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Ripe fruits of Amomum villosum Lour. are important traditional Chinese medicines and food spices. Due to similar morphological and anatomical characteristics, fruits from some Alpinia species are used clinically as substitutes or adulterants of Fructus Amomi. In this study, we determined the nrDNA ITS1 (internal transcribed space 1) sequences from Amomum villosum and ten Alpinia species, which are adulterants of Fructus Amomi. The ITS1 sequences of these species were 175~179 bp in length, and the G+C contents were 53.37~56.74%. Sequence alignment revealed that there were 55 polymorphic nucleotide sites among the tested species. The base substitution were 0.57~9.60% within the ten Aplinia species, but 17.61~21.59% between Amomum villosum and the Alpinia species. These molecular data indicated that ITS1 sequences can be used to differentiate Fructus Amomi and its substitutes or adulterants from various Alpinia species.

Five new compounds, dencryol A (1), dencryol B (2), crystalltone (3), crystallinin (4), and 3-hydroxy-2-methoxy-5,6-dimethylbenzoic acid (5), together with six known compounds, dendronobilin B (6), syringic acid (7), apigenin (8), isoviolanthin (9), 6'''-glucosyl-vitexin (10), and palmarumycin JC2 (11), have been isolated from the stems of Dendrobium crystallinum, of which compounds 9-11 were isolated from the genus Dendrobium for the first time, and all the other compounds were first obtained from this plant. Their structures were established on the basis of spectroscopic analysis and literature data.

Sensitive, selective and reliable high-performance liquid chromatography (HPLC)-diode array detection (DAD)/electrospray ionization multi-stage mass spectrometry (ESI-MSn) methods have been developed for the characterization of nine 2-glucosyloxycinnamic acid derivatives and quantitative analysis of three of the major 2-glucosyloxycinnamic acids, cis-melilotoside, trans-melilotoside and dihydromelilotoside, present in Dendrobium medicinal plants. The identities of the latter three major 2-glucosyloxycinnamic acids were confirmed by comparing their retention times, UV and mass spectra with those of the reference standards. The characteristic ESI-MSn fragmentation patterns of the remaining six 2-glucosyloxycinnamic acid derivatives, which are similar to the three major compounds, have allowed the putative elucidation of their structures. The concentrations of the cis-, trans- and dihydromelilotosides were simultaneously determined by HPLC/ESI-MS2 using the multiple reaction monitoring (MRM) mode in extracts of Dendrobium species. The method was validated with respect to the overall intra- and inter-day variation (RSD less than 8%) and the limits of quantification for the cis-, trans- and dihydromelilotosides were 0.09, 0.09 and 0.01 µg/mL, respectively. Copyright © 2007 John Wiley & Sons, Ltd.

The genus Dendrobium Sw. is composed of 74 species and two varieties in China, and 32 species carry the name "Huangcao Shihu" on the herbal medicine market, making the identification of the origin of "Huangcao Shihu" difficult for consumers. Here, the ITS regions were sequenced and evaluated to differentiate the 18 Dendrobium species used as "Huangcao Shihu". Diversity in DNA sequences among various species was found with the inter-specific sequence divergence ranging from 3.2% to 37.9% in ITS1 and 5.0% to 26.6% in ITS2. Moreover, the variations within species were very low, ranging in sequence divergence from 0 to 3.0% in ITS1 and 0 to 4.0% in ITS2. Therefore, these species could be easily distinguished at the DNA level. Furthermore, based on the divergent ITS regions, five pairs of species-specific primers were designed and used for the rapid PCR identification of five Dendrobium species listed in the Chinese Pharmacopoeia.

A novel method has been developed for simultaneous analysis for three pairs of trans - and cis -isomers of 2-glucosyloxycinnamic acids, along with their biogenic metabolites (three coumarin derivatives including scopoletin, scoparone and ayapin) in a Chinese medicinal herb Dendrobium thyrsiflorum by using high-performance liquid chromatography (HPLC)-photodiode array detection (DAD)-electrospray ionization (ESI)-tandem mass spectrometry (MS). The method was carried out by using a Polaris C 18 column with a gradient solvent system of 0.5% acetic acid aqueous solution–acetonitrile. Seven target analytes including isodensifloside, isothyrsifloside, densifloside, thyrsifloside, scoparone, ayapin and scopoletin were exclusively identified by comparing their retention behaviors, UV and MS spectra with the authentic standards, and their contents in D. thyrsiflorum were simultaneous determined by employing UV detection at 342 nm. In addition, another pair of isomers of 2-glucosyloxycinnamic acids was putatively elucidated mainly based on the MS fragmentation. The method was validated and found to be satisfactorily linear, selective and robust. Recoveries ranged from 95.56 to 97.94% for all compounds at three different spiking levels. The limits of detection (LOD) and quantitation (LOQ) ranged, respectively, from 0.02 to 0.13 μg mL −1 and 0.07 to 0.39 μg mL −1 depending on various compounds. The established quality evaluation method was successfully used for evaluating the quality of D. thyrsiflorum samples of different organs and collections.

