Purpactin A
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| Category | Enzyme inhibitors |
| Catalog number | BBF-02076 |
| CAS | |
| Molecular Weight | 414.45 |
| Molecular Formula | C23H26O7 |
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Description
Purpactin A is a cholesterol acyltransferase (ACAT) inhibitor produced by Pen. purpurogenum FO-6.
Specification
| Related CAS | 133806-59-4 |
| Synonyms | 1'-O-acetylpenicillide; Vermixocin B |
| IUPAC Name | [(1S)-1-(6-hydroxy-1-methoxy-8-methyl-12-oxo-10H-benzo[b][1,5]benzodioxocin-2-yl)-3-methylbutyl] acetate |
| Canonical SMILES | CC1=CC2=C(C(=C1)O)OC3=C(C(=C(C=C3)C(CC(C)C)OC(=O)C)OC)C(=O)OC2 |
| InChI | InChI=1S/C23H26O7/c1-12(2)8-19(29-14(4)24)16-6-7-18-20(22(16)27-5)23(26)28-11-15-9-13(3)10-17(25)21(15)30-18/h6-7,9-10,12,19,25H,8,11H2,1-5H3/t19-/m0/s1 |
| InChI Key | NUYFKDBCHFKOBT-IBGZPJMESA-N |
Properties
| Appearance | Colorless Powder |
Reference Reading
1. New penicillide derivatives isolated from Penicillium simplicissimum
Shin-Ichirou Komai, Tomoo Hosoe, Ken-Ichi Kawai, Takeshi Itabashi, Kazutaka Fukushima, Koohei Nozawa, Takashi Yaguchi J Nat Med . 2006 Jul;60(3):185-190. doi: 10.1007/s11418-005-0028-9.
Two new penicillide derivatives, secopenicillides A (3) and B (4), were isolated along with penicillide (1) and purpactin A (2), and altenusin (5) and dehydroaltenusin (6), the antifungal substances of this fungus, from the extract of Penicillium simplicissimum IFM 53375. The absolute structures of 3 and 4 were determined by spectroscopic investigation and chemical correlation to penicillide (1). The absolute configuration of purpactin A (2) was determined by the chemical method.
2. Purpactins, new inhibitors of acyl-CoA:cholesterol acyltransferase produced by Penicillium purpurogenum. II. Structure elucidation of purpactins A, B and C
S Okuda, S Omura, J Cao, H Tomoda, H Nishida J Antibiot (Tokyo) . 1991 Feb;44(2):144-51. doi: 10.7164/antibiotics.44.144.
The structure of purpactins, novel acyl-CoA:cholesterol acyltransferase (ACAT) inhibitors, was determined by spectroscopic analyses. Purpactin A was deduced to be 3-1'-acetoxy-11-hydroxy-4-methoxy-9-methyl-3'-methylbutyl-5H, 7H-dibenzo[b,g]-1,5-dioxocin-5-one, purpactin B was 5-1''-acetoxy-6'-hydroxymethyl-4-methoxy-4'-methyl-3''-methylbutyl-spiro [benzofuran-2,1'-cyclohexa-3',5'-diene]-2',3(2H)-dione and purpactin C was 5-1''-acetoxy-6'-formyl-4-methoxy-4'-methyl-3''-methylbutyl-spiro [benzofuran-2,1'-cyclohexa-3',5'-diene]-2',3(2H)-dione. Purpactin A was attributed to 1'-O-acetylpenicillide.
3. Spiroscytalin, a new tetramic acid and other metabolites of mixed biogenesis from Scytalidium cuboideum
Cedric J Pearce, Nicholas H Oberlies, David J Kroll, Maria Elena Meza Aviña, Mario Figueroa, Huzefa A Raja, Arlene A Sy-Cordero, Mansukh C Wani, Audrey F Adcock, Mitchell P Croatt Tetrahedron . 2015 Nov 25;71(47):8899-904. doi: 10.1016/j.tet.2015.09.073.
Spiroscytalin (1), a new tetramic acid that possesses an uncommon spiro-ring fusion between a polyketide-derived octalin ring system and a 2,4-pyrrolidinedione, along with two known compounds, leporin B (2) and purpactin A (3), were isolated from a solid phase culture of the fungus Scytalidium cuboideum (MSX 68345). The molecular connectivity of 1-3 was determined using NMR spectroscopy and mass spectrometry. The relative configurations of 1 and 2 were determined by NOESY experiments. The absolute configuration of 1 was determined by electronic circular dichroism (ECD) via a combination of experimental measurements and computational calculations. While leporin B was known, it displayed activities that had not been reported previously, including cytotoxicity against three human tumor cell lines and antibacterial activity against Candida albicans and Staphylococcus aureus.
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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 ╳
