Sappanin-type homoisoflavonoids from Sansevieria trifasciata Prain

Flavonoid isolation and identification of mother-in-law’s tongue leaves (sansevieria trifasciata) and the inhibitory activities to xanthine oxidase enzyme

“…It is also used for the treatment of ear pain, swellings, boils and fever [17]. Previous chemical studies on Sansevieria trifasciata led to the isolation of flavonoid [18] steroidal sapogenins namely 25S-ruscogenin and sansevierigenin [19] ,pregnane glycosides [20], and steroidal saponins [21]. Therefore, we expect a positive correlation between XO inhibitory activity and flavonoid content of plant extracts.…”

Constituents of the Rhizomes of Sansevieria cylindrica

“…S. trifasciata [4b, 10] and S. cylindrica [this paper] of dihydrocalcone 7 and sappanin-type 3-benzyl chroman-4-ones (homoisoflavanones [15]) 5 (and 6), showing the same substituent patterns in rings A and B, have suggested a plausible biogenetic relationship between these compounds. On the basis of early experiments with radioactive precursors on the biosynthesis of the 3-benzylchroman-4-one eucomin (8) in Eucomis bicolor [15], it has been proposed that the sappanin skeleton of eucomin 8, as well as trifasciatine A (5) and B (6), derives from a chalcone-like precursor 9, whose methoxy group is used to create the C(2)-C(3) bond of homoisoflavanones [10]. The proposed biosynthetic mechanism would involve the formation of the oxonium ion 10, which is then intercepted intramolecularly by the styryl double bond (Figure 2).…”

“…with preservation of the stereochemical integrity of the stereogenic center C(3). In striking contrast, instead, opposite configurations have been attributed to trifasciatine A, (R)-5 [10], and trifasciatine C, (S)-7 [4b], isolated from the same plant, S. trifasciata. Based on these observations, we tentatively propose an alternative biosynthetic pathway (path b in Figure 2), which also takes into account the enantiodivergent formation of the same homoisoflavonoid in the same or in different species.…”

“…-3-(4′hydroxybenzyl)-3,5-dihydroxy-7-methoxy chroman-4-one (4) [9], 3-(3′,4′-methyledioxybenzyl)-7-hydroxy-8-methoxy chroman-4-one (5) [10], 2′,4′-dihydroxy-3′-methoxy-3,4-methylenedioxy-8hydroxymethylene dihydrochalcone (7) [4], stigmasterol, and ergosterol peroxide. Compounds 1-4 have been isolated for the first time from the genus Sansevieria [6], while the structure of compound 5 corresponded to (R)-(-)-trifasciatine A, recently isolated from the aerial parts of S. trifasciata [10]. However, the configuration of the two samples could not be compared, because an unambiguous measurement of the optical activity of compound 5 isolated from S. cylindrica was hampered by the minute amounts in our hands.…”

“…Trifasciatine C (7) adds to the numerous known examples of the occurrence of both enantiomers or the formation of enantiomeric congeners of opposite antipodal series in the same plant or in different species [11]. Among homoisoflavanones, a recent example of biosynthetic enantiodivergence is given by trifasciatine B (6), which occurs as the (3S)-enantiomer in S. cylindrica [3], while the (3R)-antipode has been isolated from S. trifasciata [10].…”