Neoclerodane Diterpenoids from Reehal Fatima, Teucrium yemense

Mohammad  Nur-e-Alam; Muhammad Yousaf; Sarfaraz Ahmed; Ebtesam S. Al-Sheddi; Ifat Shah; David Fazakerley; Ahmed Bari; Hazem A. Ghabbour; Michael D. Threadgill; Kezia Whatley; Karl Hoffmann; Adnan J. Al-Rehaily

doi:10.1021/acs.jnatprod.7b00188

Neoclerodane Diterpenoids from Reehal Fatima, Teucrium yemense

Mohammad Nur-e-Alam, Muhammad Yousaf, Sarfaraz Ahmed, Ebtesam S. Al-Sheddi, Ifat Shah, David Fazakerley, Ahmed Bari, Hazem A. Ghabbour, Michael D. Threadgill, Kezia Whatley, Karl Hoffmann, Adnan J. Al-Rehaily

Department of Life Sciences

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Abstract

Teucrium yemense (Defl), locally known as Reehal Fatima, is a medicinal plant commonly grown in Saudi Arabia and Yemen. Phytochemical investigation of the aerial parts of T. yemense yielded six new neoclerodane diterpenoids, namely fatimanol A–E (1, 2, 3, 5, and 6) and fatimanone (4), and the known teulepicephin (7). As both the Teucrium genus and the related Lamiaceae family have previously been widely reported to possess anthelmintic and antimicrobial activities, the structural and biological characterization of the seven diterpenoids was pursued. The structures of the new compounds were elucidated from their 2D NMR and MS profiles and by comparison to related compounds. The structure of fatimanol D (5) was confirmed by X-ray crystallographic analysis. The new structures contribute to the breadth of knowledge of secondary metabolites in this genus

Original language	English
Pages (from-to)	1900-1908
Number of pages	9
Journal	Journal of Natural Products
Volume	80
Issue number	6
Early online date	05 Jun 2017
DOIs	https://doi.org/10.1021/acs.jnatprod.7b00188
Publication status	Published - 23 Jun 2017

Keywords

Candida albicans/drug effects
Crystallography, X-Ray
Diterpenes, Clerodane
Diterpenes/chemistry
Escherichia coli/drug effects
Hep G2 Cells
Humans
Lamiaceae/chemistry
Microbial Sensitivity Tests
Molecular Conformation
Molecular Structure
Mycobacterium smegmatis/drug effects
Nuclear Magnetic Resonance, Biomolecular
Plants, Medicinal/chemistry
Pseudomonas aeruginosa/drug effects
Saudi Arabia
Staphylococcus aureus/drug effects
Teucrium/chemistry

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10.1021/acs.jnatprod.7b00188

Neoclerodane Diterpenoids from Reehal Fatima, Teucrium yemenseAccepted author manuscript, 1.03 MB

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@article{188f4282945a422abb56e0c39a976a1e,

title = "Neoclerodane Diterpenoids from Reehal Fatima, Teucrium yemense",

abstract = "Teucrium yemense (Defl), locally known as Reehal Fatima, is a medicinal plant commonly grown in Saudi Arabia and Yemen. Phytochemical investigation of the aerial parts of T. yemense yielded six new neoclerodane diterpenoids, namely fatimanol A–E (1, 2, 3, 5, and 6) and fatimanone (4), and the known teulepicephin (7). As both the Teucrium genus and the related Lamiaceae family have previously been widely reported to possess anthelmintic and antimicrobial activities, the structural and biological characterization of the seven diterpenoids was pursued. The structures of the new compounds were elucidated from their 2D NMR and MS profiles and by comparison to related compounds. The structure of fatimanol D (5) was confirmed by X-ray crystallographic analysis. The new structures contribute to the breadth of knowledge of secondary metabolites in this genus",

keywords = "Candida albicans/drug effects, Crystallography, X-Ray, Diterpenes, Clerodane, Diterpenes/chemistry, Escherichia coli/drug effects, Hep G2 Cells, Humans, Lamiaceae/chemistry, Microbial Sensitivity Tests, Molecular Conformation, Molecular Structure, Mycobacterium smegmatis/drug effects, Nuclear Magnetic Resonance, Biomolecular, Plants, Medicinal/chemistry, Pseudomonas aeruginosa/drug effects, Saudi Arabia, Staphylococcus aureus/drug effects, Teucrium/chemistry",

author = "Mohammad Nur-e-Alam and Muhammad Yousaf and Sarfaraz Ahmed and Al-Sheddi, {Ebtesam S.} and Ifat Shah and David Fazakerley and Ahmed Bari and Ghabbour, {Hazem A.} and Threadgill, {Michael D.} and Kezia Whatley and Karl Hoffmann and Al-Rehaily, {Adnan J.}",

