Biosynthesis of papaverine

Tracer experiments have shown that in Papaver somniferum papaverine arises from (−)-norreticuline via norlaudanidine and norlaudanosine.     

Biosynthesis of limonoids in Citrus

Analyses of citrus leaves and fruits, and radioisotope tracer work showed that the leaves could synthesize limonoids and that the trees could translocate limonoids from leaves to the fruit. These results suggest that limonoids in citrus fruit tissues are synthesized in leaves and translocated to the fruit. No evidence was found to support the presence of limonoid biosynthetic systems in the fruit tissues.     

Spectroscopic investigation of the anticancer alkaloid piperlongumine binding to human serum albumin from the viewpoint of drug delivery

Piperlongumine (PL) is a very promising natural agent with a high potential for cancer treatment. To overcome the poor water solubility of PL, there is a need to develop a novel water‐soluble formulation in which PL is non‐covalently bound to human serum albumin (HSA). PL binding to HSA was studied by various spectroscopic techniques under simulated physiological conditions. Spectroscopic evidence showed that the interaction of PL with HSA could form a PL–HSA complex. The binding constant (K_a) values increased with increasing temperature, and a similar dependence was observed for the number of binding sites (n) values. The number of PL molecules bound to HSA reached 8.1 when the temperature was raised to 308 K. Thermodynamic calculation results suggested that the binding reaction occurred spontaneously but was an entropy‐driven process, and hydrophobic forces played a major role in stabilizing the complex. Furthermore, PL binding induced conformational and microenvironmental changes in HSA. Displacement studies indicated that PL and warfarin had separate binding regions in site I. Therefore, it would be possible to develop a novel water‐soluble formulation involving PL and HSA. This study may provide some valuable information in terms of improving the poor water solubility of PL.     

Structural and synthetic studies on the retrofractamides—amide constituents of Piper retrofractum

Two new unsaturated amides, retrofractamides A and C, were isolated from the total above-ground parts of Piper retrofractum. Retrofractamide A was shown to be N-isobutyl-9(3′,4′-methylenedioxyphenyl)2E,4E,8E-nonatrienamide from spectroscopic and chemical investigations. The structure 6 for retrofractamide C was suggested from spectroscopic and chemical studies and was confirmed by a total stereoselective synthesis. The presence of sesamin and 3,4,5-trimethoxydihydrocinnamic acid as well as two higher homologues of retrofractamide A, viz. pipericide (retrofractamide B) and retrofractamide D was demonstrated. The synthesis of pipericide was also achieved.     

Biosynthesis of cannabinoid acids

Malonic acid, mevalonic acid, geraniol and nerol were incorporated into tetrahydrocannabinolic acid and cannabichromenic acid in Cannabis sativa. The pathway from cannabigerolic acid to tetrahydrocannabinolic acid via cannabidiolic acid was established by feeding labelled cannabinoid acids. Cannabichromenic acid was shown to be formed on a side pathway from cannabigerolic acid.     

Biosynthesis of the phytoalexin wyerone in Vicia faba

In contrast to earlier results [1-¹⁴C] acetate, [2-¹⁴C] malonate and [n 9,10-³H] oleate show significant incorporations into wyerone and related Vicia faba phytoalexins, following infection by Botrytis cinerea.     

Elevated PRC1 in gastric carcinoma exerts oncogenic function and is targeted by piperlongumine in a p53‐dependent manner

