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

doi:10.1021/ol052498l

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 journal › Article › peer-review

60 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 language	English
Pages (from-to)	5709-5712
Number of pages	4
Journal	Organic Letters
Volume	7
Issue number	25
DOIs	https://doi.org/10.1021/ol052498l
Publication status	Published - 2005 Dec 8
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

Access to Document

10.1021/ol052498l

Cite this

Li, C., Lee, D., Graf, T. N., Phifer, S. S., Nakanishi, Y., Burgess, J. P., Riswan, S., Setyowati, F. M., Saribi, A. M., Soejarto, D. D., Farnsworth, N. R., Falkinham, J. O., Kroll, D. J., Kinghorn, A. D., Wani, M. C., & 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

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

@article{ab68f51ec9ef4e6b871863ed6a6d02d2,

title = "A hexacyclic ent-trachylobane diterpenoid possessing an oxetane ring from Mitrephora glabra",

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.",

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

year = "2005",

month = dec,

day = "8",

doi = "10.1021/ol052498l",

language = "English",

volume = "7",

pages = "5709--5712",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "25",

}

TY - JOUR

T1 - A hexacyclic ent-trachylobane diterpenoid possessing an oxetane ring from Mitrephora glabra

AU - Li, Chen

AU - Lee, Dongho

AU - Graf, Tyler N.

AU - Phifer, Sharnelle S.

AU - Nakanishi, Yuka

AU - Burgess, Jason P.

AU - Riswan, Soedarsono

AU - Setyowati, Fransisca M.

AU - Saribi, Achmad M.

AU - Soejarto, Djaja D.

AU - Farnsworth, Norman R.

AU - Falkinham, Joseph O.

AU - Kroll, David J.

AU - Kinghorn, A. Douglas

AU - Wani, Mansukh C.

AU - Oberlies, Nicholas H.

PY - 2005/12/8

Y1 - 2005/12/8

N2 - (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.

AB - (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.

UR - http://www.scopus.com/inward/record.url?scp=29444442408&partnerID=8YFLogxK

U2 - 10.1021/ol052498l

DO - 10.1021/ol052498l

M3 - Article

C2 - 16321028

AN - SCOPUS:29444442408

SN - 1523-7060

VL - 7

SP - 5709

EP - 5712

JO - Organic Letters

JF - Organic Letters

IS - 25

ER -

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

Abstract

ASJC Scopus subject areas

UN SDGs

Access to Document

Other files and links

Fingerprint

Cite this