Herbarin
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| Category | Antibiotics |
| Catalog number | BBF-01819 |
| CAS | 36379-67-6 |
| Molecular Weight | 304.30 |
| Molecular Formula | C16H16O6 |
| Purity | 97% |
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Description
It is produced by the strain of Torula herbarum. It is a quinone antibiotic. Herbarin complex has anti-gram-positive bacteria, negative bacteria, citrus canker xanthomonas, potato early blight, aspergillus Niger, Decaprous and other fungal activities.
Specification
| Synonyms | dehydroherbarin; Ambotz; 1H-Naphtho(2,3-c)pyran-5,10-dione,3,4-dihydro-3-hydroxy-7,9-dimethoxy-3-methyl-; 3-Hydroxy-7,9-dimethoxy-3-methyl-3,4-dihydro-1H-naphtho[2,3-c]pyran-5,10-dione |
| IUPAC Name | 3-hydroxy-7,9-dimethoxy-3-methyl-1,4-dihydrobenzo[g]isochromene-5,10-dione |
| Canonical SMILES | CC1(CC2=C(CO1)C(=O)C3=C(C=C(C=C3C2=O)OC)OC)O |
| InChI | InChI=1S/C16H16O6/c1-16(19)6-10-11(7-22-16)15(18)13-9(14(10)17)4-8(20-2)5-12(13)21-3/h4-5,19H,6-7H2,1-3H3 |
| InChI Key | MQWLANHTCHDMAR-UHFFFAOYSA-N |
Properties
| Appearance | Yellow Acicular Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria; Fungi |
| Boiling Point | 548.5 °C at 760 mmHg |
| Melting Point | 192-193 °C |
| Density | 1.39 g/cm3 |
| Solubility | Soluble in Ethyl Acetate; Insoluble in Water |
Reference Reading
1. New naphthoquinone derivatives from the ascomycete IBWF79B-90A
Heinz Kolshorn,Anja Schüffler,Till Opatz,Heidrun Anke,Johannes C Liermann Z Naturforsch C J Biosci . 2009 Jan-Feb;64(1-2):25-31. doi: 10.1515/znc-2009-1-205.
Bioactivity-guided fractionation of extracts from the fungus IBWF79B-90A resulted in the isolation of three known naphthoquinones, herbarin, dehydroherbarin, and O-methylherbarin and the azaanthraquinone scorpinone as well as three structurally related derivatives, O-phenethylherbarin and herbaridines A and B. All seven compounds exhibited cytotoxic activities against several cell lines.
2. Phaeosphspirone (1/1'), a pair of unique polyketide enantiomers with an unusual 6/5/5/6 tetracyclic ring from the desert plant endophytic fungus Phaeosphaeriaceae sp
Gang Ding,Xiang-Mei Tan,Bing-Da Sun,Shu-Bin Niu,Cai-Feng Ding,Dao-Jiang Yan,Zhen-Lu Xu,Yong-Gang Zhang,Meng Yu Phytochemistry . 2022 Feb;194:112969. doi: 10.1016/j.phytochem.2021.112969.
Phaeosphspirone, an undescribed polyketide with a unique 6/5/5/6-fused tetracyclic system, and two known analogues, herbarin and O-methylherbarin, were purified from the endophytic fungus Phaeosphaeriaceae sp. isolated from the desert plant Bassia dasyphylla. The connectivity and relative configuration of phaeosphspirone was elucidated by comprehensive HR-ESI-MS and NMR analysis together with a computer-assisted structure elucidation (CASE) method. A pair of enantiomers existing in phaeosphspirone were separated by HPLC chromatography after reacting with chiral reagents, from which the absolute configuration of phaeosphspirone was simultaneously determined based on Mosher's rule. This tandem strategy provides a useful approach for the separation and stereochemical determination of enantiomers possessing secondary hydroxyl groups. The structural feature of phaeosphspirone, herbarin and O-methylherbarin together with gene cluster analysis suggested their polyketide biosynthetic origin. Herbarin and O-methylherbarin exhibited moderate cytotoxicity against three cancer cell lines.