Gastric carcinoma is one of the most common malignancies worldwide and the second most frequent cause of cancer‐related death in China. Protein regulator of cytokinesis 1 (PRC1) is involved in cytokinesis and plays key roles in microtubule organization in eukaryotes. This study was aimed to analyse the expression and to investigate the functional role of PRC1 in gastric tumorigenesis. The expression of PRC1 was evaluated by qRT‐PCR, Western blot and immunohistochemistry. The biological function of PRC1 was determined by CCK‐8 proliferation assays, monolayer colony formation, xenografted nude mice and cell invasion assays by shRNA‐mediated knockdown in AGS and HGC27 cells. The regulation of PRC1 expression by piperlongumine was also investigated using dual‐luciferase reporter assay and ChIP‐qPCR analysis. PRC1 was up‐regulated in primary gastric cancers. Overexpression of PRC1 in gastric cancers was associated with poor disease‐specific survival and overall survival. PRC1 knockdown in AGS and HGC27 cell lines suppressed proliferation, reduced monolayer colony formation, inhibited cell invasion and migration ability and induced cell‐cycle arrest and apoptosis. Inhibition of PRC1 also suppressed tumour growth in vivo. We finally confirmed that PRC1 is a novel downstream target of piperlongumine in gastric cancer. Our findings supported the oncogenic role of PRC1 in gastric carcinogenesis. PRC1 might serve as a prognostic biomarker and potential therapeutic target for gastric carcinoma.     

Biosynthesis of amaranthin in Celosia plumosa

Seedlings of a yellow betaxanthin-producing variety of Celosia plumosa when fed with appropriate precursors are capable of synthesizing the red-violet pigment normally present in red varieties of the same species, namely amaranthin. Synthesis of amaranthin occurs in seedlings following administration of betanidin and betanin but much greater accumulation was observed after feeding cycloDOPA and its 5-O-β-d-glucoside. Possible pathways in the biosynthesis of amaranthin are discussed.     

Biosynthesis of Se-Methylselenocysteine in lima beans

It has been shown that maturing seeds of lima beans synthesize Se-methylselenocysteine, the selenium analogue of S-methyleysteine. The latter amino acid is a natural constituent of these seeds. The leaves of lima beans do not contain detectable amounts of S-methylcysteine, and in this tissue Se-methionine appears to be the principal product of selenate assimilation.     

Biosynthesis of 3-methoxycarbonylpropylglucosinolate in an Erysimum species

Incorporation of DL-2-aminohexanedioic acid, DL-2-amino-5-methoxycarbonyl-pentanoic acid and DL-methionine into 3-methoxycarbonylpropylglucosinolate have been demonstrated using an Erystmum species. The data support the following sequence of biosynthetic reactions: 2-aminohexanedioic acid is methylated by methionine; the resulting 2-amino-5-methoxycarbonyl-pentanoic acid is then converted into the glucosinolate. 2-Amino-5-methoxycarbonyl-pentanoic acid has been tentatively identified as a natural product in the plant.     

茁霉多糖生物合成的研究进展

本文综述了茁霉多糖的生物合成,简单探讨了其生物合成的机理,并从发酵工艺入手,对通过各种发酵条件的对比,分析并讨论了生物合成的一系列优化结果。同时,简要介绍了茁霉多糖的一些理化性质以及它在工业上的生产应用,并讨论了其应用前景。     

Biosynthesis of gramine in Phalaris arundinacea

The administration of L-tryptophan-[3-¹⁴C] to Phalaris arundinacea L. (Vantage strain) for 9 days resulted in the formation of radioactive gramine (8.2% absolute incorporation). A systematic degradation of the alkaloid indicated that essentially all its activity was located on the methylene group, indicating that its biosynthesis is the same as that occurring in Hordeum species and Lupinus hartwegii.     

Biosynthesis of triterpenoid sapogenols in soybean and alfalfa seedlings

By incubation of germinating soybeans with mevalonate-[2-¹⁴C] (MVA), radioactivity was incorporated into four sapogenols which were identified by TLC. Unequivocal evidence for the identity of three of the four sapogenols was provided by co-crystallization to constant specific radioactivity. The partition of incorporated radioactivity into lipid- and water-soluble fractions and the pattern of radioactivity of individual sapogenols varied with the mode of administering labeled substrates to soybean seedlings, such as incubation of germinating soybeans with MVA-[2-¹⁴C], immersion of roots into MVA-[2-¹⁴C] or foliar application of squalene-[¹⁴C]. When alfalfa seedlings were incubated with MVA-[2-¹⁴C], about two-thirds of the radioactivity incorporated into the sapogenols was associated with medicagenic acid.     

