4-Methyl-1-(1,4,5,8-tetrahydroxynaphthalen-2-yl)pent-2-en-1-one (BioDeep_00000185305)
human metabolite blood metabolite
代谢物信息卡片
4-Methyl-1-(1,4,5,8-tetrahydroxynaphthalen-2-yl)pent-2-en-1-one
化学式: C16H16O5 (288.0997686)
中文名称:
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: CC(C)C=CC(=O)C1=C(O)C2=C(O)C=CC(O)=C2C(O)=C1
InChI: InChI=1S/C16H16O5/c1-8(2)3-4-10(17)9-7-13(20)14-11(18)5-6-12(19)15(14)16(9)21/h3-8,18-21H,1-2H3
相关代谢途径
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代谢反应
0 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(0)
WikiPathways(0)
Plant Reactome(0)
INOH(0)
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1 个相关的物种来源信息
在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：
- PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
- NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
- Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
- Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。
点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。
文献列表
- Seetharaman Rajasekar, Da Jung Park, Cheol Park, Sejin Park, Young Hoon Park, Sun Tae Kim, Yung Hyun Choi, Young Whan Choi. In vitro and in vivo anticancer effects of Lithospermum erythrorhizon extract on B16F10 murine melanoma.
Journal of ethnopharmacology.
2012 Nov; 144(2):335-45. doi:
10.1016/j.jep.2012.09.017. [PMID: 22995444] - So Young Gwon, Ji Yun Ahn, Chang Hwa Chung, BoKyung Moon, Tae Youl Ha. Lithospermum erythrorhizon suppresses high-fat diet-induced obesity, and acetylshikonin, a main compound of Lithospermum erythrorhizon, inhibits adipocyte differentiation.
Journal of agricultural and food chemistry.
2012 Sep; 60(36):9089-96. doi:
10.1021/jf3017404. [PMID: 22900585] - Rubing Wang, Runting Yin, Wen Zhou, Defeng Xu, Shaoshun Li. Shikonin and its derivatives: a patent review.
Expert opinion on therapeutic patents.
2012 Sep; 22(9):977-97. doi:
10.1517/13543776.2012.709237. [PMID: 22834677] - Nadine Kretschmer, Beate Rinner, Alexander J A Deutsch, Birgit Lohberger, Heike Knausz, Olaf Kunert, Martina Blunder, Herbert Boechzelt, Helmut Schaider, Rudolf Bauer. Naphthoquinones from Onosma paniculata induce cell-cycle arrest and apoptosis in melanoma Cells.
Journal of natural products.
2012 May; 75(5):865-9. doi:
10.1021/np2006499. [PMID: 22530779] - Premysl Landa, Zsofia Kutil, Veronika Temml, Anna Vuorinen, Jan Malik, Marcela Dvorakova, Petr Marsik, Ladislav Kokoska, Marie Pribylova, Daniela Schuster, Tomas Vanek. Redox and non-redox mechanism of in vitro cyclooxygenase inhibition by natural quinones.
Planta medica.
2012 Mar; 78(4):326-33. doi:
10.1055/s-0031-1280430. [PMID: 22174077] - Jian Zhou, Xue-Mei Tang, Cong Wang, Xiao-Juan Pan. [Compare the composition and content of Arnebiae radix and the stem residues].
Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials.
2012 Mar; 35(3):361-6. doi:
". [PMID: 22876671] - Zhi-Lu Chen, Qi-Zhou Dai, Yong Wang. [Effects of shikonin on the proliferation and apoptosis of HL-60 cells].
Zhongguo Zhong xi yi jie he za zhi Zhongguo Zhongxiyi jiehe zazhi = Chinese journal of integrated traditional and Western medicine.
2012 Feb; 32(2):239-43. doi:
". [PMID: 22574601] - Yingying Fan, Shaoju Jin, Jun He, Zhenjun Shao, Jiao Yan, Ting Feng, Hong Li. Effect of β,β-dimethylacrylshikonin on inhibition of human colorectal cancer cell growth in vitro and in vivo.
International journal of molecular sciences.
2012; 13(7):9184-9193. doi:
10.3390/ijms13079184. [PMID: 22942759] - Chia-Yen Hsiao, Ching-Yi Hung, Tung-Hu Tsai, Kin-Fu Chak. A Study of the Wound Healing Mechanism of a Traditional Chinese Medicine, Angelica sinensis, Using a Proteomic Approach.
Evidence-based complementary and alternative medicine : eCAM.
2012; 2012(?):467531. doi:
10.1155/2012/467531. [PMID: 22536285] - Benjamin Wiench, Tolga Eichhorn, Malte Paulsen, Thomas Efferth. Shikonin directly targets mitochondria and causes mitochondrial dysfunction in cancer cells.
Evidence-based complementary and alternative medicine : eCAM.
