A novel Diels-Alder adduct of mulberry leaves exerts anticancer effect through autophagy-mediated cell death.

Guangsangon E (GSE) is a novel Diels-Alder adduct isolated from leaves of Morus alba L, a traditional Chinese medicine widely applied in respiratory diseases. It is reported that GSE has cytotoxic effect on cancer cells. In our research, we investigated its anticancer effect on respiratory cancer and revealed that GSE induces autophagy and apoptosis in lung and nasopharyngeal cancer cells. We first observed that GSE inhibits cell proliferation and induces apoptosis in A549 and CNE1 cells. Meanwhile, the upregulation of autophagosome marker LC3 and increased formation of GFP-LC3 puncta demonstrates the induction of autophagy in GSE-treated cells. Moreover, GSE increases the autophagy flux by enhancing lysosomal activity and the fusion of autophagosomes and lysosomes. Next, we investigated that endoplasmic reticulum (ER) stress is involved in autophagy induction by GSE. GSE activates the ER stress through reactive oxygen species (ROS) accumulation, which can be blocked by ROS scavenger NAC. Finally, inhibition of autophagy attenuates GSE-caused cell death, termed as "autophagy-mediated cell death." Taken together, we revealed the molecular mechanism of GSE against respiratory cancer, which demonstrates great potential of GSE in the treatment of representative cancer.

Study on antitubercular constituents from the seeds of Nigella glandulifera.

Two new compounds with five known compounds have been isolated from EtOH extract of the seeds of Nigella glandulifera. On the basis of their spectroscopic and chemical evidence, the new compounds were elucidated as methoxynigeglanine (1) and 6-methoxythymol-3-O-ß-D-glucopyranoside (4). Compounds 1-4 showed moderate antitubercular activity against Mycobacterium tuberculosis strain H37Rv with minimal inhibitory concentration (MIC) values of 32-250 µg/mL.

Two new guaiane-type sesquiterpene glycosides from the fruits of Daucus carota L.

Two new guaiane-type sesquiterpene glycosides, 11-O-acetyl-torilolone 8-O-beta-D-glucopyranoside (1) and 1beta-hydroxytorilolone 11-O-beta-D-glucopyranoside (2), were isolated from the fruits of Daucus carota L. Their chemical structures were elucidated on the basis of MS, NMR spectroscopic analyses coupled with chemical degradation.

UV-B induced changes in the secondary metabolites of Morus alba L. leaves.

Ultraviolet-B (UV-B) radiation is harmful to plants and human beings. Many secondary metabolites, like flavonoids, alkaloids, and lignin, are UV-B absorbing compounds, which can protect the genetic material of plants. Furthermore, they are active components of herbal drugs. UV-B radiation can activate the self-protective secondary metabolism system. The results of this paper provide a method to induce bioactive secondary metabolites from mulberry leaves (Morus alba L.) by UV-B irradiation in vitro. Five significantly different chromatographic peaks were found by HPLC fingerprint after induction, from which two active compounds were identified: One was chalcomoracin, a natural Diels-Alder type adduct with antibacterial activity; the other one was moracin N, which is a precursor of chalcomoracin. Their contents were 0.818 mg/g and 0.352 mg/g by dry weight, respectively.

One new guaiane-type sesquiterpene glycoside from the fruits of Daucus carota L.

A new guaiane-type sesquiterpene glycoside, torilolone 8-O-beta-D-glucopyranoside (1), together with a known analogue compound, torilolone 11-O-beta-D-glucopyranoside (2), was isolated from the fruits of Daucus carota L. Their chemical structures were elucidated on the basis of MS, NMR spectroscopic analyses coupled with chemical degradation. The cytotoxic activities of two isolated compounds were evaluated against two human gastric cancer cell lines BGC-823 and AGS using MTT assay.

A new sesquiterpene from the fruits of Daucus carota L.

Phytochemical investigation of the fruits of Daucus carota L. resulted in the isolation of a new sesquiterpene named as daucucarotol (1). Its structure was elucidated on the basis of 1D and 2D NMR experiments, coupled with MS studies. To our knowledge, compound 1 is the first example for a natural eudesmane sesquiterpene with a hydroxymethyl group located at a methine carbon rather than a usual quaternary carbon in the two fused six-membered ring systems.

[Studies on chemical constituents from leaves of Vaccinium bracteatum].

