General Information of Natural Product (ID: NP1331)
  Natural Product Name
Alternariol
  Synonyms
Alternariol; 641-38-3; 3,7,9-Trihydroxy-1-methyl-6H-benzo[c]chromen-6-one; UNII-KN9L4260JW; 3,7,9-trihydroxy-1-methylbenzo[c]chromen-6-one; CHEBI:64983; 3,7,9-Trihydroxy-1-methyl-6H-dibenzo[b,d]pyran-6-one; AOH; KN9L4260JW; NSC638263; 6H-DIBENZO(b,d)PYRAN-6-ONE, 1-METHYL-3,7,9-TRIHYDROXY-; CCRIS 6734; 3,7,9-Trihydroxy-1-methyl-6H-dibenzo(b,d)pyran-6-one; BRN 0244839; Alternariol from Alternaria sp.; 3,4,4'-Trihydroxy-6'-methyl-2-biphenylcarboxylic acid, gamma lactone; 5-18-04-00516 (Beilstein Handbook Reference); CHEMBL519982; MEGxm0_000137; SCHEMBL1096830; Alternariol, analytical standard; ACon0_000598; ACon1_001301; 6H-Dibenzo[b,d]pyran-6-one, 3,7,9-trihydroxy-1-methyl-; DTXSID80214305; ZINC402623; HY-N6714; BDBM50479267; MFCD00133068; AKOS015916292; CS-W020863; MCULE-2577421243; NSC-638263; Alternariol from Alternaria sp., ~96%; NCGC00180653-01; LS-14270; NCI60_012751; FT-0661536; 3,4',5-Trihydroxy-6'-methyldibenzo-a-pyrone; 3,4',5-trihydroxy-6'-methyldibenzo-alpha-pyrone; 3,7,9-trihydroxy-1-methyl-benzo[c]chromen-6-one; A867945; Q410677; BRD-K62196712-001-01-3; 1-Methyl-3,7,9-trihydroxy-6H-Dibenzo(b,D)pyran-6-one; 3,7,9-Trihydroxy-1-methyl-6H-benzo[c]chromen-6-one #; Alternariol 3,4',5-Trihydroxy-6'-methyl-dibenzo[a]pyrone; 3,7,9-Trihydroxy-1-methyl-6H-dibenzo[b,D]pyran-6-one, 9CI; BrOP ?Bromotris(dimethylamino)phosphonium Hexafluorophosphate; 3,4,4'-trihydroxy-6'-methyl-2-biphenylcarboxylic acid gamma-lactone
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  Formula C14H10O5
  Weight 258.23
  Structure Could Not Find 2D Structure
3D Structure Download 2D Structure Download
  InChI InChI=1S/C14H10O5/c1-6-2-7(15)5-11-12(6)9-3-8(16)4-10(17)13(9)14(18)19-11/h2-5,15-17H,1H3
  InChI Key CEBXXEKPIIDJHL-UHFFFAOYSA-N
  Isomeric SMILES CC1=CC(=CC2=C1C3=C(C(=CC(=C3)O)O)C(=O)O2)O
  Canonical SMILES CC1=CC(=CC2=C1C3=C(C(=CC(=C3)O)O)C(=O)O2)O
  External Links PubChem ID 5359485
CAS ID 641-38-3
NPASS ID NPC32470
CHEMBL ID CHEMBL519982
  NP Activity Charts   Click to show/hide

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Botryosphaeria dothidea strain KJ-1
  Factor Name: Rice Medium [1]
              Species Info Factor Info
               Experiment Detail
The endophytic fungal strain KJ-1 was isolated from the symptomless tissue of stem bark of M. azedarach L., which was collected at Yangling, Shaanxi province, China, in August 2011. The producing strain was cultured on a plate of potato dextrose agar (PDA) medium at 28 ± 0.5 °C for 5 days. Then one piece (approximately 7 mm2) of mycelium was inoculated aseptically to 50 mL Erlenmeyer flasks each containing 20 mL of PD liquid medium, and the seed liquids were incubated at 28 ± 0.5 °C for 3 days on a rotary shaker at 120 rpm. A suspension (100 µL) of the seed liquid was inoculated aseptically to 500 mL Erlenmeyer flasks each containing 60 g of rice and 90 mL of distilled water. There were 300 flasks in total, and the flask cultures were incubated at 28 ± 0.5 °C for 4 weeks.
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               Factor Part Location NP Content
 
