General Information of Natural Product (ID: NP1349)
  Natural Product Name
Deoxypodophyllotoxin
  Synonyms
Deoxypodophyllotoxin; 19186-35-7; Anthricin; (-)-Deoxypodophyllotoxin; Desoxypodophyllotoxin; Silicicolin; Hernandin; Hernandion; 4-Deoxypodophyllotoxin; (-)-Anthricin; NSC403148; Isodeoxypodophyllotoxin; CHEBI:4429; (-)-Desoxypodophyllotoxin; Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one, 5,8,8a,9-tetrahydro-5-(3,4,5-trimethoxyphenyl)-, (5R,5aR,8aR)-; C22H22O7; UNII-45NR8XYU1L; 45NR8XYU1L; MLS002702900; Anthriscin; (5R,5aR,8aR)-5-(3,4,5-trimethoxyphenyl)-5a,8,8a,9-tetrahydro-5H-isobenzofuro[5,6-f][1,3]benzodioxol-6-one; (5R,5aR,8aR)-5-(3,4,5-trimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one; CHEMBL63970; SCHEMBL987840; Podophyllotoxin, 7CI, 8CI); DTXSID701019944; EX-A2905; HY-N2500; ZINC1575139; AKOS032948828; NSC-403148; AC-34638; NCI60_003794; CS-0022771; W1846; J-501619; Q27106380; (10R,11R,15R)-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.03,7,011,15]hexadeca-1(9),2,7-trien-12-one; (5R,5aR,8aR)-5-(3,4,5-trimethoxyphenyl)-5,8,8a,9-tetrahydro-2H-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one; (5R,5aR,8aR)-5-(3,4,5-Trimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5a)-one; 100348-38-7; 5,8,8a,9,-Tetrahydro-5-(3,4,5-trimethoxyphenyl)furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one; Furo[3',7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one, 5,8,8a,9-tetrahydro-5-(3,4,5-trimethoxyphenyl)-,(5R,5aR,8aR)-
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  Formula C22H22O7
  Weight 398.4
  Structure Could Not Find 2D Structure
3D Structure Download 2D Structure Download
  InChI InChI=1S/C22H22O7/c1-24-17-6-12(7-18(25-2)21(17)26-3)19-14-8-16-15(28-10-29-16)5-11(14)4-13-9-27-22(23)20(13)19/h5-8,13,19-20H,4,9-10H2,1-3H3/t13-,19+,20-/m0/s1
  InChI Key ZGLXUQQMLLIKAN-SVIJTADQSA-N
  Isomeric SMILES COC1=CC(=CC(=C1OC)OC)[C@H]2[C@@H]3[C@@H](CC4=CC5=C(C=C24)OCO5)COC3=O
  Canonical SMILES COC1=CC(=CC(=C1OC)OC)C2C3C(CC4=CC5=C(C=C24)OCO5)COC3=O
  External Links PubChem ID 345501
CAS ID 19186-35-7
NPASS ID NPC80230
HIT ID C0505
CHEMBL ID CHEMBL63970
  NP Activity Charts   Click to show/hide

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Aspergillus fumigatus strain INFU/Jc/KF/6
  Factor Name: Sabouraud broth medium [1]
              Species Info Factor Info
               Experiment Detail
Collectionof plant material: As part of an effort to identify endophytic fungi that produce deoxypodophyllotoxin and/or its analogues, Juniperus plant species were collected from the natural populations at the northwestern Himalayan environments (Jammu and Kashmir, India) and the botanical gardens of Rombergpark (Dortmund, Germany). A few twigs were carefully excised from the host plant and collected in clean dry plastic bags. The twigs were transported to the Institut fur Umweltforschung (INFU), Technische Universitat Dortmund, Dortmund, Germany immediately, and processed within 4 h of collection. The twigs were washed thoroughly in running tap water followed by deionized (DI) water to remove any dirt sticking to them and stored at 4 ℃ until the isolation procedure of endophytic fungi was commenced. The endophyte was cultured in Sabouraud broth (SB; Difco, Cat. No. 238230) consisting of dextrose (2%) as the sole carbon source and enzymatic digest of casein (1%) as the sole nitrogen source. A set of 10 conical flasks of 500 ml capacity was used, each with four indentations and containing 100 ml SB, adjusted to pH 5.6 before autoclaving. The fungus was inoculated into each flask from the parent axenic culture. These flasks were incubated at 28 ℃ with shaking (200 rev/min) on a rotary shaker (Heidolph UNIMAX 2010, Germany). Each flask represented one time point of fermentation termination followed by extraction and analysis for determination of deoxypodophyllotoxin production. The first sample was taken after 2 h of inoculation (0 h) and subsequently the other samples were taken after every 24 h, up to 216 h. Three replicates of each experiment set was undertaken to get reproducible data.
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               Factor Part Location NP Content
 
Sabouraud broth (28℃ + 9 days + PH5.6)
Twigs Rombergpark, Germany
NP Content: 17719 µg/100g
 
Sabouraud broth (28℃ + 9 days + PH5.6)
Twigs Rombergpark, Germany
NP Content: 8637 µg/100g
 
Sabouraud broth (28℃ + 9 days + PH5.6)
Twigs Rombergpark, Germany
NP Content: 14249 µg/100g
 
Sabouraud broth (28℃ + 9 days + PH5.6)
Twigs Rombergpark, Germany
NP Content: 8241 µg/100g
 
Sabouraud broth (28℃ + 9 days + PH5.6)
Twigs Rombergpark, Germany
NP Content: 62 µg/100g
 
Sabouraud broth (28℃ + 9 days + PH5.6)
Twigs Rombergpark, Germany
NP Content: 188 µg/100g
 
Sabouraud broth (28℃ + 9 days + PH5.6)
Twigs Rombergpark, Germany
NP Content: 25006 µg/100g
 
Sabouraud broth (28℃ + 9 days + PH5.6)
Twigs Rombergpark, Germany
NP Content: 2882 µg/100g
 
Sabouraud broth (28℃ + 9 days + PH5.6)
Twigs Yarika, Jammu and Kashmir, India
NP Content: 1702 µg/100g
 
Sabouraud broth (28℃ + 9 days + PH5.6)
Twigs Bonera, Jammu and Kashmir, India
NP Content: 214 µg/100g
 
Sabouraud broth (28℃ + 9 days + PH5.6)
Twigs Sonamarg, Jammu and Kashmir, India
NP Content: 11301 µg/100g
References
1 Aspergillus fumigatus Fresenius, an endophytic fungus from Juniperus communis L. Horstmann as a novel source of the anticancer pro-drug deoxypodophyllotoxin