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Neolignans from Selaginella moellendorffii

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ABSTRACT

12391910188111214168111213171112: Two new neolignans selaginellol () and selaginellol 4′-O-β-d-glucopyranoside (), together with seven known compounds (–), were isolated from the whole plant of Selaginella moellendorffii. The structures of the new isolates were determined through spectroscopic data analysis. Compounds –, as well as compounds – previously isolated from the species, were measured for the activity against platelet aggregation induced by ADP or collagen. Three neoligans (, , and ), one flavanone (), and one alkaloid () showed inhibitory activity against ADP- or collagen-induced platelet aggregation as compared with tirofiban. The dihydrobenzofuran neolignans (, , and ) are more potent than the benzofuran neolignan () and other types of neolignans (–). Glucosidation of the dihydrobenzofuran neolignans ( and ) is helpful for the activity.

12: Two new neolignans selaginellol () and selaginellol 4′-O-β-d-glucopyranoside () were isolated from the whole plant of Selaginella moellendorffii. Several compounds from this plant showed the activity against platelet aggregation induced by ADP or collagen.

Electronic supplementary material: The online version of this article (doi:10.1007/s13659-016-0095-5) contains supplementary material, which is available to authorized users.

No MeSH data available.


Key 2D NMR correlations of 1 and 2
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Fig2: Key 2D NMR correlations of 1 and 2

Mentions: The 1H–1H COSY correlations (Fig. 2) exhibited two partial structures from C-7 to C-9 and C-7′ to C-9′. Based on the HMBC correlations (Fig. 2) from H-2 and H-6 to C-4, H2-7 to C-2 and C-6, H-8 to C-1, H2-8′ to C-1′, H2-7′ to C-2′ and C-6′, H-2′ and H-6′ to C-4′, 3-OMe to C-3, 5-OMe to C-5, and 5′-OMe to C-5′, two phenylpropanoid moieties, namely 4-(3-hydroxypropyl)-2,6-dimethoxyphenol and 4-(3-hydroxypropyl)-2-methoxyphenol, were confirmed. The two fragments were linked through C-8-C-3′ by the HMBC correlations from H2-7 and H2-9 to C-3′ as well as H-8 to C-2′ and H-2′ to C-8. Therefore, the relative configuration of 1 was elucidated as 3,5,5′-trimethoxy-8,3′-neoligna-4,4′,9,9′-tetraol. The absolute configuration of selaginellol (1) was elucidated as (8R)-3,5,5′-trimethoxy-8,3′-neoligna-4,4′,9,9′-tetraol by comparing its electronic circular dichroism (ECD) spectrum [Δε −0.12 (273)] with that of a known analogue secodihydrodehydrodiconiferyl alcohol tetraacetate [9].Fig. 2


Neolignans from Selaginella moellendorffii
Key 2D NMR correlations of 1 and 2
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Fig2: Key 2D NMR correlations of 1 and 2
Mentions: The 1H–1H COSY correlations (Fig. 2) exhibited two partial structures from C-7 to C-9 and C-7′ to C-9′. Based on the HMBC correlations (Fig. 2) from H-2 and H-6 to C-4, H2-7 to C-2 and C-6, H-8 to C-1, H2-8′ to C-1′, H2-7′ to C-2′ and C-6′, H-2′ and H-6′ to C-4′, 3-OMe to C-3, 5-OMe to C-5, and 5′-OMe to C-5′, two phenylpropanoid moieties, namely 4-(3-hydroxypropyl)-2,6-dimethoxyphenol and 4-(3-hydroxypropyl)-2-methoxyphenol, were confirmed. The two fragments were linked through C-8-C-3′ by the HMBC correlations from H2-7 and H2-9 to C-3′ as well as H-8 to C-2′ and H-2′ to C-8. Therefore, the relative configuration of 1 was elucidated as 3,5,5′-trimethoxy-8,3′-neoligna-4,4′,9,9′-tetraol. The absolute configuration of selaginellol (1) was elucidated as (8R)-3,5,5′-trimethoxy-8,3′-neoligna-4,4′,9,9′-tetraol by comparing its electronic circular dichroism (ECD) spectrum [Δε −0.12 (273)] with that of a known analogue secodihydrodehydrodiconiferyl alcohol tetraacetate [9].Fig. 2

View Article: PubMed Central - PubMed

ABSTRACT

12391910188111214168111213171112: Two new neolignans selaginellol () and selaginellol 4′-O-β-d-glucopyranoside (), together with seven known compounds (–), were isolated from the whole plant of Selaginella moellendorffii. The structures of the new isolates were determined through spectroscopic data analysis. Compounds –, as well as compounds – previously isolated from the species, were measured for the activity against platelet aggregation induced by ADP or collagen. Three neoligans (, , and ), one flavanone (), and one alkaloid () showed inhibitory activity against ADP- or collagen-induced platelet aggregation as compared with tirofiban. The dihydrobenzofuran neolignans (, , and ) are more potent than the benzofuran neolignan () and other types of neolignans (–). Glucosidation of the dihydrobenzofuran neolignans ( and ) is helpful for the activity.

12: Two new neolignans selaginellol () and selaginellol 4′-O-β-d-glucopyranoside () were isolated from the whole plant of Selaginella moellendorffii. Several compounds from this plant showed the activity against platelet aggregation induced by ADP or collagen.

Electronic supplementary material: The online version of this article (doi:10.1007/s13659-016-0095-5) contains supplementary material, which is available to authorized users.

No MeSH data available.