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isolation, structure elucidation and inhibitory activity against LPS-induced NO production in macrophages

Twelve new diterpenes, caryopincaolide A-L (1-4, 11-12, 16-19, 27-28), together with twenty-eight known diterpenes, have been isolated from the whole plant of Caryopteris incana (Thunb.) Miq. Their structures were elucidated on the basis of 1D and 2D NMR, IR, X-ray crystal diffraction and mass spectroscopic data, as well as ECD calculations. All compounds were tested for in vitro dipeptidyl peptidase IV (DPP-IV) inhibitory activity, with compounds 3, 4, 28, 29, and 40 exhibiting DPP-IV inhibitory effects with IC50 values ranging from 54.2 to 228.9 μM. Compounds 1, 3 and 4 also showed potent activity toward the inhibition of the growth of human cancer cells and 1 can induce apoptosis in Hey and A-549 cells.

Here, I provide an overview of the solid-state characteristics, phase transformations and chemical reactions of metoclopramide hydrochloride monohydrate (MCP HCl H2O). Three unique techniques, including thermoanalytical methods, one-step simultaneous differential scanning calorimetry (DSC) and Fourier transform infrared (FTIR) microspectroscopy, and hot-stage microscopic (HSM) imaging, have been applied to study the solid-state phase transitions of MCP HCl H2O in continuous dehydration, amorphization and recrystallization processes. I also review the effects of grinding or heating on ion-exchange reactions, milling, compression or colyophilization on Maillard reactions, and γ-ray irradiation or electron beams on radiolysis in the solid state. I also report the exposure of MCP HCl H2O in solution to light, irradiation, oxidants or π-acceptors. This review will serve as a useful keynote for the evolving realm of solid-state chemistry research.

isolation, structure elucidation and cytotoxicity of three new cassane-type diterpenes, neocaesalpin AF (I), AG (II), and AH (III)

The unique polycyclic fused ring systems of Daphniphyllum alkaloids, along with their extensive bioactivities, make this family of alkaloids especially attractive targets for total synthesis and biogenetic studies. Successive discoveries of new alkaloids with unprecedented skeletons have made a great contribution to structural diversities of alkaloids elaborated by plants of the genus Daphniphyllum. By the end of 2008, more than 200 alkaloids belonging to 14 different skeletal types have been isolated from different parts of plants of thirteen Daphniphyllum species. These alkaloids show cytotoxic, antioxidant, vasorelaxant, and antiplatelet activating factor effects. The plausible biosynthetic pathways for Daphniphyllum alkaloids have been proposed and biomimetic total syntheses of some alkaloids completed. To provide an update of the previous reviews published in 2009, new structures, synthesis, and bioactivity of Daphniphyllum alkaloids reported in recent years are presented in this article. In the meantime, an additional 54 novel alkaloids have been isolated and identified. Among them, some possess unprecedented frameworks. Several inspired organic syntheses were completed.

isolation and structure determination of platycodon A (Ia) and B (Ib), which show remarkable cytotoxic activities against HepG-2 and A549 cancer cell lines

The solid-state chemistry of drugs has seen growing importance in the pharmaceutical industry for the development of useful API (active pharmaceutical ingredients) of drugs and stable dosage forms. The stability of drugs in various solid dosage forms is an important issue because solid dosage forms are the most common pharmaceutical formulation in clinical use. In solid-state stability studies of drugs, an ideal accelerated method must not only be selected by different complicated methods, but must also detect the formation of degraded product. In this review article, an analytical technique combining differential scanning calorimetry and Fourier-transform infrared (DSC–FTIR) microspectroscopy simulates the accelerated stability test, and simultaneously detects the decomposed products in real time. The pharmaceutical dipeptides aspartame hemihydrate, lisinopril dihydrate, and enalapril maleate either with or without Eudragit E were used as testing examples. This one-step simultaneous DSC–FTIR technique for real-time detection of diketopiperazine (DKP) directly evidenced the dehydration process and DKP formation as an impurity common in pharmaceutical dipeptides. DKP formation in various dipeptides determined by different analytical methods had been collected and compiled. Although many analytical methods have been applied, the combined DSC–FTIR technique is an easy and fast analytical method which not only can simulate the accelerated drug stability testing but also at the same time enable to explore phase transformation as well as degradation due to thermal-related reactions. This technique offers quick and proper interpretations.

Neocaesalpin S (Ia), T (Ib), U (Ic) and V (II) show mild antiproliferative activities against liver cancer (HepG-2) and breast cancer (MCF-7).

by Huai-Qiong Chena), Jian-He Wei*a), Jun-Shan Yanga), Zheng Zhanga), Yun Yangb), Zhi-Hui Gaoa), Chun Suia), and Bao Gongb) a) Institute of Medicinal Plant Development (Key Laboratory of Bioactive Substances and Resources Utilization of Chinese Herbal Medicine, Ministry of Education), Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100193, P. R. China (phone: þ86-10-62818841; e-mail: wjianh@263.net) b) Hainan Branch Institute of Medicinal Plant (Hainan Provincial Key Laboratory of Resources Conservation and Development of Southern Medicine), Chinese Academy of Medical Sciences & Peking Union Medical College, Wanning 571533, P. R. China

Two new flavone C-glycosides, trollisin A (1) and trollisin B (2), along with seven known flavonoids, isoswertisin (3), isoswertiajaponin (4), orientin (5), 2″-O-β-L-galactopyranosylvitexin (6), 2″-O-β-L-galactopyranosylorientin (7), neodiosmin (8) and acacetin-7-O-neohesperidoside (9) were isolated from the flowers of Trollius ledebourii REICHB. The structures of the new compounds were elucidated based on spectral analysis, including MS, 1D- and 2D-NMR experimentation.

