Isolation, structure elucidation and cytotoxic evaluation of endiandrin B from the Australian rainforest plant Endiandra anthropophagorum

Rohan A. Davis; Emma C. Barnes; James Longden; Vicky M. Avery; Peter C. Healy

doi:10.1016/j.bmc.2008.12.030

Isolation, structure elucidation and cytotoxic evaluation of endiandrin B from the Australian rainforest plant Endiandra anthropophagorum

Rohan A. Davis^*, Emma C. Barnes, James Longden, Vicky M. Avery, Peter C. Healy

^*Corresponding author for this work

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

29 Citations (Scopus)

Abstract

Chemical investigations of the DCM extract from the roots of Endiandra anthropophagorum resulted in the isolation of a new cyclobutane lignan endiandrin B (1), together with the known natural products, endiandrin A (2), and (-)-dihydroguaiaretic acid (3). The structure of 1 was determined by extensive spectroscopic analyses, and confirmed by single crystal X-ray crystallography. Methylation of 1 using diazomethane afforded the previously reported natural product, cinbalansan (4). All compounds were evaluated for their cytotoxicity towards human lung carcinoma cells (A549) using high-content screening. (-)-Dihydroguaiaretic acid (3) was found to be the most potent cytotoxin against the A549 lung carcinoma cell line, with an IC₅₀ value of 7.49 μM.

Original language	English
Pages (from-to)	1387-1392
Number of pages	6
Journal	Bioorganic and Medicinal Chemistry
Volume	17
Issue number	3
DOIs	https://doi.org/10.1016/j.bmc.2008.12.030
Publication status	Published - 1 Feb 2009
Externally published	Yes

Keywords

(-)-Dihydroguaiaretic acid
A549
Cinbalansan
Cytotoxicity
Endiandrin A
Endiandrin B
High content screening
Natural products
NMR
Structure elucidation
X-ray

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10.1016/j.bmc.2008.12.030

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title = "Isolation, structure elucidation and cytotoxic evaluation of endiandrin B from the Australian rainforest plant Endiandra anthropophagorum",

abstract = "Chemical investigations of the DCM extract from the roots of Endiandra anthropophagorum resulted in the isolation of a new cyclobutane lignan endiandrin B (1), together with the known natural products, endiandrin A (2), and (-)-dihydroguaiaretic acid (3). The structure of 1 was determined by extensive spectroscopic analyses, and confirmed by single crystal X-ray crystallography. Methylation of 1 using diazomethane afforded the previously reported natural product, cinbalansan (4). All compounds were evaluated for their cytotoxicity towards human lung carcinoma cells (A549) using high-content screening. (-)-Dihydroguaiaretic acid (3) was found to be the most potent cytotoxin against the A549 lung carcinoma cell line, with an IC50 value of 7.49 μM.",

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AU - Barnes, Emma C.

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AU - Avery, Vicky M.

AU - Healy, Peter C.

PY - 2009/2/1

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AB - Chemical investigations of the DCM extract from the roots of Endiandra anthropophagorum resulted in the isolation of a new cyclobutane lignan endiandrin B (1), together with the known natural products, endiandrin A (2), and (-)-dihydroguaiaretic acid (3). The structure of 1 was determined by extensive spectroscopic analyses, and confirmed by single crystal X-ray crystallography. Methylation of 1 using diazomethane afforded the previously reported natural product, cinbalansan (4). All compounds were evaluated for their cytotoxicity towards human lung carcinoma cells (A549) using high-content screening. (-)-Dihydroguaiaretic acid (3) was found to be the most potent cytotoxin against the A549 lung carcinoma cell line, with an IC50 value of 7.49 μM.

KW - (-)-Dihydroguaiaretic acid

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KW - Cytotoxicity

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KW - Endiandrin B

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KW - Natural products

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IS - 3

ER -

Isolation, structure elucidation and cytotoxic evaluation of endiandrin B from the Australian rainforest plant Endiandra anthropophagorum

Abstract

Keywords

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