Fimbricalyx A, a novel phenanthrenone derivative having a rare 2H-benz[e]inden-2-one substructure

Prapairat Seephonkai; Stephen G. Pyne; Anthony C. Willis; Wilford Lie

doi:10.1016/j.tetlet.2013.02.025

Fimbricalyx A, a novel phenanthrenone derivative having a rare 2H-benz[e]inden-2-one substructure

Prapairat Seephonkai^*, Stephen G. Pyne, Anthony C. Willis, Wilford Lie

^*Corresponding author for this work

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

17 Citations (Scopus)

Abstract

Fimbricalyx A (1), a novel phenanthrenone derivative having a rare 2H-benz[e]inden-2-one substructure, was isolated from the root extract of Strophioblachia fimbricalyx. The structure of 1 was elucidated on the basis of the NMR and MS data and confirmed by X-ray crystallography. This compound showed cytotoxicity against KB, MCF7 and NCI-H187 cancer cells with IC₅₀ values of 38.4, 28.7 and 8.3 μg/mL, respectively. A possible biosynthesis of 1, via a ring-contracted p-quinone methide intermediate derived from a phenanthrenone precursor, is proposed.

Original language	English
Pages (from-to)	2085-2088
Number of pages	4
Journal	Tetrahedron Letters
Volume	54
Issue number	16
DOIs	https://doi.org/10.1016/j.tetlet.2013.02.025
Publication status	Published - 17 Apr 2013

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10.1016/j.tetlet.2013.02.025

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title = "Fimbricalyx A, a novel phenanthrenone derivative having a rare 2H-benz[e]inden-2-one substructure",

abstract = "Fimbricalyx A (1), a novel phenanthrenone derivative having a rare 2H-benz[e]inden-2-one substructure, was isolated from the root extract of Strophioblachia fimbricalyx. The structure of 1 was elucidated on the basis of the NMR and MS data and confirmed by X-ray crystallography. This compound showed cytotoxicity against KB, MCF7 and NCI-H187 cancer cells with IC50 values of 38.4, 28.7 and 8.3 μg/mL, respectively. A possible biosynthesis of 1, via a ring-contracted p-quinone methide intermediate derived from a phenanthrenone precursor, is proposed.",

keywords = "2H-Benz[e]inden-2-one, Fimbricalyx A, Phenanthrenone, Strophioblachia fimbricalyx",

author = "Prapairat Seephonkai and Pyne, \{Stephen G.\} and Willis, \{Anthony C.\} and Wilford Lie",

year = "2013",

month = apr,

day = "17",

doi = "10.1016/j.tetlet.2013.02.025",

language = "English",

volume = "54",

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journal = "Tetrahedron Letters",

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publisher = "Elsevier Ltd.",

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TY - JOUR

T1 - Fimbricalyx A, a novel phenanthrenone derivative having a rare 2H-benz[e]inden-2-one substructure

AU - Seephonkai, Prapairat

AU - Pyne, Stephen G.

AU - Willis, Anthony C.

AU - Lie, Wilford

PY - 2013/4/17

Y1 - 2013/4/17

N2 - Fimbricalyx A (1), a novel phenanthrenone derivative having a rare 2H-benz[e]inden-2-one substructure, was isolated from the root extract of Strophioblachia fimbricalyx. The structure of 1 was elucidated on the basis of the NMR and MS data and confirmed by X-ray crystallography. This compound showed cytotoxicity against KB, MCF7 and NCI-H187 cancer cells with IC50 values of 38.4, 28.7 and 8.3 μg/mL, respectively. A possible biosynthesis of 1, via a ring-contracted p-quinone methide intermediate derived from a phenanthrenone precursor, is proposed.

AB - Fimbricalyx A (1), a novel phenanthrenone derivative having a rare 2H-benz[e]inden-2-one substructure, was isolated from the root extract of Strophioblachia fimbricalyx. The structure of 1 was elucidated on the basis of the NMR and MS data and confirmed by X-ray crystallography. This compound showed cytotoxicity against KB, MCF7 and NCI-H187 cancer cells with IC50 values of 38.4, 28.7 and 8.3 μg/mL, respectively. A possible biosynthesis of 1, via a ring-contracted p-quinone methide intermediate derived from a phenanthrenone precursor, is proposed.

KW - 2H-Benz[e]inden-2-one

KW - Fimbricalyx A

KW - Phenanthrenone

KW - Strophioblachia fimbricalyx

UR - https://www.scopus.com/pages/publications/84875217865

U2 - 10.1016/j.tetlet.2013.02.025

DO - 10.1016/j.tetlet.2013.02.025

M3 - Article

SN - 0040-4039

VL - 54

SP - 2085

EP - 2088

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 16

ER -

Fimbricalyx A, a novel phenanthrenone derivative having a rare 2H-benz[e]inden-2-one substructure

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