Phytochemical and biological research of fritillaria medicine resources

Chinese Journal of Natural Medicines

Volumn 11, Issue 4, 2013, Pages 330-344

  Hao, Da Cheng ^a   Gu, Xiao Jie ^a   Xiao, Pei Gen ^b   Peng, Yong ^b  

^a DALIAN JIAOTONG UNIVERSITY   (China)

^b BEIJING UNIVERSITY OF POSTS AND TELECOMMUNICATIONS   (China)

Author keywords

Chemical components; Chemotaxonomy; Fritillaria; Medicinal resource; Molecular taxonomy; Phylogeny

Indexed keywords

(3BETA, 5ALPHA ) 20 HYDROXY 6 OXOCEVAN 3 YL ACETATE; 3ALPHA PUQIEDIN 7 OL; ALKALOID DERIVATIVE; CHLOROPLAST DNA; DELAVIDINE; HUPEHENIZIOISIDE; LICHUANINE (5ALPHA, 14ALPHA CEVANINE 3BETA, 6BETA DIOL); LICHUANISININE (5ALPHA,14ALPHA CEVANINE 3BETA, 6BETA DIOL N OXIDE); PALLIDIFLOSIDE A; PALLIDIFLOSIDE B; PALLIDIFLOSIDE C; PALLIDIFLOSIDE D; PALLIDIFLOSIDE E; PALLIDIFLOSIDE G; PALLIDIFLOSIDE H; PALLIDIFLOSIDE I; PEIMISINE 3 O BETA D GLUCOPYRANOSIDE; PENGBEIMINE B; PENGBEIMINE D; PINGBEIMUNONE; PUQIEDINE; PUQIEDINONE 3 O BETA D GLUCOPYRANOSIDE; PUQIENINE C; PUQIENINE D; PUQIENINE E; PUQIENINE F; PUQIETINEDIONE; SAPONIN; TERPENOID; UNCLASSIFIED DRUG;

ANTIOXIDANT ACTIVITY; ARTICLE; CHEMOTAXONOMY; DNA SEQUENCE; DRUG EFFICACY; DRUG RESEARCH; ELECTROSPRAY; FRITILLARIA; GENOMICS; HETERONUCLEAR MULTIPLE BOND CORRELATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MOLECULAR BIOLOGY; MOLECULAR PHYLOGENY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHYTOCHEMISTRY; SPECTROSCOPY; SYSTEMS BIOLOGY; THIN LAYER CHROMATOGRAPHY; X RAY DIFFRACTION;

EID: 84880016679     PISSN: 20956975     EISSN: 18755364     Source Type: Journal    
DOI: 10.1016/S1875-5364(13)60050-3     Document Type: Article

References (87)

