Altemicidin, a new acaricidal and antitumor substance. II. Structure determination.

Abstract

The structure of altemicidin, a new acaricidal and antitumor agent, was determined to be (l^,25,3a^,7a5)-4-carbamoyl-2-hydroxy-6-methyl-l-(sulfamoylacetamido)-2,3,3a,6,7,7a-hexahydro-6-azaindene-l-carboxylic acid by a combination of spectroscopic and X-ray crystallographic analysis of its derivatives.Altemicidin is a monoterpene alkaloid.Altemicidin, isolated from a culture broth of an actinomycete strain identified as Streptomyces sioyaensis SA-1758, is a new compound having the acaricidal and antitumor activities. We have reported the fermentation, isolation, biological properties and physico-chemical properties of altemicidin in the preceding paper1}.In this report, we describe the structure determination of altemicidin. Results and DiscussionAltemicidin (1, Fig. 1) was obtained as white powder. Its molecular formula was established to be C13H2oN407Sas described in the preceding paper1}. The IR spectrum of 1 showed the presence of amide group (1650 and 1550cm"1) and sulfonyl group (1345 and 1165cm"1)1*. In the 13C NMRspectrum (in D2O)of 1,thirteen carbon signals were observed at

SB-203207 and SB-203208, Too Novel Isoleucyl tRNA Synthetase Inhibitors from a Streptomyces sp. II. Structure Determination.

“…Addition of an isoleucyl fragment to altemicidin increases its molecular weight to 489, the observed molecular weight of (1) and further addition of a /3-methyrphenylalanyl fragment increases the molecular weight to 650, that determined for (2).…”

“…The structure determination studies of these compounds are reported in this paper. The structures of (1), (2) and (3) as well as the structures of (4) and (5), two triacetylated analogues of (2), are shown in Fig. 1.…”

“…acetamido } -2 ,4a, 5 ,6 ,7 ,7a-hexahydro-6-hydroxy-2-methyll//-2-pyrindine-7-carboxylic acid (1) and 4-(aminocarbonyl)-7-{ [(2-amino-3-methyl pentanoyl)-aminosulphonyl]acetamido } -2,4a,5,6,7,7a-hexahydro-6-(2-amino-3-phenylbutanoyl oxy)-2-methyl-l /f-2-pyrindine-7-carboxylic acid (2), respectively. SB-203207 (1) and SB-203208 (2), isolated from a fermentation broth of Streptomyces sp.…”

Ocean Dwelling Actinobacteria as Source of Antitumor Compounds

“…Streptomyces sioyaensis SA-1758 was isolated from sea mud collected at Gamo, Miyagi Prefecture, Japan. The strain SA-1758 produced a monoterpene-alkaloid, altemicidin (Takahashi et al 1989a). The compound strongly inhibited the growth of L1210 and carcinoma IMC cell lines with IC50 values of 0.84 and 0.82 μg/mL, respectively (Takahashi et al 1989b).…”

Antitumor Compounds from Marine Actinomycetes

“…Altemicidin (Figure 11) with a monoterpene-alkaloid skeleton is produced by S. sioyaensis SA-1758 isolated from sea mud collected at Gamo, Miyagi Prefecture, Japan [135]. This compound was found to inhibit the growth of murine lymphoid leukemia L1210 and carcinoma IMC cell lines with IC 50 values of 0.84 and 0.82 μg/mL, respectively, although it showed high acute toxicity in mice [136].…”