3. Modulation of polyketide biosynthetic pathway of the endophytic fungus, Anteaglonium sp. FL0768, by copper (II) and anacardic acid
Patricia Espinosa-Artiles,Maria C F de Oliveira,Felipe Hilário,Ya-Ming Xu,Jair Mafezoli,A A Leslie Gunatilaka,Brandon Freidhof,Lourdes C Dos Santos Phytochem Lett . 2018 Dec;28:157-163. doi: 10.1016/j.phytol.2018.10.011.
In an attempt to explore the biosynthetic potential of endosymbiotic fungi, the secondary metabolite profiles of the endophytic fungus,Anteagloniumsp. FL0768, cultured under a variety of conditions were investigated. In potato dextrose broth (PDB) medium,Anteagloniumsp. FL0768 produced the heptaketides, herbaridine A (1), herbarin (2), 1-hydroxydehydroherbarin (3), scorpinone (4), and the methylated hexaketide 9S,11R-(+)-ascosalitoxin (5). Incorporation of commonly used epigenetic modifiers, 5-azacytidine and suberoylanilide hydroxamic acid, into the PDB culture medium of this fungus had no effect on its secondary metabolite profile. However, the histone acetyl transferase inhibitor, anacardic acid, slightly affected the metabolite profile affording scorpinone (4) as the major metabolite together with 1-hydroxydehydroherbarin (3) and a different methylated hexaketide, ascochitine (6). Intriguingly, incorporaion of Cu2+into the PDB medium enhanced production of metabolites and drastically affected the biosynthetic pathway resulting in the production of pentaketide dimers, palmarumycin CE4(7), palmarumycin CP4(8), and palmarumycin CP1(9), in addition to ascochitine (6). The structure of the new metabolite7was established with the help of spectroscopic data and by MnO2oxidation to the known pentaketide dimer, palmarumycin CP3(10). Biosynthetic pathways to some metabolites inAnteagloniumsp. FL0768 are presented and possible effects of AA and Cu2+on these pathways are discussed.
4. Anteaglonialides A-F and Palmarumycins CE(1)-CE(3) from Anteaglonium sp. FL0768, a Fungal Endophyte of the Spikemoss Selaginella arenicola
Jana M U'Ren,A Elizabeth Arnold,Maria C F Oliveira,Ya-ming Xu,Jair Mafezoli,A A Leslie Gunatilaka J Nat Prod . 2015 Nov 25;78(11):2738-47. doi: 10.1021/acs.jnatprod.5b00717.
Anteaglonialides A-F (1-6), bearing a spiro[6-(tetrahydro-7-furanyl)cyclohexane-1,2'-naphtho[1,8-de][1,3]-dioxin]-10-one skeleton, three new spirobisnaphthalenes, palmarumycins CE1-CE3 (7-9), nine known palmarumycin analogues, palmarumycins CP5 (10), CP4a (11), CP3 (12), CP17 (13), CP2 (14), and CP1 (15), CJ-12,371 (16), 4-O-methyl CJ-12,371 (17), and CP4 (18), together with a possible artifact, 4a(5)-anhydropalmarumycin CE2 (8a), and four known metabolites, O-methylherbarin (19), herbarin (20), herbaridine B (21), and hyalopyrone (22), were encountered in a cytotoxic extract of a potato dextrose agar culture of Anteaglonium sp. FL0768, an endophytic fungus of the sand spikemoss, Selaginella arenicola. The planar structures and relative configurations of the new metabolites 1-9 were elucidated by analysis of extensive spectroscopic data, and the absolute configuration of 1 was determined by the modified Mosher's ester method. Application of the modified Mosher's ester method combined with the NOESY data resulted in revision of the absolute configuration previously proposed for 10. Co-occurrence of 1-6 and 7-18 in this fungus led to the proposal that the anteagloniolides may be biogenetically derived from palmarumycins. Among the metabolites encountered, anteaglonialide F (6) and known palmarumycins CP3 (12) and CP1 (15) exhibited strong cytotoxic activity against the human Ewing's sarcoma cell line CHP-100, with IC50 values of 1.4, 0.5, and 1.6 μM, respectively.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