1. Rix EM Fritillaria: a revised classification [M] 2001, The Fritillaria group of the Alpine Garden Society, Edinburgh.
2. Xiao PG, Jiang Y, Li P, et al. The botanical origin and pharmacophylogenetic treatment of Chinese material medica Beimu [J]. Acta Phytotaxo Sin 2007, 45(4):473-487.
3. Li HJ, Jiang Y, Li P Chemistry, bioactivity and geographical diversity of steroidal alkaloids from the Liliaceae family [J]. Nat Prod Rep 2006, 23(5):735-752.
4. Rønsted N, Savolainen V, Molgaard P, et al. Phylogenetic selection of Narcissus species for drug discovery [J]. Biochem Syst Ecol 2008, 36(5-6):417-422.
5. Jiang Y, Li P, Li HJ, et al. New steroidal alkaloids from the bulbs of Fritillaria puqiensis [J]. Steroids 2006, 71(9):843-848.
6. Zhang YH, Yang XL, Zhang P, et al. Cytotoxic alkaloids from the bulbs of Fritillaria hupehensis [J]. Chem Biodivers 2008, 5(2):259-266.
7. Zhang QJ, Zheng ZF, Yu DQ Steroidal alkaloids from the bulbs of Fritillaria unibracteata [J]. J Asian Nat Prod Res 2011, 13(12):1098-1103.
8. Pi HF, Ruan HL, Zhang YH, et al. Steroidal alkaloids from bulbs of Fritillaria lichuanensis [J]. J Asian Nat Prod Res 2006, 8(1-2):133-136.
9. Pi HF, Ruan HL, Zhang YH, et al. Two new steroidal alkaloids from bulbs of Fritillaria lichuanensis [J]. J Asian Nat Prod Res 2006, 8(3):253-257.
10. Li HJ, Jiang Y, Li P, et al. Puqienine F, a novel veratramine alkaloid from the bulbs of Fritillaria puqiensis [J]. Chem Pharm Bull 2006, 54(5):722-724.
11. Liu HN, Li F, Luo YM, et al. Two novel isosteroid alkaloids from Fritillaria monatha [J]. J Asian Nat Prod Res 2007, 9(6-8):563-567.
12. Cao XW, Chen SB, Li J, et al. Steroidal alkaloids from the bulbs of Fritillaria delavayi Franch. (Liliaceae) [J]. Biochem Syst Ecol 2008, 36(8):665-668.
13. Shou QY, Tan Q, Wu Shen Z Two 22S-solanidine-type steroidal alkaloids from Fritillaria anhuiensis [J]. Fitoterapia 2010, 81(2):81-84.
14. Lin BQ, Ji H, Li P, et al. Selective antagonism activity of alkaloids from bulbs Fritillariae at muscarinic receptors: functional studies [J]. Eur J Pharmacol 2006, 551(1-3):125-130.
15. Zhou Y, Ji H, Lin BQ, et al. The effects of five alkaloids from Bulbus Fritillariae on the concentration of cAMP in HEK cells transfected with muscarinic M(2) receptor plasmid [J]. Am J Chin Med 2006, 34(5):901-910.
16. Lin BQ, Ji H, Li P, et al. Inhibitors of acetylcholine esterase in vitro-screening of steroidal alkaloids from Fritillaria species [J]. Planta Med 2006, 72(9):814-818.
17. Wang D, Zhu J, Wang S, et al. Antitussive, expectorant and anti-inflammatory alkaloids from Bulbus Fritillariae Cirrhosae [J]. Fitoterapia 2011, 82(8):1290-1294.
18. Wang D, Wang S, Chen X, et al. Antitussive, expectorant and anti-inflammatory activities of four alkaloids isolated from bulbs of Fritillaria wabuensis [J]. J Ethnopharmacol 2012, 139(1):189-193.
19. An JJ, Zhou JL, Li HJ, et al. Puqienine E: an angiotensin converting enzyme inhibitory steroidal alkaloid from Fritillaria puqiensis [J]. Fitoterapia 2010, 81(3):149-152.
20. Xu F, Xu S, Wang L, et al. Antinociceptive efficacy of verticinone in murine models of inflammatory pain and paclitaxel induced neuropathic pain [J]. Biol Pharm Bull 2011, 34(9):1377-1382.
21. Yun YG, Jeon BH, Lee JH, et al. Verticinone induces cell cycle arrest and apoptosis in immortalized and malignant human oral keratinocytes [J]. Phytother Res 2008, 22(3):416-423.
22. Shen S, Chen CJ, Bu R, et al. Three new steroidal saponins from Fritillaria pallidiflora [J]. J Asian Nat Prod Res 2011, 13(11):1014-1022.
23. Shen S, Li G, Huang J, et al. Steroidal saponins from Fritillaria pallidiflora Schrenk [J]. Fitoterapia 2012, 83(4):785-794.
24. Xu J, Guo P, Liu C, et al. Neuroprotective kaurane diterpenes from Fritillaria ebeiensis [J]. Biosci Biotechnol Biochem 2011, 75(7):1386-1388.
