Selaginellin M,a new selaginellin derivative from Selaginella pulvinata

A new selaginellin derivative, selaginellin M (1), together with one known compound, selaginellin E (2), was isolated from Selaginella pulvinata. The structure of the new compound was elucidated and named as (R,S)-4-((4′-hydroxy-4-((2-hydroxyethoxy)methyl))-3-((4-hydroxyphenyl)ethynyl)biphenyl-2-yl)(4-hydroxyphenyl)methylene)cyclohexa-2,5-dienone on the basis of the spectroscopic data including UV, IR, 1D, and 2D NMR as well as HR-ESI-MS analysis.     

垫状卷柏炔酚类化学成分研究

目的 研究垫状卷柏中炔酚类化学成分.方法 运用色谱法分离垫状卷柏75％乙醇提取物中的炔酚类化学成分,UV、IR、MS、1H-NMR、13C-NMR波谱技术鉴定化合物的结构.结果 分离得到3个炔酚类化合物,分别是selaginellin J(1)、selaginellin K(2)和selaginellin L(3).结论 3个炔酚类化合物均为首次从该植物中分离得到.     

A new selaginellin derivative and a new triarylbenzophenone analog from the whole plant of Selaginella pulvinata

Abstract

Five selaginellin derivatives (1 and 3–6) including a new one, selaginellin T (1), and a new triarylbenzophenone analog, selagibenzophenone A (2), were isolated from the whole plants of Selaginella pulvinata. Their structures were determined by 1D- and 2D-NMR and HR-ESI-MS data. Selagibenzophenone A (2) is the first example of naturally occurring triarylbenzophenone. The results of the phosphodiesterase-4 (PDE4) inhibitory screening assays showed that compounds 1?6 exhibited potent activities with the IC₅₀ values in the range of 1.04?9.35 μM.     

Selaginellin C,a new natural pigment from Selaginella pulvinata Maxim (Hook et Grev.)

A novel compound, selaginellin C (1), was isolated from Selaginella pulvinata Maxim (Hook et Grev.) as (R,S)-4-((1,2-dihydroxyethyl)-2′,4′-dihydroxy-3-((4-hydroxyphenyl)ethynyl)biphenyl-2-yl)((4-hydroxyphenyl)methylene)cyclohexa-2,5-dienone, along with two known compounds, selaginellin (2) and selaginellin A (3). The structure of the new compound was elucidated on the basis of 1D and 2D NMR as well as HR-ESI-MS spectroscopic analysis.     

Two new selaginellin derivatives from Selaginella tamariscina (Beauv.) Spring

Two new selaginellin derivatives, selaginellins K (1) and L (2), were isolated from Selaginella tamariscina (Beauv.) Spring and characterized as 2-formyl-4,4'-dihydroxy-3-[(4-hydroxyphenyl)ethynyl]biphene and 4,4'-dihydroxy-2-methyl-3-[(4-hydroxyphenyl)ethynyl]biphene on the basis of their spectroscopic data including UV, IR, 1D, and 2D NMR as well as HR-ESI-MS spectroscopic analysis.     

Two new selaginellin derivatives from Selaginella tamariscina (Beauv.) Spring

Two new selaginellin derivatives, selaginellins K (1) and L (2), were isolated from Selaginella tamariscina (Beauv.) Spring and characterized as 2-formyl-4,4′-dihydroxy-3-[(4-hydroxyphenyl)ethynyl]biphene and 4,4′-dihydroxy-2-methyl-3-[(4-hydroxyphenyl)ethynyl]biphene on the basis of their spectroscopic data including UV, IR, 1D, and 2D NMR as well as HR-ESI-MS spectroscopic analysis.     

Isolation and cytotoxic activity of selaginellin derivatives and biflavonoids from Selaginella tamariscina

Five selaginellin derivatives, including two new selaginellins termed selaginellins M (1) and N (2), and three previously identified compounds, selaginellin (3), selaginellin A (4), and selaginellin C (5), were isolated from the Selaginella tamariscina (Beauv.) Spring plant. In addition, four known biflavonoids, namely neocryptomerin ( 6), hinokiflavone (7), pulvinatabiflavone (8), and 7'- O-methylamentoflavone (9), were also isolated. The structures of new compounds 1 and 2 were elucidated by spectroscopic analysis. The cytotoxic activity of compounds 1- 9 was evaluated against a small panel of human cancer cell lines, including U251 (human glioma cells), HeLa (human cervical carcinoma cells), and MCF-7 (human breast cancer cells). The two new selaginellins, selaginellins M (1) and N (2), showed medium activity against the human cancer cell lines.     

Uncinataflavone,a new flavonoid with a methyl benzoate substituent from Selaginella uncinata

Uncinataflavone (1), a new flavonoid, together with four known compounds (2–5), was isolated from Selaginella uncinata (Desv.) Spring. Compounds 2 and 3 were isolated from the genus selaginella for the first time. The structure of the new compound was determined as methyl 3-(5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-6-yl)-4-methoxybenzoate by means of spectroscopic evidence, including UV, IR, 1D and 2D NMR analyses as well as HR-ESI-MS. These compounds (1–5) were evaluated for the antioxidant activity in 1,1-diphenyl-2-picrylhydrazyl assay system.     