The isolation and structure elucidation of two novel sesquiterpenes, stereumin F (I) and G (II), are reported.

Four new bibenzyl derivatives, shancigusins A-D (1-4) and five known bibenzyls (5-9) were isolated from the tubers of Pleione yunnanensis (Orchidaceae). The structures of these compounds were determined by extensive analyses of their spectroscopic data.

Three new sesquiterpene glycosides, 8β,9β-epoxy-4α-hydroxy-5αH-lindan-7(11)-en-8α,12-olide-15-O-β-D-glucopyranoside (1, sarcaglaboside F), 4α-hydroxy-5α,8βH-lindan-7(11)-en-8α,12-olide-15-O-β-D-glucopyranoside (2, sarcaglaboside G), 4α-hydroxy-5α,8βH-eudesman-7(11)-en-8α,12-olide-15-O-β-D-glucopyranoside (3, sarcaglaboside H), together with five known compounds, chloranoside A (4), sarcaglaboside C (5), dihydrovomifoliol-O-β-D-glucopyranoside (6), 9-hydroxy-heterogorgiolide (7) and chloranthalactone B (8), were isolated from Sarcandra glabra THUMB. NAKAI. The structures and relative configurations of three new compounds were determined on the basis of their spectroscopic data and chemical evidence.

In the previous work we reported five lanostane-type triterpenes from the CHCl(3) soluble fraction of Fomes officinalis. In further study on the isolation of constituents from the CHCl(3) soluble fraction, four new triterpenes, fomefficinic acids F (1), G (2) and fomefficinols A (3), B (4), together with seven known compounds officinalic acid (5), fomlactone A (6), fomlactone B (7), fomlactone C (8), laricinolic acid (9), ergosterol (10), ergota-7,22,dien-3beta-ol (11) were isolated. The structures of new compounds were determined by spectroscopic analyses and chemical methods including NMR spectroscopic techniques ((13)C, (1)H, heteronuclear multiple quantum coherence (HMQC), heteronuclear multiple bonding correlation (HMBC), correlation spectroscopy (COSY) and nuclear Overhauser effect spectroscopy (NOESY)).

Two new compounds were isolated from the stems of Dendrobium candidum: (R)-3,4-dihydroxy-5,4',alpha-trimethoxybibenzyl (1), named dendrocandin A; and 4-[2-[(2S,3S)-3-(4-hydroxy-3,5-dimethoxyphenyl)-2-hydroxymethyl-8-methoxy-2,3-dihydrobenzo[1,4]dioxin-6-yl]ethyl]-1-methoxyl benzene (2), dendrocandin B. Five previously known bibenzyls were also identified: 4,4'-dihydroxy-3,5-dimethoxybibenzyl (3), 3,4-dihydroxy-5,4'-dimethoxybibenzyl (4), 3-O-methylgigantol (5), dendrophenol (6), and gigantol (7).

Two new compounds vernonioside S and vernoniether S were isolated from the stem of Vernonia cumingiana , and their structures were elucidated on the basis of spectroscopic evidences.

Three new flavanone glycosides named garccowaside A, garccowaside B, garccowaside C, and three other known compounds were isolated from the ethanol extract of the stems of Garcinia cowa. These structures were established on the basis of spectroscopic evidence. Twelve compounds isolated from the stems of Garcinia cowa were tested for cytotoxic activities.

Five new cyclolanostane triterpene glycosides, 12-deacetyloxy-15alpha-hydroxy-23-epi-26-deoxyactein, 12-deacetyloxy-23-epi-26-deoxyactein, 24-O-acetyldahurinol-3-O-beta-D-xylopyranoside, 12beta-hydroxycimigenol-3-O-beta-D-xylopyranosyl-(1--3)-beta-D-xylopyranoside, 25-anhydrocimicigenol-3-O-beta-D-(2'-O-acetyl)xylopyranoside, were isolated from the rhizome of Souliea vaginata collected in China. Their structures were elucidated by spectroscopic techniques, including 2D NMR spectra, and in the case of 5, by chemical correlation.

Five new lanostane-type triterpenes, named fomefficinic acid A-E (1-5), were isolated from the dried sclerotium of Fomes officinalis, respectively. Their structures were established as 24-methylene-3-oxo-lanost-8-en-21-oic acid (1), 3alpha,15alpha-dihydroxy-24-methylene-lanosta-7,9(11)-dien-21-oic acid (2), 3alpha,15alpha-dihydroxy-24-methylene-lanost-8-en-21-oic acid (3), 15alpha-hydroxy-3-oxo-24-methylenelanost-8-en-21-oic acid (4), 15alpha-acetoxy-3-oxo-24-methylenelanosta-7,9(11)-dien-21-oic acid (5), by spectral analysis and chemical methods as well as comparison with known compounds.