2012; 2012(?):726025. doi:
10.1155/2012/726025. [PMID: 23118796] - Chia-Yen Hsiao, Tung-Hu Tsai, Kin-Fu Chak. The molecular basis of wound healing processes induced by lithospermi radix: a proteomics and biochemical analysis.
Evidence-based complementary and alternative medicine : eCAM.
2012; 2012(?):508972. doi:
10.1155/2012/508972. [PMID: 23024692] - A Bakrudeen Ali Ahmed, A S Rao, M V Rao, Rosna Mat Taha. Production of gymnemic acid depends on medium, explants, PGRs, color lights, temperature, photoperiod, and sucrose sources in batch culture of Gymnema sylvestre.
TheScientificWorldJournal.
2012; 2012(?):897867. doi:
10.1100/2012/897867. [PMID: 22629221] - Hong-Mei Li, Ying-Lei Tang, Zhong-Hua Zhang, Chen-Jian Liu, Hai-Zhou Li, Rong-Tao Li, Xue-Shan Xia. Compounds from Arnebia euchroma and their related anti-HCV and antibacterial activities.
Planta medica.
2012 Jan; 78(1):39-45. doi:
10.1055/s-0031-1280266. [PMID: 21984340] - Su Long, Yan GuangZhi, Guan BaoJie, Xu Wei, Hao YanYong, Wang YingLi, Zhang Yang, Liu LiHua. Shikonin derivatives protect immune organs from damage and promote immune responses in vivo in tumour-bearing mice.
Phytotherapy research : PTR.
2012 Jan; 26(1):26-33. doi:
10.1002/ptr.3503. [PMID: 21538626] - Ke Gong, Wenhua Li. Shikonin, a Chinese plant-derived naphthoquinone, induces apoptosis in hepatocellular carcinoma cells through reactive oxygen species: A potential new treatment for hepatocellular carcinoma.
Free radical biology & medicine.
2011 Dec; 51(12):2259-71. doi:
10.1016/j.freeradbiomed.2011.09.018. [PMID: 22011623] - Xian Ding, Bo Yin, Li Qian, Zhirui Zeng, Zeliang Yang, Huixian Li, Yongjun Lu, Shining Zhou. Screening for novel quorum-sensing inhibitors to interfere with the formation of Pseudomonas aeruginosa biofilm.
Journal of medical microbiology.
2011 Dec; 60(Pt 12):1827-1834. doi:
10.1099/jmm.0.024166-0. [PMID: 21852522] - Huamin Han, Wen He, Wei Wang, Bin Gao. Inhibitory effect of aqueous Dandelion extract on HIV-1 replication and reverse transcriptase activity.
BMC complementary and alternative medicine.
2011 Nov; 11(?):112. doi:
10.1186/1472-6882-11-112. [PMID: 22078030] - Wen Zhou, Hu Da Gu La Jiang, Ying Peng, Shao Shun Li. Comparative study on enantiomeric excess of main akannin/shikonin derivatives isolated from the roots of three endemic Boraginaceae plants in China.
Biomedical chromatography : BMC.
2011 Oct; 25(10):1067-75. doi:
10.1002/bmc.1570. [PMID: 21308700] - Kh Zare, M Khosrowshahli, H Nazemiyeh, A Movafeghi, A Motallebi Azar, Y Omidi. Callus culture of Echium italicum L. towards production of a shikonin derivative.
Natural product research.
2011 Sep; 25(16):1480-7. doi:
10.1080/14786410902804857. [PMID: 20635302] - Wen Tan, Jinjian Lu, Mingqing Huang, Yingbo Li, Meiwan Chen, Guosheng Wu, Jian Gong, Zhangfeng Zhong, Zengtao Xu, Yuanye Dang, Jiajie Guo, Xiuping Chen, Yitao Wang. Anti-cancer natural products isolated from chinese medicinal herbs.
Chinese medicine.
2011 Jul; 6(1):27. doi:
10.1186/1749-8546-6-27. [PMID: 21777476] - Ying-jie Wei, Mo Wang, Qiu-fang Xu, Qian He, Xiao-bin Jia. [Rationality for dynamic detection of shikonin of Arnerbia euchroma in industrial process].
Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials.
2011 Jul; 34(7):1129-33. doi:
". [PMID: 22066411] - Ying-jie Wei, Mo Wang, Mu-rong Yuan, Xiao-bin Jia, Run-tong Zhang, Wei Tan. [Study on dynamic changes and stability of effective components of Arnerbia euchroma].
Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials.
2011 Apr; 34(4):611-5. doi:
". [PMID: 21809548] - Stephan Krueger, Patrick Giavalisco, Leonard Krall, Marie-Caroline Steinhauser, Dirk Büssis, Bjoern Usadel, Ulf-Ingo Flügge, Alisdair R Fernie, Lothar Willmitzer, Dirk Steinhauser. A topological map of the compartmentalized Arabidopsis thaliana leaf metabolome.
PloS one.
