, CDCl 3 , δ) 182.2, 182.1, 161.9, 162.2,152.5, 136.6, 135.7, 132.0, 131.9, 122.4, 112.0, 111.9, 29.8, 26.6, 25.7, 17.9.
Source publication
Four naphthoquinones, namely-deoxy shikonin, acetyl shikonin, β, β-dimethylacrylshikonin and isobutyl shikoninhave been isolated from the hexane extract of the root-bark of the traditional medicinal plant Lithospermum viridiflorum. The structures of the compounds were characterized by using Mass, Proton and 13C-NMR respectively.
Context in source publication
Context 1
... elution with 5% Ethylacetate in hexane yielded, isobutyl shikonin4.The compounds were carefully separated, evaporated to dryness and characterized for structural elucidation. Figure 1 clearly represents the structures of the molecules isolated from the root-bark of L.viridiflorum. Those isolated compounds have been characterized by using 1 H and 13 C NMR which is discussed below. ...
Citations
Lithospermum erythrorhizon is a native to East Asia and has been traditionally used to treat skin injuries such as burns and wounds. The extracts of this plant species contain naphthaquinones, lithospermans, and caffeic acid oligomers such as lithospermic acids, which are known to have various effects on skin as antioxidant, including UVB protection and moisturization. Naphthoquinones like shikonin are the major phytoconstituents in gromwell root. Shikonin has various pharmacological properties, acts as an anti‐inflammatory, anti‐obesity, anti‐adipogenic effect, and anticancer agent. Shikonin and its derivatives such as acetyl shikonin, deoxyshikonin, and isobutylshikonin were synthesized in the roots of Lithospermum erythrorhizon and used as an anti‐inflammatory medicine. Production of shikonin by Lithospermum erythrorhizon cells, immobilized in polyurethane foam matrices was studied. Shikonin production was observed to increase significantly when the immobilized cells were used.
