Lignans from Arum italicum

Lignans from the stems and leaves of Brandisia hancei and their effects on VEGF-induced vascular permeability and migration of HRECs and DLAV formation in zebrafish

“…These spectroscopic data were similar to those of citrusin A, an 8-O-4′ neolignan glycoside isolated from Arum italicum, 17) but the large coupling constant (J = 6.4 Hz) between C-7 and C-8 of 1, compared to that of citrusin A (J H-7/H-8 = 4.3 Hz) indicated a relative threo-configuration of the 1-phenyl-2-aryloxypropane-1,3-diol moiety in 1. 17,18) This was confirmed by the observation of crosspeaks between H-8 and H-2/H-6, and H-8 and H-7 in the NOESY spectrum. The absolute configuration at C-7 and C-8 was determined to be 7R and 8R from the circular dichroism (CD) spectrum of 1 showing a negative Cotton effect in the region 220-250 nm, compared with those of reported analogs.…”

“…The absolute configuration at C-7 and C-8 was determined to be 7R and 8R from the circular dichroism (CD) spectrum of 1 showing a negative Cotton effect in the region 220-250 nm, compared with those of reported analogs. 17,19,20) Hence, the structure of 1 was established as (7R,8R)-1-…”

Constituents of the Underground Parts of Glehnia littoralis.

“…The EtOAc fraction was chromatographed on a silica gel column to give eight known compounds (19)(20)(21)(22)(23)(24)(25)(26), while the BuOH fraction was separated by a combination of Sephadex LH-20 column chromatography and preparative TLC to afford four new compounds (1-4) and 14 known compounds (5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18). The known compounds 6-26 were identified by means of comparison with published data or with authentic samples as: citrusin A (6), 7) (Ϫ)-secoisolariciresinol (7), 8) quercetin (8), 9) isoquercetin (9), 9) rutin (10), 9) chlorogenic acid (11), 10) …”

“…The presence of D-glucose was confirmed by acid hydrolysis followed by GC analysis of the acid hydrolysate. The COSY, HMQC, and HMBC spectra suggested that 3 has a carboxylic acid instead of the allyl alcohol in citrusin A (6), 7) a known compound isolated from the same extract. The location of the glucose was determined to be at C-4 from the HMBC correlation between H-1Љ of the glucose moiety and C-4 ( Fig.…”

Neolignans, lignans and glycoside from the fruits of Melia toosendan

“…The known compounds were identified as threodihydroxydehy-drodiconiferyl alcohol (6), 1-(4-hydroxy-3-methoxyphenyl)-2-{3-[(1E)-3-hydroxy-1-propenyl]-5-methoxyphenoxy}-(1S, 2R)-1,3-propanediol (7) [37], threoguaiacylglycerol-β-O-4′-coniferyl ether (8) [36], erythroguaiacylglycerol 8′-vanillin ether (9), threo-guaiacylglycerol 8′-vanillin ether (10), erythro-guaiacylglycerol 8′-(4-hydroxymethyl-2-methoxyphenyl) ether (11), threo-guaiacylglycerol 8′-(4-hydroxymethyl-2-methoxyphenyl) ether (12) [35], (+)- pinoresinol (13) [34], evofolin-B (14) [39] and (7S,8R,8′S)-3,3′-dimethoxy-4,4′,9-trihydroxy-7,9′-epoxylignan-7′-one (15) [38], based on NMR data and mass spectrometric analysis, as well as by comparison of the spectral data with those reported. Among these known compounds, except for evofolin-B (14), all of them were isolated from this genus for the first time.…”