Akyrocrkanirrry,

Vol. 26. No. 6. pp. 1623-1625.1987. 0031~9422/x7E3.00+ 0.00

Rintai in GreatBritain. Q 1987PergamonJournalsLtd.

ANNOQUINONE-A, AN ANTIMICROBIAL AND CYTOTOXIC PRINCIPLE

FROM ANNONA MONTANA

TM-SHUNG WV, TINGTING JONG, HSIEKJU TIE*, CHANGSHENG Kuow, HIROSHI FURUKAWA$and
KUOHSIUNG LEE$

Department of Applied Chemistry, Providcncc College of Arta and Science, Taichung, Taiwan 40211, Republic of China;
*Department of Chemistry, National Cheng Kung University, Tainan, Taiwan 700. Republic of China; t Department of Biology,
National Cheng Kung University, Tainan, Taiwan 700, Republic of China; $Faculty of Pharmacy, Meijo University, Ten&u,
Nagoya 468, Japan; @chool of Pharmacy, University of North Carolina, Chapel Hill, North Carolina 27514, U.S.A.

(Revised receiwd 28 Ocrobet 1986)

Key Word Index-hnona Monroe; Annonaceae; phenanthrene-l+quinonc; annoquinonc-A; anthraquinonc;

antibacterial activity; cytotoxicity.

Abstract-A new naturally occurring phenanthrene-l+quinone, annoquinone-A, along with parietin (physcion) and
j?-sitostenone were isolated from the stem bark of Atmono montona. The structure of annoquinone-A was elucidated by
spectral methods and synthesis. Annoquinone-A demonstrated potent antimicrobial activity against Bacillus subtilis
and Micrococcus luteus as well as cytotoxicity in the KB (ED,~ = 0.16 &ml) tissue culture assay. /LSitostenone also
showed significant cytotoxicity.

INTRODU~ION thesized by condensation of styrene with methoxy-p

benzoquinone in a sealed tube at loo”.
Atuwna montana Macf. is a small evergreen tree which is
This is the first report of the occurrence of 1 in a natural
widely distributed from the West Indies to southern Brazil
source despite the fact that it was synthesized by
and is cultured for its fruit in Taiwan [ 11. Yang et al. [2],
Kakisawa in 1971 [9].
Wu et 01. [33, and CavC: et al. [4, S] have reported the
The known compounds parietin (3) [lo, 1l] and
isolation of alkaloids from the leaves, stem and root bark
/I-sitostenone (5) CL?.,133 were isolated and identified by
of this plant. We report here on the isolation, structural
IR, *H NMR and mixed melting point determination with
elucidation, and the antimicrobial and cytotoxic activities
authentic samples. This is the first report of the isolation
of a new phenanthrene-l+quinone, annoquinone-A (l),
of an anthraquinone (parietin) from Annonaceae.
as well as the known compounds, pa&in (physcion, 3)
The comoounds isolated in this studv were tested for
and /I-sitostenone (5) from the stem bark of A. nwntana antimicrobii [14] (Table 1) and cyt&oxic activities.
collected in Taiwan.

RESULTSAND DlSCU!3SION

The mass spectrum of annoquinone (1) showed a

molecular ion peak at m/z 238. The presence of a
phenanthrene-1.4quinone nucleus was suggested by UV
absorption maxima at 228, 279, 283, 317 and 370 nm
[6,7], IR bands at 1670 and 1635 cm-’ and two carbonyl
carbon signals at 6 182.4 and 185.3 in the ‘“C NMR
spectrum. The ‘H NMR spectrum of 1 contained AB type
proton signals at 68.17 and 7.89 (J = 10 Hz) which were
attributed to the onho-located protons on a tetra- 1 R- Ok, R’ - H 3 R-Me
substituted aromatic ring. The lower field signal was 2 R = H. R’ - OMe 4 R-H
assigned to H-10 as it was deshielded by the carbonyl
moiety. A double doublet centred at 69.40 was character-
istic of the C-5 proton in phenanthrenes [8]. The presence
of signals at 67.50-7.74 (2H, m) and 7.90 (lH, dd, .I = 2
and 8 Hz) were assigned to H-6, 7 and 8. respectively,
indicating that ring-A was unsubstituted. A sharp three-
proton singlet (63.92) was assigned to a methoxy group
while a singlet (66.11) was assigned lo a lone ole6nic
proton (H-2 or H-3). The above data were in excellent
accord with the structure of 1 or 2 for annoquinone-A.
Final proof for the structure of annoquinone+A was 5
provided by the demonstration that it could be syn- 6 A*

1623
 Annoquinonc-A, an antimicrobial and cytotoxic principle from Annonu montanu
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