A new sesquiterpene from Chloranthus henryi / 中国中药杂志

Eight sesquiterpenes were isolated and purified from the ethanol extract of Chloranthus henryi by column chromatographies over silica gel, ODS and Sephadex LH-20,and preparative HPLC. Their chemical structures were established by spectral data and physiochemical properties as(1S,6S,8S,10R)-8-ethoxy-10-methoxychlomultin C(1),tianmushanol(2),multistalide A(3),myrrhterpenoid N(4),1α,9α-dihydroxy-8,12-expoxy-eudesma-4,7,11-trien-6-one(5),4β,10α-aromadendranediol(6),oplopanone(7),10α-hydroxycadinan-4-en-3-one(8). Among them, compound(1) was a new compound, and compounds 2-8 were isolated from Chloranthus henryi for the first time.

Chemical constituents of sesquiterpenes from Chloranthus multistachys / 中国中药杂志

With repeated silica gel, octadecyl silica(ODS), and Sephadex LH-20 column chromatography, normal-phase and reverse-phase high performance liquid chromatography(HPLC), etc., a pair of new enantiomers and 5 known compounds were separated from the 95% ethanol extract of Chloranthus multistachys. These compounds were identified by the nuclear magnetic resonance spectroscopy(including 1 D-NMR and 2 D-NMR), single-crystal X-ray diffraction, circular dichroism(CD) spectroscopy, mass spectrometry(MS), and some other methods as(1R,4R,5R,8S,10R)-chloraeudolide H(1 a),(1S,4S,5S,8R,10S)-chloraeudolide H(1 b), hydroxyisogermafurenolide(2), 4α-hydroxy-5α,8β(H)-eudesm-7(11)-en-8,12-olide(3), chloraniolide A(4), chlorantene D(5), 4α,8β-dihydroxy-5α(H)-eudesm-7(11)-en-8,12-olide(6). Compounds 1 a and 1 b are a pair of new eudesmane-type sesquiterpene enantiomers, and compounds 2-4 were isolated from C. multistachys for the first time.

Chemical constituents and antitumor activity from stems and leaves of Dioscorea opposita / 中草药

Objective: To investigate the chemical constituents from the stems and leaves of Dioscorea opposita. Methods: The compounds were isolated and purified by various column chromatographies, and their structures were identified by physiochemical properties and spectroscopic data. The effects of the compounds on the proliferation of human breast cancer MCF-7 cells and human liver cancer HepG2 cells were investigated. Results: Twenty compounds were isolated from the 50% acetone extract of the stems and leaves of D. opposita, which were identified as 1H-indazole (1), 1H-indole-3-carboxaldehyde (2), 1H-indole-3- carboxylic acid (3), 3-(2-oxopropyl)-3-hydroxy-indolin-2-one (4), thymidine (5), uridine (6), 3-hydroxy-3-(2-oxopropyl)-2,4-(1H,3H)- quinolinedione (7), hematinic acid (8), allantoin (9), 2-ethyl-3-methyl-maleimide-N-β-D-glucopyranoside (10), paulownin (11), (+)-8-hydroxypinoresinol (12), (+)-syringaresinol (13), (-)-dihydrodehydrodiconiferyl alcohol (14), (7R,8S)-dihydrodehydro- diconiferyl alcohol-4-O-β-D-glucopyranoside (15), (2E,6S)-6,7-dihydroxy-3,7-dimethyl-2-octenoic acid (16), (2E,4S)-4-hydroxy-2- nonenoic acid (17), (2E,6S)-6-hydroxy-2,6-dimethyl-2,7-dienoic acid (18), amarantholidoside IV (19), (9Z,11E)-13-methoxy- 9,11-octadecadienoic acid methyl ester (20), and their effects on proliferation of MCF-7 cells and HepG2 cells were investigated. compounds 1, 4, 8, 11-15, 18, 20 at a dose of 25μmol/L inhibited the proliferation of MCF-7 cells, and compounds 1, 4, 8, 12-14, 18, 20 at a dose of 25 μmol/L inhibited the proliferation of HepG2 cells. Conclusion: Compounds 1, 3-5, 10-12 and 15-20 are isolated from this plant for the first time, compounds 1, 4,8, 11-15, 18, 20 inhibited the the proliferation of MCF-7 and HepG2 cellssignificantly at certain concentration, showing protent antitumor activity.