note = "This is the author accepted manuscript. The final version is available from American Chemical Society via http://dx.doi.org/10.1021/acs.jnatprod.7b00188 Funding: Biological Sciences Research Council Institute Strategic Programme Grant on Energy Grasses and Biorefining (BB/J0042/1)",

year = "2017",

month = jun,

day = "23",

doi = "10.1021/acs.jnatprod.7b00188",

language = "English",

volume = "80",

pages = "1900--1908",

journal = "Journal of Natural Products",

issn = "0163-3864",

publisher = "American Chemical Society",

number = "6",

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TY - JOUR

T1 - Neoclerodane Diterpenoids from Reehal Fatima, Teucrium yemense

AU - Nur-e-Alam, Mohammad

AU - Yousaf, Muhammad

AU - Ahmed, Sarfaraz

AU - Al-Sheddi, Ebtesam S.

AU - Shah, Ifat

AU - Fazakerley, David

AU - Bari, Ahmed

AU - Ghabbour, Hazem A.

AU - Threadgill, Michael D.

AU - Whatley, Kezia

AU - Hoffmann, Karl

AU - Al-Rehaily, Adnan J.

N1 - This is the author accepted manuscript. The final version is available from American Chemical Society via http://dx.doi.org/10.1021/acs.jnatprod.7b00188 Funding: Biological Sciences Research Council Institute Strategic Programme Grant on Energy Grasses and Biorefining (BB/J0042/1)

PY - 2017/6/23

Y1 - 2017/6/23

N2 - Teucrium yemense (Defl), locally known as Reehal Fatima, is a medicinal plant commonly grown in Saudi Arabia and Yemen. Phytochemical investigation of the aerial parts of T. yemense yielded six new neoclerodane diterpenoids, namely fatimanol A–E (1, 2, 3, 5, and 6) and fatimanone (4), and the known teulepicephin (7). As both the Teucrium genus and the related Lamiaceae family have previously been widely reported to possess anthelmintic and antimicrobial activities, the structural and biological characterization of the seven diterpenoids was pursued. The structures of the new compounds were elucidated from their 2D NMR and MS profiles and by comparison to related compounds. The structure of fatimanol D (5) was confirmed by X-ray crystallographic analysis. The new structures contribute to the breadth of knowledge of secondary metabolites in this genus

AB - Teucrium yemense (Defl), locally known as Reehal Fatima, is a medicinal plant commonly grown in Saudi Arabia and Yemen. Phytochemical investigation of the aerial parts of T. yemense yielded six new neoclerodane diterpenoids, namely fatimanol A–E (1, 2, 3, 5, and 6) and fatimanone (4), and the known teulepicephin (7). As both the Teucrium genus and the related Lamiaceae family have previously been widely reported to possess anthelmintic and antimicrobial activities, the structural and biological characterization of the seven diterpenoids was pursued. The structures of the new compounds were elucidated from their 2D NMR and MS profiles and by comparison to related compounds. The structure of fatimanol D (5) was confirmed by X-ray crystallographic analysis. The new structures contribute to the breadth of knowledge of secondary metabolites in this genus

KW - Candida albicans/drug effects

KW - Crystallography, X-Ray

KW - Diterpenes, Clerodane

KW - Diterpenes/chemistry

KW - Escherichia coli/drug effects

KW - Hep G2 Cells

KW - Humans

KW - Lamiaceae/chemistry

KW - Microbial Sensitivity Tests

KW - Molecular Conformation

KW - Molecular Structure

KW - Mycobacterium smegmatis/drug effects

KW - Nuclear Magnetic Resonance, Biomolecular

KW - Plants, Medicinal/chemistry

KW - Pseudomonas aeruginosa/drug effects

KW - Saudi Arabia

KW - Staphylococcus aureus/drug effects

KW - Teucrium/chemistry

UR - http://hdl.handle.net/2160/45244

UR - http://www.scopus.com/inward/record.url?scp=85021126873&partnerID=8YFLogxK

U2 - 10.1021/acs.jnatprod.7b00188

DO - 10.1021/acs.jnatprod.7b00188

M3 - Article

C2 - 28581290

SN - 0163-3864

VL - 80

SP - 1900

EP - 1908

JO - Journal of Natural Products

JF - Journal of Natural Products

IS - 6

ER -

Neoclerodane Diterpenoids from Reehal Fatima, Teucrium yemense

Abstract

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Ifat Parveen Shah

Energy Grasses and Biorefining (EGB) ISPG

Biorefining Centre of Excellence (BEACON)

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Neoclerodane Diterpenoids from Reehal Fatima, Teucrium yemense

Abstract

Keywords

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Profiles

Ifat Parveen Shah

Projects

Energy Grasses and Biorefining (EGB) ISPG

Biorefining Centre of Excellence (BEACON)

Cite this