1. Hussein R A and El-Anssary A A (2019) Plants secondary metabo- lites: the key drivers of the pharmacological actions of medic- inal plants. In: Builders P (ed.), Herbal Medicine, pp 11–30 (IntechOpen, Rijeka).
2. Guo C, He J, Song X, Tan L, Wang M, Jiang P, Li Y, Cao Z, and Peng C (2019) Pharmacological properties and derivatives of shikonin—a review in recent years. Pharmacol. Res. 149: 104463.
3. Yazaki K (2017) Lithospermum erythrorhizon cell cultures: present and future aspects. Plant Biotech. 34: 131–142.
4. Tabata M, Mizukami H, Hiraoka N, and Konoshima M (1974) Pigment formation in callus cultures of Lithospermum erythrorhi- zon. Phytochem 13: 927–932.
5. Shimomura K, Sudo H, Saga H, and Kamada H (1991) Shikonin production and secretion by hairy root cultures of Lithospermum erythrorhizon. Plant Cell Rep. 10: 282–285.
6. Fujita Y, Hara Y, Suga C, and Morimoto T (1981) Production of shikonin derivatives by cell suspension cultures of Lithospermum Erythrorhizon II. A new medium for the production of shikonin derivatives. Plant Cell Rep. 1: 61–63.
7. Tsukada M and Tabata M (1984) Intracellular localization and secretion of naphthoquinone pigments in cell cultures of Lithos- permum erythrorhizon. Planta Med. 50: 338–341.
8. Tatsumi K, Yano M, Kaminade K, Sugiyama A, Sato M, Toyooka K, Aoyama T, Fumihiko Sato F, and Yazaki K (2016) Characterization of shikonin derivative secretion in Lithospermum erythrorhizon hairy roots as a model of lipid-soluble metabolite secretion from plants. Front. Plant Sci. 7: 1066.
9. Korn E D (1967) A chromatographic and spectrophotometric study of the products of the reaction of osmium tetroxide with unsaturated lipids. J. Cell Biol. 34: 627–638.
10. Richards F M and Knowles J R (1968) Glutaraldehyde as a protein cross-linkage reagent. J. Mol. Biol. 37: 231–233.
11. Deetz J S and Behrman E J (1981) Reaction of osmium reagents with amino acids and proteins. Int. J. Pept. Protein Res. 17: 495–500.
12. Cope G H and Williams M A (1969) Quantitative studies on the preservation of choline and ethanolamine phosphatides during tis- sue preparation for electron microscopy I. glutaraldehyde, osmium tetroxide, araldite methods. J. Microsc. 90: 31–46.
13. Teichman R J, Cummins J M, and Takei G H (1974a) The characterization of a malachite green stainable, glutaraldehyde extractable phospholipid in rabbit spermatozoa. Biol. Reprod. 10: 565–577.
14. Angermüller S and Fahimi H D (1982) Imidazole-buffered osmium tetroxide: an excellent stain for visualization of lipids in transmis- sion electron microscopy. Histochem. J. 14: 823–835.
15. Hagstrom L and Bahr G F (1960) Penetration of osmium tetroxide with different fixation vehicles. Histchemie 2: 1–4.
16. Mersey B and McCully M E (1978) Monitoring of the course of fixation of plant cells. J. Microsc. 114: 49–76.
17. Teichman R J, Fujimoto M, and Yanagimachi R (1972) A pre- viously unrecognized material in mammalian spermatozoa as revealed by malachite green and pyronine. Bio. Reprod. 7: 73–81.
18. Ledingham J M and Simpson F O (1972) The use of p-phenylenediamine in the block to enhance osmium staining for electron microscopy. Stain. Technol. 47: 239–243.
19. Lawton J R (1986) The use of malachite green during fixation of plant tissues for the preservation of lipids. J. Microsc. 144: 201–209.
20. Lawton J R (1989) An investigation of the fixation and staining of lipids by a combination of malachite green or other triphenyl- methane dyes with glutaraldehyde. J. Microsc. 154: 83–92.
21. Bal A K (1990) Localization of plant lipids for light microscopy using p-phenylenediamine in tissues of Arachis Hypogaea L. Stain. Technol. 65: 91–94.
22. Siddique A M and Bal A K (1991) Nitrogen fixation in peanut nodules during dark periods and detopped conditions with special reference to lipid bodies. Plant Physiol. 95: 896–899.
23. Miguel E C, Pireda S, Barros C F, Zottich U, Gomes V M, Miguens F C, and Cunha M D (2017) Outer cell wall structure and the secretion mechanism of colleters of Bathysa nicholsonii K. Schum. (Rubiaceae). Acta Bot. Bras. 31: 411–419.