Biosynthesis of salep mannan

A particulate enzyme system, isolated from growing orchid tubers (Orchis morio), was shown to catalyse the transfer of mannose from guanosine-diphosphate-mannose-¹⁴C and its incorporation into alkali-insoluble mannan with the same type of linkage [β(1 → 4)-d-mannopyranosyl] as is contained in the naturally-occurring reserve polysaccharide.     

Biosynthesis of carvone in Mentha spicata

Degradation of, and measurement of isotope ratios in, (?)-carvone that had been biosynthesized in Mentha spicata from ³H- and ¹⁴C-labelled geraniol and mevalonate indicate that (a) oxidation of limonene or its biogenetic equivalent to form carvone involves shift of the endocyclic double bond; (b) (+)-limonene and (?)-carvone are biogenetically related and are probably formed on divergent pathways from a common intermediate; and (c) the exocyclic double bond of carvone is not formed regiospecifically. These results enable the mechanisms for the introduction of the carbonyl group and for the formation of the isopropenyl side-chain to be delimited.     

Biosynthesis of shikonin in callus cultures of Lithospermum erythrorhizon

Administration of various supposed precursors to the callus cultures of Lithospermum erythrorhizon grown on the Linsmaier—Skoog medium supplemented with IAA and kinetin established that the constituent shikonin is formed via shikimic acid, p-hydroxybenzoic acid, m-geranyl-p-hydroxybenzoic acid and geranylhydroquinone. In a strain of callus culture lacking the capacity to synthesize shikonin and in callus cultures which have had this capacity but lost it due to cultivation on a medium supplemented with 2,4-D, substances up to m-geranyl-p-hydroxybenzoic acid in the biosynthetic sequence have been detected. Although illumination with white light also arrested shikonin production, traces of pigment were still formed presumably because light did not reach the innermost part of the callus cultures.     

Biosynthesis of cyanidin in buckwheat hypocotyls

Aminooxyacetate (AOA), an inhibitor of phenylalanine transamination and deamination in vitro, inhibits the light-induced formation of chlorogenic acid, leucoanthocyanin, rutin and anthocyanin (cyanidin glycosides) in buckwheat hypocotyls. Anthocyanin production is inhibited 87 ± 4%, when excised hypocotyls are incubated in 0.5 mM AOA in Petri dishes. AOA is also effective when taken up through the roots or sprayed onto seedlings. In the presence of biosynthetic precursors of cyanidin (l-phenylalanine, trans-cinnamic acid, p-coumaric acid, naringenin, eriodictyol, dihydrokaempferol. and dihydroquercetin) the inhibition of anthocyanin formation caused by AOA is completely or partially reversed. The general applicability of a complementation technique involving AOA or a similar inhibitor of phenylpropane synthesis is proposed to investigate the biosynthesis of natural products derived from cinnamic acid.     

Biosynthesis of citreomontanin in Penicillium pedemontanum

The ¹³C NMR spectrum of citreomontanin has been fully assigned by analysis in the presence of a shift reagent. The intramolecular distribution patt     

Biosynthesis of withanolides in Acnistus breviflorus

Administration of [2?¹⁴C]mevalonolactone to excised leaves of Acnistus breviflorus produced labelled withaferin A and jaborosalactone A. The former was degraded leading to the isolation of glyceric acid from C-25–C-27 of the withanolide. These carbons represented only 2 % of the total radioactivity of withaferin A. The relative radioactivity of these carbons indicated that C-26 is directly derived from C-2 of mevalonolactone suggesting that the 25-pro-R-methyl group of cholesterol or any other sterol intermediate had been oxidized to form the lactone ring of the withanolide. The total radioactivity value found for C-25–C-27 was much lower than the expected 20 % of the total value for the withanolide indicating that the side chain of the sterol precursor had been partially cleaved during the biosynthetic process.