Journal of Natural Products
1160
Wol. 49, No. 6
Atranol.+2,6-Dihydroxy-4-methylbentaldehyde) uv A max nm (E) 280 (126OO), 349 (2600); 'H nmr 10.29 ( l H , s, CHO), 8.84 (2H, broad OH), 6.22 (2H, s, H 3 and H5), 2.27 (3H, s, CH,); eims (probe)70eVm/z(rel. int.) 152(M+,91), 151(1OO), 136(3), 123(2), 106(6), 95(4);alldatapreviously unreported in the literature. Antimicrobial activity of atranol, obtained using the agar plate disc diffusion method, (Fg applied), mm zone ofinhibition: against B. subtilis (ATCC 6633) (40), 17; streptomycin sulfate as control (0.6), 17; against E. coli (strain B, ATCC 11303) (40),17; streptomycin sulfate as control (6), 25; against S. cerevisiae (baker yeast) (40) 18; filipin as control (24), 24. Details ofthe procedure have been previously reported (6). The antimicrobial activity of methyl p-orcinolcarboxylate isolated from another lichen has been reported (7). Full details of the isolation and identification of the compounds are available on request to the senior author, ACKNOWLEDGMENTS We thank Dr. M. Valcuvia Passadore, Botany Institute, University of Pavia, for botanical identification. This research was supported by a grant from the Ministry of Public Education. LITERATURE CITED 1. P.J. Hylands and K. Ingolfsdottir, Phytorkmistty, 24, 127 (1985). 2. A. Bolognese, F. Chioccara, and G. Scherillo, Phytwkmistry, 13,1989 (1974). 3. C.F. Culberson, W.F. Culberson, and A. Johnson, Phytorhemistry, 16,127 (1977). 4. A. Pfau, Helv. Chim. Acta, 9 , 650 (1927). 5. Y . Solberg, Z. Natutjkch., 22, B , 777 (1967). 6. S. Caccamese and R. Azzolina, Planta Med., 37, 333 (1979). 7. S. Caccamese, R.M. Toscano, F. Bellesia, and A. Pinetti,]. Nut. Prod., 48, 157 (1985).
Receiwd 4 ApnII986.
FLAVONOIDS FROM SALVZA NICOLSONIANA ROGELIO PEREDA-MIRANDA
Departamento de Qnimica Organira, Ernrela Nacional de C k i a s Biol4gicas del lnrtituto Politirnio Nm'onal, 11340, Mexico, D . F . and GUILLERMODELGAW*
lnrtituto de Quimica, Unitwsidad Nacional A u t h o m de Mixiro, Cirruito Exterior, C i d Unimitat%z, C o y d n 04510, Mixico, D.F.
As part of a systematic chemical investigation of Mexican Iabiatae ( 1 4 ) , we previously reported several triterpenoids from Salvia nicolsoniana Ramamoorthy (2). Continuing our studies of this genus, a new
collection of this species was analyzed and resulted in the isolation and characterization of six known flavonoids. The chemistry ofS. nicolsaiana does not differ from the chemicalprofile outlined for this genus, since it contains pentacyclic triterpenes and flavonoids which are widely distributed metabolites among the members of Labiatae (4). EXPERIMENTAL
PLANTMATERIAL-S. nicolsaiana was collected in Sierra Madre del Sur, Guerrero, MCxico, in February 1985. Reference specimens are deposited in the National Herbarium, Instituto de Biologia de la
Universidad Nacional Aut6noma de Mkxico, voucher No. 619 1-M. EXTRACTION AND ISOLATION PRoCEDUREs.-Exhaustive chromatography of the Me,CO extract of the dried aerial parts (7 kg) yielded four terpenoids, namely betulinic, oleanolic, ursolic, and 3a.24 dihydroxyolean-12-en-28-oicacids, as well as p-sitosterol, which were identical in all respects (mp, tlc, ir, ms, 'H nmr) with authentic samples (2,5,6). In addition, six flavonoids were also isolated from this species in the following order from Si gel column chromatography: apigenin 4,7'-dimethyl ether (12 mg), i d u r a n e t i n (37.8 mg). acacetin(859.3 mg), genkwanin (17 mg), cirsimaritin (15.2 mg), and luteolin 3',4'dimethyl ether (7 me).
