Gilvocarcin E
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| Category | Antibiotics |
| Catalog number | BBF-01246 |
| CAS | 80937-34-4 |
| Molecular Weight | 496.50 |
| Molecular Formula | C27H28O9 |
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Description
It is produced by the strain of Streptomyces gilvotanareus, Str. anandii. It has anti-gram-positive bacterial activity and can inhibit sarcoma 180 and P388 leukemia cells.
Specification
| Synonyms | 8-Ethyl-4-(6-deoxy-α-L-galactofuranosyl)-1-hydroxy-10,12-dimethoxy-6H-benzo[d]naphtho[1,2-b]pyran-6-one; Anandimycin C; Toromycin C; dihydrotoromycin; 4-Fucofuranosyl-1-hydroxy-10,12-dimethoxy-8-ethyl-6H-benzo(d)naphtho(1,2b)pyran-6-one; 1,4-Anhydro-6-deoxy-1-(8-ethyl-1-hydroxy-10,12-dimethoxy-6-oxo-6H-benzo[d]naphtho[1,2-b]pyran-4-yl)hexitol |
| IUPAC Name | 4-[(2R,3R,4R)-3,4-dihydroxy-5-[(1R)-1-hydroxyethyl]oxolan-2-yl]-8-ethyl-1-hydroxy-10,12-dimethoxynaphtho[1,2-c]isochromen-6-one |
| Canonical SMILES | CCC1=CC2=C(C(=C1)OC)C3=C(C4=C(C=CC(=C4C(=C3)OC)O)C5C(C(C(O5)C(C)O)O)O)OC2=O |
| InChI | InChI=1S/C27H28O9/c1-5-12-8-15-19(17(9-12)33-3)14-10-18(34-4)21-16(29)7-6-13(20(21)25(14)36-27(15)32)26-23(31)22(30)24(35-26)11(2)28/h6-11,22-24,26,28-31H,5H2,1-4H3/t11-,22-,23-,24?,26-/m1/s1 |
| InChI Key | MHEQKYHSXMKYKF-CULPVLJHSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria; Neoplastics (Tumor) |
| Melting Point | 210-212 °C |
| Solubility | Soluble in Methanol, DMSO |
Reference Reading
1. Inactivation of the ketoreductase gilU gene of the gilvocarcin biosynthetic gene cluster yields new analogues with partly improved biological activity
Tao Liu, Madan K Kharel, Lili Zhu, Samuel A Bright, Cynthia Mattingly, Val R Adams, Jürgen Rohr Chembiochem. 2009 Jan 26;10(2):278-86. doi: 10.1002/cbic.200800348.
Four new analogues of the gilvocarcin-type aryl-C-glycoside antitumor compounds, namely 4'-hydroxy gilvocarcin V (4'-OH-GV), 4'-hydroxy gilvocarcin M, 4'-hydroxy gilvocarcin E and 12-demethyl-defucogilvocarcin V, were produced through inactivation of the gilU gene. The 4'-OH-analogues showed improved activity against lung cancer cell lines as compared to their parent compounds without 4'-OH group (gilvocarcins V and E). The structures of the sugar-containing new mutant products indicate that the enzyme GilU acts as an unusual ketoreductase involved in the biosynthesis of the C-glycosidically linked deoxysugar moiety of the gilvocarcins. The structures of the new gilvocarcins indicate substrate flexibility of the post-polyketide synthase modifying enzymes, particularly the C-glycosyltransferase and the enzyme responsible for the sugar ring contraction. The results also shed light into biosynthetic sequence of events in the late steps of biosynthetic pathway of gilvocarcin V.
2. Engineered biosynthesis of gilvocarcin analogues with altered deoxyhexopyranose moieties
Micah D Shepherd, Tao Liu, Carmen Méndez, Jose A Salas, Jürgen Rohr Appl Environ Microbiol. 2011 Jan;77(2):435-41. doi: 10.1128/AEM.01774-10. Epub 2010 Nov 12.
A combinatorial biosynthetic approach was used to interrogate the donor substrate flexibility of GilGT, the glycosyltransferase involved in C-glycosylation during gilvocarcin biosynthesis. Complementation of gilvocarcin mutant Streptomyces lividans TK24 (cosG9B3-U(-)), in which the biosynthesis of the natural sugar donor substrate was compromised, with various deoxysugar plasmids led to the generation of six gilvocarcin analogues with altered saccharide moieties. Characterization of the isolated gilvocarcin derivatives revealed five new compounds, including 4-β-C-D-olivosyl-gilvocarcin V (D-olivosyl GV), 4-β-C-D-olivosyl-gilvocarcin M (D-olivosyl GM), 4-β-C-D-olivosyl-gilvocarcin E (D-olivosyl GE), 4-α-C-L-rhamnosyl-gilvocarcin M (polycarcin M), 4-α-C-L-rhamnosyl-gilvocarcin E (polycarcin E), and the recently characterized 4-α-C-L-rhamnosyl-gilvocarcin V (polycarcin V). Preliminary anticancer assays showed that D-olivosyl-gilvocarcin and polycarcin V exhibit antitumor activities comparable to that of their parent drug congener, gilvocarcin V, against human lung cancer (H460), murine lung cancer (LL/2), and breast cancer (MCF-7) cell lines. Our findings demonstrate GilGT to be a moderately flexible C-glycosyltransferase able to transfer both D- and L-hexopyranose moieties to the unique angucyclinone-derived benzo[D]naphtho[1,2b]pyran-6-one backbone of the gilvocarcins.
3. Combined directed remote metalation-transition metal catalyzed cross coupling strategies: the total synthesis of the aglycones of the gilvocarcins V, M, and E and arnottin I
Clint A James, Victor Snieckus J Org Chem. 2009 Jun 5;74(11):4080-93. doi: 10.1021/jo9001454.
A key directed remote metalation (DreM)-carbamoyl migration strategy was applied in an efficient synthesis of the naturally occurring 6H-naphtho[1,2-b]benzopyran-6-one defucogilvocarcin V (1a, Scheme 11). The required biarylcarbamate 33d was best prepared by a high yielding Suzuki coupling reaction of 31a with the differentially protected trioxygenated naphthalene coupling partner 32d which was synthesized using a selective acylation of a juglone derivative. In the late stages of the synthesis, the triflate 39 served as the common intermediate to install the required C-8 vinyl group of 1a (Stille coupling) as well as the required substituents for the preparation of defucogilvocarcins M (1b) and E (1c). A variety of protecting group strategies were investigated and provided insight into which groups are preferred for the DreM-carbamoyl migration process. The strategic lessons learned from this total synthesis were applied in the successful total synthesis of the structurally similar natural product arnottin I (2).
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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 ╳