Chemical compositions and anticancer activity of Mollugo pentaphylla / 中草药

Objective: To investigate the chemical compositions and anticancer activity of Mollugo pentaphylla. Methods: These compounds were isolated by various technologies, such as silica gel, Sephadex LH-20 and high performance liquid chromatography. Their structures were elucidated on the basis of physicochemical properties and spectroscopic data. The cytotoxic activities of compounds 1-5 against five cancer cell lines were tested by MTT. Results: Six compounds were isolated from this plant and identified as mollugoside E (1), 3-O-[α-L-rhamnopyranosy1 (1→2)-α-L-arabinopyranosyl]-28-O-[β-D-glucopyranosyl (1→6)-β-D- glucopyranosyl]oleanolic acid (2), raddeanoside R8 (3), raddeanin A (4), mollugogenol A (5), and oleanolic acid (6). The cytotoxic activities results showed that compounds 1-5 had certain inhibitory effects on human prostate cancer DU145 cell lines, cervical cancer Hela cell lines and early-juvenile leukemia HL 60 cell lines, especially on HL 60 cells with IC50 value of 10.21, 38.43, 40.28, 20.59, and 83.16 μmol/L, respectively. Conclusion: Compound 1 is a new triterpenoid saponin and compounds 2-4 are isolated first time from M. pentaphylla. The cytotoxic activities results showed that compounds 1-5 had certain inhibitory effects on DU145, Hela and HL 60 cell lines.

A new lignan from Gleditsiae spina / 药学学报

The chemical constituents from ethyl acetate extract of Gleditsiae spina were isolated and purified by various chromatographic methods such as MCI gel CHP-20, ODS, Sephadex LH-20, silica gel and semi-preparative HPLC. Seven lignans were isolated and identified by spectroscopic data analyses as (7R,8S,7'E,7''S,8''R)-buddlenol P (1), (+)-syringaresinol (2), (+)-isolariciresinol (3), (7S,8R)-cedrusin (4), (7S,8R)-4,9,9'-trihydroxy-3,3'-dimethoxy-7,8-dihydrobenzofuran-1'-propylneolignan (5), 3',4-O-dimethylcedrusin (6), balanophonin (7). Among them, compound 1 is a new lignan, compounds 2-7 are isolated from the Gleditsia L. for the first time. MTT method was used to investigate the effect of compounds 2-7 on LPS-induced injury of NRK-52e cells. As a result, compounds 2, 3 and 7 exhibit protective effects against LPS-induced damage to NRK-52e cells.

Two new terpenoids from Reduning Injection / 中草药·英文版

Objective: To study the antipyretic and anti-inflammatory constituents from the active fraction of Reduning (RDN) Injection. Methods: In this study, the active fraction of RDN Injection was screened by the LPS-induced mouse endotoxin shock model. The chemical constituents were isolated by chromatography on HP-20 macroporous adsorptive resins, silica gel, ODS columns and reverse phase MPLC and HPLC repeatedly, and their structures were elucidated based on spectroscopic analysis (HR-ESI-MS, NMR, ECD) and chemical methods. Meanwhile, we evaluated the anti-inflammatory activities of the isolates by measuring their inhibitory effects on TNF-α production in LPS stimulated RAW 264.7 macrophages. Results: The 95% ethanol eluate of RDN Injection by the macroporous adsorption resin column was proved to be the antipyretic and anti-inflammatory active fraction of this injection. A novel iridoid, named jasminoide A (1), and a new guaiane sesquiterpenoid, named (1R,7R,8S,10R)-7,8,11-trihydroxy-4-guaien-3-one (2), were isolated from Reduning injection, and compound 2 can inhibit TNF-α production with IC50 values of 72.24 µmol/L. Conclusion: In this study, two new terpenoids were isolated from Reduning Injection, and compound 2 showed inhibitory activity against LPS-activated TNF-α production in RAW 264.7 cells in vitro.