OBJECTIVE: To investigate the chemical constituents from the leaves of Vaccinium bracteatum. METHOD: Many column chromatographic techniques were used for the isolation and separation of chemical constituents. Their structures were elucidated on the basis of spectral analysis and chemical evidences. RESULT: Twelve compounds were isolated from the plant, and they were identified as chrysoeriol (1), scopoletin (2), trans-p-hydroxycinnamic acid (3), trans-p-hydroxycinnamic acid ethyl ester (4), cafeic acid ethyl ester (5), beta-sitosterol (6), iuteolin (7), quercetin (8), esculetin (9), cafeic acid (10), isolariciresinol-9-O-beta-D-xyloside (11), 10-O-trans-p-coumaroylsandoside (12). CONCLUSION: Compounds 4, 5, 11, 12 were isolated from the genus Vaccinium for the first time, and compounds 1, 2, 9, 10 were isolated from this plant for the first time.

Cytotoxic triterpenoid saponins from the roots of Platycodon grandiflorum.

Bioguided fractionation of the ethanol extracts obtained from Platycodon grandiflorum roots led to isolation of two new triterpenoid saponins, characterized as 3-O-beta-D-glucopyranosyl-2beta,12alpha,16alpha,23,24-pentahydroxyoleanane-28(13)-lactone (1) and 3-O-beta-D-glucopyranosyl-(1-->3)-beta-D-glucopyranosyl-2beta,12alpha,16alpha,23alpha-tetrahydroxyoleanane-28(13)-lactone (2) by 1D- and 2D-NMR and MS techniques, as well as chemical means. Both compounds showed cytotoxic activity against human ECA-109 cells.

[Studies on the extraction process of total saponins from Paris polyphylla Smith].

OBJECTIVE: To optimize the extraction process of total saopnins from Paris polyphylla Smith. METHODS: The single factor test and orthogonal experiment were used to determine the optimum extraction process. RESULTS: The optimum extraction process was obtained as follows: the plant materials were extracted with 70% ethanol twice, respectively with 10BV for 2 hours and then with 8BV the solvents for 1.5 hours. The yield of total saponins could be up to 4.24% and the total extraction rate of Paris polyphylla I and Paris polyphylla II was 93.28%. CONCLUSION: The optimum process obtained is steady, reasonable and feasible.

[GC-MS analysis of volatile oil from the ear of Schizonepeta tenifolia Briq].

Volatile oil was extracted from the ear of Schizonepeta tenifollia Briq. by supercritical carbon dioxide extraction and steam distillation, then GC-MS was used to analyse their components and determine the content. There were 41 components identified from products of supercritical carbon dioxide extraction, while 32 from those of steam distillation. The content of the main component, pulegone, was also different in the two extracts. It showed that the two extractions have differences in component and content to a certain extent.

[Chemical constituents from roots of Platycodon grandiflorum].

OBJECTIVE: To study the chemical constituents from roots of Platycodon grandiflorum. METHOD: Column chromatography (silica gel, macroporous resin, sephadex LH - 20 and the preparative RP - HPLC were used to isolate the constituents. Their structures were elucidated by physical and spectral data. RESULT: Eight compounds were isolated and identified as tangeritin (1), 3-O-beta-D-glucopyranosylplatycodigenin methyl ester (2), 3-O-beta-D-glucopyranosylplaticogenic acid A lactone (3), 3-O-beta-D-glucopyranosylplatycodigenin (4), deapio-platyconic acid A lactone (5), deapio-platycodin-D (6), platycoside-G1 (7) and platycoside-E (8). CONCLUSION: Compounds 1,3 and 5 were isolated from this plant for the first time.

Two new eudesmane-type glucopyranosides from the fruits of Daucus carota L.

Two new eudesmane-type glucopyranosides have been isolated from the fruits of Daucus carota L. On the basis of their spectroscopic and chemical evidence, the new compounds were elucidated as daucucarotol-10-O-ß-D-glucopyranoside (1) and decahydro-7-[(2-O-ß-D-glucopyranosyl)-isopropyl]-1ß,4aα-dimethyl-(1α,4α,8aß)-naphthalenetriol (2). Compounds 1 and 2 showed moderate antitumour activity against human ECA-109 and gave IC50 values of 23.22 and 26.76 µM, respectively.

[Two new triterpenoid saponins from Lysimachia capillipes Hemsl].

AIM: To study the triterpenoid saponins in the whole plants of Lysimachia capillipes Hemsl.. METHODS: Column chromatography (including AB-8 macroporous resin, silica gel and ODS) was used to separate triterpenoid saponins whose structures were elucidated by ESI-MS, NMR (1D and 2D) and hydrolysis methods. RESULTS: Two new triterpenoid saponins were isolated and established as 3beta, 22alpha-dihydroxy-16alpha-angeloyloxy-28-->13-lactone-oleanane-3-O-[beta-D-glucopyranosyl-(1-->2)-alpha-L-arabinpyranosyl]-22-O-(6-acetyl)-beta-D-glucopyranoside (I), 3beta, 13beta, 22alpha-trihydroxy-16alpha-acetyloxyoleanane-28-oic acid Na-3-O-[beta-D-glucopyranosyl-(1-->2)-alpha-L-arabinpyranosyl]-22-O-beta-D-glucopyranoside (II). CONCLUSION: Compounds I and II are new compounds and named as capilliposide I and capilliposide J.

