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Structure type: monomer
Trivial name: ginsenoside-F1, 20(S)-ginsenoside-Rh1, ginsenoside F1
Compound class: saponin glycoside, glycoside, triterpenoid glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 7266
  Liu X, Qiao LR, Xie D, Dai JG "Microbial deglycosylation and ketonization of ginsenosides Rg1 and Rb1 by Fusarium oxysporum" - Journal of Asian Natural Products Research 13(7) (2011) 652-658
  

  Two major ginsenosides, ginsenoside-Rg1 (1) and ginsenoside-Rb1 (2), were transformed by the fungus Fusarium oxysporum f. sp. Lycopersici (Z-001). 1 was converted into five metabolites, ginsenoside-F1 (3), 6α,12β-dihydroxydammar-3-one-20(S)-O- β-D-glucopyranoside (4), 3a-oxa-3a-homo-6α,12β-dihydroxydammar- 3-one-20(S)-O-β-D-glucopyranoside (5), 20(S)-protopanaxatriol (6), and 3-oxo-20(S)-protopanaxatriol (7). 2 was converted into four metabolites, ginsenoside-Rd (8), ginsenoside-F2 (9), compound K (10), and 12β-hydroxydammar-3-one-20(S)-O-β-D-glucopyranoside (11). The structures of these metabolites were determined by the analysis of extensive spectroscopic data. Among them, 4 and 5 were two new compounds. Deglycosylation and ketonization at C-3 were recognized as the characteristic reactions of this strain.

  deglycosylation, Fusarium oxysporum, ginsenosides, ketonization

  Publication DOI: 10.1080/10286020.2011.585607
  Journal NLM ID: 100888334
  Publisher: Harwood Academic Publishers; London: Informa Healthcare
  Correspondence: jgdai@imm.ac.cn
  Institutions: Key Laboratory of Biosynthesis of Natural Products, Ministry of Public Health, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, China, Key Laboratory of Bioactive Substances and Resources Utilization of Chinese Herbal Medicine, Ministry of Education, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, China
  Methods: 13C NMR, 1H NMR, TLC, ESI-MS, FTIR, HPLC, extraction, CC, HR-ESI-MS
  
   
  
  Fusarium oxysporum f.sp. lycopersici Z-001
  CSDB ID 43449 (all data & tools)
• Article ID: 7290
  Liu X, Qiao L, Xie D, Zhang Y, Zou J, Chen X, Dai J "Microbial transformation of ginsenoside-Rg1 by Absidia coerulea and the reversal activity of the metabolites towards multi-drug resistant tumor cells" - Fitoterapia 82(8) (2011) 1313-1317
  

  Biotransformation of ginsenoside-Rg1 (1) by the fungus Absidia coerulea AS 3.2462 yielded five metabolites (2-6). On the basis of spectroscopic data analyses, the metabolites were identified as ginsenoside-F1 (2), 6α,12β-dihydroxydammar-3-one-20(S)-O-β-D-glucopyranoside (3), 3-oxo-20(S)-protopanaxatriol (4), 3-oxo-7β-hydroxy-20(S)-protopanaxatriol (5), and 3-oxo-7β,15α-dihydroxy-20(S)-protopanaxatriol (6), respectively. Among them, 5 and 6 are new compounds. These results indicated that Absidia coerulea AS 3.2462 could catalyze the specific C-3 dehydrogenation of derivatives of ginsenoside-Rg1, as well as hydroxylation at the 7β and 15α positions. Metabolites 2, 4 and 5 exhibited moderate reversal activity towards A549/taxol MDR tumor cells in vitro.

  hydroxylation, microbial transformation, ginsenoside-Rg1, Absidia coerulea AS 3.2462, dehydrogenation, tumor MDR reversal activity

  NCBI PubMed ID: 21946057
  Publication DOI: 10.1016/j.fitote.2011.09.001
  Journal NLM ID: 16930290R
  Publisher: Elsevier
  Correspondence: jgdai@imm.ac.cn
  Institutions: State Key Laboratory of Bioactive Substances and Functions of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Ministry of Public Health, Beijing, China, Key Laboratory of Biosynthesis of Natural Products, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Ministry of Public Health, Beijing, China
  Methods: 13C NMR, 1H NMR, TLC, FTIR, HPLC, extraction, HR-ESI-MS, antitumor activity assay
  
   
  
  Absidia coerulea AS 3.2462
  CSDB ID 43509 (all data & tools)
• Article ID: 10728
  Samukawa K, Yamashita H, Matsuda H, Kubo M "Simultaneous analysis of saponins in Ginseng Radix by high performance liquid chromatography" - Chemical and Pharmaceutical Bulletin 43 (1995) 137-141
  

  The presence of about 25 ginsenosides in Ginseng Radix and their structures have already been elucidated. Although some important neutral- and acidic-saponins have been detected by high performance liquid chromatography (HPLC), other saponins have not yet been examined by HPLC. Our present improved method for the detection of ginsenosides by HPLC with a C_<18> column and a CH_3CN-H_2O gradient system enabled the measurement of not only the representative ginsenosides in Red Ginseng [20(R)-ginsenoside-Rg_2 and -Rh_1,20(S, R)-ginsenosides-Rg_3 and -Rs_1] but also the minor ginsenosides [ginsenosides-Rb_3,-Rg_2,-Rh_1 and quinquenoside-R1]. Furthermore, the application of this method after a little modification of the eluent in particular to an extract of Ginseng Radix achieved simultaneous separation of 22 neutral- and acidic-ginsenosides. The qualitative and quantitative analysis of ginsenosides using the present method offers an efficient means of evaluating Ginseng Radix and commercial products containing it.