25. Xu J, Liu C, Guo P, et al. Neuroprotective labdane diterpenes from Fritillaria ebeiensis [J]. Fitoterapia 2011, 82(5):772-776.
26. Atta-ur-Rahman, Akhtar MN, Choudhary MI, et al. New diterpene isopimara-7,15-dien-19-oic acid and its prolyl endopeptidase inhibitory activity [J]. Nat Prod Res 2005, 19(1):13-22.
27. Liu C, Chang J, Zhang L, et al. Purification and antioxidant activity of a polysaccharide from bulbs of Fritillaria ussuriensis Maxim [J]. Int J Biol Macromol 2012, 50(4):1075-1080.
28. Zhou JL, Jiang Y, Bi ZM, et al. Study on nucleosides from Fritillaria puqiensis [J]. Chin Pharm J 2008, 43(12):894-896.
29. Zhang J, Song C, Chen B, et al. Simultaneous determination of 5 nucleotides in Bulbus Fritillariae by RP-HPLC [J]. China J Chin Materia Med 2010, 35(1):67-70.
30. Cao XW, Li J, Chen SB, et al. Simultaneous determination of nine nucleosides and nucleobases in different Fritillaria species by HPLC-diode array detector [J]. J Sep Sci 2010, 33(11):1587-1594.
31. Huang L, Duan B, Wang L, et al. Simultaneous determination of 7 nucleosides and nucleobases in aqueous extracts of Fritillaria taipaiensis by HPLC-DAD [J]. China J Chin Materia Med 2011, 36(5):585-588.
32. Duan B, Huang L, Chen S Chemical fingerprint analysis of Fritillaria delavayi Franch. by high-performance liquid chromatography [J]. J Sep Sci 2012, 35(4):513-518.
33. Liang J, Cao X, Li J, et al. Analysis of volatile components of flowers of Fritillaria thunbergii by GC-TOF-MS [J]. China J Chin Mater Med 2011, 36(19):2689-2692.
34. Helsper JP, Bücking M, Muresan S, et al. Identification of the volatile component(s) causing the characteristic foxy odor in various cultivars of Fritillaria imperialis L. (Liliaceae) [J]. J Agric Food Chem 2006, 54(14):5087-5091.
35. Yuan X, Shi J, Yang Y, et al. Establishment of element fingerprint and multielement analysis of Fritillaria thunbergii by inductively coupled plasma optical emission spectrometry [J]. Biol Trace Elem Res 2010, 135(1-3):304-313.
36. Yao YH, Xu GH, Zhang JD, et al. Determination of trace elements in traditional Chinese medicine from Changbai Mountain by ICP-MS [J]. Spectrosc Spectral Anal 2008, 28(5):1165-1167.
37. Kim SH, Shin DS, Oh MN, et al. Inhibition of sortase, a bacterial surface protein anchoring transpeptidase, by beta-sitosterol-3-O-glucopyranoside from Fritillaria verticillata [J]. Biosci Biotechnol Biochem 2003, 67(11):2477-2479.
38. Li F, Yan DM, Liu HN, et al. Review on chemical components research on domestic Fritillaria plants of China [J]. World Sci Technol Mod Tradit Chin Med 2005, 7(2):26-31.
39. Yu SC, Xiao PG The existence of isosteroidal alkaloids in Fritillaria L. (Liliaceae) and its taxonomical significance [J]. Acta Phytotaxon Sin 1992, 30(5):450-459.
40. Li SL, Li P, Lin G, et al. 1999 Existence of 5α-cevanine isosteroidal alkaloids in bulbs of Fritillaria L. [J]. Acta Pharm Sin 1999, 34(11):842-847.
41. Xiao PG A review on the study of Hu Bei Bei Mu [J]. China J Chin Mater Med 2002, 27(10):726-728.
42. Li HJ, Jiang Y, Li P Characterizing distribution of steroidal alkaloids in Fritillaria spp. and related compound formulas by liquid chromatography-mass spectrometry combined with hierarchial cluster analysis [J]. J Chromatogr A 2009, 1216(11):2142-2149.
43. Yu SC, Xiao PG On the taxonomical state of Fritillaria sulcisquamosa and F. puqiensis [J]. Acta Phytotaxon Sin 1992, 30(3):277-278.
44. Luo K, Ma P, Yao H, et al. Molecular identification of Fritillariae Cirrhosae Bulbus and its adulterants [J]. World Sci Technol Mod Tradit Chin Med 2012, 14(1):1-6.
