lignans and balanophonin

A new (propylphenyl)bibenzyl derivative, dendrowillol A (1), along with 22 known compounds were isolated from the whole plants of Dendrobium williamsonii. Their structures were elucidated by means of extensive spectroscopic analysis. Cytotoxicity evaluation against five human tumour lines showed that all the compounds tested displayed very weak cytotoxicity when compared with the positive control taxol, but selective inhibitory effects on HL-60 for several compounds tested were observed, with IC

Topics: Antineoplastic Agents, Phytogenic; Benzyl Compounds; Bibenzyls; Cell Line, Tumor; Dendrobium; Drug Screening Assays, Antitumor; HL-60 Cells; Humans; Inhibitory Concentration 50; Lignans; Magnetic Resonance Spectroscopy; Molecular Structure

Topics: Antineoplastic Agents; Apoptosis; Cell Line, Tumor; Humans; Lignans; Phenols; Picrasma; Plant Stems; Reactive Oxygen Species; Stereoisomerism

While analyzing the fruit composition of nine European Cirsium species representing three sections (i.e., Cephalonoplos, Chamaeleon and Eriolepis), four lignans, three neolignans and three sesquineolignans were determined and used as chemotaxonomic markers. Among them, desmethyl balanophonin and desmethyl picrasmalignan were determined for the first time in the plant kingdom, as the main metabolites of the Chamaeleon section. Prebalanophonin and prepicrasmalignan, identified so far exclusively in C. eriophorum, were also confirmed in C. boujartii and C. vulgare, highlighting the chemotaxonomic significance of these compounds in the Eriolepis section. The antiproliferative assay of the compounds isolated from their optimum sources, confirmed a dose-dependent inhibitory effect of the structures bearing the 4',7-epoxy moiety (balanophonin, picrasmalignan, desmethyl balanophonin, desmethyl picrasmalignan) against SW480 colon cancer cells, while those bearing the 4',7-dihydroxy motif (prebalanophonin, prepicrasmalignan) were inactive.

Topics: Antineoplastic Agents, Phytogenic; Cell Line, Tumor; Cirsium; Fruit; Humans; Lignans; Molecular Structure; Phytochemicals

Sixteen lignanoids were isolated from an aqueous extract of the commonly used Chinese traditional medicine Dangshen, the dried roots of Codonopsis pilosula, by using a combination of various chromatographic techniques, including silica gel, macroporous adsorbent resin, MCI resin, sephadex LH-20, and reversed phase semi-preparative HPLC. On the basis of spectral data analysis, their structures were elucidated and identified as（-）-（7R,7’R,8R,8’S）-4,4’-dihydroxy-3,3’,5,5’,7-pentamethoxy-2,7’-cyclolignane（1）,（-）-（7R,8S）- dihydrodehydrodiconiferyl alcohol 4-O-β-D-glucopyranosyl-（1’’’→2’’）-β-D-glucopyranoside（2）,（-）-（7R,8S）- dihydrodehydrodiconiferyl alcohol（3）,（+）-（7S,8R）-dehydrodiconiferyl alcohol（4）,（+）-balanophonin（5）,（+）- demethoxypinoresinol（6）,（+）-pinoresinol（7）,（+）-epipinoresinol（8）,（-）-syringaresinol（9）,（-）-medioresinol（10）,（-）-lariciresinol（11）,（-）-secoisolariciresinol（12）,（-）-ent-isolariciresinol（13）,（+）-（7S,8S）-3-methoxy-3’,7- expoxy-8,4’-neolignan-4,9,9’-triol（14）,（+）-（7S,8R）-3’,4-dihydroxy-3-methoxy-8,4’-neolignan（15）, and（-）-（7R,8R）-3’,4-dihydroxy-3-methoxy-8,4’-neolignan（16）. All these compounds were isolated from C. pilosula for the first time, while compound 1 is a new natural product of 2,7’-cyclolignan and 2 is a new 4’,7-epoxy- 8,3’-neolignan diglucoside. Compound 12 showed activity against Fe(2+)-cysteine induced rat liver microsomal lipid peroxidation with an inhibition ratio of（63.4 ± 8.3） % at 1×10(-5) mol·L(-1).

