q
IICT Communication No. 4371.
*Corresponding author. Tel.:#91-40-7170512; fax:#91-40-73757/7173387.
E-mail address:luchem@iict.ap.nic.in (Y. Venkateswarlu).
Biochemical Systematics and Ecology 28 (2000) 1035}1037
S
-(
#
)-methyl ester of hanishin from the marine
sponge
Agelas ceylonica
qN. Srinivasa Reddy, Y. Venkateswarlu
*
Natural Products Laboratory, Organic Chemistry Division-I, Indian Institute of Chemical Technology, Hyderabad 500 007, India
Received 8 November 1999; accepted 8 February 2000
Keywords: Agelas ceylonica; Agelasidae; Bromopyrrole alkaloids; Optical isomers; Antibacterial assay
1. Subject and source
In a continuation of a search for biologically active molecules from marine organ-isms (Venkateswarlu et al., 1999) we investigated the spongeAgelas ceylonica belong-ing to the family Agelasidae. The sponge was collected at a depth of 30 f by skin divbelong-ing near the Mandapam coast (N 173, E 833) India, during October 1997. A voucher specimen (IIC } 338) has been deposited at the museum of National Institute of Oceanography, Goa, India.
2. Previous work
Sponges of the genusAgelasproduce a variety of secondary metabolites such as bromopyrrole alkaloids (Ca"eri et al., 1998a), agelasines (D'Ambrosio et al., 1993), agelastatins (Hattori et al., 1997), diterpenoids (Shoji et al., 1996) and betaines (Ca"eri et al., 1998b). No chemical examination has been reported on the sponge Agelas ceylonica.
3. Present study
The 1 : 1 dichloromethane}methanol extract of the sponge was concentrated to obtain a viscous gummy residue which was extracted with ethyl acetate and concentrated.
The extract was chromatographed on Sephadex LH-20, (1 : 1 DCM}MeOH) fol-lowed by silica gel chromatography, eluting with hexane through hexane}ethyl acetate mixtures and"nally with ethyl acetate to a!ord compounds1,2in a mixture and compound3. The mixture of compounds 1and 2was separated using reverse phase HPLC eluting with 20 : 80 water-methanol to yield compounds1and2. The structures of compound1, 2and3were con"rmed on the basis of spectral studies. Compound1showed mild antibacterial activity againstBacillus subtitles.
S-(#)-methyl ester of hanishin (1): White solid; 40 mg (0.008% dry wt.) m.p. 2153C;
The methyl ester of hanishin (1), was previously isolated from the sponge
Homaxinellasp., as a racemic mixture of both R and S isomers (Umeyama et al., 1998). The previous authors did not report a m.p., or 13C NMR data for the mixture. Compound2has been previously isolated from the spongeAcanthella carteri (Man-cini et al., 1997) and compound3from the sponge Axinella tenuidigitata(Srinivasa Reddy et al., 1999).
Acknowledgements
We are thankful to the Department of Ocean Development for"nancial assistance, NSR is grateful to CSIR (New Delhi) for providing a Fellowship.
References
Ca"eri, F., Fattorusso, E., Taglialatela-Scafati, O., 1998a. J. Nat. Prod. 61, 122. Ca"eri, F., Fattorusso, E., Taglialatela-Scafati, O., 1998b. J. Nat. Prod. 61, 1171.
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Venkateswarlu, Y., Ramesh, P., Srinivasa Reddy, N., Prabhakara Rao, T., 1999. Nat. Prod. Lett. 13 (1), 11. Umeyama, A., Ito, S., Yuasa, E., Arihara, S., Yamada, T., 1998. J. Nat. Prod. 61, 1433.