  Panax ginseng, Ginseng saponin, simultaneous HPLC analysis, Ginseng Radix, White Ginseng, Red Ginseng

  Journal NLM ID: 0377775
  WWW link: http://ci.nii.ac.jp/naid/110003631301
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Faculty of Pharmaceutical Sciences, Kinki University, Japan, Ginseng Institute, Japan Korea Red Ginseng Co., Ltd., Japan
  Methods: HPLC
  
   
  
  Panax ginseng
  CSDB ID 120545 (all data & tools)
• Article ID: 11125
  Yoshikawa M, Murakami T, Ueno T, Yashiro K, Hirokawa N, Murakami N, Yamahara J, Matsuda H, Saijoh R, Tanaka O "Bioactive saponins and glycosides. VIII. Notoginseng (1): new dammarane-type triterpene oligoglycosides, notoginsenosides-A, -B, -C, and -D, from the dried root of Panax notoginseng (Burk) F.H. Chen" - Chemical and Pharmaceutical Bulletin 45(6) (1997) 1039-1045
  

  The glycosidic fraction from the dried roots of Panax notoginseng (BURK.) F. H. CHEN was found to show protective effect on liver injury induced by D-galactasamine and lipopolysaccharide. From the glycosidic fraction with hepatoprotective effect, nine new dammarane-type triterpene oligoglycosides, notoginsenosides-A, -B, -C, -D, -E, -G, -H, -I, and -J and an acetylenic fatty acid glycoside, notoginsenic acid β-sophoroside, were isolated together with fourteen known dammarane-type triterpene oligoglycosides. The structures of notoginsenosides-A, -B, -C, and -D were determined on the basis of chemical and physicochemical evidence, which included the chemical correlation with ginsenoside-Rb, using photosensitized oxygenation, as follows: notoginsenoside A; 3-O-[β-D-glucopyranosyl(1→2)-β-D-glucopyranosyl]-20-O-[β-D-glucopyranosyl(1→6)-β-D-glucopyranosyl] 3β,12β,20(S),25-tetrahydroxydammar-23-ene, B; 3-O-[β-D-glucopyranosyl(1→2)-β-D-glucopyranosyl]-20-O-[β-D-glucpyranosyl(1→6)-β-D-glucopyranosyl] 3β,12β,20(S)-trihydroxydammar-25-en-24-one C; 3-O-[β-D-glucopyranosyl(1→2)-β-D-glucopyranosyl]-20-O-[β-D-glucopyranosyl(1→6)-β-D-glucopyranosyl] 3β,12β,20(S)-trihydroxy-24 ξ-hydroperoxydammar-25-ene , and D; 3-O-[β-D-xylopyranosyl(1→2)-β-D-glucopyranosyl(1→2)-β-D-glucopyranosyl]-20-O-[β-D-xylopyranosyl(1→6)-β-D-glucopyranosyl(1→6)-β-D-glucopyranosyl] 20(S)-protopanaxadiol, respectively.

  Panax notoginseng, bioactive saponin, notoginsenoside, liver injury protective, dammarane-type triterpene oligoglycoside, notoginseng

  NCBI PubMed ID: 9214709
  Publication DOI: 10.1248/cpb.45.1039
  Journal NLM ID: 0377775
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Kyoto Pharmaceutical University, Kyoto, Japan
  Methods: 13C NMR, 1H NMR, IR, FAB-MS, acid hydrolysis, GLC, chemical methods, biological assays, methanolysis, HPLC, extraction
  
   
  
  Panax notoginseng
  CSDB ID 60221 (all data & tools)
• Article ID: 11812
  Atopkina LN, Malinovskaya GV, Elyakov GB, Uvarova NI, Woerdenbag HJ, Koulman A, Pras N, Potier P "Cytotoxicity of natural Ginseng glycosides and semisynthetic analogues" - Planta Medica 65(1) (1999) 30-34
  

  The cytotoxicity of natural glycosides from Ginseng, semisynthetic analogues and related triterpenes of the dammarane series, isolated from the leaves of the Far-East species of the genus Betula was studied in order to elucidate structure-activity relationships. Some of the compounds studied were active against the human lung carcinoma GLC4 and adenocarcinoma COLO 320 cell lines. The natural glycosides displayed the lowest cytotoxicity. The triterpenes of the dammarane series used as starting aglycones for semisynthetic derivatives were moderately cytotoxic. The dammarane triterpenes possessing keto groups and their semisynthetic glucosides were the most active compounds tested. Cytotoxic effects of the dammarane glucosides were inversely proportional both to the number of sugars attached to the aglycones and to the number of hydroxy groups of the aglycones. The type of side chain and the configuration of the hydroxy group at C-3 in aglycones did not have a significant influence on the cytotoxicity.

