Coronarin K and L: Two Novel Labdane Diterpenes From Roscoea purpurea : An Ayurvedic Crude Drug

The main objective of cancer treatment with chemotherapy is to kill the cancerous cells without affecting the healthy normal cells. In the present study, bioactivity-guided purification of the -chloroform soluble fraction from the methanol extract of resulted in the identification of two new labdane...

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Published in:Frontiers in chemistry Vol. 9; p. 642073
Main Authors: Singamaneni, Venugopal, Lone, Bashir, Singh, Jasvinder, Kumar, Pankaj, Gairola, Sumeet, Singh, Shashank, Gupta, Prasoon
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Published: Switzerland Frontiers Media S.A 21-04-2021
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Abstract The main objective of cancer treatment with chemotherapy is to kill the cancerous cells without affecting the healthy normal cells. In the present study, bioactivity-guided purification of the -chloroform soluble fraction from the methanol extract of resulted in the identification of two new labdane diterpenes: coronarin K ( ) and coronarin L ( ), along with eight known compounds, coronarin A ( ), bisdemethoxycurcumin ( ), kaempferol 3- -methyl ether ( ), kaempferol ( ), fenozan acid ( ), 3-(3-methoxy,4-hydroxyphenyl)-2-propenoic acid ferulic acid ( ), caffeic acid ( ), and gallic acid ( ). The structural identification of new compounds ( and ) were determined by detailed analysis of 1D ( H and C) and 2D NMR (COSY, HSQC, and HMBC) spectroscopic data. The relative configurations of 1 and 2 were determined with the help of NOESY correlations and comparison of optical rotations with known labdane diterpenes, with established stereochemistry, while structure of known compounds was established by direct comparison of their NMR data with those reported in the literature. This is the first report of isolation of this labdane diterpenes and phenolic classes of secondary metabolites in . In the preliminary screening, the methanol extract and its fractions were tested for the cytotoxic activity against a panel of four cancer cell lines (A549, HCT-116, Bxpc-3, and MCF-7); extract and its chloroform fraction were found to be active against the lung cancer cell line, A-549, with IC value <25 μg/ml. Owing to the notable cytotoxic activity of the chloroform fraction, the compounds ( ) were screened for their cytotoxicity against all the cell lines by MTT assay. Coronarin K, showed significant cytotoxic potential against lung cancer cell lines (A-549), with IC value of 13.49 μM, while other compounds did not show activity below 22 μM.
AbstractList The main objective of cancer treatment with chemotherapy is to kill the cancerous cells without affecting the healthy normal cells. In the present study, bioactivity-guided purification of the n -chloroform soluble fraction from the methanol extract of Roscoea purpurea resulted in the identification of two new labdane diterpenes: coronarin K ( 1 ) and coronarin L ( 2 ), along with eight known compounds, coronarin A ( 3 ), bisdemethoxycurcumin ( 4 ), kaempferol 3- O -methyl ether ( 5 ), kaempferol ( 6 ), fenozan acid ( 7 ), 3-(3-methoxy,4-hydroxyphenyl)-2-propenoic acid ferulic acid ( 8 ), caffeic acid ( 9 ), and gallic acid ( 10 ). The structural identification of new compounds ( 1 and 2 ) were determined by detailed analysis of 1D ( 1 H and 13 C) and 2D NMR (COSY, HSQC, and HMBC) spectroscopic data. The relative configurations of 1 and 2 were determined with the help of NOESY correlations and comparison of optical rotations with known labdane diterpenes, with established stereochemistry, while structure of known compounds was established by direct comparison of their NMR data with those reported in the literature. This is the first report of isolation of this labdane diterpenes and phenolic classes of secondary metabolites in R. purpurea . In the preliminary screening, the methanol extract and its fractions were tested for the cytotoxic activity against a panel of four cancer cell lines (A549, HCT-116, Bxpc-3, and MCF-7); extract and its chloroform fraction were found to be active against the lung cancer cell line, A-549, with IC 50 value <25 μg/ml. Owing to the notable cytotoxic activity of the chloroform fraction, the compounds ( 1–5 ) were screened for their cytotoxicity against all the cell lines by MTT assay. Coronarin K, 1 showed significant cytotoxic potential against lung cancer cell lines (A-549), with IC 50 value of 13.49 μM, while other compounds did not show activity below 22 μM.
