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Anhydroophiobolin A

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Anhydroophiobolin A
Category Bioactive by-products
Catalog number BBF-04280
CAS 6026-65-9
Molecular Weight 382.54
Molecular Formula C25H34O3
Purity >95% by HPLC

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Capabilities & Facilities

Fermentation Lab

4 R&D and scale-up labs

2 Preparative purification labs

Fermentation Plant

Semi pilot, pilot and industrial plant 4 Manufacturing sites 7 Production lines at pilot scale 100+ Reactors of 30-4000 L; 170+ reactors of 20 KL-30 KL; 24+ reactors of >100 KL 2 Hydrogenation reactors (200 L, 4Mpa and 1000L, 4Mpa)

Product Description

It is the dehydrated analogue of ophiobolin A and a major member of the ophiobolin complex of phytotoxic metabolites produced by many species of the genus bipolaris. It possesses a broad biological profile with antibacterial, antifungal, antitumour, herbicidal and nematocidal activities.

  • Specification
  • Properties
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Synonyms 14,17-Epoxy-5-oxo-3,7,18-ophiobolatrien-21-al; Anhydroophiobolin; (18R)-5-Oxo-14,18-epoxy-3,4-didehydroophiobola-7,19-diene-25-al; (2'S,3'S,3aR,5'R,6aS,9aS,10aR)-2,3a,4,4',5',6a,7,9a,10,10a-Decahydro-3',9,10a-trimethyl-5'-(2-methyl-1-propen-1-yl)-7-oxospiro[dicyclopenta[a,d]cyclooctene-3(1H),2'(3'H)-furan]-6-carboxaldehyde; [3S-[3α(3'R*,5'S*),3aα,6aβ,9aβ,10aβ]]-1,3a,4,4',5',6a,7,9a,10,10a-Decahydro-3',9,10a-trimethyl-5'-(2-methyl-1-propenyl)-7-oxo-spiro[dicyclopenta[a,d]cyclooctene-3(2H),2'(3'H)-furan]-6-carboxaldehyde; 3-Anhydro-cochliobolin; 3-Anhydroophiobolin A
Storage Store at -20°C
IUPAC Name (1'R,2S,3S,3'S,5R,7'S,8'E,11'R)-1',3,4'-trimethyl-5-(2-methylprop-1-enyl)-6'-oxospiro[oxolane-2,12'-tricyclo[9.3.0.03,7]tetradeca-4,8-diene]-8'-carbaldehyde
Canonical SMILES CC1CC(OC12CCC3(C2CC=C(C4C(C3)C(=CC4=O)C)C=O)C)C=C(C)C
InChI InChI=1S/C25H34O3/c1-15(2)10-19-12-17(4)25(28-19)9-8-24(5)13-20-16(3)11-21(27)23(20)18(14-26)6-7-22(24)25/h6,10-11,14,17,19-20,22-23H,7-9,12-13H2,1-5H3/b18-6-/t17-,19-,20+,22+,23+,24+,25-/m0/s1
InChI Key MDYSLOGZXCWLSL-CWPAWFJGSA-N
Source Bipolaris sp.
Appearance White Solid
Antibiotic Activity Spectrum Neoplastics (Tumor); Fungi; Parasites; Bacterial
Boiling Point 520.6±50.0°C (Predicted)
Melting Point 136°C
Density 1.10±0.1 g/cm3 (Predicted)
Solubility Soluble in Ethanol, Methanol, DMF, DMSO; Poorly soluble in Water
1. Microbial metabolites of ophiobolin A and antimicrobial evaluation of ophiobolins
D P Rotella, A M Clark, C D Hufford, E Li J Nat Prod . 1995 Jan;58(1):74-81. doi: 10.1021/np50115a009.
Ophiobolin A [1], 3-anhydroophiobolin A [2], ophiobolin B [3], and ophiobolin L [4] were isolated from fermentation broths of Cochliobolus heterostrophus. Preliminary screening showed that a number of organisms were capable of metabolizing the sesterterpene ophiobolin A [1]. Large-scale transformations of ophiobolin A [1] with Polyangium cellulosum produced 6 and 7 while Pseudomonas aeruginosa produced 8. Resting-cell preparations of Penicillium patulum afforded 9 and 10. The structures of these metabolites were established by spectroscopic methods and by comparison of the spectral data with those of the starting material. The antimicrobial activity of the ophiobolins was also evaluated.
2. Characterization of 6-epi-3-anhydroophiobolin B from Cochliobolus heterostrophus
D M Gibson, B G Turgeon, S W Lu, S B Krasnoff, C D Dunbar, J O'Neal, M T Hamann, O C Yoder, X Shen J Nat Prod . 1999 Jun;62(6):895-7. doi: 10.1021/np980462e.
The new sesterterpenoid 6-epi-3-anhydroophiobolin B (1) and six known ophiobolins were isolated from the extracts of the fungus Cochliobolus heterostrophus race O. The structure of 6-epi-3-anhydroophiobolin B was deduced from analysis of spectral data and the structural characterization of dehydration and dimerization products. Ophiobolin A (2) showed potent activity in cytotoxicity assays and marginal activity in antimalarial assays.

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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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