Tumor targeting and suppression effect in nude mice induced by rgd and r8 peptides modifieds liposomes loading ergosterol and cisplatin / 中国药学杂志

OBJECTIVE: To preliminarily evaluate the targeting and anti-lung cancer effect in vivo in nude mice induced by Cyclo (RGD) and R8 peptides modified ergosterol combined cisplatin liposomes. METHODS: The first step, injected RGD cyclo peptide and R8 peptide-modified, single modified or no modified ergosterol combined cisplatin liposome in the caudal vein of nude mouse bearing the tumor, the body distribution and targeting of each group under the different time points through small animals living imager were observed. The second step, continuously, dose every other day for 14 d, observating the weight of mice and the tumor growth situation. The animals were drawed blood and then were put to death, removing the tumor, the spleen and the lung tissue of all the mice. As the index of the tumor weight, the tumor suppression effect, the level of TGF-β1, TIMPs and TNF-α in serum, the spleen index and changes of the tumor and lung tissue, investigate the tumor suppression effect in mice of the liposomes preliminary. RESULTS: The targeting result of tumor-bearing nude mice displays that the fluorescence intensity of RGD and R8 peptides-modified liposome is the highest and the targeting is most obvious under high concentration and other group of liposome are weaker. Preliminary pharmacodynamics results show that each dosage group of mice have no obvious change in body weight and the high and middle dose group of RGD and R8 peptides-modified liposomes has tumor suppression effect obviously. The high dose group of RGD and R8 peptides-modified liposome is the most significant. It has high expression of cytokines (TNF-α) in serum. The spleen index of middle and low dose group of RGD and R8 peptides-modified liposomes significantly increased compared with positive medicine group. CONCLUSION: RGD cyclo peptide and R8 peptide-modified ergosterol combined cisplatin targeting liposome drug delivery system further improves the tumor targeting and anti-lung cancer effect in vivo.

Chemical Constituents from the Aerial Part of Sibiraea angustata / 中国药学杂志

OBJECTIVE: To study the chemical constituents of the aqueous extract from the aerial part of Sibiraea angustata. METHODS: The constituents were isolated by various chromatographic techniques(HP - 20 macroporous absorption resin, Sephadex LH - 20 gel, Reverse-phase silical gel and PHPLC) and their structures were determined on the basis of physicochemical properties and their spectroscopic data, as well as the literatures. RESULTS: Twelve compounds were separated and identified as veratric acid (1), (+) -cycloolivil(2), 3, 7-dimethyl-3(E) -6-octadien-5-one-1-O-β-D-glucoside(3), 3, 7-dimethyl-3(Z) -6-octadien-5-one-1-O- β-D-glucoside(4), 1-O-β-D-glucopyranosyl(1→2) -β-D-glucopyranosyl-3, 7 -dimethyl-2(E) -6-heptdiene(5), (7R, 8 S) -dihydrodehydrodiconiferyl alcohol-9'-O-β-D-glucopyranoside(6), (+) -1-hydroxypinoresinol-1-β-D-glucoside(7), skimmin(8), kaempferol 3-O-α- L-arabinopyranosyl-(1→6) -β-D-galactopyranoside (9), isorhamnetin-3-O-β-D-galactopyranosyl (1→6) -β-D-glucopyranoside (10), isorhamnetin 3-O-α-arabinopyranosyl-(1→6) -β-galactopyranoside(11), and quercetin 3-O-[2‴ -O-(E)-caffeoyl]-α-L-arabinopyranosyl-(1→6) -β-D-galactopyranoside(12). CONCLUSION: All compounds are obtained from the genus of Sibiraea for the first time.

