Anguinomycin A

Anguinomycin A

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Anguinomycin A
Category Antibiotics
Catalog number BBF-00689
CAS 111278-01-4
Molecular Weight 512.68
Molecular Formula C31H44O6
Purity >95% by HPLC

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Description

It is produced by the strain of Streptomyces sp. R2827 and R2827-2. It has anti-rat Lewis lung cancer and P388 leukemia activity. It has been reported that it can cause normal cell growth to stop and deformable cell death.

Specification

Synonyms 5-Demethylleptomycin A, KR 2827A
Storage -20°C
IUPAC Name 6-hydroxy-3,5,7,9,11,15,17-heptamethyl-8-oxo-19-(6-oxo-2,3-dihydropyran-2-yl)nonadeca-2,10,12,16,18-pentaenoic acid
Canonical SMILES CC(CC=CC(=CC(C)C(=O)C(C)C(C(C)CC(=CC(=O)O)C)O)C)C=C(C)C=CC1CC=CC(=O)O1
InChI InChI=1S/C31H44O6/c1-20(16-22(3)14-15-27-12-9-13-29(34)37-27)10-8-11-21(2)17-24(5)30(35)26(7)31(36)25(6)18-23(4)19-28(32)33/h8-9,11,13-17,19-20,24-27,31,36H,10,12,18H2,1-7H3,(H,32,33)
InChI Key SGYKTDIJCLHSET-UHFFFAOYSA-N
Source Streptomyces sp.

Properties

Appearance Colorless Oily Matter
Antibiotic Activity Spectrum neoplastics (Tumor)
Boiling Point 714.9±60.0 °C (Predicted)
Density 1.095±0.06 g/cm3 (Predicted)
Solubility Soluble in ethanol or methanol. Poor water solubility. Ethanol recommended. Unstable in DMSO.

Reference Reading

1. New Antimicrobial Phenyl Alkenoic Acids Isolated from an Oil Palm Rhizosphere-Associated Actinomycete, Streptomyces palmae CMU-AB204T
Kanaporn Sujarit, Saisamorn Lumyong, Mihoko Mori, Kazuyuki Dobashi, Kazuro Shiomi, Wasu Pathom-Aree Microorganisms . 2020 Mar 1;8(3):350. doi: 10.3390/microorganisms8030350.
Basal stem rot (BSR), orGanodermarot disease, is the most serious disease associated with the oil palm plant of Southeast Asian countries. A basidiomycetous fungus,Ganoderma boninense, is the causative microbe of this disease. To control BSR in oil palm plantations, biological control agents are gaining attention as a major alternative to chemical fungicides. In the course of searching for effective actinomycetes as potential biological control agents for BSR,Streptomyces palmaeCMU-AB204Twas isolated from oil palm rhizosphere soil collected on the campus of Chiang Mai University. The culture broth of this strain showed significant antimicrobial activities against several bacteria and phytopathogenic fungi includingG. boninense. Antifungal and antibacterial compounds were isolated by antimicrobial activity-guided purification using chromatographic methods. Their structures were elucidated by spectroscopic techniques, including Nuclear Magnetic Resonance (NMR), Mass Spectrometry (MS), Ultraviolet (UV), and Infrared (IR) analyses. The current study isolated new phenyl alkenoic acids1-6and three known compounds, anguinomycin A (7), leptomycin A (8), and actinopyrone A (9) as antimicrobial agents. Compounds1and2displayed broad antifungal activity, though they did not show antibacterial activity. Compounds3and4revealed a strong antibacterial activity against both Gram-positive and Gram-negative bacteria including the phytopathogenic strainXanthomonas campestrispv.oryzae. Compounds7-9displayed antifungal activity againstGanoderma. Thus, the antifungal compounds obtained in this study may play a role in protecting oil palm plants fromGanodermainfection with the strainS. palmaeCMU-AB204T.
2. Nuclear export inhibition through covalent conjugation and hydrolysis of Leptomycin B by CRM1
Youcai Hu, Qingxiang Sun, Hamid Mirzaei, Yuh Min Chook, Xiaofeng Guo, John Macmillan, Yazmin P Carrasco Proc Natl Acad Sci U S A . 2013 Jan 22;110(4):1303-8. doi: 10.1073/pnas.1217203110.
The polyketide natural product Leptomycin B inhibits nuclear export mediated by the karyopherin protein chromosomal region maintenance 1 (CRM1). Here, we present 1.8- to 2.0-Å-resolution crystal structures of CRM1 bound to Leptomycin B and related inhibitors Anguinomycin A and Ratjadone A. Structural and complementary chemical analyses reveal an unexpected mechanism of inhibition involving covalent conjugation and CRM1-mediated hydrolysis of the natural products' lactone rings. Furthermore, mutagenesis reveals the mechanism of hydrolysis by CRM1. The nuclear export signal (NES)-binding groove of CRM1 is able to drive a chemical reaction in addition to binding protein cargoes for transport through the nuclear pore complex.

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