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Alkaloids from Mongolian species Hypecoum lactiflorum Kar. et Kir. Pazij

A new secoberbine alkaloid (-)-N-methylcorydalisol was isolated from the aerial parts of Hypecoum lactiflorum Kar. et Kir. Pazij. (Papaveraceae) of Mongolian origin and was characterised. The known alkaloids of protopine and protoberberine type protopine, allocryptopine, (-)-N-methylcanadine and (-)-N-methylstylopine were also isolated. (-)-N-methylstylopine is a new alkaloid for the genus, while (-)-N-methylcanadine is new for the species. All structures were established by physical and spectral analysis.

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ALKALOIDS FROM Corydalis nobilis (L.) Pers. AND C. intermedia (L.) MERAT

Rhizomes of Corydalis nobilis (L.) Pers. (3percent of alkaloids) contain (+)-tetrahydropalmitine, (+)-bicuculline and (+)-corytuberine as the main constituents of the tertiary alkaloid fraction.Protopine, (+)-corypalmine and (+)-stylopine, which also belong to the dominant alkaloids, were isolated in lesser amounts.As minor alkaloids were isolated (+/-)-tetrahydropalmatine, (+)-corydaline, allocryptopine, cryptopine, (-)-scoulerine, (+)-adlumidine, (+)-sinactine, (+/-)-corlumine, isoboldine, (+)-corybulbine, (+/-)-stylopine and (-)-isocorypalmine.The fraction of quaternary protoberberine alkaloids afforded coptisine, dehydrocorydaline, palmatine, corysamine, jatrorrhyzine and cis-N-methylstylopinium hydroxide.Aobamidine (Z-adlumidiceine enol lactone), isolated as the principal alkaloid of aerial parts (0.3 percent of alkaloids), is obviously an artifact arising from bicuculline N-metho salt during the isolation process.Further dominant alkaloids of the tertiary fraction were adlumidine, bicuculline, protopine, (+/-)-tetrahydropalmatine and (+/-)-corlumine; as minor alkaloids were isolated corytuberine, scoulerine, corypalmine, cryptopine, isocorypalmine, corybulbine, (+)-corydalidzine, and unidentified alkaloids CN 1 (C23H25NO5, m.p.211 deg C) and CN 2 (m.p.261 deg C).Quternary protoberberine fraction afforded coptisine and palmatine.Nineteen of the mentioned alkaloids were isolated froom this species for the first time.Tubers of C.intermedia (L.) Merat (0.7 percent of alkaloids) afforded protopine, tetrahydropalmatine and corydaline as the main alkaloids and allocryptopine, canadine, stylopine, palmatine, dehydrocorydaline, berberine, coptisine as minor alkaloids, together with traces of bicuculline and magnoflorine.Dominant alkaloids of the aerial part (0.73 percent of alkaloids) were bicuculline, bulbocapnine, protopine, stilopine and an unidentified phenolic base, m.p. 258 deg C.Isoboldine, scoulerine, allocryptopine, corydaline, canadine, coptisine, palmatine and berberine were identified as the minor alkaloids.

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Structural characterization and identification of major constituents in jitai tablets by high-performance liquid chromatography/diode-array detection coupled with electrospray ionization tandem mass spectrometry

In the present study a universally applicable HPLC-DAD/ESI-MS/MS method was developed for carrying out the comprehensive characterization of Jitai tablets (JTT). Based on the ESI-MSn fragmentation patterns of the reference standards, a total of 101 components were identified or tentatively characterized by comparing their retention times, UV and MS spectra with those of reference standards or through the matching of empirical information with those of published components in the in-house library. The characteristic fragmentation pattern of alkaloids, phenolic acids, tanshinones, flavonoid glycosides, cyanogenic glycosides, ginsenosides, 2-(2-phenylethyl) chromones, phthalides and gingerol-related compounds were tentatively elucidated using structurally-relevant product ions. It was observed that neutral losses of C9H10O3 and C9H8O 2 were the characteristic product ions of scopola alkaloids. Neutral fragment mandelonitrile was the characteristic ion of cyanogenic glycosides. To our knowledge, tropylium ion and C4H2O unit were the characteristic ions of 2-(2-phenylethyl) chromone, which resulted from the Retro-Diels-Alder (RDA) cleavage of the C ring. The results indicated that the developed analysis method could be employed as a rapid, effective technique for structural characterization of chemical constituents in TCM. This work is expected to provide comprehensive information for the quality evaluation and pharmacokinetic studies of JTT.

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Isolation and characterization of a cDNA encoding (S)-cis-N-methylstylopine 14-hydroxylase from opium poppy, a key enzyme in sanguinarine biosynthesis

Sanguinarine is a benzo[. c]phenenthridine alkaloid with potent antimicrobial properties found commonly in plants of the Papaveraceae, including the roots of opium poppy (. Papaver somniferum). Sanguinarine is formed from the central 1-benzylisoquinoline intermediate (. S)-reticuline via the protoberberine alkaloid (. S)-scoulerine, which undergoes five enzymatic oxidations and an N-methylation. The first four oxidations from (. S)-scoulerine are catalyzed by cytochromes P450, whereas the final conversion involves a flavoprotein oxidase. All but one gene in the biosynthetic pathway from (. S)-reticuline to sanguinarine has been identified. In this communication, we report the isolation and characterization of (. S)-. cis-. N-methylstylopine 14-hydroxylase (MSH) from opium poppy based on the transcriptional induction in elicitor-treated cell suspension cultures and root-specific expression of the corresponding gene. Along with protopine 6-hydroxylase, which catalyzes the subsequent and penultimate step in sanguinarine biosynthesis, MSH is a member of the CYP82N subfamily of cytochromes P450. The full-length MSH cDNA was expressed in Saccharomyces cerevisiae and the recombinant microsomal protein was tested for enzymatic activity using 25 benzylisoquinoline alkaloids representing a wide range of structural subgroups. The only enzymatic substrates were the N-methylated protoberberine alkaloids N-methylstylopine and N-methylcanadine, which were converted to protopine and allocryptopine, respectively.

