Details of Natural Product (NP)

General Information of Natural Product (ID: NP1347)
  Natural Product Name
Podofilox
  Synonyms
podophyllotoxin; Podofilox; 518-28-5; Condylox; Condyline; (-)-Podophyllotoxin; Wartec; Podophyllinic acid lactone; Podophyllotoxin 7; Warticon; Podophyllum; Podofilox [USAN]; UNII-L36H50F353; NSC24818; CHEMBL61; MFCD00075290; (10R,11R,15R,16R)-16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1(9),2,7-trien-12-one; (5R,5aR,8aR,9R)-5-hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one; MLS000069495; (5R,5aR,8aR,9R)-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one; CHEBI:50305; Podofilox (USAN); NSC-24818; L36H50F353; NCGC00022001-05; Podofilm; SMR000059121; NSC 24818; DSSTox_CID_25645; DSSTox_RID_81023; DSSTox_GSID_45645; (5R,5aR,8aR,9R)-5,8,8a,9-Tetrahydro-9-hydroxy-5-(3,4,5-trimethoxyphenyl)furo(3',4':6,7)naphtho(2,3-d)-1,3-dioxol-6(5aH)-one; (5R,5aR,8aR,9R)-5-hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-isobenzofuro[5,6-f][1,3]benzodioxol-8-one; Podocon-25; Podophilox; (5R,5aR,8aR,9R)-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-5,5a,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(8H)-one; CCRIS 565; HSDB 7238; SR-05000001749; MLS002702981; EINECS 208-250-4; Podofillina; Podophylotoxin; AI3-50456; Mayapple isolate; Condylox (TN); (5R,5aR,8aR,9R)-5,8,8a,9-Tetrahydro-9-hydroxy-5-(3,4,5-trimethoxyphenyl)furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one; CAS-518-28-5; Podophyllotoxin,(S); Prestwick_1018; Furo(3',4':6,7)naphtho(2,3-d)-1,3-dioxol-6(5aH)-one, 5,8,8a,9-tetrahydro-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-, (5R-(5alpha,5abeta,8aalpha,9alpha))-; Podofillina [Italian]; Podophyllotoxin (BAN); Podophyllotoxin, 95%; Spectrum_000199; Opera_ID_1397; Prestwick0_000782; Prestwick1_000782; Prestwick2_000782; Prestwick3_000782; Spectrum2_000878; Spectrum4_000592; Spectrum5_001368; UPCMLD-DP035; SCHEMBL42243; BSPBio_000884; BSPBio_002352; KBioGR_001084; KBioSS_000679; MLS001148204; MLS002172467; MLS006010754; MLS006011412; BIDD:GT0123; DivK1c_000292; UNII-16902YVY2B; SPBio_000955; SPBio_002823; BPBio1_000974; CCRIS 4391; DTXSID3045645; UPCMLD-DP035:001; UPCMLD-DP035:002; BCBcMAP01_000165; HMS500O14; KBio1_000292; KBio2_000679; KBio2_003247; KBio2_005815; AMY2648; NINDS_000292; 16902YVY2B; HMS1570M06; HMS2093P16; HMS2097M06; HMS2235A23; HMS3259J19; HMS3714M06; Pharmakon1600-02300332; (5R,5aR,8aR,9R)-5,8,8a,9-Tetrahydro-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-furo(3',4':6,7)naphtho[2,3-d]-1,3-dioxol-6(5aH)-one; 9-Hydroxy-5-(3,4,5-trimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5ah)-one; ALBB-020906; BCP24085; Podophyllotoxin, analytical standard; ZINC3861806; EINECS 232-546-2; Tox21_110874; Tox21_202922; B18-5C; BBL033695; BDBM50035218; CCG-39894; NSC759591; STK801918; AKOS000265559; Tox21_110874_1; AC-1656; CS-1185; DB01179; KS-1281; MCULE-9617461427; NC00675; ND-1185; NSC-759591; SDCCGMLS-0066888.P001; IDI1_000292; SMP1_000243; NCGC00022001-03; NCGC00022001-07; NCGC00022001-08; NCGC00022001-09; NCGC00022001-10; NCGC00022001-11; NCGC00022001-13; NCGC00022001-14; NCGC00260468-01; (5R,9R,5aR,8aR)-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-5,8,9,5a,8a-pentahydro-2H -isobenzofurano[5',6'-2,1]benzo[4,5-d]1,3-dioxolan-6-one; 1,3,3a,4,9,9a-Hexahydro-9-hydroxy-6,7-(methylenedioxy)-4-(3',4',5'-trimethoxyphenyl)benz(f)isobenzofuran-3-one; HY-15552; NCI60_001981; RD4-6269; EN300-52746; D05529; P-6980; 518P285; A828801; Q421193; SR-01000003030; SR-01000003030-3; SR-05000001749-1; SR-05000001749-2; BRD-K47869605-001-05-6; BRD-K47869605-001-18-9; Z1258578359; (10R,11R,15R,16R)-16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0?,?.0??,??]hexadeca-1(9),2,7-trien-12-one; (5R,5aR,8aR,9R)-5-hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-isobenzofuro[6,5-f][1,3]benzodioxol-8-one; (5R,5aR,8aR,9R)-5-oxidanyl-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one; 11016-28-7; 5,8,8a,9-Tetrahydro-9-hydroxy-5-(3,4,5-trimethoxyphenyl)furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one, [5R-(5.alpha.,5a.beta.,8a.alpha.,9.alpha.)]; furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one, 5,8,8a,9-tetrahydro-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-, (5R,5aR,8aR,9R)-; Furo[3',7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one, 5,8,8a,9-tetrahydro-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-, [5R-(5.alpha.,5a.beta.,8a.alpha.,9.alpha.)]-; Naphtho[2,3-dioxole-6-carboxylic acid, 5,6,7,8-tetrahydro-8-hydroxy-7-(hydroxymethyl)-5-(3,4,5-trimethoxyphenyl-, .gamma.-lactone
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  Formula C22H22O8
  Weight 414.4
  Structure Could Not Find 2D Structure
3D Structure Download 2D Structure Download
  InChI InChI=1S/C22H22O8/c1-25-16-4-10(5-17(26-2)21(16)27-3)18-11-6-14-15(30-9-29-14)7-12(11)20(23)13-8-28-22(24)19(13)18/h4-7,13,18-20,23H,8-9H2,1-3H3/t13-,18+,19-,20-/m0/s1
  InChI Key YJGVMLPVUAXIQN-XVVDYKMHSA-N
  Isomeric SMILES COC1=CC(=CC(=C1OC)OC)[C@H]2[C@@H]3[C@H](COC3=O)[C@H](C4=CC5=C(C=C24)OCO5)O
  Canonical SMILES COC1=CC(=CC(=C1OC)OC)C2C3C(COC3=O)C(C4=CC5=C(C=C24)OCO5)O
  External Links PubChem ID 10607
CAS ID 518-28-5
NPASS ID NPC237946
CHEMBL ID CHEMBL61
  NP Activity Charts   Click to show/hide
  Activity Info  