2011 Mar; 6(3):e17806. doi:
10.1371/journal.pone.0017806. [PMID: 21423574] - W Zhang, A Zou, J Miao, Y Yin, R Tian, Y Pang, R Yang, J Qi, Y Yang. LeERF-1, a novel AP2/ERF family gene within the B3 subcluster, is down-regulated by light signals in Lithospermum erythrorhizon.
Plant biology (Stuttgart, Germany).
2011 Mar; 13(2):343-8. doi:
10.1111/j.1438-8677.2010.00375.x. [PMID: 21309981] - Haeyong Lee, Sungmin Bae, Kijeong Kim, Wonyong Kim, Sang-In Chung, Young Yang, Yoosik Yoon. Shikonin inhibits adipogenesis by modulation of the WNT/β-catenin pathway.
Life sciences.
2011 Feb; 88(7-8):294-301. doi:
10.1016/j.lfs.2010.12.004. [PMID: 21146546] - Yi Zhang, Ping-Ping Li. Assessment of shikonin for potential estrogenic activity by dual-luciferase reporter based bioluminescent measurements in vitro.
Die Pharmazie.
2011 Feb; 66(2):141-3. doi:
". [PMID: 21434578] - Sonia Malik, Shashi Bhushan, Madhu Sharma, Paramvir Singh Ahuja. Physico-chemical factors influencing the shikonin derivatives production in cell suspension cultures of Arnebia euchroma (Royle) Johnston, a medicinally important plant species.
Cell biology international.
2011 Feb; 35(2):153-8. doi:
10.1042/cbi20090459. [PMID: 20977433] - Anette I Öberg, Kamal Yassin, Robert I Csikasz, Nodi Dehvari, Irina G Shabalina, Dana S Hutchinson, Mona Wilcke, Claes-Göran Östenson, Tore Bengtsson. Shikonin increases glucose uptake in skeletal muscle cells and improves plasma glucose levels in diabetic Goto-Kakizaki rats.
PloS one.
2011; 6(7):e22510. doi:
10.1371/journal.pone.0022510. [PMID: 21818330] - Hong Gao, Lei Liu, Zhang-Yi Qu, Feng-Xiang Wei, Shu-Qiu Wang, Guang Chen, Le Qin, Fu-Yang Jiang, Ying-Chen Wang, Lei Shang, Chun-Yan Gao. Anti-adenovirus activities of shikonin, a component of Chinese herbal medicine in vitro.
Biological & pharmaceutical bulletin.
2011; 34(2):197-202. doi:
10.1248/bpb.34.197. [PMID: 21415527] - K Haghbeen, S Pourmolaei, M J Mareftjo, A Mousavi, K Akbari Noghabi, F Hosseini Shirazi, A Meshkat. Detailed investigations on the solid cell culture and antimicrobial activities of the Iranian Arnebia euchroma.
Journal of biomedicine & biotechnology.
2011; 2011(?):165852. doi:
10.1155/2011/165852. [PMID: 21772789] - Yusai Ito, Kenichi Onobori, Takeshi Yamazaki, Yoko Kawamura. Tigloylshikonin, a new minor Shikonin derivative, from the roots and the commercial root extract of lithospermum erythrorhizon.
Chemical & pharmaceutical bulletin.
2011; 59(1):117-9. doi:
10.1248/cpb.59.117. [PMID: 21212559] - Rupesh Thakur, Nitika Jain, Raghvendra Pathak, Sardul Singh Sandhu. Practices in wound healing studies of plants.
Evidence-based complementary and alternative medicine : eCAM.
2011; 2011(?):438056. doi:
10.1155/2011/438056. [PMID: 21716711] - Ravi S Singh, Rishi K Gara, Pardeep K Bhardwaj, Anish Kaachra, Sonia Malik, Ravi Kumar, Madhu Sharma, Paramvir S Ahuja, Sanjay Kumar. Expression of 3-hydroxy-3-methylglutaryl-CoA reductase, p-hydroxybenzoate-m-geranyltransferase and genes of phenylpropanoid pathway exhibits positive correlation with shikonins content in arnebia [Arnebia euchroma (Royle) Johnston].
BMC molecular biology.
2010 Nov; 11(?):88. doi:
10.1186/1471-2199-11-88. [PMID: 21092138] - Shao-Chih Chiu, Shan-Wen Tsao, Pei-Ing Hwang, Staniforth Vanisree, Yi-An Chen, Ning-Sun Yang. Differential functional genomic effects of anti-inflammatory phytocompounds on immune signaling.
BMC genomics.
2010 Sep; 11(?):513. doi:
10.1186/1471-2164-11-513. [PMID: 20868472] - Rong Deng, Jun Tang, Bing-Fen Xie, Gong-Kan Feng, Yu-Han Huang, Zong-Chao Liu, Xiao-Feng Zhu. SYUNZ-16, a newly synthesized alkannin derivative, induces tumor cells apoptosis and suppresses tumor growth through inhibition of PKB/AKT kinase activity and blockade of AKT/FOXO signal pathway.
International journal of cancer.