Topics: Animals; Butylene Glycols; Codonopsis; Drugs, Chinese Herbal; Furans; Lignans; Microsomes, Liver; Molecular Structure; Plant Extracts; Plant Roots; Rats

To study the chemical constituents from Serissa japonica.. The constituents were isolated by various chromatographic techniques and their structures were determined on the basis of spectroscopic data,as well as literatures.. Eleven compounds were obtained and identified as 3-hydroxy-1,2-dimethoxyanthraquinone( 1),1,2,4-trimethoxy-3-hydroxy-6-methyl anthraquinone( 2),emodin( 3),pinoresinol( 4),medioresinol( 5),( 7S,8R)-balanophonin-4-O-β-D-glucopyranoside( 6),lupeol( 7),icariside F2( 8),gallic acid( 9),methyl caffeate( 10) and 4-hydroxy-3-methoxyphenyl-β-D-glucopyranoside( 11).. Compounds 4and 5 are isolated from this plant for the first time,compounds 1 ~ 3 and 6 ~ 11 are isolated from Serissa genus for the first time.

Topics: Drugs, Chinese Herbal; Furans; Lignans; Rubiaceae

A new (propylphenyl)bibenzyl, bambusifolol (1), along with six known compounds, batatasin III (2), tristin (3), 3-hydroxy-5-methoxy bibenzyl (4), gigantol (5), 3',5-dimethoxy-9,9'-diacetyl-4,7'-epoxy-3,8'-bilign-7-ene-4'-methol (6) and balanophonin (7) were isolated from the whole plants of Eria bambusifolia. Their structures were elucidated by the means of extensive spectroscopic analysis. 3-7 were isolated from the genus Eria for the first time and 2 obtained originally from E. bambusifolia. All the compounds isolated were evaluated for their cytotoxicity against human tumour HL-60, SMMC-7721, A-549, MCF-7 and SW-480 cell lines, but none showed significant activity.

Topics: Antineoplastic Agents, Phytogenic; Bibenzyls; Cell Line, Tumor; Dendrobium; Guaiacol; Humans; Lignans; Stilbenes

To study the chemical constituents of Eucommia ulmoides in Guizhou Province.. Silica gel, Sephadex LH-20, RP-18, MCI and semi-preparative HPLC were used to study the chemical constituents of Eucommia ulmoides, and the chemical structures were elucidated by application of spectral data.. 16 compounds were isolated from the bark of Eucommia ulmoides. Their structures were identified as β-sitosterol (1), cycloeucalenol (2), betulinic acid (3), 24-methylenecycloartenone (4), cycloeucalenone (5), salicifoliol (6), pinoresinol (7), genipin (8) , alternariol (9), balanophonin (10), eucommidiol (11), pinoresinol-4'-O-β-D-glucopyranoside (12), eucommiol (13), deoxyeucommiol (14), 8-hydroxypinoresinol (15), and dehydrodiconiferyl alcohol -γ'-O-β-D-glucopyranoside (16).. Seven compounds, including compounds 2,4 - 6,9, 10 and 15 are isolated from Eucommia ulmoides for the first time, and compound 14 is isolated from the bark of Eucommia ulmoides for the first time.

Topics: Betulinic Acid; Chromatography, High Pressure Liquid; Eucommiaceae; Furans; Lignans; Pentacyclic Triterpenes; Phenols; Phytochemicals; Plant Bark; Sitosterols; Triterpenes

In order to identify and quantify fruit-lignans of Cirsium vulgare - authors introduced a special analysis system: with particular attention to the lignans enrichment/separation course. These synchronized, germination and enzymatic hydrolysis processes were followed by complementary gas and liquid chromatography, coupled with special mass selective detections (GC-MS, LC-MS/MS, LC-TOF/MS) and confirmed by nuclear magnetic resonance (NMR) spectroscopy. Mass fragmentations and NMR evidences, proved that the two main medicinal lignan constituents of the fruits of Cirsium vulgare are the neolignan-type, free balanophonin and the butyrolactone-type tracheloside. As novelty to the field, these two lignans of different chemical structures could be quantitatively extracted, separately from each others, without impurities. Balanophonin and tracheloside do accumulate in the fruits of C. vulgare, separately: balanophonin was found, in enormous high concentrations, in the fruit wall (23.2-24.9 mg/g), while in embryo part tracheloside was determined (20.3mg/g), exclusively. Consequently, the optimum source of balanophonin proved to be the fruit wall, while tracheloside, - providing trachelogenin upon enzymatic hydrolysis, - could be obtained from the embryo parts of fruits. As further novelties of the study balanophonin was identified and quantified at the first time with on-line chromatographic technique, in free form, without authentic standard compound.

Topics: Chromatography, Gas; Chromatography, Liquid; Cirsium; Lignans; Magnetic Resonance Spectroscopy; Mass Spectrometry; Spectrophotometry, Ultraviolet