ANTIMICPROBIAL AGENTS AND CHEMOTHERAPY, Mar. 1975, p. 320-321 Vol. 7. No.

3
Copyright 0 1975 American Society for Microbiology Printed in U.S.A.

Antimicrobial Agents from Marine Algae

JAMES J. SIMS, MARK S. DONNELL, JOHN V. LEARY,* AND GEORGE H. LACY
Department of Plant Pathology, University of California, Riverside, California 92502
Received for publication 16 December 1974

The antimicrobial activity of five compounds extracted from marine algae was
tested against Staphylococcus aureus, Salmonella choleraesuis, Mycobacterium
smegmatis, Candida albicans, and Escherichia coli. Three of the compounds,
cycloeudesmol, laurinterol, and debromolaurinterol, exhibited activity at con-
centrations approaching that of streptomycin. None of the compounds inhibited
all of the organisms tested. There appeared to be selectivity for gram-positive
microbes.
There have been a number of reports of this period was interpreted as inhibition. Control
antibiotic activity from marine algae (1, 2, 7, plates of tryptic soy agar not containing the algal
10). For the most part, these reports represented compounds were streaked with each of the test
preliminary studies of crude extracts and little organisms and scored along with the test plates. In all
follow-up work has been done to isolate the cases, visible growth was observed after 48 h.
substance(s) responsible for the activity. We RESULTS AND DISCUSSION
have been examining the secondary metabolites
from a number of such algae and have found Each of the five compounds was tested at
compounds with potent antimicrobial activity. varying concentrations to determine that con-
Described here are the results of preliminary centration at which growth was completely
tests of chondriol (4) and cycloeudesmol (3) inhibited when assayed 48 h after inoculation
from Chondria oppositiclada, pre-pacifenol (9) (Table 1). In each test, streptomycin sulfate was
from Laurencia filiformis, and laurinterol and included for comparison. The most active com-
debromolaurinterol from Laurencia pacifica (5, pound of the five tested was laurinterol, which
8). gave complete inhibition of S. aureus and M.
smegmatis at concentrations comparable to
MATERIALS AND METHODS those of streptomycin. The five compounds
Compounds. Five natural products from marine tested exhibited an interesting selectivity since
algae were tested; the structures are given in Fig. 1. primary activity was against gram-positive or-
The methods for extraction, purification, and struc- ganisms. Only one compound, cycloeudesmol,
tural determination of these compounds have been significantly inhibited a gram-negative bacte-
described previously (3-5, 8, 9). The desired amounts rium.
of the compounds were dissolved in 1:1 dimethyl The greater activity of debromolaurinterol
sulfoxide and ethanol added to 10 ml of melted agar to compared with laurinterol against C. albicans
give a constant concentration of 0.04 ml of solvent per ATCC 10321 is noteworthy since the bromine
ml of agar. Control plates contained the same concen-
tration of solvent.
Organisms. The American Type Culture Collec- CI
tion names and numbers of the organisms used in
these studies are as follows: Staphylococcus aureus, HO-
0
6538 and 12600; Salmonella choleraesuis, 13312; My- OH
cobacterium smegmatis, 14468; Candida albicans, BrII
2
10231; and Escherichia coli, 11775. A second isolate of
C. albicans, CA-5, was obtained from Frank E.
Swatek at California State University, Long Beach.
Screening methods. The procedure was adapted OH O
from that of Mitscher et al. (6) as follows. Compounds
to be tested were mixed well with 10 ml of sterile Oi R= Br
liquid tryptic soy agar and poured into petri plates. 5 R= H
The test organisms were streaked on the surface of the Br CI
agar. These organisms had been grown previously for FIG. 1. Structures of five algal natural products.
48 h in tryptic soy broth at 36 C. The plates were then (1) Chondriol; (2) cycloeudesmol; (3) pre-pacifenol;
incubated at 36 C for 48 h, and lack of growth after (4) laurinterol; (5) debromolaurinterol.
320
VOL. 7, 1975 ANTIMICROBIAL AGENTS FROM MARINE ALGAE 321
TABLE 1. Antimicrobial activity of the algal natural products
Concn (Ag/ml) for complete inhibition after 48 h
Compound Staphylococcus aureus Salmonella C. albicans E. coli
cholraeuis M. smegmatis
6538 12600 choleraesuts 10231 CA-5
Chondriol 10-100 > 1,000 10-100 > 1,000 > 1,000
Pre-pacifenol 10-100 > 1,000 10-100 > 1,000 > 1,000
Laurinterol .1-5 1-5 > 1,000 1-5 10-100 10-30 > 1,000
Debromolaurinterol 10-30 10-30 > 1,000 10-50 10-50 10-30 > 1,000
Cycloeudesmol 10-50 50-100 10-50 10-50 > 1,000
Streptomycin sulfate 1-10 10-20 < 10 < 100 < 10

atom was not required for antibiosis. However,
when retested with CA-5, it was found that both
compounds were equally active. The differential
susceptibility of ATCC 10321 may have been a
character of that isolate.
The study of natural products, especially
from terrestrial plants, has long been the source
of pharmaceuticals. The studies reported here
extend earlier studies to compounds for which
the structures are known.
LITERATURE CITED
1. Baslow, M. H. 1969. Marine pharmacology. The Williams
& Wilkins Co., Baltimore.
2. Chisters, C. G. C., and J. A. Stott. 1956. The production
of antibiotic substances by seaweeds, p. 49. In Proc.
2nd Int. Seaweed Symp. Pergamon Press, New York.
3. Fenical, W., and J. J. Sims. 1974. Cycloeudesmol, an
antibiotic cyclopropane containing sesquiterpene from
the marine alga, Chondria oppositiclada Dawson. Te-
trahedron Lett. p. 1137-1140.
4. Fenical, W., J. Sims. and P. Radlick. 1973. Chondriol, a
halogenated acetylene from the marine alga Chondria
oppositiclada. Tetrahedron Lett. p. 313-316.
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1973. Marine natural products. IV. Prepacifenol, a
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properties of marine algae. J. Bacteriol. 83:97-99.