2010 Jul; 127(1):220-9. doi:
10.1002/ijc.25032. [PMID: 19904742] - Yuan Yao, Qun Zhou. A novel antiestrogen agent Shikonin inhibits estrogen-dependent gene transcription in human breast cancer cells.
Breast cancer research and treatment.
2010 May; 121(1):233-40. doi:
10.1007/s10549-009-0547-2. [PMID: 19760501] - Keiko Murakami, Miyako Haneda, Shouko Iwata, Masataka Yoshino. Effect of hydroxy substituent on the prooxidant action of naphthoquinone compounds.
Toxicology in vitro : an international journal published in association with BIBRA.
2010 Apr; 24(3):905-9. doi:
10.1016/j.tiv.2009.11.018. [PMID: 19961919] - Haeyong Lee, Ryunhwa Kang, Yoosik Yoon. Shikonin inhibits fat accumulation in 3T3-L1 adipocytes.
Phytotherapy research : PTR.
2010 Mar; 24(3):344-51. doi:
10.1002/ptr.2942. [PMID: 19610030] - Huanjie Yang, Jinbao Liu, Q Ping Dou. Targeting tumor proteasome with traditional Chinese medicine.
Current drug discovery technologies.
2010 Mar; 7(1):46-53. doi:
10.2174/157016310791162785. [PMID: 20156140] - I-Chang Chang, Yu-Jen Huang, Tsay-I Chiang, Chi-Wei Yeh, Li-Sung Hsu. Shikonin induces apoptosis through reactive oxygen species/extracellular signal-regulated kinase pathway in osteosarcoma cells.
Biological & pharmaceutical bulletin.
2010; 33(5):816-24. doi:
10.1248/bpb.33.816. [PMID: 20460760] - Jie Han, Tian-Xiang Chen, Christopher J Branford-White, Li-Min Zhu. Electrospun shikonin-loaded PCL/PTMC composite fiber mats with potential biomedical applications.
International journal of pharmaceutics.
2009 Dec; 382(1-2):215-21. doi:
10.1016/j.ijpharm.2009.07.027. [PMID: 19660536] - Yi Zhang, Rui-Qin Qian, Ping-Ping Li. Shikonin, an ingredient of Lithospermum erythrorhizon, down-regulates the expression of steroid sulfatase genes in breast cancer cells.
Cancer letters.
2009 Oct; 284(1):47-54. doi:
10.1016/j.canlet.2009.04.008. [PMID: 19419812] - Nandini Sharma, Upendra K Sharma, Ajai P Gupta, Arun K Sinha, Brij Lal, Paramvir S Ahuja. Simultaneous densitometric determination of shikonin, acetylshikonin, and beta-acetoxyisovaleryl-shikonin in ultrasonic-assisted extracts of four Arnebia species using reversed-phase thin layer chromatography.
Journal of separation science.
2009 Sep; 32(18):3239-45. doi:
10.1002/jssc.200900129. [PMID: 19697311] - Xin Chang Wang, Jian Feng, Feng Huang, Yong Sheng Fan, Yan Yan Wang, Ling Yong Cao, Cheng Pin Wen. Effects of shikonin isolated from zicao on lupus nephritis in NZB/W F1 mice.
Biological & pharmaceutical bulletin.
2009 Sep; 32(9):1565-70. doi:
10.1248/bpb.32.1565. [PMID: 19721233] - Xia Liu, Yuan-Peng Jing, Yan-Ping Shi. Bothriodumin, a shikonin derivative from Bothriospermum secundum Maxim.
Die Pharmazie.
2009 Sep; 64(9):619-21. doi:
". [PMID: 19827309] - Kazuaki Ohara, Ayumu Muroya, Nobuhiro Fukushima, Kazufumi Yazaki. Functional characterization of LePGT1, a membrane-bound prenyltransferase involved in the geranylation of p-hydroxybenzoic acid.
The Biochemical journal.
2009 Jun; 421(2):231-41. doi:
10.1042/bj20081968. [PMID: 19392660] - Huanjie Yang, Ping Zhou, Hongbiao Huang, Di Chen, Ningfang Ma, Qiuzhi Cindy Cui, Shouxing Shen, Weihua Dong, Xiaoyan Zhang, Wen Lian, Xuejun Wang, Q Ping Dou, Jinbao Liu. Shikonin exerts antitumor activity via proteasome inhibition and cell death induction in vitro and in vivo.
International journal of cancer.
2009 May; 124(10):2450-9. doi:
10.1002/ijc.24195. [PMID: 19165859] - Alen Albreht, Irena Vovk, Breda Simonovska, Marija Srbinoska. Identification of shikonin and its ester derivatives from the roots of Echium italicum L.
Journal of chromatography. A.
2009 Apr; 1216(15):3156-62. doi:
10.1016/j.chroma.2009.01.098. [PMID: 19233376] - Rachel A Okrent, Matthew D Brooks, Mary C Wildermuth. Arabidopsis GH3.12 (PBS3) conjugates amino acids to 4-substituted benzoates and is inhibited by salicylate.
