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Norstaminane- and isopimarane-type diterpenes of Orthosiphon stamineus from Okinawa

From National Research Council Canada

DOIResolve DOI: https://doi.org/10.1016/S0040-4020(02)00508-2
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FormatText, Article
SubjectOrthosiphon stamineus; staminane; norstaminolactone A; isopimarane; secoorthosiphol; antiproliferative activity
Abstract
Nine novel highly oxygenated and structurally diverse diterpenes, named norstaminolactone A (1), norstaminols B and C (2 and 3), secoorthosiphols A–C (4–6) and orthosiphols R–T (7–9) have been isolated from the aerial part of Orthosiphon stamineus cultivated in Okinawa Prefecture, Japan. Norstaminolactone A (1) is the first representative of a biogenetically unusual norstaminane-type diterpene bearing a nitrogen atom. Norstaminol C (3) possessed a framework presumed to be biosynthesized from the staminane-type diterpene. Secoorthosiphols A–C (4–6) possessed an unprecedented structural feature of the opened ring A system, encountered for the first time in isopimarane-type diterpenes. Secoorothosiphol C (6) also represents the first example of biogenetically unique and unconventional secoisopimarane-type diterpene bearing a cyano group. Norstaminolactone A (1) showed a potent antiproliferative activity with an IC(50) value of 2.16 μg/mL against highly liver metastatic colon 26-L5 carcinoma cell line.
Publication date
In
  • Tetrahedron 58, no. 27 (1 July 2002): 5503–5512.
LanguageEnglish
Peer reviewedYes
NRC publication
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"Non-NRC publications" are publications authored by NRC employees prior to their employment by NRC.

NPARC number21274777
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Record identifier53ac4c36-060b-49bb-b670-f96772287e83
Record created2015-04-08
Record modified2020-03-30
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