Semi-synthesis and cytotoxicity evaluation of pyrimidine, thiazole, and indole analogues of argentatins A–C from guayule (Parthenium argentatum) resin

Chandrashekhar Madasu; Ya Ming Xu; E. M.Kithsiri Wijeratne; Manping X. Liu; István Molnár; A. A.Leslie Gunatilaka

doi:10.1007/s00044-021-02835-1

Semi-synthesis and cytotoxicity evaluation of pyrimidine, thiazole, and indole analogues of argentatins A–C from guayule (Parthenium argentatum) resin

Chandrashekhar Madasu
, Ya Ming Xu
, E. M.Kithsiri Wijeratne
, Manping X. Liu
, István Molnár
, A. A.Leslie Gunatilaka^*

^*Corresponding author for this work

Not published at VTT

University of Arizona

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

29 Citations (Scopus)

Abstract

Argentatins A–C (1–3), the major cycloartane-type triterpenoids of guayule resin, a byproduct of commercial rubber production, were converted into their pyrimidine (7–12), thiazole (13–15), and indole (16–18) analogues by a molecular hybridization approach. The cytotoxic activities of these fused heterocyclic analogues 7–18 were compared with those of argentatins A–C (1–3) against a panel of three sentinel human cancer cell lines [NCI-H460 (non-small cell lung), MCF-7 (breast adenocarcinoma), and SF-268 (central nervous system glioma)], and normal human fibroblast (WI-38) cells. The cytotoxicity data suggest that the pyrimidine analogues 7 and 8 (derived from 1), 9 and 10 (derived from 2), and 12 (derived from 3) had significantly enhanced activity compared to the parent compounds or their thiazole (13–15) and indole (16–18) analogues. These findings indicate that triterpenoid constituents of guayule resin may be exploited to obtain value-added products with potential applications in anticancer drug discovery. [Figure not available: see fulltext.]

Original language	English
Pages (from-to)	1088-1098
Number of pages	11
Journal	Medicinal Chemistry Research
Volume	31
Issue number	7
DOIs	https://doi.org/10.1007/s00044-021-02835-1
Publication status	Published - Jul 2022
MoE publication type	A1 Journal article-refereed

Funding

This project was supported by the USDA-NIFA (Grant # 2017-68005-26867; Kimberly Ogden, PI) and Hatch projects ARZT-1005072 (AALG) and ARZT-1361640-H12-224 (IM), and the University of Arizona College of Agriculture. We thank Dr. Lijiang Xuan, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, P. R. China for HRMS data.

UN SDGs

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

SDG 3 Good Health and Well-being

Keywords

Argentatins A–C
Cytotoxic activity
Guayule resin
Indole analogues
Pyrimidine analogues
Thiazole analogues

Access to Document

10.1007/s00044-021-02835-1

Cite this

@article{e58b0b4172574445ba82c2c3ec746a7f,

title = "Semi-synthesis and cytotoxicity evaluation of pyrimidine, thiazole, and indole analogues of argentatins A–C from guayule (Parthenium argentatum) resin",

abstract = "Argentatins A–C (1–3), the major cycloartane-type triterpenoids of guayule resin, a byproduct of commercial rubber production, were converted into their pyrimidine (7–12), thiazole (13–15), and indole (16–18) analogues by a molecular hybridization approach. The cytotoxic activities of these fused heterocyclic analogues 7–18 were compared with those of argentatins A–C (1–3) against a panel of three sentinel human cancer cell lines [NCI-H460 (non-small cell lung), MCF-7 (breast adenocarcinoma), and SF-268 (central nervous system glioma)], and normal human fibroblast (WI-38) cells. The cytotoxicity data suggest that the pyrimidine analogues 7 and 8 (derived from 1), 9 and 10 (derived from 2), and 12 (derived from 3) had significantly enhanced activity compared to the parent compounds or their thiazole (13–15) and indole (16–18) analogues. These findings indicate that triterpenoid constituents of guayule resin may be exploited to obtain value-added products with potential applications in anticancer drug discovery. [Figure not available: see fulltext.]",

keywords = "Argentatins A–C, Cytotoxic activity, Guayule resin, Indole analogues, Pyrimidine analogues, Thiazole analogues",