The Journal of biological chemistry.
2009 Apr; 284(15):9742-54. doi:
10.1074/jbc.m806662200. [PMID: 19189963] - Andreana N Assimopoulou, Sonja Sturm, Hermann Stuppner, Vassilios P Papageorgiou. Preparative isolation and purification of alkannin/shikonin derivatives from natural products by high-speed counter-current chromatography.
Biomedical chromatography : BMC.
2009 Feb; 23(2):182-98. doi:
10.1002/bmc.1101. [PMID: 18816456] - Shu-Jing Wu, Jin-Liang Qi, Wen-Ju Zhang, Shao-Hua Liu, Feng-Hui Xiao, Ming-Sheng Zhang, Guo-Hua Xu, Wei-Guo Zhao, Ming-Wang Shi, Yan-Jun Pang, Heng-Guan Shen, Yong-Hua Yang. Nitric oxide regulates shikonin formation in suspension-cultured Onosma paniculatum cells.
Plant & cell physiology.
2009 Jan; 50(1):118-28. doi:
10.1093/pcp/pcn178. [PMID: 19022805] - Hyo-Jung Lee, Hyo-Jeong Lee, Venkataraman Magesh, Dongwoo Nam, Eun-Ok Lee, Kwang Seok Ahn, Min-Hyung Jung, Kyoo-Seok Ahn, Dae-Keun Kim, Ji-Young Kim, Sung-Hoon Kim. Shikonin, acetylshikonin, and isobutyroylshikonin inhibit VEGF-induced angiogenesis and suppress tumor growth in lewis lung carcinoma-bearing mice.
Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan.
2008 Nov; 128(11):1681-8. doi:
10.1248/yakushi.128.1681. [PMID: 18981704] - Jie Liu, Wen Zhou, Shao-Shun Li, Zhe Sun, Bingzhen Lin, Yuan-Yuan Lang, Jia-You He, Xihua Cao, Tingdong Yan, Li Wang, Jiongming Lu, Young-Hoon Han, Yu Cao, Xiao-kun Zhang, Jin-Zhang Zeng. Modulation of orphan nuclear receptor Nur77-mediated apoptotic pathway by acetylshikonin and analogues.
Cancer research.
2008 Nov; 68(21):8871-80. doi:
10.1158/0008-5472.can-08-1972. [PMID: 18974131] - Pei-Fen Su, Vanisree Staniforth, Chin-Jin Li, Chien-Yu Wang, Ming-Tsang Chiao, Sheng-Yang Wang, Lie-Fen Shyur, Ning-Sun Yang. Immunomodulatory effects of phytocompounds characterized by in vivo transgenic human GM-CSF promoter activity in skin tissues.
Journal of biomedical science.
2008 Nov; 15(6):813-22. doi:
10.1007/s11373-008-9266-7. [PMID: 18622761] - Jin-Liang Qi, Wen-Ju Zhang, Shao-Hua Liu, Hong Wang, Deng-Yun Sun, Guo-Hua Xu, Ming-Wang Shi, Zhi Liu, Ming-Sheng Zhang, Hui-Ming Zhang, Yong-Hua Yang. Expression analysis of light-regulated genes isolated from a full-length-enriched cDNA library of Onosma paniculatum cell cultures.
Journal of plant physiology.
2008 Sep; 165(14):1474-82. doi:
10.1016/j.jplph.2007.11.003. [PMID: 18242776] - Hwa-Young Lee, Yoon-Jung Kim, Eun-Jung Kim, Young-Keun Song, Sang Yo Byun. Red pigment from Lithospermum erythrorhizon by supercritical CO2 extraction.
Journal of cosmetic science.
2008 Sep; 59(5):431-40. doi:
". [PMID: 18841307] - Gianni Sagratini, Gloria Cristalli, Dario Giardinà, Giorgio Gioventù, Filippo Maggi, Massimo Ricciutelli, Sauro Vittori. Alkannin/shikonin mixture from roots of Onosma echioides (L.) L.: extraction method study and quantification.
Journal of separation science.
2008 Apr; 31(6-7):945-52. doi:
10.1002/jssc.200700408. [PMID: 18327849] - Nandini Sharma, Upendra Kumar Sharma, Sonia Malik, Shashi Bhushan, Vinod Kumar, Subash Chandra Verma, Naina Sharma, Madhu Sharma, Arun Kumar Sinha. Isolation and purification of acetylshikonin and beta-acetoxyisovalerylshikonin from cell suspension cultures of Arnebia euchroma (Royle) Johnston using rapid preparative HPLC.
Journal of separation science.
2008 Mar; 31(4):629-35. doi:
10.1002/jssc.200700489. [PMID: 18264989] - A N Assimopoulou, M Ganzera, H Stuppner, V P Papageorgiou. Simultaneous determination of monomeric and oligomeric alkannins and shikonins by high-performance liquid chromatography-diode array detection-mass spectrometry.
