Synthesis, chemical transformation, and application of isoxazole derivatives in the total chemical synthesis of natural compounds (review)

Microbes constitute important platforms for the biosynthesis of numerous molecules of pharmaceutical interest such as antitumor, anticancer, antiviral, antihypertensive, antiparasitic, antioxidant, immunological agents, and antibiotics as well as hormones, belonging to various chemical families, for instance, terpenoids, alkaloids, polyphenols, polyketides, amines, and proteins. Engineering microbial factories offers rich opportunities for the production of natural products that are too complex for cost-effective chemical synthesis and whose extraction from their originating plants needs the use of many solvents. Recent progresses that have been made since the millennium beginning with metabolic engineering of microorganisms for the biosynthesis of natural products of pharmaceutical significance will be reviewed.

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Chemical Synthesis of Validamycin and Related Natural Compounds

Validamycin and its Derivatives ◽

10.1016/b978-0-08-100999-4.00004-6 ◽

2017 ◽

pp. 165-235

Author(s):

Xiaolong Chen ◽

Yuele Lu ◽

Yongxian Fan ◽

Yinchu Shen

Keyword(s):

Chemical Synthesis ◽

Natural Compounds

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The chemical synthesis of glucosaminylphosphatidylglycerol. Comparison with a new phospholipid isolated from Bacillus megaterium

Biochemical Journal ◽

10.1042/bj1080211 ◽

1968 ◽

Vol 108 (2) ◽

pp. 211-219 ◽

Cited By ~ 12

Author(s):

M I Gurr ◽

P. P. M. Bonsen ◽

J. A. F. OP Den Kamp ◽

L. L. M. Van Deenen

Keyword(s):

Chemical Synthesis ◽

Bacillus Megaterium ◽

Natural Compound ◽

Silver Salt ◽

Natural Compounds ◽

Protecting Groups ◽

Hydrogen Phosphate ◽

Hydrolysis Products ◽

Catalytic Hydrogenolysis

1. We describe the synthesis of a glucosamine derivative of phosphatidylglycerol having the same structure as that of the natural compound isolated from Bacillus megaterium. 2. 2-O-(3,4,6-Tri-O-acetyl-2-deoxy-2-phthalimido-d-glucopyranosyl)-3-O-benzyl-1-iodo-sn-glycerol was prepared by a Königs–Knorr condensation between 3-O-benzyl-1-toluene-p-sulphonyl-sn-glycerol and 3,4,6-tri-O-acetyl-1-bromo-2-deoxy-2-phthalimido-d-glucopyranose followed by replacement of the toluene-p-sulphonyl group with iodine. The iodide was treated with the silver salt of 2-isolauroyl-1-oleoyl-sn-glycerol 3-(monobenzyl hydrogen phosphate) to form the fully protected phosphoglycolipid. 3. Removal of benzyl protecting groups by catalytic hydrogenolysis, phthaloyl group with hydrazine and acetyl groups with pH10 buffer furnished 2-O-(2-amino-2-deoxy-d-glucopyranosyl)-1-(2-isolauroyl-1-stearoyl-sn-glycero-3-phosphoryl)-sn-glycerol. 4. The synthetic and natural compounds appeared identical when compared by chromatography and by identification of hydrolysis products from chemical and enzymic degradations.

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Natural products for plant protection

Hemijska industrija ◽

10.2298/hemind0606113c ◽

2006 ◽

Vol 60 (5-6) ◽

pp. 113-119

Author(s):

Zivorad Cekovic

Keyword(s):

Natural Products ◽

Secondary Metabolites ◽

Chemical Synthesis ◽

Secondary Metabolite ◽

Industrial Production ◽

Plant Protection ◽

Natural Compounds ◽

Ecological Studies ◽

Ecological Criteria ◽

Biotechnological Processes

The advantage applying natural products, such as a secondary metabolites, in plant protection is shortly presented. Acceptable solutions for the enhanced ecological criteria, which are requested by the users of pesticides and consumers of agricultural goods, could be the replacement of classical pesticides by natural products in plant protection. Some natural products are already in use as insecticides, herbicides and fungicides because new biotechnological processes, fermentation and biotransformations provide procedures for their industrial production. In addition to biotechnical processes natural compounds possessing pesticide activities are also prepared by chemical synthesis. An active secondary metabolite must first be isolated from natural sauces and then, based on biological toxicological and ecological studies, acceptable compounds are selected for laboratory and industrial chemical synthesis. Several compounds possessing insecticidal, herbicidal and fungicidal activities, which have been successfully applied for plan protection are presented.

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Semi-synthesis as a tool for broadening the health applications of bioactive olive secoiridoids: a critical review

Natural Product Reports ◽

10.1039/d0np00084a ◽

2021 ◽

Author(s):

Manuela Oliverio ◽

Monica Nardi ◽

Maria Luisa Di Gioia ◽

Paola Costanzo ◽

Sonia Bonacci ◽

...

Keyword(s):

Critical Review ◽

Natural Compounds ◽

Effective Strategy ◽

Synthetic Analogues ◽

Health Applications ◽

Natural And Synthetic

Semi-synthesis is an effective strategy to obtain both natural and synthetic analogues of the olive secoiridoids, starting from easy accessible natural compounds.

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