60657-37-6

Usage

Uses

Used in Environmental Monitoring:
rac Pterosin B is used as a detection agent for identifying the presence of Ptaquiloside, a carcinogenic pollutant derived from bracken fern. Its application aids in assessing environmental contamination and potential health risks associated with exposure to this carcinogen.
Used in Pharmaceutical Research:
As a pterosin derivative, rac Pterosin B is used as a research compound in the development of potential pharmaceuticals targeting cancer and other diseases. Its structural relationship to Ptaquiloside allows for the exploration of novel therapeutic approaches and the understanding of the mechanisms of action of related compounds.

Upstream product

• 68373-73-9 dihydropterosin-B 
• 57283-34-8 6-(β-hydroxy)ethyl-2,5,7-trimethyl-3-methoxy-1-indenone 
• 65848-78-4 5,7-dimethyl-6-<2'-hydroxyethyl>-indan-1-one 
• 74-88-4 methyl iodide 
• 576-83-0 2,4,6-trimethylphenyl bromide 
• 6950-92-1 2-(2,4,6-trimethylphenyl)ethanol 
• 65848-80-8 2-(4,6-dimethyl-3-oxo-2,3-dihydro-1H-inden-5-yl)ethyl acetate 
• 87625-62-5 ptaquiloside 
• 89103-85-5 (+/-)-pterosin-E 
• 52528-75-3 3-(4-Carboxymethyl-3,5-dimethyl-phenyl)-2-methyl-propionic acid 
• 131750-27-1 6-bromo-5,7-dimethyl-indan-1-one 
• 39815-61-7 6-[2'-(benzoyloxy)ethyl]-(2R)-2,5,7-trimethyl-1-indanone 
• 576-22-7 2-Bromo-m-xylene 
• 89042-98-8 (3-Hydroxy-2,4,6-trimethyl-indan-5-yl)-acetic acid ethyl ester 

Relevant academic research and scientific papers

PTAQUILOSIDE, A NOVEL NORSESQUITERPENE GLUCOSIDE FROM BRACKEN, PTERIDIUM AQUILINUM VAR. LATIUSCULUM

An unstable norsesquiterpene glucoside with a novel illudane skeleton, ptaquiloside (1) has been isolated from bracken fern, Pteridium aquilinum var. latiusculum and the planar structure has been established on the basis of spectral and chemical means.

Isolation and structure of wallichoside, a novel pteroside from Pteris wallichiana

Wallichoside has been isolated from the rhizomes of Pteris wallichiana and its structure and absolute configuration has been established as the 3-β-d-glucoside of 2S, 3S-pterosin C on the basis of UV, IR, NMR and MS data of wallichoside and its derivatives.

A concise stereoselective synthesis of pterosin B

Pterosin B is a naturally occurring indanone found in bracken fern (Pteridium aquilinum) that displays a variety of interesting pharmacological properties, but for which few stereoselective syntheses exist. Herein we describe a 7-step stereoselective synthesis of (2R)-pterosin B via 6-bromo-5,7-dimethylindan-1-one whose structure was confirmed by NOE analysis and structure determination by X-ray crystallography. The hydroxyethyl chain was introduced via a Suzuki-Miyaura cross-coupling reaction. The 2-methyl group was introduced stereoselectively by methylation of a SAMP [(S)-1-amino-2-methoxymethyl)pyrrolidine] hydrazone and the chiral auxiliary was removed to produce (2R)-pterosin B. The structure of pterosin B was confirmed by specific rotation and structural determination by X-ray crystallography.

Total synthesis of pterosines B and C via a photochemical key step

A total synthesis of pterosines B and C is reported. Starting with a fourfold substituted benzene derivative, the introduction of the remaining substituents is mainly based on Sonogashira couplings followed by different transformations of the ethyne moiety. The key step is a photochemical ring-closure of an α-mesyloxy ketone forming the 1-indanone skeleton. Georg Thieme Verlag Stuttgart.

PTAQUILOSIDE, A POTENT CARCINOGEN ISOLATED FROM BRACKEN FERN PTERIDIUM AQUILINUM VAR. LATIUSCULUM: STRUCTURE ELUCIDATION BASED ON CHEMICAL AND SPECTRAL EVIDENCE, AND REACTIONS WITH AMINO ACIDS, NUCLEOSIDES, AND NUCLEOTIDES

The structure of ptaquiloside (I), a potent carcinogenic compound isolated from bracken fern, Pteridium aquilinum var. latiusculum has been elucidated on the basis of chemical and spectral evidence.The dienone 3 generated from 1 under alkaline conditions was shown to be a strong alkylating agent.For the purpose of obtaining the preliminary information on chemical modification of biopolymers such as proteins and DNA with the dienone 3, reactions of 3 with amino acids, nucleosides, and nucleotides have been carried out and the alkylated products have been characterized.

Studies in Terpenoids: Part LXI - Synthesis of (+/-)-Pterosin-B

(+/-)-Pterosin-B (1), a sesquiterpene constituent of several ferns, has been synthesized in excellent yield by the regiospecific oxidation of the diol (12) obtained by LAH reduction of the dihydroderivatives (10 and 11) of (+/-)-pterosin-E (2).