Notoptol

Isolation of the minor and rare constituents from fruits of Peucedanum alsaticum L. using high-performance counter-current chromatography.[Pubmed:22532346]

J Sep Sci. 2012 Apr;35(7):790-7.

A high-performance counter-current chromatography (HPCCC) method was applied for the first time for the preparative separation and purification of three rare compounds which occur as minor constituents in the fruits of Peucedanum alsaticum L.: 5-substituted coumarin Notoptol and two dihydropyranochromones: divaricatol and ledebouriellol. A scale-up process from analytical to preparative in a very short time was developed. In order to purify a range of rare and minor compounds with different polarity two separate experiments were performed, one in reverse phase, the other in normal phase, using the same crude extract. A two-phase solvent system composed of n-hexane/ethyl acetate/methanol/water (1:1:1:1) was developed. The components purified and collected were analyzed by high-performance liquid chromatography. The method yielded 0.7 mg of Notoptol, 1.46 mg of ledebouriellol at purity of 99.5%, and 10 mg of mixtures of divaricatol, alsaticol and alsaticocoumarin, where divaricatol present 22% by peak area. These amounts were obtained from 1 g of the crude extract in a single run. This is the first time when minor Notoptol, ledebouriellol, and divaricatol were isolated in a single run using HPCCC method and first time when these were identified in plant from Peucedanum genus.

Coumarins from Seseli hartvigii.[Pubmed:20734942]

Nat Prod Commun. 2010 Jul;5(7):1067-70.

Linear-type furocoumarins, 5-[(2"E,6"R)-6"-hydroxy-3",7"-dimethylocta-2",7"-dienyloxy]psoralen and 5-[(2"E,6"S)-6"-hydroxy-3",7"-dimethylocta-2",7"-dienyloxy]psoralen (1) were first isolated from whole plants of Seseli hartvigii together with one new natural product 6-(3'-methyl-2'-oxo-3'-butenyl)-7-methoxycoumarin (2), and four known compounds (tamarin, bergaptol, Notoptol, and a mixture of beta-sitosterol and stigmasterol). The structure of 1 was elucidated by extensive spectroscopic analysis and chemical conversion. The modified Mosher's method and HPLC were applied to determine its stereochemistry. Both R- and S-configurations exist in 1; after modification by Mosher's reagent, they were effectively separated, and their ratio was deduced to be 59% and 41%, respectively.

[Studies on chemical constituents in roots and rhizomes of Notopterygium incisum].[Pubmed:19294850]

Zhongguo Zhong Yao Za Zhi. 2008 Dec;33(24):2918-21.

OBJECTIVE: To study the chemical constituents in the roots and rhizomes of Notopterygium incisum. METHOD: The chemical constituents were isolated by various column chromatographic methods and structurally elucidated by NMR and MS evidences. RESULT: Twenty-four compounds were obtained and identified as isocalamenediol (1), pregnenolone (2), beta-sitosterol (3), bergapten (4), bergaptol (5), cnidilin (6), isoimperatorin (7), bergamottin (8), demethylfuropinnarin (9), nodakenetin (10), 7'-O-methylNotoptol (11), notopterol (12), Notoptol (13), pabulenol (14), phenethylferulate (15), p-hydroxyphenethyl anisate (16), trans-ferulic acid (17), nodakenin (18), sucrose (19), 2-methoxy-4-(3-methoxy-1-propenyl)-phenol (20), 3, 4, 5 trimethoxy-trans-cinnamic acid (21), p-methoxycinnamic acid (22), 4-acetoxy-3-methoxy-trans-cinnamic acid (23), and p-hydroxy-trans-cinnamic acid (24). CONCLUSION: Compounds 1, 14, 20-24 were isolated from the roots and rhizomes of N. incisum for the first time. Compounds 1 and 14 are sesquiterpenoid and coumarin, respectively, and 20-24 were phenylpropanoid compounds.