Isolation and structure of ruprechstyril from Ruprechtia tangarana

George Pettit, Yanhui Meng, Delbert L. Herald, Keith A N Graham, Robin Pettit, Dennis L. Doubek

Research output: Contribution to journalArticle

57 Citations (Scopus)

Abstract

Bioassay (P388 lymphocytic leukemia cell line and human cancer cell lines)-guided separation of an extract prepared from the stem bark and twigs of the previously uninvestigated Ruprechtia tangarana led to the isolation of a new isocarbostyril designated ruprechstyril (1), secalonic acid A (2), 2′-O-methylevernic acid (3), 3,3′,4-tri-O-methylflavellagic acid (4), lichexanthone (5), methyl asterrate (6), and 3β,22E,24S-stigmasta-5,22-dien-3-ol (7). Only secalonic acid A exhibited cancer cell and microbial growth inhibition. The structure of ruprechstyril (1) was determined by HRMS and 1D and 2D NMR spectra and confirmed by single-crystal X-ray analysis. The structures and absolute stereochemistry of five of the other compounds were also established by X-ray crystal structure determination.

Original languageEnglish (US)
Pages (from-to)1065-1069
Number of pages5
JournalJournal of Natural Products
Volume66
Issue number8
DOIs
StatePublished - Aug 1 2003

Fingerprint

Cells
X-Rays
Lymphoid Leukemia
Cell Line
Acids
acids
Biological Assay
Neoplasms
Stereochemistry
X-radiation
Bioassay
cell lines
X ray analysis
lymphocytic leukemia
stereochemistry
Growth
crystal structure
Crystal structure
Nuclear magnetic resonance
Single crystals

ASJC Scopus subject areas

  • Plant Science
  • Chemistry (miscellaneous)
  • Drug Discovery
  • Organic Chemistry
  • Pharmacology

Cite this

Isolation and structure of ruprechstyril from Ruprechtia tangarana. / Pettit, George; Meng, Yanhui; Herald, Delbert L.; Graham, Keith A N; Pettit, Robin; Doubek, Dennis L.

In: Journal of Natural Products, Vol. 66, No. 8, 01.08.2003, p. 1065-1069.

Research output: Contribution to journalArticle

Pettit, George ; Meng, Yanhui ; Herald, Delbert L. ; Graham, Keith A N ; Pettit, Robin ; Doubek, Dennis L. / Isolation and structure of ruprechstyril from Ruprechtia tangarana. In: Journal of Natural Products. 2003 ; Vol. 66, No. 8. pp. 1065-1069.
@article{36d24e9479dc461abffa561002ec4b74,
title = "Isolation and structure of ruprechstyril from Ruprechtia tangarana",
abstract = "Bioassay (P388 lymphocytic leukemia cell line and human cancer cell lines)-guided separation of an extract prepared from the stem bark and twigs of the previously uninvestigated Ruprechtia tangarana led to the isolation of a new isocarbostyril designated ruprechstyril (1), secalonic acid A (2), 2′-O-methylevernic acid (3), 3,3′,4-tri-O-methylflavellagic acid (4), lichexanthone (5), methyl asterrate (6), and 3β,22E,24S-stigmasta-5,22-dien-3-ol (7). Only secalonic acid A exhibited cancer cell and microbial growth inhibition. The structure of ruprechstyril (1) was determined by HRMS and 1D and 2D NMR spectra and confirmed by single-crystal X-ray analysis. The structures and absolute stereochemistry of five of the other compounds were also established by X-ray crystal structure determination.",
author = "George Pettit and Yanhui Meng and Herald, {Delbert L.} and Graham, {Keith A N} and Robin Pettit and Doubek, {Dennis L.}",
year = "2003",
month = "8",
day = "1",
doi = "10.1021/np0300986",
language = "English (US)",
volume = "66",
pages = "1065--1069",
journal = "Journal of Natural Products",
issn = "0163-3864",
publisher = "American Chemical Society",
number = "8",

}

TY - JOUR

T1 - Isolation and structure of ruprechstyril from Ruprechtia tangarana

AU - Pettit, George

AU - Meng, Yanhui

AU - Herald, Delbert L.

AU - Graham, Keith A N

AU - Pettit, Robin

AU - Doubek, Dennis L.

PY - 2003/8/1

Y1 - 2003/8/1

N2 - Bioassay (P388 lymphocytic leukemia cell line and human cancer cell lines)-guided separation of an extract prepared from the stem bark and twigs of the previously uninvestigated Ruprechtia tangarana led to the isolation of a new isocarbostyril designated ruprechstyril (1), secalonic acid A (2), 2′-O-methylevernic acid (3), 3,3′,4-tri-O-methylflavellagic acid (4), lichexanthone (5), methyl asterrate (6), and 3β,22E,24S-stigmasta-5,22-dien-3-ol (7). Only secalonic acid A exhibited cancer cell and microbial growth inhibition. The structure of ruprechstyril (1) was determined by HRMS and 1D and 2D NMR spectra and confirmed by single-crystal X-ray analysis. The structures and absolute stereochemistry of five of the other compounds were also established by X-ray crystal structure determination.

AB - Bioassay (P388 lymphocytic leukemia cell line and human cancer cell lines)-guided separation of an extract prepared from the stem bark and twigs of the previously uninvestigated Ruprechtia tangarana led to the isolation of a new isocarbostyril designated ruprechstyril (1), secalonic acid A (2), 2′-O-methylevernic acid (3), 3,3′,4-tri-O-methylflavellagic acid (4), lichexanthone (5), methyl asterrate (6), and 3β,22E,24S-stigmasta-5,22-dien-3-ol (7). Only secalonic acid A exhibited cancer cell and microbial growth inhibition. The structure of ruprechstyril (1) was determined by HRMS and 1D and 2D NMR spectra and confirmed by single-crystal X-ray analysis. The structures and absolute stereochemistry of five of the other compounds were also established by X-ray crystal structure determination.

UR - http://www.scopus.com/inward/record.url?scp=0042423380&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0042423380&partnerID=8YFLogxK

U2 - 10.1021/np0300986

DO - 10.1021/np0300986

M3 - Article

C2 - 12932125

AN - SCOPUS:0042423380

VL - 66

SP - 1065

EP - 1069

JO - Journal of Natural Products

JF - Journal of Natural Products

SN - 0163-3864

IS - 8

ER -