  cytotoxicity, ginsenosides, Panax ginseng, araliaceae, Betulaceae, Betula, chikusetsusaponin-LT8, dammarane type triterpenes, betulafolienetriol

  NCBI PubMed ID: 10083841
  Publication DOI: 10.1055/s-1999-13957
  Journal NLM ID: 0066751
  Publisher: George Thieme
  Correspondence: Elyakov GB
  Institutions: Pacific Institute of Bioorganic Chemistry, Far East Division of the Russian Academy of Sciences, Vladivostok, Russia, Department of Pharmaceutical Biology, University Centre for Pharmacy, Groningen, The Netherlands, Centre National de la Pecherche Scientifigue, Institute de Chimie des Substances Naturelles, Gif-sur-Yvette, France, Present address: Groningen Biomolecular Sciences and Biotechnology Institute, University of Groningen, Groningen, The Netherlands
  Methods: 13C NMR, 1H NMR, IR, TLC, cytotoxicity assay
  
   
  
  Panax ginseng
  CSDB ID 63091 (all data & tools)
• Article ID: 12012
  Awang DVC "The neglected ginsenosides of North American ginseng (Panax quinquefolius L.)" - Journal of Herbs, Spices and Medicinal Plants 7(2) (2000) 103-109
  

  The high performance liquid chromatographic (HPLC) procedures commonly employed for the assay of ginsenosides in Panax quinquefolius L. (North American Ginseng) neglect assessment of acidic, mainly malonyl, ginsenosides. As such, total ginsenoside values for this species, in contrast with corresponding values for Panax ginseng C.A. Meyer (Asian Ginseng) in which the level of acidic ginsenosides is much lower, are usually gross underestimates of total ginsenoside content. Malonyl ginsenosides are readily susceptible to hydrolysis, a process accelerated by heat and catalyzed under both basic and acidic conditions. There can be little question that these acidic ginsenosides, more polar and water soluble than their neutral progenitors, are significant active constituents of ginseng root and should be as routinely evaluated as the seven or six neutral ginsenosides normally assessed.

  analysis, medicinal plant, saponins, herb

  Publication DOI: 10.1300/J044V07N02_09
  Journal NLM ID: 9302329
  Publisher: Binghamton Ny: Food Products Press
  Institutions: Medi-Plant, White Rock, Canada
  Methods: HPLC, extraction
  
   
  
  Panax quinquefolius, Panax ginseng
  CSDB ID 64801 (all data & tools)

Show legend Show as text

Structure type: monomer
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 7290
  Liu X, Qiao L, Xie D, Zhang Y, Zou J, Chen X, Dai J "Microbial transformation of ginsenoside-Rg1 by Absidia coerulea and the reversal activity of the metabolites towards multi-drug resistant tumor cells" - Fitoterapia 82(8) (2011) 1313-1317
  

  Biotransformation of ginsenoside-Rg1 (1) by the fungus Absidia coerulea AS 3.2462 yielded five metabolites (2-6). On the basis of spectroscopic data analyses, the metabolites were identified as ginsenoside-F1 (2), 6α,12β-dihydroxydammar-3-one-20(S)-O-β-D-glucopyranoside (3), 3-oxo-20(S)-protopanaxatriol (4), 3-oxo-7β-hydroxy-20(S)-protopanaxatriol (5), and 3-oxo-7β,15α-dihydroxy-20(S)-protopanaxatriol (6), respectively. Among them, 5 and 6 are new compounds. These results indicated that Absidia coerulea AS 3.2462 could catalyze the specific C-3 dehydrogenation of derivatives of ginsenoside-Rg1, as well as hydroxylation at the 7β and 15α positions. Metabolites 2, 4 and 5 exhibited moderate reversal activity towards A549/taxol MDR tumor cells in vitro.

  hydroxylation, microbial transformation, ginsenoside-Rg1, Absidia coerulea AS 3.2462, dehydrogenation, tumor MDR reversal activity

  NCBI PubMed ID: 21946057
  Publication DOI: 10.1016/j.fitote.2011.09.001
  Journal NLM ID: 16930290R
  Publisher: Elsevier
  Correspondence: jgdai@imm.ac.cn
  Institutions: State Key Laboratory of Bioactive Substances and Functions of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Ministry of Public Health, Beijing, China, Key Laboratory of Biosynthesis of Natural Products, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Ministry of Public Health, Beijing, China
  Methods: 13C NMR, 1H NMR, TLC, FTIR, HPLC, extraction, HR-ESI-MS, antitumor activity assay
  
   
  
  Absidia coerulea AS 3.2462
  CSDB ID 43510 (all data & tools)