14017-71-1

Basic information

• Product Name: (-)-Praeruptorin A
• Synonyms: Isopteryxin;Peupraerin I
• CAS NO: 14017-71-1
• Molecular Formula: C₂₁H₂₂O₇
• Molecular Weight: 386.39518
• Mol File: 14017-71-1.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (-)-Praeruptorin A(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-Praeruptorin A(14017-71-1)
• EPA Substance Registry System: (-)-Praeruptorin A(14017-71-1)

Safety Data

• Hazardous Substances Data: 14017-71-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(-)-Praeruptorin A is used as a therapeutic agent for respiratory conditions due to its anti-inflammatory, bronchodilator, and anti-allergic effects, which can help in the treatment of asthma and chronic obstructive pulmonary disease (COPD).
Used in Neurodegenerative Disease Treatment:
(-)-Praeruptorin A is used as a neuroprotective agent for the potential treatment of neurodegenerative diseases, owing to its antioxidant properties that may protect neurons from damage and degeneration.
Research is ongoing to further investigate the mechanisms of action of (-)-Praeruptorin A and to explore additional applications in medicine.

Upstream product

• 565-63-9 Angelic acid 
• 4955-21-9 (+/-)-cis-4'-acetylkhellactone 
• 35660-94-7 (Z)-2-methyl-2-butenoyl chloride 
• 523-59-1 seseline 
• 518-76-3 (±)-cis-khellactone 
• 80-59-1 Tiglic acid 
• 35660-94-7 (E)-2-methylbut-2-enoyl chloride 
• 4955-21-9 (+/-)-trans-4'-acetylkhellactone 
• 108-24-7 acetic anhydride 
• 20098-05-9 2-methylbut-(2Z)-enoic acid (9R,10R)-10-hydroxy-8,8-dimethyl-9,10-dihydro-2H,8H-benzo[1,2-b:3,4-b']dipyran-2-one-9-yl ester 
• 75-36-5 acetyl chloride 

Downstream Products

• 54712-23-1 (-)-cis-(3'S,4'S)-khellactone 
• 518-76-3 (+)-(3'S,4'R)-trans-khellactone 
• 84579-96-4 (-)-(3'R,4'S)-3'-angeloylkhellactone 
• 518-76-3 (+)-cis-khellactone 
• 518-76-3 trans-kellactone 
• 518-76-3 (±)-cis-khellactone 

Relevant articles and documents

The antagonistic effects of khellactones on platelet-activating factor, histamine, and leukotriene D4

Khellactones of Peucedanum praeruptorum Duun., including praeruptorins A (= Pd-Ia, 2) and B (= Pd-II, 11), had an antagonistic effect specifically on platelet aggregation induced by platelet activating factor (PAF) among various aggregating agents examined, and represent a new class of PAF antagonists. We examined the effects of twenty compounds on PAF-induced platelet aggregation and on histamine- and leukotriene D4 (LTD4)-induced contractions in isolated guinea pig ileum. Compounds 2, (±)-cis-3',4'-diacetylkhellactone (3), (±)-cis-4'-acetyl-3'-crotonoylkhellactone (5), (±)-cis-4'-acetyl-3'-tetrolylkhellactone (6), (±)-cis-4'-acetyl-3'-tigloylkhellactone (7), (±)-cis-4'-acetyl-3'-(2''-methylbutyryl)khellactone (8), (±)-cis-3',4'-ditigloylkhellactone (10), and 11 all strongly inhibited PAF-induced platelet aggregation. (±)-cis-4'-Acetyl-3'-(2''-methyl-2''-dodecenoyl)khellactone (9), (±)-cis-4'-ethyl-3'-tigloylkhellactone (13), (±)-cis-4'-ethyl-3'-[N-(2''-triethylammonio)ethylcarbamoyl]khellacton e iodide (16), (±)-trans-3',4'-diacetylkhellactone (18), (±)-trans-4'-acetyl-3'-crotonoylkhellactone (19), (±)-trans-4'acetyl-3'-valerylkhellactone (20), (±)-trans-4'-acetyl-3'-isovalerylkhellactone (21), and (±)-trans-4'-acetyl-3'-tigloylkhellactone (22) were weakly inhibitory. Most of the compounds exhibited noncompetitive antagonist actions on histamine- and LTD4-induced contractions. The potencies of the antagonistic effects on histamine action were in the order 7 = 22 ≥ 2 = 8 = 10 > 6 = 11 = 13 ≥ 5 > 19 = 9 and those on LTD4 action were in the order 6 = 22 = 2 > 10 = 8 > 7 = 9 = 11 ≥ 13. Thus, compounds with potent PAF-antagonistic activities have the following features: cis isomers of khellactone at the C-3' and C-4' positions are more favorable than trans isomers, and the acyl moiety at the C-3' position of khellactone must be of an appropriate molecular size. In the case of histamine- and LTD4-antagonistic activities, both isomers show similar effects and acyl moieties of appropriate size are required at the C-3' and C-4' positions. These results are of interest in regard to the medicinal uses of Peucedanum species as a herbal drug.

SYNTHESIS OF (+/-)-PRAERUPTORIN A AND RELATED KHELLACTONE DERIVATIVES

The first synthesis of the pyranocoumarin natural product, (+/-)-praeruptorin A (= Pd-Ia), is described.A general method for the preparation of various khellactone derivatives is reported.

PYRANOCOUMARINS FROM ARRACACIA NELSONII

(+)-Suksdorfin, (-)-isosamidin, (-)-3'-angeloyl-cis-khellactone, and a new pyranocoumarin, (3'S)-3'-angeloyl-4'-oxo-khellactone, were isolated from the aerial parts of Arracacia nelsonii.Their structures were established by chemical and spectroscopic means. - Key Word Index: Arracacia nelsonii; Umbelliferae; angular pyranocoumarins; khellactone derivatives; 3'-angeloyl-4'-oxo-khellactone.

COUMARINS FROM SESELI BOCCONI

Key Word Index - Seseli bocconi; Apiaceae; khellactones ester; bocconin. A new khellactone, bocconin, in addition to known compounds, have been isolated from Seseli bocconi subsp. bocconi and subsp. praecox Gamisans.Their structures were elucidated on the basis of spectral analyses and hydrolytic studies.