Two novel triterpenes (1 and 2) were isolated from the orchid Pholidota yunnanensis Rolfe. Using chemical and spectral analyses (UV, IR, MS,1D-NMR and 2D-NMR), these two triterpenes were established as 25-methylenecyclopholidonyl p-hydroxy-trans-cinnamate (1; named pholidotine A) and 25-methylenecyclopholidonyl p-hydroxy-cis-cinnamate (2; named pholidotine B). ( Managing editor: Wei WANG)

The Euphorbiaceae is an extensive family of plants that includes about 300 genera and 5000 species and is mainly distributed in tropical areas. For a long time this family has been recognized and reported for its anti-cancer components, anti-hepatitis B components and carcinogenic factors. In the literature of ancient traditional Chinese medicine (TCM), 33 species of plants from 17 genera of Euphorbiaceae have been mentioned as medicines. We report here the results of our recent investigation. The locations under investigation were in Guangdong Province, Guangxi Zhuang Nationality Autonomous Region and Hainan Province in southeastern China. There were 111 species within 35 genera of medicinal Euphorbiaceous plants reported, along with their folk usages. Among them, 17 species are used to treat snakebites. It was observed that most of the species within the Euphorbiaceae family contained toxic components. In fact, only a few species are employed as widespread medicines throughout China—most specie...

Two novel compounds, (9R)-4-methoxy-9H-fluorene-2,5,9-triol (1a) and 2,7-dihydroxy-8-methoxyphenanthro[4,5-bcd]pyran-5(5H)-one (2) were isolated from the stems of the orchid Dendrobium chrysotoxum Lindl. Their structures were established spectroscopically, by chemical derivatization, and by single-crystal X-ray diffraction analysis. The absolute configuration of 1a was determined by Mosher's method. Neither compound showed antitumoral activity.

Bio-guided fractionation of the stems of Dendrobium aurantiacum var. denneanum using a 1,1-diphenyl-2-picryl-hydrazyl (DPPH) radical scavenging assay, led to the isolation of three 2-glucosyloxycinnamic acid derivates, namely, cis-melilotoside, trans-melilotoside and dihydromelilotoside, respectively. Their structures were elucidated through the analysis of uni- and bi-dimensional NMR, UV, IR and MS data. All these three compounds were first reported from the genus Dendrobium and exhibited potent antioxidant activities.

The whole plant of Ixeris sonchifolia afforded two new guaianolide sesquiterpene lactones named 8-desoxyartelin [3-hydroxy-1(10),3-guaiadiene-12,6-olide-2-one] and ixerin Z [1(10),3,11(13)-guaiatriene-12,6-olide-2-one-3- O -glucopyranoside], along with the known compound 9α-hydroxyzaluzalin C, whose structure and stereochemistry wee determined by spectroscopic methods.

An extract from the entire Ixeris denticulata f. pinnatipartita plant afforded the guaianolide sesquiterpene lactone glucoside, 8 beta,15-dihydroxy-1(10),3,11(13)-guaiatrien-12,6-olide-15-O- glucopyranoside, along with the known flavonoids luteolin-7-O-glucoside and luteolin-7-O-glucuronide-6'-methyl ester; their structures were determined by spectroscopic methods. Ixerin Y inhibited the growth of human breast cancer MCF7 and MDA468 cell lines.

Two new dammarane triterpene glycosides named notoginsenosides Rw 1 (1) and Rw 2 (2) were isolated from the rhizomes of Panax notoginseng, together with 20 known compounds including protopanaxadiol (3), protopanaxatriol (4), ginsenosides Rb1 (5), Rd (6), Re (7), Rg1 (8), Rg2 (9), 20-(S)-Rg3 (10), 20-(R)-Rg(3) (11), Rh1 (12), Rh4 (13), Rf (14), 20-O-glucopyranosyl Rf (15), notoginsenosides R1 (16), R2 (17), T5 (18), S (19), T (20), and Fa (21), and koryoginsenoside R1 (22). Based on FABMS, HRFABMS, IR, (1)H, 13C, and 2D-NMR (HSQC, HMBC, and COSY) spectral data, the structures of the new compounds were elucidated as 6-O-beta-d-xylopyranosyl-20-O-beta-d-xylopyranosyl-(1 --6)-beta-d-glucopyranosyldammar-24-ene-3beta,6alpha,12beta,20(S)tetraol (1) and 6-O-beta-d-xylopyranosyl-(1 --2)-beta-d-glucopyranosyldammar-22-ene-(trans)-3beta,6alpha,12beta,20(S), 25-pentaol (2). Compounds 3, 4, 13, and 22 were isolated from P. notoginseng for the first time.

Two new bibenzyl derivatives, named dengraols A 1 and B 2, are isolated from stems of Dendrobium gratiosissimum Rchb. (Orchidaceae), together with seven known compounds: 3,5,4'-trihydroxybibenzyl 3, 3,4'-dihydroxy- 5-methoxybibenzyl 4, 3, 4 -dihydroxy-5, 4' - dimethoxy bibenzyl 5, 3, 4' - dihydroxy - 4, 5, 3'-trimethoxybibenzyl (moscatilin) 6 and 5, 4'- dihydroxy -3, 3'-dimethoxybibenzyl (gigantol) 7, 5, 3', 4'-trihydroxy - 3- methoxy-bibenzyl (tristin) 8 and 5, 3'- dihydroxy- 3-methoxybibenzyl (batatasin III) 9. Among the isolated compounds, dengraols A 1 and B 2, moscatilin 6 and gigantol 7 showed inhibitory activity of proliferation on HL-60 cells with IC 50 values at 2.1, 6.4, 0.082 and 10.6 (μM, respectively.

