Structures of cleomiscosins, coumarinolignoids of cleome viscosa seeds

Hyosgerin, a New Optically Active Coumarinolignan, from the Seeds of Hyoscyamus niger

“…8) Consistent with this observation, C-8Ј of hyosgerin (1) appeared at a lower field than that of venkatasin (2) by about 0.5 ppm indicating that hyosgerin is related to venkatasin in the same manner as cleomiscosin B is to cleomiscosin A.…”

“…The two compounds showed essentially identical UV absorption maxima near 232, 287 and 322 nm. The 1 H-and 13 C-NMR data (Table 1) for 1 and 2 were closely similar to each other, and resembled cleomiscosins A 8,9) and B, 8) except for the signals of an acetyl group, not discernible in the spectra of cleomiscosins. Careful comparison of the 1 H-and 13 C-NMR data of 2 with the published data for venkatasin 10) (durantin-A 11) ) led to the assignment of 2 as venkatasin, while hyosgerin (1) was suggested to be a structural isomer of venkatasin.…”

Cleome viscosa(wild mustard): A review on ethnobotany, phytochemistry, and pharmacology

“…A novel umbelliferone derivative, designated as cleosandrin, has been isolated from the ethanol extract of the seeds (Ramchandran, 1979). The seeds are also reported to contain cleomiscosin A, a coumarino-lignoid (Ray et al, 1980); cleomiscosin B (Ray et al, 1982); and cleomiscosin C (Ray et al, 1985) and its regioisomer cleomiscosin D, a minor coumarino-lignan (Kumar et al, 1988). Chattopadhyay et al (2007) have developed a simple, accurate, and reproducible reverse-phase high performance liquid chromatography (HPLC) method for identification and quantification of two isomeric coumarino-lignoids, cleomiscosin A and B, in different extracts of the seeds using photodiode array detection at 326 nm.…”

A New Isoflavone Glycoside from the Stems of Tilia taquetii Schneider

“…By the analysis of 1D and 2D NMR spectra, the compounds 3 and 4 were identified as coumarinolignans, cleomiscosin A and B respectively. 7 The compound 5 isolated from a nonpolar fraction was oleic acid, whose identification was made by comparing its NMR data to those obtained from authentic sample. Even though the isolates 2-5 were known metabolites from natural sources, this is the first example of their isolations from T. taquetii.…”