Venturicidin C, a new 20-membered macrolide produced by Streptomyces sp. TS-2-2

Khaled A. Shaaban; Shanteri Singh; Sherif I. Elshahawi; Xiachang Wang; Larissa V. Ponomareva; Manjula Sunkara; Gregory C. Copley; James C. Hower; Andrew J. Morris; Madan K. Kharel; Jon S. Thorson

doi:10.1038/ja.2013.113

Venturicidin C, a new 20-membered macrolide produced by Streptomyces sp. TS-2-2

Khaled A. Shaaban, Shanteri Singh, Sherif I. Elshahawi, Xiachang Wang, Larissa V. Ponomareva, Manjula Sunkara, Gregory C. Copley, James C. Hower, Andrew J. Morris, Madan K. Kharel, Jon S. Thorson

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37 Scopus citations

Abstract

Venturicidin C (1), a new 20-membered macrolide along with the known venturicidins A (2) and B (3) were isolated from the crude extract of the Appalachian bacterial strain Streptomyces sp. TS-2-2. Additionally, nine other known compounds namely nocardamine, dehydroxynocardamine, desmethylenylnocardamine, ferrioxamine E, adenosine, riboflavin, cyclo(D)-trans-4-OH-Pro-(D)-Phe, cyclo(D)-Pro-(D)-Phe and N-(2-phenylethyl)- acetamide were also isolated and identified. The structure of the new macrolide 1 was elucidated by the cumulative analyses of NMR spectroscopy and HR-MS data. Complete NMR assignments for the known venturicidins A (2) and B (3) are also provided, for the first time, in this report. Venturicidins A-C did not inhibit the proliferation of A549 lung cancer cell line but all displayed potent antifungal activity.

Original language	English
Pages (from-to)	223-230
Number of pages	8
Journal	Journal of Antibiotics
Volume	67
Issue number	3
DOIs	https://doi.org/10.1038/ja.2013.113
State	Published - Mar 2014

Bibliographical note

Funding Information:
This work was supported in part by the University of Kentucky College of Pharmacy, the University of Kentucky Markey Cancer Center and the National Center for Advancing Translational Sciences (UL1TR000117). We also thank Professor Jürgen Rohr (University of Kentucky, College of Pharmacy) for access to routine HPLC-MS and Professor Joseph Chappell (University of Kentucky, College of Pharmacy) for providing the fungal strain Cladosporium cucumerinum.

Keywords

Apoptolidin
Microbial
Natural products
Secondary metabolites
Streptomyces

ASJC Scopus subject areas

Pharmacology
Drug Discovery

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1038/ja.2013.113

Cite this

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title = "Venturicidin C, a new 20-membered macrolide produced by Streptomyces sp. TS-2-2",

abstract = "Venturicidin C (1), a new 20-membered macrolide along with the known venturicidins A (2) and B (3) were isolated from the crude extract of the Appalachian bacterial strain Streptomyces sp. TS-2-2. Additionally, nine other known compounds namely nocardamine, dehydroxynocardamine, desmethylenylnocardamine, ferrioxamine E, adenosine, riboflavin, cyclo(D)-trans-4-OH-Pro-(D)-Phe, cyclo(D)-Pro-(D)-Phe and N-(2-phenylethyl)- acetamide were also isolated and identified. The structure of the new macrolide 1 was elucidated by the cumulative analyses of NMR spectroscopy and HR-MS data. Complete NMR assignments for the known venturicidins A (2) and B (3) are also provided, for the first time, in this report. Venturicidins A-C did not inhibit the proliferation of A549 lung cancer cell line but all displayed potent antifungal activity.",

keywords = "Apoptolidin, Microbial, Natural products, Secondary metabolites, Streptomyces",

author = "Shaaban, {Khaled A.} and Shanteri Singh and Elshahawi, {Sherif I.} and Xiachang Wang and Ponomareva, {Larissa V.} and Manjula Sunkara and Copley, {Gregory C.} and Hower, {James C.} and Morris, {Andrew J.} and Kharel, {Madan K.} and Thorson, {Jon S.}",

note = "Funding Information: This work was supported in part by the University of Kentucky College of Pharmacy, the University of Kentucky Markey Cancer Center and the National Center for Advancing Translational Sciences (UL1TR000117). We also thank Professor J{\"u}rgen Rohr (University of Kentucky, College of Pharmacy) for access to routine HPLC-MS and Professor Joseph Chappell (University of Kentucky, College of Pharmacy) for providing the fungal strain Cladosporium cucumerinum.",

year = "2014",

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doi = "10.1038/ja.2013.113",

language = "English",

volume = "67",

pages = "223--230",

number = "3",

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AU - Shaaban, Khaled A.

AU - Singh, Shanteri

AU - Elshahawi, Sherif I.

AU - Wang, Xiachang

AU - Ponomareva, Larissa V.

AU - Sunkara, Manjula

AU - Copley, Gregory C.

AU - Hower, James C.

AU - Morris, Andrew J.

AU - Kharel, Madan K.

AU - Thorson, Jon S.

N1 - Funding Information: This work was supported in part by the University of Kentucky College of Pharmacy, the University of Kentucky Markey Cancer Center and the National Center for Advancing Translational Sciences (UL1TR000117). We also thank Professor Jürgen Rohr (University of Kentucky, College of Pharmacy) for access to routine HPLC-MS and Professor Joseph Chappell (University of Kentucky, College of Pharmacy) for providing the fungal strain Cladosporium cucumerinum.

PY - 2014/3

Y1 - 2014/3

N2 - Venturicidin C (1), a new 20-membered macrolide along with the known venturicidins A (2) and B (3) were isolated from the crude extract of the Appalachian bacterial strain Streptomyces sp. TS-2-2. Additionally, nine other known compounds namely nocardamine, dehydroxynocardamine, desmethylenylnocardamine, ferrioxamine E, adenosine, riboflavin, cyclo(D)-trans-4-OH-Pro-(D)-Phe, cyclo(D)-Pro-(D)-Phe and N-(2-phenylethyl)- acetamide were also isolated and identified. The structure of the new macrolide 1 was elucidated by the cumulative analyses of NMR spectroscopy and HR-MS data. Complete NMR assignments for the known venturicidins A (2) and B (3) are also provided, for the first time, in this report. Venturicidins A-C did not inhibit the proliferation of A549 lung cancer cell line but all displayed potent antifungal activity.

AB - Venturicidin C (1), a new 20-membered macrolide along with the known venturicidins A (2) and B (3) were isolated from the crude extract of the Appalachian bacterial strain Streptomyces sp. TS-2-2. Additionally, nine other known compounds namely nocardamine, dehydroxynocardamine, desmethylenylnocardamine, ferrioxamine E, adenosine, riboflavin, cyclo(D)-trans-4-OH-Pro-(D)-Phe, cyclo(D)-Pro-(D)-Phe and N-(2-phenylethyl)- acetamide were also isolated and identified. The structure of the new macrolide 1 was elucidated by the cumulative analyses of NMR spectroscopy and HR-MS data. Complete NMR assignments for the known venturicidins A (2) and B (3) are also provided, for the first time, in this report. Venturicidins A-C did not inhibit the proliferation of A549 lung cancer cell line but all displayed potent antifungal activity.

KW - Apoptolidin

KW - Microbial

KW - Natural products

KW - Secondary metabolites

KW - Streptomyces

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ER -

Venturicidin C, a new 20-membered macrolide produced by Streptomyces sp. TS-2-2

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

UN SDGs

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