author = "Chandrashekhar Madasu and Xu, \{Ya Ming\} and Wijeratne, \{E. M.Kithsiri\} and Liu, \{Manping X.\} and Istv{\'a}n Moln{\'a}r and Gunatilaka, \{A. A.Leslie\}",

year = "2022",

month = jul,

doi = "10.1007/s00044-021-02835-1",

language = "English",

volume = "31",

pages = "1088--1098",

journal = "Medicinal Chemistry Research",

issn = "1054-2523",

publisher = "Birkhauser Boston",

number = "7",

}

Semi-synthesis and cytotoxicity evaluation of pyrimidine, thiazole, and indole analogues of argentatins A–C from guayule (Parthenium argentatum) resin. / Madasu, Chandrashekhar; Xu, Ya Ming; Wijeratne, E. M.Kithsiri et al.
In: Medicinal Chemistry Research, Vol. 31, No. 7, 07.2022, p. 1088-1098.

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

TY - JOUR

T1 - Semi-synthesis and cytotoxicity evaluation of pyrimidine, thiazole, and indole analogues of argentatins A–C from guayule (Parthenium argentatum) resin

AU - Madasu, Chandrashekhar

AU - Xu, Ya Ming

AU - Wijeratne, E. M.Kithsiri

AU - Liu, Manping X.

AU - Molnár, István

AU - Gunatilaka, A. A.Leslie

PY - 2022/7

Y1 - 2022/7

N2 - Argentatins A–C (1–3), the major cycloartane-type triterpenoids of guayule resin, a byproduct of commercial rubber production, were converted into their pyrimidine (7–12), thiazole (13–15), and indole (16–18) analogues by a molecular hybridization approach. The cytotoxic activities of these fused heterocyclic analogues 7–18 were compared with those of argentatins A–C (1–3) against a panel of three sentinel human cancer cell lines [NCI-H460 (non-small cell lung), MCF-7 (breast adenocarcinoma), and SF-268 (central nervous system glioma)], and normal human fibroblast (WI-38) cells. The cytotoxicity data suggest that the pyrimidine analogues 7 and 8 (derived from 1), 9 and 10 (derived from 2), and 12 (derived from 3) had significantly enhanced activity compared to the parent compounds or their thiazole (13–15) and indole (16–18) analogues. These findings indicate that triterpenoid constituents of guayule resin may be exploited to obtain value-added products with potential applications in anticancer drug discovery. [Figure not available: see fulltext.]

AB - Argentatins A–C (1–3), the major cycloartane-type triterpenoids of guayule resin, a byproduct of commercial rubber production, were converted into their pyrimidine (7–12), thiazole (13–15), and indole (16–18) analogues by a molecular hybridization approach. The cytotoxic activities of these fused heterocyclic analogues 7–18 were compared with those of argentatins A–C (1–3) against a panel of three sentinel human cancer cell lines [NCI-H460 (non-small cell lung), MCF-7 (breast adenocarcinoma), and SF-268 (central nervous system glioma)], and normal human fibroblast (WI-38) cells. The cytotoxicity data suggest that the pyrimidine analogues 7 and 8 (derived from 1), 9 and 10 (derived from 2), and 12 (derived from 3) had significantly enhanced activity compared to the parent compounds or their thiazole (13–15) and indole (16–18) analogues. These findings indicate that triterpenoid constituents of guayule resin may be exploited to obtain value-added products with potential applications in anticancer drug discovery. [Figure not available: see fulltext.]

KW - Argentatins A–C

KW - Cytotoxic activity

KW - Guayule resin

KW - Indole analogues

KW - Pyrimidine analogues

KW - Thiazole analogues

UR - https://www.scopus.com/pages/publications/85123086130

U2 - 10.1007/s00044-021-02835-1

DO - 10.1007/s00044-021-02835-1

M3 - Article

AN - SCOPUS:85123086130

SN - 1054-2523

VL - 31

SP - 1088

EP - 1098

JO - Medicinal Chemistry Research

JF - Medicinal Chemistry Research

IS - 7

ER -

Semi-synthesis and cytotoxicity evaluation of pyrimidine, thiazole, and indole analogues of argentatins A–C from guayule (Parthenium argentatum) resin

Abstract

Funding

UN SDGs

Keywords

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