A New 3-Benzylchroman Derivative from Sappan Lignum (Caesalpinia sappan)

Abstract

3'-Deoxy-4-O-methylepisappanol, a new 3-benzylchroman derivative, was isolated from Sappan Lignum, together with thirteen known chemical compounds identified as protosappanin A, sappanchalcone, sappanone B, palmitic acid, (+)-(8S,8'S)-bisdihydrosiringenin, brazilein, 3-deoxysappanchalcone, (+)-lyoniresinol, 3-deoxy-sappanone B, protosappanin B, isoprotosappanin B, 3'-O-methylbrazilin and brazilin, respectively. Among these known compounds, this is the first time that (+)-(8S,8'S)-bis-dihydrosiringenin was obtained from the family Caesalpiniaceae.

Protective effects of 3′‐deoxy‐4‐O‐methylepisappanol from Caesalpinia sappan against glutamate‐induced neurotoxicity in primary cultured rat cortical cells

“…These compounds were identifi ed as sappanchalcone and 3′-deoxy-4-O-methylepisappanol ( paring physicochemical and spectroscopic data with literature values. All spectral data for these compounds were in good agreement with those previously reported in literature (Baek et al, 2000;Fu et al, 2008). Furthermore, to investigate and compare the neuroprotective activities of these compounds isolated from the methanol extracts of C. sappan, the activities of sappanchalcone and 3′-deoxy-4-O-methylepisappanol were evaluated in glutamate-injured primary cultured rat cortical cells at concentrations ranging from 0.1 to 10 μM (Table 1).…”

“…The reported main phenolic compounds in C. sappan were divided into to four structural subtypes: i.e., brazilin, chalcone, protosappanin and homisofl avonoid. Even though several compounds have been isolated from the wood of C. sappan (Fu et al, 2008), and many experiments regarding biological activities, such as inhibitory activity in central nervous system (Nagai et al, 1986), have been carried out, the principal component of the drugs manifesting neuroprotective activity has not yet been reported.…”

Homoisoflavonoids from <i>Caesalpinia sappan</i> Displaying Viral Neuraminidases Inhibition

“…The chemical structures of 2-11 were elucidated by their spectroscopic data. [20][21][22][23][24][25][26] The biological activities of 1-12 were assessed against Table 1.…”

Isolation and antitrichomonal activity of the chemical constituents of the leaves of Maytenus phyllanthoides Benth. (Celastraceae)

“…16 These facts suggest that compound 1 isolated from M. phyllanthoides is an enantiomeric mixture in which the (+)-lyoniresinol enantiomer (with relative configuration 7'S, 8'R, 8R) is predominant. Similarly, other authors have also reported low optical rotation values [α] D for (+)-lyoniresinol isolated from other species such as Quercus petraea (Fagaceae), 17 Dendrobium chrysanthum (Orchidaceae), 18 and Caesalpinia sappan (Fabaceae) 19 ([α] D +13.3°, +11.0° and + 2.08°, respectively), indicating that lyoniresinol is commonly isolated as a racemic mixture.…”