[Two new triterpenoid saponins from Lysimachia davurica].

AIM: To study the triterpenoid saponins in the whole plant of Lysimachia davurica Ledeb. METHODS: Column chromatography (including AB-8 macroporous resin, silica gel and ODS) was used to separate triterpenoid saponins whose structures were elucidated by ESI-MS, NMR (1D and 2D) and hydrolysis methods. RESULTS: Two new triterpenoid saponins were isolated and established as 3beta, 16alpha, 28-trihydroxy-olean-12-en-3-0-(beta-D-glucopyranosyl-(1 --> 2)-beta-D-glucuronopyranosyl)-28-0-beta-D-glucopyranoside) (I), 3beta, 16alpha, 28-trihydroxy-olean-12-en-3-O-(beta-D-glucopyranosyl-(1 --> 2)-beta-D-glucuronopyranosyl)-28-0-beta-D-glucopyranoside) (II). CONCLUSION: Compounds I and II are new compounds and named as davuricosides D and J.

[Studies on chemical constituents in herba of Lysimachia davurica].

OBJECTIVE: To study the chemical constituents from the whole plant of Lysimachia davurica. METHOD: The constituents were separated and purified by column chromatograph, and identified by spectral analysis and physical data. RESULT: Six compounds were isolated and identified as triacontanoic acid(I), palmitic acid(II), beta-amyrin(III), stigmasterol(IV), oleanolic acid(V), soya-cerebroside I (VI). CONCLUSION: I, III, VI were isolated from this gene for the first time.

A new indole alkaloidal glucoside from the aerial parts of Clematis terniflora DC.

A new indole alkaloidal glucoside together with three known compounds aurantiamide acetate (2), eleutheroside E (3) and 1-O-caffeoyl-ß-D-glucopyranoside (4) has been isolated from ethanol extract of the aerial parts of Clematis terniflora DC. On the basis of their spectroscopic and chemical evidence, the new compound was elucidated as (6-O-ß-D-glucopyranosyl-1H-indol-3-yl) carboxylic acid methyl ester (1). Compounds 1 and 3 showed significant cytotoxicity against human ECA-109.

Two new guaiane-type sesquiterpenoids from the fruits of Daucus carota L.

Two new guaiane-type sesquiterpenoids containing an interesting epoxy unit, daucuside (1) and daucusol (2) were isolated from the fruits of Daucus carota L. Their chemical structures were elucidated on the basis of MS, NMR spectroscopic analyses coupled with chemical degradation and they were also evaluated for the cytotoxic effects against two human gastric cancer cell lines BGC-823 and AGS.

Two new indolopyridoquinazoline alkaloidal glycosides from Ranunculus ternatus.

Two new indolopyridoquinazoline alkaloidal glycosides, 11-O-beta-D-glucopyranosyl rutaecarpine (ternatoside C) and 11-O-alpha-L-rhamnosyl-(1-->6)-beta-D-glucopyranosyl rutaecarpine (ternatoside D) were isolated from the roots of Ranunculus ternatus. Their structures were determined on the basis of spectroscopic and chemical methods.

Chemical constituents from the roots of Ranunculus ternatus.

Two new glycosides named as ternatoside A (1) and ternatoside B (2), with four known constituents sternbin (3), methylparaben (4), 4-O-D-glucopyranosyl-p-coumaric acid (5) and linocaffein (6) were isolated from the roots of Ranunculus ternatus, The structures of new compounds were determined by 1D and 2D NMR, MS techniques, and chemical methods.

Triterpenoid saponins from Lysimachia davurica.

Three new saponins were isolated from the whole plants of Lysimachia davurica. On the basis of 1D and 2D NMR ((1)H-(1)HCOSY, HMBC, HMQC, and TOCSY) techniques, MS, and hydrolysis, their structures were found to be 3-O-beta-D-glucopyranosyl-(1-->2)-[beta-D-glucopyranosyl-(1-->4)]-alpha-L-arabinopyranosyl-13,28-epoxy-3beta-hydroxy-16-oleanaone (1), 3-O-beta-D-glucopyranosyloxyuronic acid-(1-->2)-beta-D-xylopyranosyl-cyclamiretin A (2), and 3-O-beta-D-glucopyranosyl-(1-->2)-alpha-L-arabinopyranosyl-cyclamiretin A (3), respectively. Compounds 2 and 3 showed significant cytotoxicities against human A-2780 cells.