Biomedical chromatography : BMC.
2008 Feb; 22(2):173-90. doi:
10.1002/bmc.912. [PMID: 18059064] - Rajesh L Thangapazham, Anoop K Singh, Pankaj Seth, Namita Misra, Vijayavitthal T Mathad, Kanwal Raj, Radha K Maheshwari. Shikonin analogue (SA) 93/637 induces apoptosis by activation of caspase-3 in U937 cells.
Frontiers in bioscience : a journal and virtual library.
2008 Jan; 13(?):561-8. doi:
10.2741/2701. [PMID: 17981569] - M Rajbhandari, T H Schoepke, R Mentel, U Lindequist. Antibacterial and antiviral naphthazarins from Maharanga bicolor.
Die Pharmazie.
2007 Aug; 62(8):633-5. doi:
". [PMID: 17867562] - Weidong Han, Ling Li, Shuang Qiu, Qinghua Lu, Qiangrong Pan, Ying Gu, Jianhong Luo, Xun Hu. Shikonin circumvents cancer drug resistance by induction of a necroptotic death.
Molecular cancer therapeutics.
2007 May; 6(5):1641-9. doi:
10.1158/1535-7163.mct-06-0511. [PMID: 17513612] - Takahiro Ishida, Ikuyo Sakaguchi. Protection of human keratinocytes from UVB-induced inflammation using root extract of Lithospermum erythrorhizon.
Biological & pharmaceutical bulletin.
2007 May; 30(5):928-34. doi:
10.1248/bpb.30.928. [PMID: 17473437] - Thomas Efferth, Hayato Miyachi, Helmut Bartsch. Pharmacogenomics of a traditional Japanese herbal medicine (Kampo) for cancer therapy.
Cancer genomics & proteomics.
2007 Mar; 4(2):81-91. doi:
". [PMID: 17804870] - Gulseren Pekin, Markus Ganzera, Serdar Senol, Erdal Bedir, Kemal S Korkmaz, Hermann Stuppner. Determination of naphthazarin derivatives in endemic Turkish Alkanna species by reversed phase high performance liquid chromatography.
Planta medica.
2007 Mar; 73(3):267-72. doi:
10.1055/s-2007-967110. [PMID: 17318780] - Sojin An, Yong-Dae Park, Young-Ki Paik, Tae-Sook Jeong, Woo Song Lee. Human ACAT inhibitory effects of shikonin derivatives from Lithospermum erythrorhizon.
Bioorganic & medicinal chemistry letters.
2007 Feb; 17(4):1112-6. doi:
10.1016/j.bmcl.2006.11.024. [PMID: 17157006] - A N Assimopoulou, I Karapanagiotis, A Vasiliou, S Kokkini, V P Papageorgiou. Analysis of alkannin derivatives from Alkanna species by high-performance liquid chromatography/photodiode array/mass spectrometry.
Biomedical chromatography : BMC.
2006 Dec; 20(12):1359-74. doi:
10.1002/bmc.705. [PMID: 17080496] - Yue Hou, Tao Guo, Chunfu Wu, Xiang He, Minghong Zhao. Effect of shikonin on human breast cancer cells proliferation and apoptosis in vitro.
Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan.
2006 Dec; 126(12):1383-6. doi:
10.1248/yakushi.126.1383. [PMID: 17139164] - A Pietrosiuk, K Sykłowska-Baranek, H Wiedenfeld, R Wolinowska, M Furmanowa, E Jaroszyk. The shikonin derivatives and pyrrolizidine alkaloids in hairy root cultures of Lithospermum canescens (Michx.) Lehm.
Plant cell reports.
2006 Oct; 25(10):1052-8. doi:
10.1007/s00299-006-0161-2. [PMID: 16670900] - U Ozgen, M Ikbal, A Hacimuftuoglu, P J Houghton, F Gocer, H Dogan, M Coskun. Fibroblast growth stimulation by extracts and compounds of Onosma argentatum roots.
Journal of ethnopharmacology.
2006 Mar; 104(1-2):100-3. doi:
10.1016/j.jep.2005.08.052. [PMID: 16226418] - T Kundakovic, N Fokialakis, S Dobric, H Pratsinis, D Kletsas, N Kovacevic, I Chinou. Evaluation of the anti-inflammatory and cytotoxic activities of naphthazarine derivatives from Onosma leptantha.
Phytomedicine : international journal of phytotherapy and phytopharmacology.
2006 Mar; 13(4):290-4. doi:
10.1016/j.phymed.2004.10.009. [PMID: 16492534] - Woo Hoi Choi, Seong Su Hong, Seon A Lee, Xiang Hua Han, Kyong Soon Lee, Myung Koo Lee, Bang Yeon Hwang, Jai Seup Ro. Monoamine oxidase inhibitory naphthoquinones from the roots of Lithospermum erythrorhizon.