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Antiparasitic activity of certain isoquinoline alkaloids and their hypothetical complexes with oligonucleotides

The antiparasitic activity of two tetrahydrodiisoquinoline alkaloids 2, 3, beta-allocryptopine (4), protopine (5), and a substituted phenylethylamine 6 was studied. Compounds 2 and 6 inhibited the growth of the parasite Leishmania donovani. The capability of the examined compounds to bind DNA was estimated by molecular modeling. It has been shown that binding occurs in the small groove and primarily at the AT-enriched part of the oligonucleotide.

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ALKALOIDS OF Corydalis paniculigera

The alkaloid composition of the roots of Corydalis paniculigera Rgl., collected in the flowering phase in the Alai range, has been studied.Chloroform extraction yielded 0.39percent of total alkaloids, from which were isolated wilsonirine, thalicmidine, coclaurine, stylopine, dihydrosanguinarine, sanguinarine, oxosanguinarine, adlumine, adlumidine, bicucculine, sibiricine, protopine, pancorine, and corunnine, and new alkaloids which have been called pancoridine (I) and pancorinine (II).The structures of (I) and (II) have been established on the basis of spectral characteristics and also the production of wilsonirine on their reduction in sulfuric acid.

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Conversion of Protopine into the Secoberbines Corydalisol and Hypecorine

Pyrolysis of protopine N-oxide (6) leads to the dibenzoxazacycloundecine (7) whose reduction with palladium catalyst affords (+/-)-corydalisol (2).Alternatively, zinc in acetic acid treatment of (7) leads to (+/-)-hypecorine (3) and (+/-)-corydalisol (2).

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Isoquinoline alkaloids from Thalictrum delavayi

Two new protoberberine alkaloids, 2,3,9,10-dimethylenedioxy-8-oxoprotoberberine (1) and 2,3,9,10-dimethylenedioxy-l,8-dihydroxyprotoberberine (2), together with nine known isoquinoline-type alkaloids were isolated from the roots of Thalictrum delavayi. Their structures were elucidated by spectral methods. Among these compounds, pseudoprotopine showed competitive inhibition activity by DA receptor binding assay (D1) in vitro. The competitive inhibitions were 87.5% (10-4 M) and 15.6% (10-6 M), respectively.

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Systems pharmacology-based dissection of the active ingredients and targets of Yiqi Zishen formula for application to COPD

In this work, a systems pharmacology model based on the pharmacokinetic analysis, drug targeting, and drug-target-disease network analyses, was applied specifically to uncover the active ingredients and therapeutic targets of Yiqi Zishen formula (YZF). Furthermore, a rat model of cigarette smoke-and bacterial infection-induced chronic obstructive pulmonary disease (COPD) was applied to evaluate the effects of YZF on COPD and its comorbidity. The expression of interleukin (IL)-1beta, IL-6, tumor necrosis factor (TNF)-alpha, soluble TNF-alpha receptor (sTNFR2), matrix metalloproteinase (MMP)-2, MMP-9, tissue inhibitor of MMP (TIMP)-1, endothelin (ET)-1, transforming growth factor (TGF)-beta, vascular endothelial growth factor (VEGF), and basic fibroblast growth factor (bFGF) were analyzed by immunohistochemistry. The pharmacological system efficiently generated 158 active compounds from YZF, and predicted 192 potential targets. The result showed that there was a significant target overlap between the 12 herbs in the YZF formula, which means that each herb of YZF connected with the similar targets, implying the synergistic effects among them. The target-disease network results indicated that YZF was effective in treating various pathological conditions, including respiratory tract diseases, cardiovascular disease, immune system diseases, and nervous system diseases. The therapeutic mechanisms of YZF were probably associated with modulation of inflammatory response, immune responses, matrix metalloproteinases expression, among others. In follow-up experiments, we found that YZF was effective for the treatment of COPD and its comorbidity such as ventricular hypertrophy, by inhibiting the expression of inflammatory cytokine, matrix metalloproteinases, and hypertrophic stimuli and collagen, in vivo.

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ON ALKALOIDS OF THREE Papaver SPECIES FROM THE SECTION Scapiflora REICHB.

The main alkaloid of the aerial part of P. croceum LEDEB. was nudaurine (I), isolated for the first time.In addition to amurine, known to be present in this species, oxysanguinarine (II) and corydine (IIIa) were also newly isolated and the presence of papaverrubine D demonstrated.In the fraction of tertiary bases from P.kerneri HAYEK allocryptopine and epialpinine (IV) were isolated as further alkaloids in addition to the already known alkaloids amurensine (the main alkaloid), amurensinine, amurine, alpinigenine, muramine, protopine, mecambridine, nudaurine, cryptopine and papaverrubines B, D, and G.In the fraction of quaternary bases the presence of traces of coptisine was detected, and in addition to alborine (alkaloid PO-5) cis-N-methyltetrahydropalmatinium hydroxide (V) was isolated for the first time in the form of iodide from P. kerneri.In P. tatricum (NYAR.) EHREND. allocryptopine, epialpinine, and amurensinine were identified as the dominant alkaloids, while among the minor components protopine, amurensine, muramine, palmatine, coptisine, corytuberine (IIIb), N-methyltetrahydropalmatinium hydroxide, and N-methylamurensinium hydroxide could be demonstrated.Corydine (IIIa) and corytuberine (IIIb) represent the first two aporphine alkaloids found in the Scapiflora section.

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