Astonishing Diversity of Natural Surfactants: 2. Polyether Glycosidic Ionophores and Macrocyclic Glycosides

Overview

Journal Lipids

Specialty Biochemistry

Date 2005 Jun 17

PMID 15957249

Citations 7

Authors

Valery M Dembitsky

Affiliations

Soon will be listed here.

Abstract

Polyether glycosidic ionophores and macrocyclic glycosides are of great interest, especially for the medicinal and pharmaceutical industries. These biologically active natural surfactants are good prospects for the future chemical preparation of compounds useful as antibiotics, anticancer agents, or in industry. More than 300 interesting and unusual natural surfactants are described in this review article, including their chemical structures and biological activities.

Citing Articles

Natural Polyether Ionophores and Their Pharmacological Profile.

Dembitsky V Mar Drugs. 2022; 20(5).

PMID: 35621943 PMC: 9144361. DOI: 10.3390/md20050292.

Antiprotozoal and Antitumor Activity of Natural Polycyclic Endoperoxides: Origin, Structures and Biological Activity.

Dembitsky V, Ermolenko E, Savidov N, Gloriozova T, Poroikov V Molecules. 2021; 26(3).

PMID: 33525706 PMC: 7865715. DOI: 10.3390/molecules26030686.

Chemical Diversity of Soft Coral Steroids and Their Pharmacological Activities.

Ermolenko E, Imbs A, Gloriozova T, Poroikov V, Sikorskaya T, Dembitsky V Mar Drugs. 2020; 18(12).

PMID: 33276570 PMC: 7761492. DOI: 10.3390/md18120613.

Simple glycolipids of microbes: Chemistry, biological activity and metabolic engineering.

Abdel-Mawgoud A, Stephanopoulos G Synth Syst Biotechnol. 2018; 3(1):3-19.

PMID: 29911195 PMC: 5884252. DOI: 10.1016/j.synbio.2017.12.001.

Surfactants tailored by the class Actinobacteria.

Kugler J, Le Roes-Hill M, Syldatk C, Hausmann R Front Microbiol. 2015; 6:212.

PMID: 25852670 PMC: 4365757. DOI: 10.3389/fmicb.2015.00212.

References

Muroi M, Izawa M, Asai M, Kishi T, Mizuno K . Maridomycin, a new macrolide antibiotic. II. Isolation and characterization. J Antibiot (Tokyo). 1973; 26(4):199-205. DOI: 10.7164/antibiotics.26.199. View

Muroi M, Izawa M, Kishi T . Maridomycin, a new macrolide antibiotic. XI. The structures of maridomycin components. Chem Pharm Bull (Tokyo). 1976; 24(3):463-78. DOI: 10.1248/cpb.24.463. View

Jensen K, Madsen P . Candicidin treatment of prostatism: a prospective double-blind placebo-controlled study. Urol Res. 1983; 11(1):7-10. DOI: 10.1007/BF00272701. View

Moore B, Hopke J . Discovery of a new bacterial polyketide biosynthetic pathway. Chembiochem. 2002; 2(1):35-8. DOI: 10.1002/1439-7633(20010105)2:1<35::AID-CBIC35>3.0.CO;2-1. View

Tynan 3rd E, NELSON T, Davies R, Wernau W . The production of semduramicin by direct fermentation. J Antibiot (Tokyo). 1992; 45(5):813-5. DOI: 10.7164/antibiotics.45.813. View

Majer J, McAlpine J, Egan R, CORCORAN J . Antibiotic glycosides. VII 10,11-dihydropicromycin: another metabolite of Streptomyces venezuelae. J Antibiot (Tokyo). 1976; 29(7):769-70. DOI: 10.7164/antibiotics.29.769. View

Nakayama H, Seto H, Otake N, Yamagishi M, Kawashima A, Mizutani T . Studies on the ionophorous antibiotics. XXVIII. Moyukamycin, a new glycosylated polyether antibiotic. J Antibiot (Tokyo). 1985; 38(10):1433-6. DOI: 10.7164/antibiotics.38.1433. View

Martin J, DEVAULT R, SINCLAIR A, Stanaszek R, Johnson P . A new naturally occurring erythromycin: erythromycin F. J Antibiot (Tokyo). 1982; 35(4):426-30. DOI: 10.7164/antibiotics.35.426. View

Hong J, Park S, Choi C, Sohng J, Yoon Y . New olivosyl derivatives of methymycin/pikromycin from an engineered strain of Streptomyces venezuelae. FEMS Microbiol Lett. 2004; 238(2):391-9. DOI: 10.1016/j.femsle.2004.08.002. View

10.

Luesch H, Yoshida W, Harrigan G, Doom J, Moore R, Paul V . Lyngbyaloside B, a new glycoside macrolide from a Palauan marine cyanobacterium, Lyngbya sp. J Nat Prod. 2002; 65(12):1945-8. DOI: 10.1021/np0202879. View

11.

Robinson J . Chemical and biochemical aspects of polyether-ionophore antibiotic biosynthesis. Fortschr Chem Org Naturst. 1991; 58:1-81. DOI: 10.1007/978-3-7091-9141-5_1. View

12.

Ricketts A, Dirlam J, Shively J . Anticoccidial efficacy and chicken toleration of potent new polyether ionophores. 2. The portmicin relative CP-84,657. Poult Sci. 1992; 71(10):1631-6. DOI: 10.3382/ps.0711631. View

13.

CORONELLI C, White R, LANCINI G, Parenti F . Lipiarmycin, a new antibiotic from Actinoplanes. II. Isolation, chemical, biological and biochemical characterization. J Antibiot (Tokyo). 1975; 28(4):253-9. DOI: 10.7164/antibiotics.28.253. View

14.

Martin J, Egan R, GOLDSTEIN A, Mueller S, KELLER-SCHIERLEIN W, Mitscher L . 3'-de-o-methyl-2', 3'-anhydro-lankamycin, a new macrolide antibiotic from Streptomyces violaceoniger. Helv Chim Acta. 1976; 59(5):1886-94. DOI: 10.1002/hlca.19760590545. View

15.

Koshiyama H, Okanishi M, Ohmori T, Miyaki T, TSUKIURA H, Matsuzaki M . Cirramycin, a new antibiotic. J Antibiot (Tokyo). 1963; 16:59-66. View

16.

Somani P, Kabell G, Saini R, Hester R . The effect of monensin, a Na+-selective carboxylic ionophore, on coronary circulation. Adv Myocardiol. 1980; 2:435-47. View

17.

Dembitsky V . Astonishing diversity of natural surfactants: 1. Glycosides of fatty acids and alcohols. Lipids. 2005; 39(10):933-53. DOI: 10.1007/s11745-004-1316-1. View

18.

Huber G, WALLHAEUSSER K, Fries L, Steigler A, WEIDENMUELLER H . [Niddamycin, a new macrolide antibiotic]. Arzneimittelforschung. 1962; 12:1191-5. View

19.

Sun Y, Zhou X, Liu J, Bao K, Zhang G, Tu G . 'Streptomyces nanchangensis', a producer of the insecticidal polyether antibiotic nanchangmycin and the antiparasitic macrolide meilingmycin, contains multiple polyketide gene clusters. Microbiology (Reading). 2002; 148(Pt 2):361-371. DOI: 10.1099/00221287-148-2-361. View

20.

Oscarson J, Bordner J, CELMER W, CULLEN W, Huang L, Maeda H . Endusamycin, a novel polycyclic ether antibiotic produced by a strain of Streptomyces endus subsp. aureus. J Antibiot (Tokyo). 1989; 42(1):37-48. DOI: 10.7164/antibiotics.42.37. View