45. Zhou JL, Xin GZ, Shi ZQ, et al. Characterization and identification of steroidal alkaloids in Fritillaria species using liquid chromatography coupled with electrospray ionization quadrupole time-of-flight tandem mass spectrometry [J]. J Chromatogr A 2010, 1217(45):7109-7122.
46. Duan BZ, Huang LF, Chen SL Simultaneous determination of peimisine and sipeimine in Fritillaria walujewii Regel and Fritillaria pallidiflora Schrenk by UPLC-ELSD [J]. Acta Pharm Sin 2010, 45(12):1541-1544.
47. Yu RP, Cheng ZF, Gong XQ Determination and comparison of trace elements in four sorts of Bulbus Fritillariae by microwave digestion-atomic absorption spectrometry [J]. Spectrosc Spectral Anal 2007, 27(12):2591-2594.
48. Hao DC, Chen SL, Xiao PG, et al. Authentication of medicinal plants by DNA-based markers and genomics [J]. Chin Herb Med 2010, 2(4):250-261.
49. Li YF, Tang L, Chen F RAPD analysis of eight Fritillaria species [J]. Chin Tradit Patent Med 2006, 28(10):1527-1529.
50. Yin CP, Liu WT, Xu SQ, et al. Discriminating Chuan Bei Mu and Hu Bei Bei Mu by RAPD [J]. Her Med 2007, 26(4):359-361.
51. Lu H, Zhu SH, Zhou SJ, et al. Specific RAPD screening of breeds in Fritillaria thunbergii and genetic diversity analysis of five species of Fritillaria [J]. J Ningbo Univ 2009, 22(1):44-47.
52. Li Q, Chen X, Wang S Study on the relative in molecular biology among Fritillariae of Sichuan species [J]. West China J Pharm Sci 2010, 25(2):140-143.
53. Celebi A, Teksen M, Acik L, et al. Taxonomic relationships in genus Fritillaria (Liliaceae): evidence from RAPD-PCR and SDS-PAGE of seed proteins [J]. Acta Bot Hun 2008, 50(3-4):325-343.
54. Li KQ, Wu W, Zheng Y, et al. Genetic diversity of Fritillaria from Sichuan Province based on ISSR [J]. China J Chin Mater Med 2009, 34(17):2149-2154.
55. Wu XQ, Cheng HZ, Zhou YZ, et al. Analysis of genetic relationship ornamental Fritillaria germplasm resources by ISSR markers [J]. North Horti 2010, (18):157-160.
56. Li S, Hu K, Guo J, et al. Genetic diversity and relationship of Fritillaria thunbergii Miq. landraces and related taxa [J]. Biochem Syst Ecol 2011, 39(4-6):725-731.
57. Liu XX, Chen C, Pan LL, et al. Genetic diversity of bulbus Fritillariae Thunbergii Miq. varieties based on ISSR markers [J]. J Zhejiang Univ (Agric & Life Sci) 2010, 36(3):246-254.
58. Zhou J, Wang ZH ISSR analysis of genetic diversity of F. thunbergii [J]. J Zhejiang Agri Sci 2012, (2):156-159.
59. Zhang DQ, Gao LM, Yang YP Genetic diversity and structure of a traditional Chinese medicinal plant species, Fritillaria cirrhosa (Liliaceae) in southwest China and implications for its conservation [J]. Biochem Syst Ecol 2010, 38(2):236-242.
60. Xu JZ, Zhang HY, Ma XY, et al. AFLP analysis on genetic diversity for germplasm resources of Fritillaria thunbergii cultivated in Zhejiang Province [J]. Chin Tradit Herb Drug 2010, 41(1):109-113.
61. Yang FS, Wang XQ, Hong DY Unexpected high divergence in nrDNA ITS and extensive parallelism in floral morphology of Pedicularis (Orobanchaceae) [J]. Plant Syst Evol 2003, 240(1-4):91-105.
62. Luo Y, Zhang FM, Yang QE Phylogeny of Aconitum subgenus Aconitum (Ranunculaceae) inferred from ITS sequences [J]. Plant Syst Evol 2005, 252(1-2):11-25.
63. Xie L, Wen J, Li LQ Phylogenetic analyses of Clematis (Ranunculaceae) based on sequences of nuclear ribosomal ITS and three plastid regions [J]. Syst Bot 2011, 36(4):907-921.
64. Luo YB, Chen XQ A revision of Fritillaria L. (Liliaceae) in the Hengduan Mountains and adjacent regions, China (II) [J]. Acta Phytotaxon Sin 1996, 34(5):547-553.
65. Zhang S, Wei J, Chen SL, et al. Floral dynamic and pollination habit of Fritillaria cirrhosa [J]. China J Chin Mater Med 2010, 35(1):27-29.
66. Tan Y, Zhang LH, Li MC, et al. Identification of Chinese herb Fritillaria cirrhosa D. Don by DNA fingerprint [J]. China Pharm J 2011, 46(1):14-16.