Nov-D~c 19861
Brief Reports
1161
All the flavonoids were identified by standard spectral data (uv, ir, ms, 'H nmr) as well as by authentic sample comparison (mp, tlc) (7- 12).Full details of the isolation and identification of the compounds are available on request to the senior author. ACKNOWLEDGMENTS We thank Esteban Manuel Martinez, National Herbarium, Instituto de Biologia de la Univenidad Nacional Aut6noma de MCxico, for collection and botanical identification of the plant material.
LITERATURE CITED 1. G. Delgado, R. Pereda-Miranda, and A. Romo de Vivar, Hetemycler, 23, 1869 (1985). 2. R. Pereda-Miranda, G.Delgado, and A. Romo de Vivar,]. Nat. Prod., 49,225 (1986). 3. G. Delgado, X.Girdenas, L. Alvarez, A. Romo de Vivar, and R. Pereda-Miranda,]. C h . Res., (S) 268,( M ) 2565 (1986). 4. R. Pereda-Miranda, G. Delgado, and A. Romo de Vivar, Phytorkistry, 2 5 , 1931 (1986). 5. P. MOMCOand L. Previtera,]. Nat. Prod., 47,673 (1984). 6. A. Romo de Vivar, J.M. G o d l e z , and A.L. PCrez, Rev. Latinoam. Q x i m . , 16,5 1 (1985). 7 . K.H. Bauer and H . Dietrich, C h . Ber., 66, 1053 (1933). 8. M. Hasegawa and T. Shirato, J . Am. C h . SK., 79,450(1957). 9. W.Baker, R. Hemming, and W. Dollis,]. C h .Sor., 691 (1951). 10. M. Nakao and K.F. Tseng,]. P h m . Sor. Japan, 5 2 , 148 (1932). 11. M.M. Rao, D.G.I. Kingston, and T.D. Spitter, Phytorhistry, 9,227 (1970). 12. T. Nakanishi, J. Ogaki, A. Inada, H . Murata, and M. Nishi,]. Nat. Prod., 48,49 1 (1985).
Received 21 April I986
BIOLOGICALLY ACTIVE COUMARINS FROM ENKLEZA SIAMENSZS &WANLuo, LADDAWAN BOONYARATANAKORNKIT,CHUN-TAOCHE,
CLEMENSA.J. ERDELMEIER, HARRY H.S. FONG, and N.R. FARNSWORTH
Programfw Colkaboratiw Reseunh in the Pharnurcutical Sciences, College of Pharnucry, UniwrIity of Illinois at Chicago, Chicago, Illinois 60612 Enkleia siamenrir Kurz (Thymeliaceae) is a climbing shrub commonly distributed throughout the northeastern region ofThailand. An ethanolic extract ofthe dried roots was found to be active in the P-388 in vitro cytotoxicity assay (ED,, 0.1Fg/ml). Bioassaydirected fractionation of the total alcoholic extract resulted in the isolation of three coumarins, clausarin, nordentatin, and daphnoretin. Clausarin and nordentatin were obtained from the petroleum ether fraction of the ethanolic extract. Clausarin was identified by comparing its spectra('H nmr,uv, ir, ms)withpublished data(l,2). Nordentatin exhibited spectral properties ('H nmr, ir, uv, ms)indicating a demethylponcitrin structure. When methylated with CH,N,, it gave poncitrin (co-tlc). Since dentatin has been proved to be identical with poncitrin (l), which is a linear structure (3-8), nordentatin must also have a linear structure (2) rather than OR
1 R=CH, 2
R=H
'Present Address: Deparcmenc of Pharmaceutical Botany, Faculty of Pharmaceutical Sciences, Chulalongkorn University, Bangkok, Thailand.