Lignan Constituents of Patrinia villosa (Thunb.) Juss / 中国药学杂志

OBJECTIVE: To study the chemical constituents of Patrinia villosa (Thunb.) Juss. METHODS: The compounds were isolated by a combination of various chromatographic techniques including column chromatography over macroporous resin, Sephadex LH-20, and reversed-phase HPLC. Their structures were elucidated by physiochemical property and spectral analysis. RESULTS: Eleven compounds were isolated and identified as(7R, 8S)-3, 3', 5-trimethoxy-4', 7-epoxy-8, 5'-neolignan-4, 9, 9'-triol-9-O-β-D-glucopyranoside(1), massonianoside D(2), (7R, 8S)-dihydroxydehydrodiconiferyl alcohol-4-O-β-D-glucopyranoside(3), (7S, 8R)-dihydroxydehydrodiconiferyl alcohol-4-O-β-D-glucopyranoside(4), 7R, 8S-glochidioboside(5), lariciresinol-4-O-β-D-glucopyranoside(6), lariciresinol-9-O-β-D-glucopyranoside(7), lariciresinol-4'-O-β-D-glucopyranoside(8), tortoside B(9), tanegool(10), and tanegool-7'-methyl ether(11). CONCLUSION: All compounds are isolated from Patrinia genus for the first time.

Chemical constituents from Spiraea pubescens / 中草药

Objective: To investigate the chemical constituents from the ethanol extract of Spiraea pubescens. Methods: The compounds were isolated and purified by chromatography on silica gel, ODS, and preparative HPLC. Their structures were elucidated on the basis of chemical and spectroscopic methods, including MS, 1D, and 2D NMR spectral techniques. Results : Fourteen compounds were isolated and identified as β-sitosterol (1), tricosyl alcohol (2), stigmast-4-en-3-one (3), pentacosyl alcohol (4), stigmastanol (5), (+)-cyclo-olivil (6), (+)-africannal (7), (+)-lyoniresinol (8), 5-methoxy-(+)-isolariciresinol (9), (+)-isolariciresinol (10), (7R,8R)-4,7,9,9'-tetrahydroxy-3,3'-dimethoxy-8-O-4'-neolignan (11), (6S,9R)-6-hydroxy-3-one-α-ionol-9-O-β-D-glucopyranoside (12), (+)-lyoniresinol 9-O-β-D-xylopyranoside (13), and (-)-lyoniresinol 9-O-β-D-xylopyranoside (14). Conclusion: Compounds 2-5 and 7-14 are isolated from the plants of Spiraea L. for the first time, and compounds 1 and 6 are obtained from this plant for the first time.

Diterpenoids from a kind of soft coral Lobophytum sp / 中草药

Objective: To study the chemical constituents of a kind of soft coral Lobophytum sp. collected from Xisha islands of China. Methods: Isolation and purification of the chemical constituents were performed by silica gel and ODS gel column chromatographies as well as HPLC. Their structures were determined on the basis of physicochemical properties and spectroscopic methods. Results: Six diterpenoids were obtained in 95% ethanol extract from Lobophytum sp., including chilobolide B (1), (1S*,3S*,4S*,7E,11E)-3,4-epoxy-13-oxo-7,11,15-cembratriene (2), (2E,4E,7R,8S,12Z)-1-isopropylcyclotetradeca-4,8-dimethyl-7-hydroxy-1,3,11-triene-8,12-carbolactone (3), (2E,4E,8S,12Z)-1-isopropyl-4,8-dimethyl-7-oxocyclotetradeca-l,3,11-triene-8,12-carbolactone (4), sarcrassin D (5), and laevigatol B (6). Conclusion: Compound 1 is a new compound named chilobolide B. Compounds 2-4 are obtained from Lobophytum sp. for the first time.

Investigação do papel de SIGIRR/IL-1R8 no crosstalk entre células tumorais e o infiltrado leucocitário / Investigating the role of SIGIRR/IL-1R8 in the crosstalk between tumor cells and the immune system