Rice Medium (28 ± 0.5 degrees Celsius + 28Days)
tissue of stem bark Yangling, Shaanxi province, China
NP Content: 9.5 mg
      Species Name: Hyalodendriella sp. Ponipodef 12
  Factor Name: Rice Medium [2]
              Species Info Factor Info
               Experiment Detail
The endophytic fungus Hyalodendriella sp. Ponipodef12 (GenBank accession number HQ731647) was isolated from the healthy stems of the 'Neva' hybrid of Populus deltoides Marsh × P. nigra L.. The fungus was cultured on PDA (potato 200 g/L, dextrose 20 g/L and agar 20 g/L) medium in Petri dishes at 25 °C for 10 days. For seed culture, two to three plugs of agar medium (0.5 × 0.5 cm) with fungal cultures were inoculated in each 250-mL Erlenmeyer flask containing 100 mL potato dextrose broth (PDB) medium, and incubated on a rotary shaker at 150 rpm and 25 °C for 5 days. For fermentation culture, about 50 mycelium pellets were inoculated in each 1,000-mL Erlenmeyer flask containing 300 mL PDB medium, and incubated on a rotary shaker at 150 rpm and 25 °C for 20 days.
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               Factor Part Location NP Content
 
Rice Medium (25 degrees Celsius + 45Days)
healthy stems China
NP Content: 6 mg
      Species Name: Penicillium citrinum strain TPDTF1.4
  Factor Name: Beans medium [3]
              Species Info Factor Info
               Experiment Detail
Fungal material: The fungus P. citrinum (strain no. TPDTF1.4) was isolated under sterile conditions from the flowers of O. tenuiflorum (Lamiaceae) collected in Denpasar, Bali, Indonesia in 2011. The fungal strain was cultivated on rice or white beans, which were prepared by autoclaving 100 g rice or beans and 100 mL water in a 1 L Erlenmeyer flask. Fermentation was performed on rice medium in one flask for 27 days at room temperature under static conditions. Meanwhile a static cultivation was conducted on beans medium in two flasks for 17 days at room temperature.
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               Factor Part Location NP Content
 
Beans medium (25℃ + 17 days)
Flowers Denpasar, Bali, Indonesia
NP Content: 4.6 mg
      Species Name: Phomopsis sp. strain CAM240
  Factor Name: Rice medium [4]
              Species Info Factor Info
               Experiment Detail
Isolation of endophytic fungus: The fungus was isolated from the nut of Garcinia kola bought at Mokolo local market in Yaounde (Cameroon). Phomopsis sp. was cultured in 12 flat culture bottles containing 100 g rice and 100 mL water enriched with 0.3% peptone each, autoclaved at 121 ℃ for 45 min. Each flask received about 5 small pieces of mycelium from PDA plate under sterile conditions. After 40 days of growth at 25 ℃ , ethyl acetate (12 × 500 mL) was added to each bottle, homogenized and filtered after 24 h and taken to dryness to afford 11.6 g of crude extract.
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               Factor Part Location NP Content
 
Solid rice medium (25℃ + 40 days)
Nuts Yaounde, Cameroon
NP Content: 5.3 mg
      Species Name: Rhizopycnis sp. Nitaf22
  Factor Name: Rice Medium [5]
              Species Info Factor Info
               Experiment Detail
The endophytic fungus (strain Nitaf22) was isolated from the inner tissue of the healthy root of a three-year-old tobacco N. tabacum L. grown in the greenhouse of the campus at China Agricultural University (CAU) in July 2014. The fungus was cultured on PDA (potato dextrose agar) medium for 5 days at 25 °C, and then a slice of agar containing fungal hyphae was transferred to a 250 mL Erlenmeyer flask containing 150 mL of PDB (potato dextrose broth). The cultivation was performed in a rotatory shaker for another 7 days at 150 rpm and 25 °C to produce the seed culture, which was used to inoculate the autoclaved rice media in 1 L Erlenmeyer flasks each containing 100 g of rice and 110 mL of distilled water. The scale-up fermentation was carried out using a total of 4.5 kg of rice under static conditions at room temperature (RT) in the dark for 35 days.
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               Factor Part Location NP Content
 
Rice Medium (25 degrees Celsius + 35Days)
healthy root China Agricultural University, Beijing, China
NP Content: 4.2 mg
References
1 Secondary metabolites from the endophytic Botryosphaeria dothidea of Melia azedarach and their antifungal, antibacterial, antioxidant, and cytotoxic activities
2 Dibenzo-alpha-pyrones: a new class of larvicidal metabolites against Aedes aegypti from the endophytic fungus Hyalodendriella sp. Ponipodef12
3 Bioactive polyketides and alkaloids from Penicillium citrinum, a fungal endophyte isolated from Ocimum tenuiflorum
4 Antibacterial and cytotoxic cytochalasins from the endophytic fungus Phomopsis sp. harbored in Garcinia kola (Heckel) nut
5 Bioactive Dibenzo-alpha-pyrone Derivatives from the Endophytic Fungus Rhizopycnis vagum Nitaf22