Two rare antioxidative prenylated terpenoids from loop-root Asiatic mangrove Rhizophora mucronata (Family Rhizophoraceae) and their activity against pro-inflammatory cyclooxygenases and lipoxidase
CMFRI Repository
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Relation |
http://eprints.cmfri.org.in/11345/
http://www.tandfonline.com/doi/abs/10.1080/14786419.2016.1174232?journalCode=gnpl20 |
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Title |
Two rare antioxidative prenylated terpenoids from loop-root Asiatic mangrove Rhizophora mucronata (Family Rhizophoraceae) and their activity against pro-inflammatory cyclooxygenases and lipoxidase |
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Creator |
Raola, Vamshi Krishna
Chakraborty, Kajal |
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Subject |
Bioactive compound
Fish Biotechnology |
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Description |
Two new biogenic prenylated terpenoids were isolated from the methanol extract of Rhizophora mucronata. The extended C20 sesquiterpenoid with prenylated guaiane framework was characterised as (4E, 8Z)-3, 3a, 6, 7-tetrahydro-3, 9-dimethyl-5-(6-methylheptan-2-yl) cycloocta[b] furan-2-(9aH)-one (1). (35E)-1,2,3,5,6,6-icosahydro-4,4,8b,10,14,17,20,20- octamethylpicen-3-yl-34,35-dimethyloct-31-enoate (2) represents the first example of naturally occurring C40 prenylated oleanane-type triterpenoid, whereas one 4,5-dimethyloct-5-enoate side chain remains attached at C-3 position of the oleanane framework formed by the E-ring closure of C30 saccharide moiety. The structures of the compounds were elucidated using NMR and mass spectrometric analysis. Compound 1 was found to have significantly greater antioxidant activities (IC50 ~ 0.75 mg/ mL) compared to 2 (IC50 > 0.80 mg/mL). No significant differences in anti-cyclooxygenase-2 of these compounds were discernable (IC50 0.8 – 0.9 mg/mL), whilst compound 1 showed greater anti-5-lipoxidase activities (IC50 ~ 0.8 mg/mL) those that of 2 (IC50 0.96 mg/mL). Bioactivities of the prenylated terpenoids were inversely proportional to lipophilic and bulk descriptors. |
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Publisher |
Taylor and Francis
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Date |
2016
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Type |
Article
PeerReviewed |
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Format |
text
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Language |
en
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Identifier |
http://eprints.cmfri.org.in/11345/1/Two%20rare%20antioxidative%20prenylated%20terpenoids%20from_Natural%20Product%20Research_Kajal%20Chakraborty_2016.pdf
Raola, Vamshi Krishna and Chakraborty, Kajal (2016) Two rare antioxidative prenylated terpenoids from loop-root Asiatic mangrove Rhizophora mucronata (Family Rhizophoraceae) and their activity against pro-inflammatory cyclooxygenases and lipoxidase. Natural Product Research. pp. 1-10. ISSN 1478-6427 (Online) |
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