Células tumorais desenvolvem diversas estratégias para escapar da identificação e eliminação pelo sistema imune. Dessa forma, a investigação dos mecanismos envolvidos na comunicação celular no microambiente tumoral e na desregulação local do sistema imune é crítica para uma melhor compreensão da progressão da doença e para o desenvolvimento de alternativas terapêuticas mais eficazes. Nós aqui demonstramos que SIGIRR/IL-1R8, um importante regulador negativo de receptores de Interleucina-1 (ILRs) e receptores do tipo Toll (TLRs), apresenta expressão aumentada em uma linhagem celular epitelial mamária transformada pela superexpressão do oncogene HER2 e em tumores primários de mama, e promove o crescimento tumoral e metástase através da modulação da inflamação associada ao câncer e da atenuação da resposta imune antitumoral. Observamos que IL-1R8 tem sua expressão correlacionada com HER2 em tecidos mamários e sua alta expressão é fator de pior prognóstico em câncer de mama de baixo grau. Notavelmente, níveis aumentados de IL-1R8 foram observados especialmente nos subtipos HER2+ e Luminais de tumores de mama, e sua expressão aumentada em células epiteliais de mama transformadas por HER2 diminui a ativação da via de NF-κB e a expressão de diferentes citocinas pro-inflamatórias (IL-6, IL-8, TNF, CSF2, CSF3 e IFN-ß1). Meio condicionado de células transformadas por HER2, mas não de variantes celulares com o gene IL-1R8 silenciado, induz a polarização de macrófagos para o fenótipo M2 e inibe a ativação de células NK. Em um modelo murino transgênico de tumorigênese espontânea mediada por HER2, MMTV-neu, verificamos que a deficiência de IL-1R8 (IL-1R8-/-neu) retardou o aparecimento de tumores e reduziu a incidência, a carga tumoral e a disseminação metastática. Contudo, não foram observadas diferenças significativas no crescimento tumoral quando animais IL-1R8-/-neu receberam medula óssea de animais IL-1R8+/+, confirmando um papel importante da expressão de IL-1R8 em células não hematopoiéticas na tumorigênese da mama. Tumores IL-1R8+/+neu apresentaram maiores níveis de citocinas pró-inflamatórias como IL-1ß e VEGF, e menores níveis da citocina imunomodulatória IFN-γ. Além disso, tumores que expressavam IL-1R8 apresentaram menor infiltrado de células NK maduras, células dendríticas (DCs) e linfócitos T-CD8+ e um maior infiltrado de macrófagos M2 e linfócitos T-CD4+. Coletivamente, esses resultados indicam que a expressão de IL-1R8 em tumores de mama pode representar um novo mecanismo de escape da resposta imune e suportam IL-1R8 como potencial alvo terapêutico

Tumor cells develop numerous strategies to fine-tune inflammation and avoid detection and eradication by the immune system. Identification of new players that regulate the cellular crosstalk within the tumor microenvironment and promote local immune dysregulation is critical to understand disease progression and to improve therapeutic strategies. Here, we demonstrate that SIGIRR/IL-1R8, a negative regulator of IL-1R and TLRs, is up-regulated in a HER2-transformed epithelial mammary cell line and in primary breast tumors and promotes tumor growth and metastasis by modulating cancer-related inflammation and impairing anti-tumor immunity. IL-1R8 expression is correlated with HER2 in mammary tissue, and higher tumor IL-1R8 expression is a poor prognostic factor in lower grade breast tumors. Notably, higher levels of IL-1R8 expression were observed in HER2+ and Luminal breast tumor subtypes and IL-1R8 up-regulation in HER2-transformed mammary epithelial cells inhibited NF-κB activation and the expression of pro-inflammatory cytokines (IL-6, IL-8, TNFα, CSF2, CSF3, IFN-ß1). Conditioned medium from HER2-transformed cells, but not from IL-1R8 knockdown variants, induced M2-macrophage polarization and inhibited natural-killer (NK) cell activation. IL-1R8 deficiency in a transgenic mouse model of breast tumorigenesis (MMTV-neu) significantly delayed tumor onset and reduced tumor incidence, burden and metastasis. No significant differences in tumor growth were observed when IL-1R8-/-neu mice were transplanted with bone marrow from IL-1R8+/+ animals, confirming an important role for IL-1R8 expression in non-hematopoietic cells during breast tumorigenesis. IL-1R8+/+neu mammary tumors presented higher levels of pro-inflammatory cytokines such as IL-1ß and VEGF, but lower levels of IFN-γ. Besides, a lower infiltrate of mature NK cells, dendritic cells (DCs) and CD8+ T cells but higher infiltrate of M2-macrophages and CD4+ T cells were present in IL-1R8 expressing tumors. Collectively, our results support IL-1R8 expression as a novel tumor immune escape mechanism in breast cancer and putative target for immunotherapy