Archives of pharmacal research.
2005 Apr; 28(4):400-4. doi:
10.1007/bf02977668. [PMID: 15918512] - Kaori Touno, Jin Tamaoka, Yuko Ohashi, Koichiro Shimomura. Ethylene induced shikonin biosynthesis in shoot culture of Lithospermum erythrorhizon.
Plant physiology and biochemistry : PPB.
2005 Feb; 43(2):101-5. doi:
10.1016/j.plaphy.2005.01.004. [PMID: 15820656] - A N Assimopoulou, V P Papageorgiou. Radical scavenging activity of Alkanna tinctoria root extracts and their main constituents, hydroxynaphthoquinones.
Phytotherapy research : PTR.
2005 Feb; 19(2):141-7. doi:
10.1002/ptr.1645. [PMID: 15852495] - Kenichiro Inoue. [Cytochrome P450 enzymes in biosyntheses of some plant secondary metabolites].
Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan.
2005 Jan; 125(1):31-49. doi:
10.1248/yakushi.125.31. [PMID: 15635280] - O A Poronnik, V A Kunakh. [Biosynthesis of naphthoquinoine pigments in plants from Boraginaceae family in nature and in vitro culture].
Ukrains'kyi biokhimichnyi zhurnal (1999 ).
2005; 77(6):24-36. doi:
. [PMID: 19618739] - Banasri Hazra, Madhushree Das Sarma, Utpal Sanyal. Separation methods of quinonoid constituents of plants used in Oriental traditional medicines.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2004 Dec; 812(1-2):259-75. doi:
10.1016/j.jchromb.2004.08.007. [PMID: 15556503] - Hisashi Hemmi, Kyohei Shibuya, Yoshihiro Takahashi, Toru Nakayama, Tokuzo Nishino. (S)-2,3-Di-O-geranylgeranylglyceryl phosphate synthase from the thermoacidophilic archaeon Sulfolobus solfataricus. Molecular cloning and characterization of a membrane-intrinsic prenyltransferase involved in the biosynthesis of archaeal ether-linked membrane lipids.
The Journal of biological chemistry.
2004 Nov; 279(48):50197-203. doi:
10.1074/jbc.m409207200. [PMID: 15356000] - A N Assimopoulou, V P Papageorgiou. Study on isohexenylnaphthazarins polymerization in alkaline media.
Biomedical chromatography : BMC.
2004 Oct; 18(8):508-22. doi:
10.1002/bmc.347. [PMID: 15386522] - Zhen Wu, Li-Jun Wu, Lin-Hao Li, Shin-Ichi Tashiro, Satoshi Onodera, Takashi Ikejima. Shikonin regulates HeLa cell death via caspase-3 activation and blockage of DNA synthesis.
Journal of Asian natural products research.
2004 Sep; 6(3):155-66. doi:
10.1080/1028602032000169622. [PMID: 15224412] - A Pietrosiuk, E Skopińska-Rózewska, M Furmanowa, H Wiedenfeld, E Sommer, I Sokolnicka, E Rogala, D Radomska-Leśniewska, J Bany, M Malinowski. Immunomodulatory effect of shikonin derivatives isolated from Lithospermum canescens on cellular and humoral immunity in Balb/c mice.
Die Pharmazie.
2004 Aug; 59(8):640-2. doi:
. [PMID: 15378856] - A N Assimopoulou, V P Papageorgiou. Encapsulation of isohexenylnaphthazarins in cyclodextrins.
Biomedical chromatography : BMC.
2004 May; 18(4):240-7. doi:
10.1002/bmc.310. [PMID: 15162386] - A N Assimopoulou, V P Papageorgiou. Preparation and release studies of alkannin-containing microcapsules.
Journal of microencapsulation.
2004 Mar; 21(2):161-73. doi:
10.1080/02652040310001637839. [PMID: 15198428] - Vanisree Staniforth, Sheng-Yang Wang, Lie-Fen Shyur, Ning-Sun Yang. Shikonins, phytocompounds from Lithospermum erythrorhizon, inhibit the transcriptional activation of human tumor necrosis factor alpha promoter in vivo.
The Journal of biological chemistry.
2004 Feb; 279(7):5877-85. doi:
10.1074/jbc.m309185200. [PMID: 14645256] - B Singh, P M Sahu, S C Jain, S Singh. Estimation of naphthaquinones from Arnebia hispidissima (Lehm.) DC. In vivo and in vitro. I. Anti-inflammatory screening.
Phytotherapy research : PTR.
2004 Feb; 18(2):154-9. doi:
10.1002/ptr.1385. [PMID: 15022169] - Zhen Wu, Lijun Wu, Linhao Li, Shin-Ichi Tashiro, Satoshi Onodera, Takashi Ikejima. p53-mediated cell cycle arrest and apoptosis induced by shikonin via a caspase-9-dependent mechanism in human malignant melanoma A375-S2 cells.
Journal of pharmacological sciences.