The whole plant of Ixeris sonchifolia afforded two new guaianolide sesquiterpene lactones named 8-desoxyartelin [3-hydroxy-1(10),3-guaiadiene-12,6-olide-2-one] and ixerin Z [1(10),3,11(13)-guaiatriene-12,6-olide-2-one-3- O -glucopyranoside], along with the known compound 9α-hydroxyzaluzalin C, whose structure and stereochemistry wee determined by spectroscopic methods.

One bi-bicyclic and two bi-tricyclic derivatives of coumarin-benzofuran, phenanthrene-phenanthrene and phenanthrene-phenanthraquinone, along with seven known compounds, were isolated from stems of Dendrobium thyrsiflorum Rchb.f. (Orchidaceae). On the basis of chemical, NMR (1H, 13C, HMQC, HMBC and NOESY) and mass spectrometry data, their structures were elucidated as denthyrsin [3-(5',6'-dimethoxybenzofuran-2'-yl)-6,7-dimethoxy-2H-chromen-2-one; 1], denthyrsinol (4,5'-dimethoxy-[1,1']biphenanthrenyl-2,5,4',7'-tetraol; 2), and denthyrsinone (7,4',7'-trihydroxy-2,2',8'-trimethoxy-[5,1']biphenanthrenyl-1,4-dione; 3). Compounds 1-3 and denthyrsinin (1,5,7-trimethoxyphenanthrene-2,6-diol; 4) showed significant cytotoxic activities against Hela (13.5, 9.3, 9.9 and 2.7 microM, respectively), K-562 (0.45, 1.6, 6.0 and 2.3 microM, respectively) and MCF-7 (18.1, not tested, 3.5 and 4.8 microM, respectively) cell lines.

The rhizomes of Alpinia jianganfeng are used as a traditional Chinese medicine, Jian Gan Feng, to cure rheumatism in Guangdong, China. The rhizomes of some other species of the genus Alpinia such as A. japonica, A. suishaensis and A. nanchuanensis are also used as Jian Gan Feng in Southwest China. However, the identification of the original plants of the crude drugs is difficult. The internal transcribed spacers and the 5.8S coding region of nuclear ribosomal DNA of the four species were sequenced and analyzed. The DNA markers have been determined and they can be used for the molecular identification of these medicinal plants.

A new beta-carboline alkaloid, 1-acetyl-8-hydroxy-beta-carboline, was isolated from the fern, Hypodematium squamuloso-pilosum, along with a known compound, 1-acetyl-beta-carboline. Their structures were elucidated from spectral evidence. This is the first report of this type of alkaloid being found in ferns.

An extract from the entire Ixeris denticulata f. pinnatipartita plant afforded the guaianolide sesquiterpene lactone glucoside, 8 beta,15-dihydroxy-1(10),3,11(13)-guaiatrien-12,6-olide-15-O- glucopyranoside, along with the known flavonoids luteolin-7-O-glucoside and luteolin-7-O-glucuronide-6'-methyl ester; their structures were determined by spectroscopic methods. Ixerin Y inhibited the growth of human breast cancer MCF7 and MDA468 cell lines.

The whole plant of Ixeris denticulata f. pinnatipartita and I. sonchifofia respectively afforded a new guaianolide sesquiterpene lactone glucoside named ixerin X, 8(,15-dihydroxy-1(10), 3,11(13)-guaiatriene-12,6-olide-15-O-β-D-glucopyranoside ( 1 ), ixerin Z, 1(10),3,11(13)-guaiatriene-12,6-olide-2-one-3-O- β -D-glucopyranoside ( 2 ), whose structure and stereo-chemistry were determined by spectroscopic methods. 1 inhibited the growth of human breast cancer MCF7 & MDA468 cell lines.

Based on rDNA ITS sequences of D. officinale and the other 37 species of Dendrobium, a pair of allele-specific diagnostic primers, TP-JB01S and TP-JB01X, were designed to authenticate D. officinale from the other species. Before the diagnostic PCR, the primer pair, P1 and P2, for amplifying the whole ITS region was used to validate template DNA and to obtain the appropriate template DNA for the diagnostic PCR. Diagnostic PCRs were performed using the diagnostic primers with the total DNAs of the original plants as a template. When the annealing temperature was raised to 66 degrees C, only the template DNA of D. officinale could be amplified whereas the diagnostic PCRs of the other Dendrobium species were all negative. The diagnostic PCRs have been repeated many times and have played an important role in authenticating the stems of D. officinale in China. Compared with the authentication method by sequencing DNA fragments, the allele-specific diagnostic PCR is not only simpler and time-saving but also practical and effective.