Chemical constituents in n-butanol extract from pine needles of Cedrus deodara / 中草药

Objective: To investigate the chemical constituents in the n-butanol extract of pine needles of Cedrus deodara. Methods: Chemical constituents were separated and purified by silica gel and Sephadex LH-20 chromatography column. The structures were elucidated on the basis of physicochemical properties and spectral data (1H-NMR, 13C-NMR, and DEPT). Results: The compounds were identified as 1-(4'-hydroxy-3'-methoxyphenyl)-2-[4″-(3-hydroxypropyl)-2″-methoxyphenoxy]-1, 3-propanediol (1), (7S, 8R)-9, 9'-dihydroxy-3, 3'-dimethoxy-7, 8-dihydro-benzofuran-1'-propanol base neolignan-4-O-β-D-glucoside (2), (7R, 8R)-3', 9, 9'- trihydroxy-3-methoxy-7, 8-dihydro-benzofuran-1'-propanol base neolignans-9-O-α-L-rhamnoside (3), (6R, 9R)-6-hydroxy-3-oxo-α- ionol-9-O-β-D-glucopyranoside (4), (6R, 9R)-3-oxo-α-ionol-9-O-β-D-glucopyranoside (5), shikimic acid butyl ester (6), quinic acid butyl ester (7), (6S, 9R)-6-hydroxy-3-oxo-α-ionol-9-O-β-D-glucopyranoside (8), 5-p-trans-coumaroylguinic acid (9), and (E)-1-O-p- coumaroyl-α-D-glucopyranoside (10). Conclusion: Compounds 1-7 are isolated from C. Trew for the first time.

Preparation of transferrin and R8 co-modified liposome and study on its targeting to hepatoma / 中国生化药物杂志

Objective To prepare transferring and R8 co-modified liposome (TF/R8-LP)for forhepatoma targeting.Methods The co-modified liposome were prepared by film-ultrasonic method.The appearance,particle size,Zeta potential were evaluated.The cellular uptake by HepG2 cell in vitro was used to evaluate the targeting efficiency and in vivo imaging were used to evaluate the targeting efficiency. Results The particle diameter of the co-modified liposome was(108.5 ±12.6)nm and the Zeta potential was(24.15 ±4.78)mV.The liposome kept stable in 50% FBS at 24 h.The result demonstrated that the co-modified liposome uptaken by HepG2 were 2.4,2.6 times higher than that of R8-LP and TF-LP,respectively(P<0.05).The evaluation of tumor spheroid penetration and in vivo imaging results showed the co-modified liposome had the strongest fluorescence intensity. Conclusion The co-modified liposome might serve as a promising hepatoma delivery system of antitumor drugs.

Study on chemical constituents in shells of Juglans sigillata / 中草药

Objective: To investigate the chemical constituents in the shells of Juglans sigillata. Methods: The chemical constituents were isolated by silica gel, RP18, Sephadex LH-20, and MCI column chromatography and semi-preparative HPLC and so on. The structures were identified on the basis of spectroscopic analysis and chemical evidence. Results: Fifteen compounds were isolated and identified in the 70% ethanol extract from the shells of J. sigillata including seven phenolic glycosides: tachioside (1), mudanoside A (2), 4-O-β-D-glucopyranosylvanillc acid (3), breynioside A (4), 1-O-vanilloyl-β-D-glucose (5), 6'-O-vanilloyltachioside (6), and 6'-O-vanilloylisotachioside (7); three phenylpropanoide acid glycosides: 6-O-feruloyl-D-glucopyranose (8), methyl-4-O-coumaroylquinate (9), and 5-p-cis-coumaroylquinic acid (10); two tetralone glycosides: juglanin A (11) and juglanin E (12); one norsesquiterpenes glycoside: roseoside (13); one flavone: toxifolin (14); and one glucosylated abscisic acid derivate: (1'R, 3'R, 5'R, 8'S)-epi-dihydrophaseic acid β-D-glucoside (15). Conclusion: Except compound 14, the other compounds are isolated from the shells of J. sigillata for the first time. And compounds 1-4, 13, and 15 are reported for the first time from the plants in genus of Juglans L.