2004 Feb; 94(2):166-76. doi:
10.1254/jphs.94.166. [PMID: 14978355] - Hai-Tao Lu, Yue Jiang, Feng Chen. Preparative high-speed counter-current chromatography for purification of shikonin from the Chinese medicinal plant Lithospermum erythrorhizon.
Journal of chromatography. A.
2004 Jan; 1023(1):159-63. doi:
10.1016/j.chroma.2003.09.022. [PMID: 14760860] - Chien-Ming Hu, Yu-Wen Cheng, Hui-Wen Cheng, Jaw-Jou Kang. Impairment of vascular function of rat thoracic aorta in an endothelium-dependent manner by shikonin/alkannin and derivatives isolated from roots of Macrotomia euchroma.
Planta medica.
2004 Jan; 70(1):23-8. doi:
10.1055/s-2004-815450. [PMID: 14765288] - H Mani, G S Sidhu, A K Singh, J Gaddipati, K K Banaudha, K Raj, R K Maheshwari. Enhancement of wound healing by shikonin analogue 93/637 in normal and impaired healing.
Skin pharmacology and physiology.
2004 Jan; 17(1):49-56. doi:
10.1159/000074063. [PMID: 14755128] - Ching-Hsein Chen, Chi-Liang Chern, Chun-Ching Lin, Fung-Jou Lu, Ming-Kuei Shih, Pei-Ying Hsieh, Tsan-Zon Liu. Involvement of reactive oxygen species, but not mitochondrial permeability transition in the apoptotic induction of human SK-Hep-1 hepatoma cells by shikonin.
Planta medica.
2003 Dec; 69(12):1119-24. doi:
10.1055/s-2003-45193. [PMID: 14750028] - A N Assimopoulou, V P Papageorgiou, C Kiparissides. Synthesis and release studies of shikonin-containing microcapsules prepared by the solvent evaporation method.
Journal of microencapsulation.
2003 Sep; 20(5):581-96. doi:
10.1080/0265204031000148031. [PMID: 12909543] - Nikolaos K Andrikopoulos, Andriana C Kaliora, Andreana N Assimopoulou, Vassilios P Papapeorgiou. Biological activity of some naturally occurring resins, gums and pigments against in vitro LDL oxidation.
Phytotherapy research : PTR.
2003 May; 17(5):501-7. doi:
10.1002/ptr.1185. [PMID: 12748987] - Yoshimi Yamamura, F Pinar Sahin, Akito Nagatsu, Hajime Mizukami. 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 physiology.
2003 Apr; 44(4):437-46. doi:
10.1093/pcp/pcg057. [PMID: 12721385] - B Singh, M K Sharma, P R Meghwal, P M Sahu, S Singh. Anti-inflammatory activity of shikonin derivatives from Arnebia hispidissima.
Phytomedicine : international journal of phytotherapy and phytopharmacology.
2003; 10(5):375-80. doi:
10.1078/0944-7113-00262. [PMID: 12834001] - Chien-Chang Shen, Wan-Jr Syu, Shyh-Yuan Li, Chia-Hung Lin, Gum-Hee Lee, Chang-Ming Sun. Antimicrobial activities of naphthazarins from Arnebia euchroma.
Journal of natural products.
2002 Dec; 65(12):1857-62. doi:
10.1021/np010599w. [PMID: 12502328] - Annegret Köhle, Susanne Sommer, Kazufumi Yazaki, Albert Ferrer, Albert Boronat, Shu-Ming Li, Lutz Heide. High level expression of chorismate pyruvate-lyase (UbiC) and HMG-CoA reductase in hairy root cultures of Lithospermum erythrorhizon.
Plant & cell physiology.
2002 Aug; 43(8):894-902. doi:
10.1093/pcp/pcf106. [PMID: 12198192] - Hirobumi Yamamoto, Ping Zhao, Kazufumi Yazaki, Kenichiro Inoue. Regulation of lithospermic acid B and shikonin production in Lithospermum erythrorhizon cell suspension cultures.
Chemical & pharmaceutical bulletin.
2002 Aug; 50(8):1086-90. doi:
10.1248/cpb.50.1086. [PMID: 12192141] - Dayuan Gao, Makoto Hiromura, Hiroyuki Yasui, Hiromu Sakurai. Direct reaction between shikonin and thiols induces apoptosis in HL60 cells.
Biological & pharmaceutical bulletin.
2002 Jul; 25(7):827-32. doi:
10.1248/bpb.25.827. [PMID: 12132652] - Angeliki P Kourounakis, Andreana N Assimopoulou, Vassilios P Papageorgiou, Antonis Gavalas, Panos N Kourounakis. Alkannin and shikonin: effect on free radical processes and on inflammation - a preliminary pharmacochemical investigation.
Archiv der Pharmazie.
2002 Jun; 335(6):262-6. doi:
10.1002/1521-4184(200208)335:6<262::aid-ardp262>3.0.co;2-y. [PMID: 12210768]