The main objective of cancer treatment with chemotherapy is to kill the cancerous cells without affecting the healthy normal cells. In the present study, bioactivity-guided purification of the -chloroform soluble fraction from the methanol extract of resulted in the identification of two new labdane diterpenes: coronarin K ( ) and coronarin L ( ), along with eight known compounds, coronarin A ( ), bisdemethoxycurcumin ( ), kaempferol 3- -methyl ether ( ), kaempferol ( ), fenozan acid ( ), 3-(3-methoxy,4-hydroxyphenyl)-2-propenoic acid ferulic acid ( ), caffeic acid ( ), and gallic acid ( ). The structural identification of new compounds ( and ) were determined by detailed analysis of 1D ( H and C) and 2D NMR (COSY, HSQC, and HMBC) spectroscopic data. The relative configurations of 1 and 2 were determined with the help of NOESY correlations and comparison of optical rotations with known labdane diterpenes, with established stereochemistry, while structure of known compounds was established by direct comparison of their NMR data with those reported in the literature. This is the first report of isolation of this labdane diterpenes and phenolic classes of secondary metabolites in . In the preliminary screening, the methanol extract and its fractions were tested for the cytotoxic activity against a panel of four cancer cell lines (A549, HCT-116, Bxpc-3, and MCF-7); extract and its chloroform fraction were found to be active against the lung cancer cell line, A-549, with IC value <25 μg/ml. Owing to the notable cytotoxic activity of the chloroform fraction, the compounds ( ) were screened for their cytotoxicity against all the cell lines by MTT assay. Coronarin K, showed significant cytotoxic potential against lung cancer cell lines (A-549), with IC value of 13.49 μM, while other compounds did not show activity below 22 μM.
The main objective of cancer treatment with chemotherapy is to kill the cancerous cells without affecting the healthy normal cells. In the present study, bioactivity-guided purification of the n-chloroform soluble fraction from the methanol extract of Roscoea purpurea resulted in the identification of two new labdane diterpenes: coronarin K (1) and coronarin L (2), along with eight known compounds, coronarin A (3), bisdemethoxycurcumin (4), kaempferol 3-O-methyl ether (5), kaempferol (6), fenozan acid (7), 3-(3-methoxy,4-hydroxyphenyl)-2-propenoic acid ferulic acid (8), caffeic acid (9), and gallic acid (10). The structural identification of new compounds (1 and 2) were determined by detailed analysis of 1D (1H and 13C) and 2D NMR (COSY, HSQC, and HMBC) spectroscopic data. The relative configurations of 1 and 2 were determined with the help of NOESY correlations and comparison of optical rotations with known labdane diterpenes, with established stereochemistry, while structure of known compounds was established by direct comparison of their NMR data with those reported in the literature. This is the first report of isolation of this labdane diterpenes and phenolic classes of secondary metabolites in R. purpurea. In the preliminary screening, the methanol extract and its fractions were tested for the cytotoxic activity against a panel of four cancer cell lines (A549, HCT-116, Bxpc-3, and MCF-7); extract and its chloroform fraction were found to be active against the lung cancer cell line, A-549, with IC50 value <25 μg/ml. Owing to the notable cytotoxic activity of the chloroform fraction, the compounds (1–5) were screened for their cytotoxicity against all the cell lines by MTT assay. Coronarin K, 1 showed significant cytotoxic potential against lung cancer cell lines (A-549), with IC50 value of 13.49 μM, while other compounds did not show activity below 22 μM.
Author Singamaneni, Venugopal
Kumar, Pankaj
Gupta, Prasoon
Singh, Jasvinder
Singh, Shashank
Lone, Bashir
Gairola, Sumeet
AuthorAffiliation 2 Academy of Scientific & Innovative Research (AcSIR) , Ghaziabad , India
3 Cancer Pharmacology Division, Indian Institute of Integrative Medicine , Jammu , India
4 Plant Science Division, Indian Institute of Integrative Medicine , Jammu , India
1 Natural Products and Medicinal Chemistry Division, Indian Institute of Integrative Medicine , Jammu , India
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Copyright Copyright © 2021 Singamaneni, Lone, Singh, Kumar, Gairola, Singh and Gupta.
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Keywords labdane diterpenes
coronarin k
coronarin L
Roscoea purpurea
Astavarga
cytotoxic
Zingiberaceae
Language English
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This article was submitted to Organic Chemistry, a section of the journal Frontiers in Chemistry
Edited by: Ramon Rios, University of Southampton, United Kingdom
Reviewed by: Guoxu Ma, Institute of Medicinal Plant Development, China; Muhammad Adnan Iqbal, University of Agriculture, Faisalabad, Pakistan
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SubjectTerms Astavarga
Chemistry
coronarin k
cytotoxic
labdane diterpenes
Roscoea purpurea
Zingiberaceae
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Title Coronarin K and L: Two Novel Labdane Diterpenes From Roscoea purpurea : An Ayurvedic Crude Drug
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