67. Wang CZ, Li P, Ding JY, et al. Simultaneous identification of Bulbus Fritillariae cirrhosae using PCR-RFLP analysis [J]. Phytomedicine 2007, 14(9):628-632.
68. Xu CL, Li HJ, Li P, et al. Molecular method for the identification of Bulbus Fritillariae Cirrhosae [J]. J China Pharm Univ 2010, 41(3):226-230.
69. Gao YD, Zhou SD, He XJ, et al. Chromosome diversity and evolution in tribe Lilieae (Liliaceae) with emphasis on Chinese species [J]. J Plant Res 2012, 125(1):55-69.
70. Rønsted N, Law S, Thornton H, et al. Molecular phylogenetic evidence for the monophyly of Fritillaria and Lilium (Liliaceae; Liliales) and the infrageneric classification of Fritillaria [J]. Mol Phylogenet Evol 2005, 35(3):509-527.
71. Li KQ Studies on genetic diversity of genus Fritillaria from Sichuan province and effects of temperature and light on the growth and development of Fritillaria cirrhosa [M]. 2009, Sichuan Agricultural University, Master degree thesis.
72. Wang Q, Zhou SD, Deng XY, et al. Comparative morphology of the leaf epidermis in Fritillaria (Liliaceae) from China [J]. Bot J Linn Soc 2009, 160(1):93-109.
73. Hill L A taxonomic history of Japanese endemic Fritillaria (Liliaceae) [J]. Kew Bull 2011, 66(2):227-240.
74. Wink M, Botschen F, Gosmann C, et al. Chemotaxonomy seen from a phylogenetic perspective and evolution of secondary metabolism. Annual Plant Reviews, Volume 40, Biochemistry of Plant Secondary Metabolism [M] 2010, Wiley-Blackwell. 2nd Edition. M. Wink (Ed.).
75. Shi JY, Yuan XF, Lin HR, et al. 2011 Differences in soil properties and bacterial communities between the rhizosphere and bulk soil and among different production areas of the medicinal plant Fritillaria thunbergii [J]. Int J Mol Sci 2011, 12(6):3770-3785.
76. Hao DC, Yang L, Xiao PG The first insight into the Taxus genome via fosmid library construction and end sequencing [J]. Mol Genet Genomics 2011, 285(3):197-205.
77. Ambrozová K, Mandáková T, Bures P, et al. Diverse retrotransposon families and an AT-rich satellite DNA revealed in giant genomes of Fritillaria lilies [J]. Ann Bot 2011, 107(2):255-268.
78. Hao DC, Chen SL, Xiao PG, et al. Application of high-throughput sequencing in the medicinal plant transcriptome studies [J]. Drug Dev Res 2012, 73(8):487-498.
79. Sun C, Sun YQ, Song JY, et al. Discovery of genes related to steroidal alkaloid biosynthesis in Fritillaria cirrhosa by generating and mining a dataset of expressed sequence tags (ESTs) [J]. J Med Plant Res 2011, 5(21):5307-5314.
80. Hao DC, Ma P, Mu J, et al. De novo characterization of the root transcriptome of a traditional Chinese medicinal plant Polygonum cuspidatum [J]. Sci China Life Sci 2012, 55(5):452-466.
81. Hao DC, Ge GB, Xiao PG, et al. The first insight into the tissue specific taxus transcriptome via Illumina second generation sequencing [J]. PLoS One 2011, 6(6):e21220.
82. Yang ZD, Duan DZ A new alkaloid from Fritillaria ussuriensis Maxim [J]. Fitoterapia 2012, 83(1):137-141.
83. Kang L, Zhou JX, Shen ZW A new diterpenoid from Fritillaria anhuiensis [J]. Acta Pharm Sin 2007, 42(1):58-60.
84. Liu HN, Li F, Luo YM, et al. Diterpenoids from bulbus of Fritillaria monanth [J]. Acta Pharm Sin 2007, 42(11):1152-1154.
85. Zhang YH, Ruan HL, Pi HF, et al. Structural elucidation of fritillahupehin from bulbs of Fritillaria hupehensis Hsiao et K. C. Hsia [J]. J Asian Nat Prod Res 2004, 6(1):29-34.
86. Pi HF, Zhang P, Ruan HL, et al. Two new triterpenoids from the leaves and stems of Fritillaria hupehensis [J]. J Asian Nat Prod Res 2009, 11(9):779-782.
87. Tamura K, Peterson D, Peterson N, et al. MEGA5: Molecular evolutionary genetics analysis using maximum likelihood, evolutionary distance, and maximum parsimony methods [J]. Mol Biol Evol 2011, 28(10):2731-2739.