Chemical constituents from Syringa pinnatifolia / 中草药

Objective: To investigate the chemical constituents from the stems of Syringa pinnatifolia. Methods: The chemical constituents were isolated and identified by chromatography on silica gel, ODS, and Sephadex LH-20 columns, as well as RP-HPLC. Their structures were elucidated on the basis of physicochemical properties and spectral analyses. Results: Eleven compounds were isolated from S. pinnatifolia and their structures were identified as secoisolariciresinol (1), (8R, 8'R, 9R)-4, 4'-dihydroxy-3, 3', 9-trimethoxy-9, 9'-epoxylignan (2), (8R, 8'R, 9S)-4, 4'-dihydroxy-3, 3', 9-trimethoxy-9, 9'-epoxylignan (3), (-)-pinoresinol (4), (8R, 8'R, 9'S)-4, 4'-dihydroxy-3, 3', 9'-trimethoxy-9, 9'-epoxylignan (5), (8R, 8'R, 9'R)-4, 4'-dihydroxy-3, 3', 9'-trimethoxy-9, 9'-epoxylignan (6), (9S)-9-O-methylcubebin (7), dibutylphthalate (8), piperphilippinin VI (9), balanophonin (10), and larixnaphthaone (11). Conclusion: Compounds 2-11 are isolated from the plant for the first time.

Chemical constituents of antineoplastic actinomycete strain (N2010-37) of bottom mud in mangrove (I) / 中草药

Objective: To study the chemical constituents in the cultured filaments of an antitumor actinomycete strain (N2010-37). Methods: Compounds were isolated and purified by chromatographic techniques and recrystallization, and the structures were identified by spectral methods together with physicochemical analysis. The antitumor effects of these compounds were tested in vitro by MTT method. Results: Three compounds were identified including two anthrones and one novel macrolide. They were (3S, 4R, 7R, 8R, 9S)-3, 8-dihydroxy-4, 7,9-trimethyl-2,6-cyclononanediiolacetone (1), 2-hydroxy-1-methoxy-3- methylanthraquinone (2), and 1, 6, 8-thihydroxy-3-methylanthraquinone (3). Conclusion: Compound 1 is a new compound, and compounds 1 and 3 show the favorable cytotoxic activity against human chronic granulocytic leukemia cell line K562 strain by MTT method in vitro.

Protection by Chrysanthemum zawadskii extract from liver damage of mice caused by carbon tetrachloride is maybe mediated by modulation of QR activity

Our previous study demonstrated that methanolic extract of Chrysanthemum zawadskii Herbich var. latilobum Kitamura (Compositae) has the potential to induce detoxifying enzymes such as NAD(P)H:(quinone acceptor) oxidoreductase 1 (EC 1.6.99.2) (NQO1, QR) and glutathione S-transferase (GST). In this study we further fractionated methanolic extract of Chrysanthemum zawadskii and investigated the detoxifying enzyme-inducing potential of each fraction. The fraction (CZ-6) shown the highest QR-inducing activity was found to contain (+)-(3S,4S,5R,8S)-(E)-8-acetoxy-4-hydroxy-3-isovaleroyloxy-2-(hexa-2,4-diynyliden)-1,6-dioxaspiro [4,5] decane and increased QR enzyme activity in a dose-dependent manner. Furthermore, CZ-6 fraction caused a dose-dependent enhancement of luciferase activity in HepG2-C8 cells generated by stably transfecting antioxidant response element-luciferase gene construct, suggesting that it induces antioxidant/detoxifying enzymes through antioxidant response element (ARE)-mediated transcriptional activation of the relevant genes. Although CZ-6 fraction failed to induce hepatic QR in mice over the control, it restored QR activity suppressed by CCl4 treatment to the control level. Hepatic injury induced by CCl4 was also slightly protected by pretreatment with CZ-6. In conclusion, although CZ-6 fractionated from methanolic extract of Chrysanthemum zawadskii did not cause a significant QR induction in mice organs such as liver, kidney, and stomach, it showed protective effect from liver damage caused by CCl4.