scholarly journals Recent progress in the synthesis of homotropane alkaloids adaline, euphococcinine and N-methyleuphococcinine

2021 ◽  
Vol 17 ◽  
pp. 28-41
Author(s):  
Dimas J P Lima ◽  
Antonio E G Santana ◽  
Michael A Birkett ◽  
Ricardo S Porto

The 9-azabicyclo[3.3.1]nonane ring system is present in several insect- and plant-derived alkaloids. (−)-Adaline (1) and (+)-euphococcinine (2), found in secretions of Coccinelid beetles, and (+)-N-methyleuphococcinine (3), isolated from the Colorado blue spruce Picea pungens, are members of this alkaloid family. Their unique bicyclic system with a quaternary stereocenter, and the potent biological activity exerted by these homotropane alkaloids, make them attractive synthetic targets. This work aims briefly to review the chemical ecology of Adalia bipunctata and the recent methodologies to obtain adaline (1), euphococcinine (2), and N-methyleuphococcinine (3).

1999 ◽  
Vol 7 ◽  
pp. 85-94
Author(s):  
G.A. Lane

Neotyphodium spp. fungi in pasture grasses synthesise a diverse range of metabolites. In this report, recent progress in extending knowledge of the diversity of endophyte metabolites is reviewed, in particular the elucidation of indole-diterpenes and ergot alkaloids. Some 20 indole-diterpenes have been identified from N. lolii-infected perennial ryegrass, and several ergot alkaloids additional to ergovaline have been identified in perennial ryegrass and other grasses infected with Neotyphodium spp. endophytes. While lolitrem B, ergovaline, and peramine remain significant factors in understanding the biological activity of N. loliiinfected perennial ryegrass, a more complex and complete view of endophyte chemical ecology must now be developed. Keywords: chanoclavine-I, dehydroergovaline, endophyte, ergine, ergot alkaloid, indolediterpene, Neotyphodium spp., perennial ryegrass, tall fescue


1983 ◽  
Vol 61 (4) ◽  
pp. 1194-1198 ◽  
Author(s):  
John B. Sutherland ◽  
Anthony L. Pometto III ◽  
Don L. Crawford

Eighteen strains of fungi in the genus Fusarium, including varieties of F. episphaeria, F. lateritium, F. moniliforme, F. nivale, F. oxysporum, F. rigidiusculum, F. roseum, F. solani, and F. tricinctum, slowly degraded lignocelluloses from blue spruce (Picea pungens) and wheat (Triticum aestivum). When grown with [lignin-14C]lignocellulose from blue spruce, 15 of the Fusarium strains converted 2.2 to 4.3% of the [14C]lignin in 60 days to 14CO2 and 3.9 to 8.4% to labeled water-soluble products. When grown with unlabeled lignocellulose from wheat straw, the strains caused total weight losses in 60 days of 7 to 25%, acid-insoluble (Klason) lignin losses of 2 to 17%, and carbohydrate losses of 3 to 33%. Crude protein contents of degraded wheat-straw lignocellulose samples were 3.2 to 5.1%. Among the aromatic degradation products from wheat-straw lignocellulose degraded by different strains, as shown by gas chromatography, were p-coumaric acid, vanillic acid, vanillin, syringaldehyde, and p-hydroxybenzaldehyde.


2003 ◽  
Vol 64 (2) ◽  
pp. 385-393 ◽  
Author(s):  
Peter J. Houghton ◽  
Abraham Y Mensah ◽  
Noha Iessa ◽  
Liao Yong Hong

2019 ◽  
Vol 10 (1) ◽  
Author(s):  
Masakazu Nambo ◽  
Jacky C.-H. Yim ◽  
Luiza B. O. Freitas ◽  
Yasuyo Tahara ◽  
Zachary T. Ariki ◽  
...  

Abstract α-Fluoromethylarenes are common substructures in pharmaceuticals and agrochemicals, with the introduction of fluorine often resulting in improved biological activity and stability. Despite recent progress, synthetic routes to α-fluorinated diarylmethanes are still rare. Herein we describe the Pd-catalyzed Suzuki-Miyaura cross-coupling of α-fluorinated benzylic triflones with arylboronic acids affording structurally diverse α-fluorinated diarylmethanes. The ease of synthesis of fluorinated triflones as the key starting materials enables powerful late-stage transformations of known biologically active compounds into fluorinated analogs.


2020 ◽  
Vol 66 (No. 8) ◽  
pp. 309-317
Author(s):  
Jiri Sefl ◽  
Veronika Mottlová ◽  
Iva Schořálková

A survey was carried out in 2013–2019 on the life cycle of the bud blight Gemmamyces piceae (Borthw.) Casagrande and the trend assessment in the infestation of the Colorado blue spruce Picea pungens Engelm. stands. Four ecologically different plots were chosen in the Fláje region in the Eastern part of the Krušné hory Mountains. The pycnidia were formed at the beginning of June on buds infested the previous year. Later, in the second half of June, they formed on the spring attack buds. Conidia occurred in the first week of July on the buds of the old infestation, or later in the case of the spring attack buds, in the middle of July. The production of conidia lasted till the end of September. Ascospores occurred in the middle of July and were produced until the end of September. The ability of host trees to sprout became continually weaker, along with the defoliation progress. A distinct decline in the sprouting ability was noticed on stands with a dense crown canopy and on stands with competition of broad-leaved trees – with an admixture of birch.


2014 ◽  
Vol 79 (11) ◽  
pp. 4948-4962 ◽  
Author(s):  
Masahiro Kunitake ◽  
Takahiro Oshima ◽  
Keiichi Konoki ◽  
Makoto Ebine ◽  
Kohei Torikai ◽  
...  

2018 ◽  
Vol 31 (4) ◽  
pp. 357-365 ◽  
Author(s):  
Nikita Maksimov ◽  
Anastasia Evmenyeva ◽  
Maria Breygina ◽  
Igor Yermakov

1983 ◽  
Vol 63 (4) ◽  
pp. 1097-1098
Author(s):  
W. H. CRAM

Albino seedlings from self-pollinated seed were attributed to a simple and lethal recessive gene, which was utilized to estimate the occurrence of 0–18% natural self-pollination in blue spruce (Picea pungens Engelm.).Key words: Albinism, natural selfing, Picea pungens


1969 ◽  
Vol 47 (11) ◽  
pp. 1693-1700 ◽  
Author(s):  
James W. Hanover ◽  
Ronald C. Wilkinson

Controlled pollinations were made within and between blue spruce (Picea pungens Engelm.) and white spruce (Picea glauca (Moench) Voss) in 1967 and 1968. Interspecific hybrids were obtained and verified by comparative measurements of several traits. The cross was successful when either species was used as the female parent. Hybrid seed germinated more rapidly than that of either species and hybrid seedlings showed some heterosis for early growth. Also, hybrid seedlings had needles intermediate between, and significantly different from, the parental seedlings. Growth form of the hybrid was quite variable compared with that of either species. Further evidence for the successful crossing of blue spruce and white spruce was provided by biochemical analyses of monoterpene compounds in the parents and progeny.


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