Neolignans and Caffeoyl Derivatives from Selaginella moellendorffii

Abstract

Ten new phenolic compounds including the six neolignans 1 -3 and 6 -8 and four caffeoyl derivatives, i.e., myo-inositol 1-caffeate (9), myo-inositol 6-caffeate (10), myo-inositol 5-caffeate (11), and paucine 3'-b-d-glucopyranoside (12) were isolated from the whole plants of Selaginella moellendorffii (caffeic acid ¼ 3-(3,4-dihydroxyphenyl)prop-2-enoic acid). Their structures were established by spectroscopic and chemical methods.Introduction. -Selaginella moellendorffii Hieron. (Selaginellaceae), a perennial herb, is mainly distributed in the southern area of the Changjiang River in China and has been used to treat jaundice, gonorrhea, bleeding, acute hepatitis, and idiopathic thrombocytopenic purpura (ITP) [5] biflavones in this plant. In our recent research, a series of pyrrolidinoindoline alkaloids were found from this plant [6]. In continuation of the studies on this plant, ten new phenolic derivatives, 1 -3 and 6 -12, and four known ones, compounds 4 and 5, paucine (¼ (2E)-N-(4-aminobutyl)-3-(3,4-dihydroxyphenyl)prop-2-enamide 13) [7], and N

Theagalloflavic Acid, a New Pigment Derived from Hexahydroxydiphenoyl Group, and Lignan Oxidation Products Produced by Aerobic Microbial Fermentation of Green Tea

“…32) The electron-circular dichroism spectrum showed a negative Cotton effect at 280 nm (Δε−0.24), the sign of which was opposite of the Cotton effect of the related compound (7S,8R)-4,9-dihydroxy-3,3′,5-trimethoxy-4′,7-epoxy-8,5′-neolignan-9′-oic acid methyl ester [Δε+0.13 at 282 nm], 32) indicating 7R,8S configuration of 3. Thus, compound 3 was characterized as (7R,8S)-dihydro-3′-hydroxy-8-hydroxymethyl-7-(4,5-dihydroxy-3-methoxyphenyl)-1′-benzofuranpropanol.…”

Phenolic Compounds from Arundina graminifolia and Their Anti-Tobacco Mosaic Virus Activity

“…This crude extract was subjected repeatedly to column chromatography on Si gel, Sephadex LH-20, RP-18 and preparative HPLC to afford compounds 1-6 (Figure 1), including two new phenolic compounds, gramniphenol A and B (1-2), together with four known phenols, 9'-dehydroxy-vladinol F (3), 6 vladinol F (4), 7 9-O-β-D-xylopyranoside-vladinol F (5), 8 and 4,9-dihydroxy-4',7-epoxy-8',9'-dinor-8,5'-neolignan-7'-oic acid (6). 9 The structures of the compounds 1-6 were as shown in Figure 1, and the NMR data of 1 and 2 were listed in Table 1 ) could also be observed in its IR spectrum. The UV spectrum of 1 showed absorption maxima at 268, 210 nm which confirmed the existence of the aromatic functions.…”

A new phenolic glycoside from Spiraea prunifolia var. simpliciflora twigs

“…Etoposide was used as a positive control. (Otsuka et al 2000), 7R,8S-dihydrodehydrodiconiferyl alcohol (15) (Fang et al 1992), 7R,8S-5-methoxydihydrodehydroconiferyl alcohol (16) (Wang et al 2010), and dihydrodehydrodiconiferyl alcohol 4-O-b-Dglucopyranoside (17) (Matsuda et al 1996) by comparing the spectroscopic data with those in the literature.…”