A hexacyclic ent-trachylobane diterpenoid possessing an oxetane ring from Mitrephora glabra

Chen Li, Dongho Lee, Tyler N. Graf, Sharnelle S. Phifer, Yuka Nakanishi, Jason P. Burgess, Soedarsono Riswan, Fransisca M. Setyowati, Achmad M. Saribi, Djaja D. Soejarto, Norman R. Farnsworth, Joseph O. Falkinham, David J. Kroll, A. Douglas Kinghorn, Mansukh C. Wani, Nicholas H. Oberlies

Research output: Contribution to journalArticle

41 Citations (Scopus)

Abstract

(Chemical Equation Presented) Three new ent-trachylobane diterpenoids (1-3) were isolated and structures elucidated from Mitrephora glabra Scheff. (Annonaceae). Mitrephorone A (1) possesses a hexacyclic ring system with adjacent ketone moieties and an oxetane ring, both of which are unprecedented among trachylobanes. All compounds were evaluated for cytotoxicity against a panel of cancer cells, where 1 displayed the most potent and broadest activity, and against a battery of antimicrobial assays, where all compounds were approximately equipotent.

Original languageEnglish
Pages (from-to)5709-5712
Number of pages4
JournalOrganic Letters
Volume7
Issue number25
DOIs
Publication statusPublished - 2005 Dec 8
Externally publishedYes

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Annonaceae
Diterpenes
Cytotoxicity
Ketones
Assays
Cells
rings
ketones
electric batteries
Neoplasms
cancer
oxetane
mitrephorone A

ASJC Scopus subject areas

  • Molecular Medicine

Cite this

Li, C., Lee, D., Graf, T. N., Phifer, S. S., Nakanishi, Y., Burgess, J. P., ... Oberlies, N. H. (2005). A hexacyclic ent-trachylobane diterpenoid possessing an oxetane ring from Mitrephora glabra. Organic Letters, 7(25), 5709-5712. https://doi.org/10.1021/ol052498l

A hexacyclic ent-trachylobane diterpenoid possessing an oxetane ring from Mitrephora glabra. / Li, Chen; Lee, Dongho; Graf, Tyler N.; Phifer, Sharnelle S.; Nakanishi, Yuka; Burgess, Jason P.; Riswan, Soedarsono; Setyowati, Fransisca M.; Saribi, Achmad M.; Soejarto, Djaja D.; Farnsworth, Norman R.; Falkinham, Joseph O.; Kroll, David J.; Kinghorn, A. Douglas; Wani, Mansukh C.; Oberlies, Nicholas H.

In: Organic Letters, Vol. 7, No. 25, 08.12.2005, p. 5709-5712.

Research output: Contribution to journalArticle

Li, C, Lee, D, Graf, TN, Phifer, SS, Nakanishi, Y, Burgess, JP, Riswan, S, Setyowati, FM, Saribi, AM, Soejarto, DD, Farnsworth, NR, Falkinham, JO, Kroll, DJ, Kinghorn, AD, Wani, MC & Oberlies, NH 2005, 'A hexacyclic ent-trachylobane diterpenoid possessing an oxetane ring from Mitrephora glabra', Organic Letters, vol. 7, no. 25, pp. 5709-5712. https://doi.org/10.1021/ol052498l
Li, Chen ; Lee, Dongho ; Graf, Tyler N. ; Phifer, Sharnelle S. ; Nakanishi, Yuka ; Burgess, Jason P. ; Riswan, Soedarsono ; Setyowati, Fransisca M. ; Saribi, Achmad M. ; Soejarto, Djaja D. ; Farnsworth, Norman R. ; Falkinham, Joseph O. ; Kroll, David J. ; Kinghorn, A. Douglas ; Wani, Mansukh C. ; Oberlies, Nicholas H. / A hexacyclic ent-trachylobane diterpenoid possessing an oxetane ring from Mitrephora glabra. In: Organic Letters. 2005 ; Vol. 7, No. 25. pp. 5709-5712.
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