STRUCTURE OF ISOCHAMAEJASMIN FROM STELLERA CHAMAEJASME L.

Abstract

A new C-3/C-3″-biflavanone named isochamaejasmin has been isolated from Stellera chamaejasme L. (Thymelaeaceae) and its structure has been elucidated by spectroscopic and chemical methods. Furthermore, the stereochemistry of some C-3/C-3″-biflavanones including isochamaejasmin was discussed.

Flavonoids from Daphne aurantiaca and Their Inhibitory Activities against Nitric Oxide Production

“…1) and 29 known flavonoids. By comparing physical and spectroscopic data with reported data, the 29 known compounds were identified as chamaechromone (4), 6) neochamaejasmin B (5), 7) neochamaejasmin A (6), 7) 7-methoxy neochamaejasmin A (7), 8) daphnodorin A (8), 9,10) daphnodorin B (9), 9,10) daphnodorin C (10), 10,11) dihydrodaphnodorin B (11), 12) daphnodorin I (12), 13) daphnodorin J (13), 12) afzelechin (14), 14) epiafzelechin (15), 15,16) farrerol (16), 17) naringenin (17), 18) sakuranetin (18), 19) sakuranin (19), 20) genkwanin (20), 21) apigenin (21), 22) kaempferol (22), 23) luteolin (23), 24) Chrysoeriol (24), 25) 7,4Ј-dimethylether-luteolin (25), 21) luteolin-5-O-b-glucoside (26), 26) 5,7,4Ј-trihydroxy-3Ј-methoxyflavone (27), 27) diosmetin (28), 28) 5,3Ј,4Ј-trihydroxy-7-methoxyflavone (29), 29) genk wanin-5-O-b-glucopyranoside (30), 29) 30) and yuankanin (32). 31 (Table 1) were very similar to those of 5-methoxy-2,8-bis-(3,4-dimethoxyphenyl)-2,3-cis-7,8-trans-3,4,6,7-tetrahy...…”

Antimitotic and Antifungal C-3/C-3"-Biflavanones from Stellera chamaejasme

“…1) The 1 H-NMR spectrum of 1 ( Table 1) )] suggested that the linkage of the two flavanones was only at the C-3/C-3Љ positions, which was confirmed by comparison of the 1 H-and 13 C-NMR data of 1 with those of known C-3/C-3Љ biflavanones. [4][5][6] The HMBC correlations of one methoxyl group ( (Table 1), IR and UV data suggested 2 to be a C-3/C-3Љ biflavanone like 1, and its structure was highly symmetric, which was also indicated by the EI-MS [m/z 570 (M …”

“…4) However, the chirality of C-3/C-3Љ remains uncertain, like those known biflavanones. 1,[4][5][6] In previous studies, the meso-form and d-or l-form biflavanones as 2 and chamaejasmenin B were commonly reported, such as isochamaejasmin (mesoform) 7) and chamaejasmenin (l-form), 8) isoneochamaejasmin A (meso-form) 9) and neochamaejasmin A (d-form) 5) isolated from the same plant. The structure of 2 was thus established to be [3,3Ј-Bi-4H-1-benzopyran]-4,4Ј-dione, 2,2Ј,3,3Ј-tetrahydro-5,5Ј,7Ј,7-tetrahydroxy-2,2Ј-bis(4-methoxyphenyl)-(meso), and named isochamaejasmenin B.…”

“…Compounds 3-7 were identified as chamaejasmenin A (3), 4) chamaejasmenin B (4), 4) neochamaejasmin A (5), 5) sikokianin A (6), 6) and chamaejasmenin C ( Morphological deformations of mycelia or conidia of microorganisms, such as curling, swelling, hyperdivergence, bead formation, and inhibition of germination, are often induced in the presence of bioactive substances. 10) A new screening bioassay detecting deformation of mycelia germinated from conidia of Pyricularia oryzae, a phytopathogenic fungus, was developed for quantitative application in screening antimitotic and antifungal agents by Kobayashi et al 11) This bioassay method is quick, easy to perform, and has been efficiently used in the screening of antimitotic, antineoplastic, and antifungal agents, 12) such as rhizoxin 13) and fusarielin A 14) from fungal metabolites.…”

Hepatic Glucuronidation of Isoneochamaejasmin A from the Traditional Chinese Medicine Stellera Chamaejasme L. Root

“…Stellera chamaejasme L., a traditional Chinese medicine, is widely used for the treatment of scabies, ringworm, stubborn skin ulcers, chronic tracheitis, and liver and lung cancers in China and in other Asian countries (Niwa et al, 1984;Yang, 1993). Pharmacological studies have revealed that S. chamaejasme L. possesses multiple bioactivities, including antiviral, antitumor, antimitotic, antifungal, and immunomodulating activities (Yoshida et al, 1996;Endo et al, 1998;Yang et al, 2005;Liu and Zhu, 2012).…”