A new glucoside from Selaginella sinensis

A new glucoside, selaginoside (1), together with two known compounds, hinokiflavone (2) and 2,3-dihydroamentoflavone (3), were isolated from the whole plants of Selaginella sinensis. Their structures were elucidated by means of spectroscopic methods.     

Two new flavonoids from Selaginella uncinata

Two new flavonoids, uncinataflavones A (1) and B (2), along with one known compound 6-(5-carboxyl-2-methoxyphenyl)-apigenin (3), were isolated from Selaginella uncinata (Desv.) Spring. All these compounds belong to apigenin derivatives with aryl substituents at C-6 position. The structures of new compounds were elucidated on the basis of comprehensive spectroscopic analyses (UV, IR, 1D, and 2D NMR as well as HR-ESI-MS).     

Paniculacin, a new coumarin derivative from Murraya paniculata

Paniculacin (1), a new coumarin derivative, has been isolated from the ethyl acetate soluble fraction of the ethanolic extract of Murraya paniculata along with umbelliferone, scopoletin, 4-hydroxybenzoic acid, trans-cinnamic acid, and β-sitosterol. Their structures were elucidated on the basis of spectral data.     

Paniculacin,a new coumarin derivative from Murraya paniculata

Paniculacin (1), a new coumarin derivative, has been isolated from the ethyl acetate soluble fraction of the ethanolic extract of Murraya paniculata along with umbelliferone, scopoletin, 4-hydroxybenzoic acid, trans-cinnamic acid, and β-sitosterol. Their structures were elucidated on the basis of spectral data.     

A new norlignan lignanoside from Selaginella moellendorffii Hieron

This study reports an investigation into the chemical constituents of the whole plant of Selaginella moellendorffii Hieron. Ten compounds, isolated and purified by column chromatography, were identified on the basis of spectral analysis and their physicochemical properties to be: (8R)-3,5-dimethoxy-4-hydroxyphenylpropylalcohol-8-(1-acetyl-3-methoxy-4-hydroxyphenyl)-9-O-β-d-glucopyranoside (moellenoside B) (1), amentoflavone (2), hinokiflavone (3), apigenin-7-O-β-neohesperidoside (4), apigenin-8-C-β-d-glucopyranoside (5), adenosine (6), uridine (7), 2,3,4,9-tetrahydro-1H-pyrido[3, 4-b]indole-3-carboxylic acid (8), vanillic acid (9), and lariciresinol (10). Compound 1 is a new norlignan lignanoside and compounds 4–10 were isolated from this plant for the first time.     

Cyclobakuchiol C, a new bakuchiol derivative from Psoralea coryllfolia

A new compound, cyclobakuchiol C (1), together with four known bakuchiol derivatives, 2-5, was isolated from the non-polar fraction of the seeds of Psoralea corylifolia, and compounds 3-5 were identified from this plant for the first time. The structure of 1 was determined by spectroscopic methods, especially 2D NMR experiments.     

Griseusin D, a new pyranonaphthoquinone derivative from a alkaphilic Nocardiopsis sp

A new pyranonaphthoquinone antibiotic, griseusin D (1) was isolated from the cultural fluid of the alkaphilic Nocardiopsis sp. The structure was determined as 5'-one-4-hydroxy-12-methoxygriseusin by spectroscopic methods, comparison with reported data and single-crystal X-ray analysis. 1 displayed strong cytotoxicity against human leukemia cells (HL60) and modest cytotoxicity against human lung adenocarcinoma cell lines (AGZY) with IC(50) values of 0.23 and 19.6 microg/ml, respectively. It also exhibited weak antifungal activity against Alternaria alternate with MIC of 140 microg/ml.     

Lepidepyrone, a new gamma-pyrone derivative, from Neolentinus lepideus, inhibits hyaluronidase

In the course of screening for hyaluronidase (HAase) inhibitory agents, a new gamma-pyrone derivative, lepidepyrone, C(8)H(10)O(5), was isolated from the cultured mycelium of the mushroom Neolentinus lepideus TMC-1102 as a major HAase inhibitory compound (IC(50) 3.3 mM). The structure of lepidepyrone was established on the basis of spectroscopic investigation.     

Two new secolignans from Selaginella sinensis (Desv.) Spring

Two new secolignans, 3,4-trans-3-hydroxymethyl-4-[bis(4-hydroxyphenyl)methyl]butyrolactone (1) and 2,3-trans-3,4-trans-2-methoxy-3-hydroxymethyl-4-[bis(4-hydroxyphenyl)methyl]tetrahydrofuran (2), together with six known compounds, were isolated from the whole grass of Selaginella sinensis (Desv.) Spring. Their structures were elucidated by NMR and MS experiments.     

Kakispyrol, a new biphenyl derivative from the leaves of Diospyros kaki

A new biphenyl derivative, 4',5-dimethoxy-3-beta-D-glucopyranosyloxy-4-hydroxy-biphenyl, named kakispyrol (1), has been isolated from the leaves of Diospyros kaki, together with three known compounds, vitexin (2), 2'-O-rhamnosyl vitexin (3) and isorhamnetin-3-O-beta-D-glucopyranoside (4). The structure of compound 1 has been determined on the basis of spectroscopic evidence.