In Vivo Activity of Benzoyl Ester Clerodane Diterpenoid Derivatives from Dodonaea polyandra

Bradley Simpson; David Claudie; Jacobus Gerber; Simon Pyke; Jiping Wang; Ross McKinnon; Susan Semple

doi:10.1021/np100701s

In Vivo Activity of Benzoyl Ester Clerodane Diterpenoid Derivatives from Dodonaea polyandra

Bradley Simpson, David Claudie, Jacobus Gerber, Simon Pyke, Jiping Wang, Ross McKinnon, Susan Semple

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

28 Citations (Scopus)

Abstract

Four new benzoyl ester clerodane diterpenoids, 15,16-epoxy-8α- (benzoyloxy)methylcleroda-3,13(16),14-trien-18-oic acid (1), 15,16-epoxy-8α-(benzoyloxy)methyl-2α-hydroxycleroda-3,13(16), 14-trien-18-oic acid (2), 15,16-epoxy-8α-(benzoyloxy)methyl-2-oxocleroda- 3,13(16),14-trien-18-oic acid (3), and 15,16-epoxy-2α-benzoyloxycleroda-3, 13(16),14-trien-18-oic acid (4), have been isolated from the leaves and stems of Dodonaea polyandra. The anti-inflammatory activities of compounds 1, 2, and 4 were evaluated by means of 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced mouse ear edema. Compounds 2 and 4 exhibited maximum inhibition of inflammation (70-76%) at doses of 0.22 and 0.9 μmol/ear, respectively. Modest activity (45% inhibition) was maintained at nanomole/ear doses.

Original language	English
Pages (from-to)	650-657
Number of pages	8
Journal	Journal of Natural Products
Volume	74
Issue number	4
DOIs	https://doi.org/10.1021/np100701s
Publication status	Published - 25 Apr 2011

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title = "In Vivo Activity of Benzoyl Ester Clerodane Diterpenoid Derivatives from Dodonaea polyandra",

abstract = "Four new benzoyl ester clerodane diterpenoids, 15,16-epoxy-8α- (benzoyloxy)methylcleroda-3,13(16),14-trien-18-oic acid (1), 15,16-epoxy-8α-(benzoyloxy)methyl-2α-hydroxycleroda-3,13(16), 14-trien-18-oic acid (2), 15,16-epoxy-8α-(benzoyloxy)methyl-2-oxocleroda- 3,13(16),14-trien-18-oic acid (3), and 15,16-epoxy-2α-benzoyloxycleroda-3, 13(16),14-trien-18-oic acid (4), have been isolated from the leaves and stems of Dodonaea polyandra. The anti-inflammatory activities of compounds 1, 2, and 4 were evaluated by means of 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced mouse ear edema. Compounds 2 and 4 exhibited maximum inhibition of inflammation (70-76%) at doses of 0.22 and 0.9 μmol/ear, respectively. Modest activity (45% inhibition) was maintained at nanomole/ear doses.",

author = "Bradley Simpson and David Claudie and Jacobus Gerber and Simon Pyke and Jiping Wang and Ross McKinnon and Susan Semple",

year = "2011",

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T1 - In Vivo Activity of Benzoyl Ester Clerodane Diterpenoid Derivatives from Dodonaea polyandra

AU - Simpson, Bradley

AU - Claudie, David

AU - Gerber, Jacobus

AU - Pyke, Simon

AU - Wang, Jiping

AU - McKinnon, Ross

AU - Semple, Susan

PY - 2011/4/25

Y1 - 2011/4/25

N2 - Four new benzoyl ester clerodane diterpenoids, 15,16-epoxy-8α- (benzoyloxy)methylcleroda-3,13(16),14-trien-18-oic acid (1), 15,16-epoxy-8α-(benzoyloxy)methyl-2α-hydroxycleroda-3,13(16), 14-trien-18-oic acid (2), 15,16-epoxy-8α-(benzoyloxy)methyl-2-oxocleroda- 3,13(16),14-trien-18-oic acid (3), and 15,16-epoxy-2α-benzoyloxycleroda-3, 13(16),14-trien-18-oic acid (4), have been isolated from the leaves and stems of Dodonaea polyandra. The anti-inflammatory activities of compounds 1, 2, and 4 were evaluated by means of 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced mouse ear edema. Compounds 2 and 4 exhibited maximum inhibition of inflammation (70-76%) at doses of 0.22 and 0.9 μmol/ear, respectively. Modest activity (45% inhibition) was maintained at nanomole/ear doses.

AB - Four new benzoyl ester clerodane diterpenoids, 15,16-epoxy-8α- (benzoyloxy)methylcleroda-3,13(16),14-trien-18-oic acid (1), 15,16-epoxy-8α-(benzoyloxy)methyl-2α-hydroxycleroda-3,13(16), 14-trien-18-oic acid (2), 15,16-epoxy-8α-(benzoyloxy)methyl-2-oxocleroda- 3,13(16),14-trien-18-oic acid (3), and 15,16-epoxy-2α-benzoyloxycleroda-3, 13(16),14-trien-18-oic acid (4), have been isolated from the leaves and stems of Dodonaea polyandra. The anti-inflammatory activities of compounds 1, 2, and 4 were evaluated by means of 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced mouse ear edema. Compounds 2 and 4 exhibited maximum inhibition of inflammation (70-76%) at doses of 0.22 and 0.9 μmol/ear, respectively. Modest activity (45% inhibition) was maintained at nanomole/ear doses.

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ER -

In Vivo Activity of Benzoyl Ester Clerodane Diterpenoid Derivatives from Dodonaea polyandra

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