Thalictrum minus

Fig. 2.21 Compounds 79-87, alkaloids from Thalictrum minus collected near Vojvodina, Serbia...

Popovlc, M., Djurkovlc, R., Gaslc, O., Pal, B., Dutchewska, H. and Kuzmanov, B. 1992. Chemical and cytological investigation of Thalictrum minus from Vojvodina region. Biochem. Syst. Ecol. 20 255-258. 

Berberine Berberis wilsoniae Coptis japonica Thalictrum minus... 

Magnoflorine Coptis japonica Corydalis incisa Eschscholzia califomica Fumaria capreolata Papaver bracteatum Papaver somniferum Thalictrum minus... 

A recent addition to the pavine series may be thalipoline, C has been isolated from Thalictrum minus 28). The pavine framework was deduced from spectral data which, however, were not described. 

Thaliracebine (324), C39H44N207, amorphous, mp 83-84°C, [a] >6 +121° (c 0.28, MeOH), was isolated from Thalictrum minus Race B. The UV max of 278 nm shows no change in acid or alkali, in accord with a nonphenolic bis tetrahy-dro base. A positive chromotropic acid test confirmed the NMR evidence (8... 

Thalictrum minus L. var. microphyllum (Ranunculaceae) was the source of the amorphous base (+)-uskudaramine (358), C39H44N208, [a] 5 +84° (c 0.15, MeOH). The structure proof of uskudaramine was simplified by comparison of its properties with those of the isomeric (+)-istanbulamine (173, Section II,C,47), isolated from the same source. Notably, the NMR spectrum of 358 lacks the H-8 (8 6.84) singlet of 173, and its UV spectrum shows not only a bathochromic base shift but also a hyperchromic effect, characteristic of a 3- or 9-hydroxyaporphine. 

A high-performance liquid chromatographic (HPLC) method has enabled the determination of thalicarpine and its metabolites hemandaline, hemandalinol, and dehydrothalicarpine, in urine (262). Thalmelatine, thalipine, and thalicarpine were quantitated in Thalictrum minus (335). HPLC methods for quantitation of tubocurarine in curare (335a) and in human plasma (335b,335c) have been described. 

The cycleanine (112) content of Stephania glabra tubers was increased by addition of boron and molybdenum to the soil (357). The thalicarpine (94) yield of various cultivars of Thalictrum minus was determined in order to select the best plants for commercial production (352). 

Although earlier described from 3-year-old Thalictrum minus extracts as a probable artifact of air oxidation (555) of thalmelatine (314a), 6a,7-dehydrothalmelatine (474), C A, was only recently isolated as a natural product from Hernandia peltata. Identification was by comparison of spectral data with published values (549). 

Thaligrisine (517), C37H42N206, [a] ,5 +57° (c 0.13, MeOH), from Thalictrum minus var. microphyllum, showed the same NMR and mass spectra as (—)-grisabine (159) but opposite rotation. It is accordingly the enantiomer 517 (538). 

Thaliphylline (518), C37H40N206, [ot]g,5 +198° (c 0.12, MeOH), also from Thalictrum minus var. microphyllum, gave with diazomethane O-methylthalicberine (274), previously reported from this plant. MS and NMR evidence established the substitution pattern (538). 

Thalictrum minus var. minus provided thalivarmine (519), C36H38N206. NMR comparison with the co-occurring known alkaloid thalicberine (520) showed thalivarmine to be 7-0-desmethylthalicberine. Diazomethane converted 519 to 0-methylthalicberine (274), proving the stereochemistry. No optical rotation data, however, are cited for these compounds (569). 

Along with thalivarmine (519), Thalictrum minus var. minus yielded the new alkaloid thalsivasine (521), C36H36N206. MS and NMR data showed 521 to be 7-0-desmethyl-O-methylthalmethine. Methylation (CH2N2) of 521 gave the known O-methylthalmethine (522), a co-occurring alkaloid (569). 

Feeding experiments on Thalictrum minus with ( )-[l-14C]-reticuline (444) and with [8 -3H]-thalicarpine (527) showed that both are incorporated into adiantifoline (233) and thalmelatidine (528), supporting the biosynthetic sequence reticuline to thalmelatine to thalicarpine to adiantifoline, thalmelatidine (607). 

If 02 consumption were indeed zero order for a particular plant species, then it would appear that any phytoproduction process involving that species would require only that a minimum dissolved 02 concentration be maintained any concentration increase beyond that would be irrelevant. In the case of tobacco cells, any concentration greater than 15 % of air saturation would yield the same metabolic rate and, presumably, the same productivity of all metabolites. If, on the other hand, consumption is first order in the concentration range achievable in a practical bioreactor (equivalently, if Kf is comparable to working concentrations), then its concentration is an important control parameter in the bioreactor. However, Kobayashi et al. studied berberine production by suspended and immobilized cells of Thalictrum minus [50]. They assert that 02 uptake is a zero-order process but observed that berberine production depended on 02 availability. They controlled that availability by adjusting the speed of shaking of the culture flasks, thus varying the mass transfer coefficient for absorption of 02. 

Secondary metabolites produced by plant cell culture are commonly accumulated in the cells. With few exceptions such as Capsicum frutescens, Thalictrum minus (9) and Vanilla planifolia (Knorr, D. and Romagnoli, L., Univ. of Delaware, unpublished data) cultures, which release valuable compounds such as capsaicin, berberine and vanillin, respectively, into the medium, procedures to induce product release are required to develop continuous production processes. Reported permeabilization methods include treatment with dimethylsulfoxide (DMSO), isopropanol, toluene, phenethyl alcohol or chloroform (9, 28). But as Fontanel and Tabata (9) pointed out, such treatments with organic solvents are severe and other methods of permeabilization need to be developed. 

Occurrence Platicapnos spicata (42a), Thalictrum hazarica (54), Thalictrum minus (55), Thalictrum rugosum (51), Thalictrum strictum (56), Thalictrum thunbergii (55), Unonopsis stipitata (48) Synthesis see Refs. 29, 52, and 55 Pharmacology see Ref. 5/... 

Thalicarpine (LX), C41H48O8N2 (mp 160°-161°) was first isolated from Thalictrum dasycarpum Fisch. and Lall. (30). Later it was obtained from Thalictrum minus L. var. datum Jacq. (31) and from Hernandia ovigera (Auth. ) (32). 

Thelmelatine (LXI), C40H46O8N2 (mp 131°-135°) was isolated from Thalictrum minus L. var. datum Jacq. (31). 

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