Isolation of shikonin fromOnosma caucasicum andEchium rubrum

The Chemistry and Biology of Alkannin, Shikonin, and Related Naphthazarin Natural Products

“…[36] 48,49] A. hispidissima, [32] A. guttata, [49,50] A. tibetiana, [51±53] Cynoglossum officinale, [36] Echium lycopsis, [54] E. rubrum, [55,69] E. vulgare, [36] Eritrichium incanum, [36] E. sichotenze, [36] Jatropha glandulifera, [56] Lappula consanguinera, [36] L. echinata, [36] Lithospermum erythrorhizon , [48, 57±61, 77] L. officinale, [58±62] Macrotomia echioides, [63] M. ugamensis, [52,53,64] M. euchroma, [36,65,66] Mertensia maritima, [36] Onosma caucasicum, [52,55] O. conferitum, [78] O. hookeri, [42] O. livanovii, [63] O. polyphyllum, [67] O. tauricum, [68] O. sericium, [63] O. setosum, [63] O. visianii, [69] O. zerizaminium. [52±53, 70] cell cultures: Arnebia euchroma, [107e,f] Echium lycopsis, [26] Lithospermum erythrorhizon, [91, 99a] Onosma paniculatum.…”

“…[26] and geranyl pyrophosphate (GPP, 54). These components are unified in a reaction mediated by the enzyme PHB geranyltransferase to yield m-geranylPHB (55). In general, far more is known about the early stages of the biosynthetic route to 2 than the later ones.…”

“…Feeding experiments have been used to show that shikimic acid (37), l-phenylalanine (38), cinnamic acid (39), PHB (45), m-geranylPHB (55), mgeranylhydroquinone (56), and mevalonic acid (50) are all intermediates in the biosynthetic route. [115] Furthermore, PHB (45), m-geranylPHB (55), and m-geranylhydroquinone (56) have been isolated from shikonin-free cell cultures of LE grown in LS liquid medium (in which shikonin biosynthesis is (48), [116] which is speculated to be a defense mechanism since 45 is known to be toxic to the cells. [117] Intermediates up to m-geranylPHB (55) have been detected from these shikoninfree cells, from which it was suggested that its conversion into m-geranylhydroquinone (56) is repressed by ammonium ions.…”

Chemie und Biologie von Alkannin, Shikonin und verwandten Naphthazarin-Naturstoffen

“…O O (nicht benannt) Wurzeln: Cynoglossum officinale, [36] Eritrichium incanum, [36] E. sichotenze, [36] Lappula consanguinea, [36] Lappula echinata, [36] Mertensia maritima [36] 48,49] A. hispidissima, [32] A. guttata, [49,50] A. tibetiana, [51±53] Cynoglossum officinale, [36] Echium lycopsis, [54] E. rubrum, [55,69] E. vulgare, [36] Eritrichium incanum, [36] E. sichotenze, [36] Jatropha glandulifera, [56] Lappula consanguinera, [36] L. echinata, [36] Lithospermum erythrorhizon, [48, 57±61, 77] L. Officinale,…”

“…[58±62] Macrotomia echioides, [63] M. ugamensis, [52,53,64] M. euchroma, [36,65,66] Mertensia maritima, [36] Onosma caucasicum, [52,55] O. conferitum, [78] O. hookeri, [42] O. livanovii, [63] O. polyphyllum, [67] O. tauricum, [68] O. sericium, [63] O. setosum, [63] O. visianii, [69] O. zerizaminium [52±53, 70] Zellkulturen: Arnebia euchroma, [107e,f] Echium lycopsis, [26] Lithospermum erythrorhizon, [91, 99a] Onosma paniculatum [105] Biologische Wirkung: Antitumorwirkung (Abschnitt 5.2), antiamöbisch (Abschnitt 5.3), antipyretisch und analgetisch (Abschnitt 5.1), antimykotisch und antibakteriell (Abschnitt 5.3), wundheilend (Abschnitt 5.1), chemoprophylaktisch (Abschnitt 5.2), entzündungshemmend (Abschnitt 5.1), Inhibierung der Topoisomerase II (Abschnitt 5.2), Inhibierung der mikrosomalen Monooxygenase, [71] Stimulierung der Peroxidase, [72] Schutz vor UV-Strahlung, [73] Inhibierung von Testosteron-a-Reduktase, [19f] Induktion und Sekretion des Nervenwachstumsfaktors [74] 15 O O…”