24. Yamamura Y, Sahin F P, Nagatsu A, and Mizukami H (2003) Molecular cloning and characterization of a cDNA encoding a novel apoplastic protein preferentially expressed in a shikonin- producing callus strain of Lithospermum erythrorhizon. Plant Cell Physiol. 44: 437–446.
25. Linsmaier E M and Skoog F (1965) Organic growth fac- tor requirements of tobacco tissue cultures. Physiol. Plant. 18: 100–127.
26. Yazaki K, Matsuoka H, Ujihara T, and Sato F (1999) Shikonin biosynthesis in Lithospermum erythrorhizon: light-induced neg- ative regulation of secondary metabolism. Plant Biotech. 16: 335–342.
27. Reynolds E S (1963) The use of lead citrate at high pH as an electron-opaque stain in electron microscopy. J. Cell Biol. 17: 208–212.
28. Teichman R J, Takei G H, and Cummins J M (1974b) Detection of fatty acids, fatty aldehydes, phospholipids, glycolipids and choles- terol, on thin-layer chromatograms stained with malachite green. J. Chromat. 88: 425–427.
29. Cleare M J, Hydes P C, Griffith W P, and Wright M J (1977) Studies on transition-metal oxo- and nitrido-complexes. Part 3. Complexes of osmium tetraoxide with tertiary amines, and their reactions with alkenes. J. Chem. Soc., Dalton Trans. 941–944.
30. Emerman M and Behrman E J (1982) Cleavage and cross-linking of proteins with osmium (VIII) reagents. J. Histochem. Cytochem. 30: 395–397.
31. Becker D E and Reed K L (2006) Essentials of local anesthetic pharmacology. Anesth. Prog. 53: 98–109.
32. Neiss W F (1983) Extraction of osmium-containing lipids by section staining for TEM. Histochemistry 79: 245–250.
33. Boshier D P, Holloway H, and Kitchin L F (1984) A comparison of standard lipid staining techniques used in electron microscopic studies of mammalian tissues. Stain. Technol. 59: 83–89.
34. Ledingham J M and Simpson F O (1970) Intensification of osmium staining by p-phenylenediamine: paraffin and epon embedding. Stain. Technol. 45: 255–260.
35. Nakao I, Okada H, Senzaki R, Nishimura N, Fujita N, Shikata N, and Morii S (1992) A mixture of paraphenylenediamine and imi- dazole: its effect on the extraction of lipid droplets during electron microscopy staining. Biotech. Histochem. 67: 219–223.
36. Adams C W M, Abdulla Y H, and Bayliss O B (1967) Osmium tetroxide as a histochemical and histological reagent. Histochemie 9: 68–77.
37. Merriam R W (1958) The contribution of lower oxides of osmium to the density of biological specimens in electron microscopy. J. Biophys. Biochem. Cytol. 4: 579–582.
38. Tabata M (1996) The mechanism of shikonin biosynthesis in cell cultures. Plant Tissue Cult. Lett. 13: 117–125.
39. Nanninga N (1971) The mesosome of Bacillus subtilis as affected by chemical and physical fixation. J. Cell Biol. 48: 219–224.
40. Ebersold H R, Cordier J L, and Ltithy P (1981) Bacterial meso- somes: method dependent artifacts. Arch. Microbiol. 130: 19–22.
41. Yazaki K, Inushma K, Kataoka M, and Tabata M (1995) Intra- cellular localization of UDPG: p-hydroxybenzoate glucosyltrans- ferase and its reaction product in Lithospermum cell cultures. Phytochem 38: 1127–1130.
42. Yamamoto H, Tsukahara M, Yamano Y, Wada A, and Yazaki K (2020) Alcohol dehydrogenase activity converts 3”- hydroxygeranylhydroquinone to an aldehyde intermediate for shikonin and benzoquinone derivatives in Lithospermum ery- throrhizon. Plant Cell Physiol. 61: 1798–1806.
43. Oshikiri H, Watanabe B, Yamamoto H, Yazaki K, and Takanashi K (2020) Two BAHD acyltransferases catalyze the last step in the shikonin/alkannin biosynthetic pathway. Plant Physiol. 184: 753–761.
44. Ueoka H, Sasaki K, Miyawaki T, Ichino T, Tatsumi K, Suzuki S, Yamamoto H, Sakurai N, Suzuki H, Shibata D, and Yazaki K (2020) A cytosol-localized geranyl diphosphate synthase from Lithospermum erythrorhizon and its molecular evolution. Plant Physiol. 182: 1933–1945.
45. H¨ausler E, Petersen M, and Alfermann A W (1993) Isolation of protoplasts and vacuoles from cell suspension cultures of Coleus blumei Benth. Plant Cell Rep. 12: 510–512.
論文の公開元へ
