Biosynthesis and Molecular Actions of Specialized 1,4-naphthoquinone Natural Products Produced by Horticultural Plants

Overview

Journal Hortic Res

Publisher Oxford University Press

Date 2016 Oct 1

PMID 27688890

Citations 48

Authors

Joshua R Widhalm

David Rhodes

Affiliations

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Abstract

The 1,4-naphthoquinones (1,4-NQs) are a diverse group of natural products found in every kingdom of life. Plants, including many horticultural species, collectively synthesize hundreds of specialized 1,4-NQs with ecological roles in plant-plant (allelopathy), plant-insect and plant-microbe interactions. Numerous horticultural plants producing 1,4-NQs have also served as sources of traditional medicines for hundreds of years. As a result, horticultural species have been at the forefront of many basic studies conducted to understand the metabolism and function of specialized plant 1,4-NQs. Several 1,4-NQ natural products derived from horticultural plants have also emerged as promising scaffolds for developing new drugs. In this review, the current understanding of the core metabolic pathways leading to plant 1,4-NQs is provided with additional emphasis on downstream natural products originating from horticultural species. An overview on the biochemical mechanisms of action, both from an ecological and pharmacological perspective, of 1,4-NQs derived from horticultural plants is also provided. In addition, future directions for improving basic knowledge about plant 1,4-NQ metabolism are discussed.

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References

Palmer D, Garrett J, Sharma V, Meganathan R, Babbitt P, Gerlt J . Unexpected divergence of enzyme function and sequence: "N-acylamino acid racemase" is o-succinylbenzoate synthase. Biochemistry. 1999; 38(14):4252-8. DOI: 10.1021/bi990140p. View

Yamamoto H, Inoue K, Li S, Heide L . Geranylhydroquinone 3"-hydroxylase, a cytochrome P-450 monooxygenase from Lithospermum erythrorhizon cell suspension cultures. Planta. 2000; 210(2):312-7. DOI: 10.1007/PL00008139. View

Bringmann G, Rischer H, Wohlfarth M, Schlauer J, Assi L . Droserone from cell cultures of Triphyophyllum peltatum (Dioncophyllaceae) and its biosynthetic origin. Phytochemistry. 2000; 53(3):339-43. DOI: 10.1016/s0031-9422(99)00543-9. View

Bolton J, Trush M, Penning T, Dryhurst G, Monks T . Role of quinones in toxicology. Chem Res Toxicol. 2000; 13(3):135-60. DOI: 10.1021/tx9902082. View

Yao J, Kops O, Lu P, Lu K . Functional conservation of phosphorylation-specific prolyl isomerases in plants. J Biol Chem. 2000; 276(17):13517-23. DOI: 10.1074/jbc.M007006200. View

Meganathan R . Biosynthesis of menaquinone (vitamin K2) and ubiquinone (coenzyme Q): a perspective on enzymatic mechanisms. Vitam Horm. 2001; 61:173-218. DOI: 10.1016/s0083-6729(01)61006-9. View

Chao S, Greenleaf A, Price D . Juglone, an inhibitor of the peptidyl-prolyl isomerase Pin1, also directly blocks transcription. Nucleic Acids Res. 2001; 29(3):767-73. PMC: 30403. DOI: 10.1093/nar/29.3.767. View

Yazaki K, Matsuoka H, Shimomura K, Bechthold A, Sato F . A novel dark-inducible protein, LeDI-2, and its involvement in root-specific secondary metabolism in Lithospermum erythrorhizon. Plant Physiol. 2001; 125(4):1831-41. PMC: 88839. DOI: 10.1104/pp.125.4.1831. View

Bringmann G, Feineis D . Stress-related polyketide metabolism of Dioncophyllaceae and Ancistrocladaceae. J Exp Bot. 2001; 52(363):2015-22. DOI: 10.1093/jexbot/52.363.2015. View

10.

Lobstein A, Brenne X, Feist E, Metz N, Weniger B, Anton R . Quantitative determination of naphthoquinones of Impatiens species. Phytochem Anal. 2001; 12(3):202-5. DOI: 10.1002/pca.574. View

11.

Wildermuth M, Dewdney J, Wu G, Ausubel F . Isochorismate synthase is required to synthesize salicylic acid for plant defence. Nature. 2001; 414(6863):562-5. DOI: 10.1038/35107108. View

12.

Yazaki K, Kunihisa M, Fujisaki T, Sato F . Geranyl diphosphate:4-hydroxybenzoate geranyltransferase from Lithospermum erythrorhizon. Cloning and characterization of a ket enzyme in shikonin biosynthesis. J Biol Chem. 2001; 277(8):6240-6. DOI: 10.1074/jbc.M106387200. View

13.

Han Y, van der Heijden R, Lefeber A, Erkelens C, Verpoorte R . Biosynthesis of anthraquinones in cell cultures of Cinchona 'Robusta' proceeds via the methylerythritol 4-phosphate pathway. Phytochemistry. 2002; 59(1):45-55. DOI: 10.1016/s0031-9422(01)00296-5. View

14.

Rischer H, Hamm A, Bringmann G . Nepenthes insignis uses a C2-portion of the carbon skeleton of L-alanine acquired via its carnivorous organs, to build up the allelochemical plumbagin. Phytochemistry. 2002; 59(6):603-9. DOI: 10.1016/s0031-9422(02)00003-1. View

15.

Gao D, Hiromura M, Yasui H, Sakurai H . Direct reaction between shikonin and thiols induces apoptosis in HL60 cells. Biol Pharm Bull. 2002; 25(7):827-32. DOI: 10.1248/bpb.25.827. View

16.

Chen X, Yang L, Oppenheim J, Howard M . Cellular pharmacology studies of shikonin derivatives. Phytother Res. 2002; 16(3):199-209. DOI: 10.1002/ptr.1100. View

17.

Yamamoto H, Zhao P, Yazaki K, Inoue K . Regulation of lithospermic acid B and shikonin production in Lithospermum erythrorhizon cell suspension cultures. Chem Pharm Bull (Tokyo). 2002; 50(8):1086-90. DOI: 10.1248/cpb.50.1086. View

18.

Loscher R, Heide L . Biosynthesis of p-Hydroxybenzoate from p-Coumarate and p-Coumaroyl-Coenzyme A in Cell-Free Extracts of Lithospermum erythrorhizon Cell Cultures. Plant Physiol. 1994; 106(1):271-279. PMC: 159525. DOI: 10.1104/pp.106.1.271. View

19.

Lin L, Yang L, Chou C . Cytotoxic naphthoquinones and plumbagic acid glucosides from Plumbago zeylanica. Phytochemistry. 2003; 62(4):619-22. DOI: 10.1016/s0031-9422(02)00519-8. View

20.

Lame M, Jones A, Wilson D, Segall H . Protein targets of 1,4-benzoquinone and 1,4-naphthoquinone in human bronchial epithelial cells. Proteomics. 2003; 3(4):479-95. DOI: 10.1002/pmic.200390062. View