 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: 623 µg/100g
 
Sabouraud broth (28℃ + 9 days + PH5.6)
 Twigs Rombergpark, Germany
NP Content:
 
Sabouraud broth (28℃ + 9 days + PH5.6)
 Twigs Rombergpark, Germany
NP Content: 1492 µg/100g
 
Sabouraud broth (28℃ + 9 days + PH5.6)
 Twigs Rombergpark, Germany
NP Content:
 
Sabouraud broth (28℃ + 9 days + PH5.6)
 Twigs Rombergpark, Germany
NP Content:
 
Sabouraud broth (28℃ + 9 days + PH5.6)
 Twigs Rombergpark, Germany
NP Content:
 
Sabouraud broth (28℃ + 9 days + PH5.6)
 Twigs Rombergpark, Germany
NP Content: 100100 µg/100g
 
Sabouraud broth (28℃ + 9 days + PH5.6)
 Twigs Rombergpark, Germany
NP Content: 4611 µg/100g
 
Sabouraud broth (28℃ + 9 days + PH5.6)
 Twigs Yarika, Jammu and Kashmir, India
NP Content: 819 µg/100g
 
Sabouraud broth (28℃ + 9 days + PH5.6)
 Twigs Bonera, Jammu and Kashmir, India
NP Content: 5522 µg/100g
 
Sabouraud broth (28℃ + 9 days + PH5.6)
 Twigs Sonamarg, Jammu and Kashmir, India
NP Content: 3230 µg/100g
      Species Name: Mucor fragilis isolate TW5
  Factor Name: PDB medium [2]
              Species Info Factor Info
               Experiment Detail
The intact plant was collected from an altitude of 2600 m in the Taibai Mountains of Shaanxi, China in August 2009. The plant was identified morphologically and phylogenetically to be S. hexandrum. Strain TW5 was inoculated into 300 flasks (500 mL) containing 200 mL of fermentation medium and incubated at 26 ℃ on a reciprocal shaker at 180 rpm. After 7-d incubation, 60 L of culture liquid containing 4250 g of mycelia (wet weight) was obtained.
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               Factor Part Location NP Content
 
PDB medium (26℃ + 7 days)
 Roots; Stems Shaanxi, China
NP Content: 12.5 mg
References
1 Aspergillus fumigatus Fresenius, an endophytic fungus from Juniperus communis L. Horstmann as a novel source of the anticancer pro-drug deoxypodophyllotoxin
2 Mucor fragilis as a novel source of the key pharmaceutical agents podophyllotoxin and kaempferol