The native production of the sesquiterpene isopterocarpolone by Streptomyces sp. RM-14-6

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:10.1080/14786419.2013.855932

The native production of the sesquiterpene isopterocarpolone by Streptomyces sp. RM-14-6

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

Research output: Contribution to journal › Article › peer-review

19 Citations (SciVal)

Abstract

We report the production, isolation and structure elucidation of the sesquiterpene isopterocarpolone from an Appalachian isolate Streptomyces species RM-14-6. While isopterocarpolone was previously put forth as a putative plant metabolite, this study highlights the first native bacterial production of isopterocarpolone and the first full characterisation of isopterocarpolone using 1D and 2D NMR spectroscopy and HR-ESI mass spectrometry. Considering the biosynthesis of closely related metabolites (geosmin or 5-epiaristolochene), the structure of isopterocarpolone also suggests the potential participation of one or more unique enzymatic transformations. In this context, this work also sets the stage for the elucidation of potentially novel bacterial biosynthetic machinery.

Original language	English
Pages (from-to)	337-339
Number of pages	3
Journal	Natural Product Research
Volume	28
Issue number	5
DOIs	https://doi.org/10.1080/14786419.2013.855932
State	Published - Mar 4 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 (No. UL1TR000117).

Keywords

bacteria
biosynthesis
cyclase
isoprenoid
natural products
terpene

ASJC Scopus subject areas

Analytical Chemistry
Biochemistry
Plant Science
Organic Chemistry

Access to Document

10.1080/14786419.2013.855932

Cite this

@article{ad3a3ff26afd4a9ba58936aaffd297f3,

title = "The native production of the sesquiterpene isopterocarpolone by Streptomyces sp. RM-14-6",

abstract = "We report the production, isolation and structure elucidation of the sesquiterpene isopterocarpolone from an Appalachian isolate Streptomyces species RM-14-6. While isopterocarpolone was previously put forth as a putative plant metabolite, this study highlights the first native bacterial production of isopterocarpolone and the first full characterisation of isopterocarpolone using 1D and 2D NMR spectroscopy and HR-ESI mass spectrometry. Considering the biosynthesis of closely related metabolites (geosmin or 5-epiaristolochene), the structure of isopterocarpolone also suggests the potential participation of one or more unique enzymatic transformations. In this context, this work also sets the stage for the elucidation of potentially novel bacterial biosynthetic machinery.",

keywords = "bacteria, biosynthesis, cyclase, isoprenoid, natural products, terpene",

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 (No. UL1TR000117).",

year = "2014",

month = mar,

day = "4",

doi = "10.1080/14786419.2013.855932",

language = "English",

volume = "28",

pages = "337--339",

number = "5",

}

TY - JOUR

T1 - The native production of the sesquiterpene isopterocarpolone by Streptomyces sp. RM-14-6

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 (No. UL1TR000117).

PY - 2014/3/4

Y1 - 2014/3/4

N2 - We report the production, isolation and structure elucidation of the sesquiterpene isopterocarpolone from an Appalachian isolate Streptomyces species RM-14-6. While isopterocarpolone was previously put forth as a putative plant metabolite, this study highlights the first native bacterial production of isopterocarpolone and the first full characterisation of isopterocarpolone using 1D and 2D NMR spectroscopy and HR-ESI mass spectrometry. Considering the biosynthesis of closely related metabolites (geosmin or 5-epiaristolochene), the structure of isopterocarpolone also suggests the potential participation of one or more unique enzymatic transformations. In this context, this work also sets the stage for the elucidation of potentially novel bacterial biosynthetic machinery.

AB - We report the production, isolation and structure elucidation of the sesquiterpene isopterocarpolone from an Appalachian isolate Streptomyces species RM-14-6. While isopterocarpolone was previously put forth as a putative plant metabolite, this study highlights the first native bacterial production of isopterocarpolone and the first full characterisation of isopterocarpolone using 1D and 2D NMR spectroscopy and HR-ESI mass spectrometry. Considering the biosynthesis of closely related metabolites (geosmin or 5-epiaristolochene), the structure of isopterocarpolone also suggests the potential participation of one or more unique enzymatic transformations. In this context, this work also sets the stage for the elucidation of potentially novel bacterial biosynthetic machinery.

KW - bacteria

KW - biosynthesis

KW - cyclase

KW - isoprenoid

KW - natural products

KW - terpene

UR - http://www.scopus.com/inward/record.url?scp=84896389019&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84896389019&partnerID=8YFLogxK

U2 - 10.1080/14786419.2013.855932

DO - 10.1080/14786419.2013.855932

M3 - Article

C2 - 24237421

AN - SCOPUS:84896389019

SN - 1478-6419

VL - 28

SP - 337

EP - 339

JO - Natural Product Research

JF - Natural Product Research

IS - 5

ER -

The native production of the sesquiterpene isopterocarpolone by Streptomyces sp. RM-14-6

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this