Short Reports 2021 product was extracted twice with an equal vol. of C6H6 and hried over anhydrous Na,SO,. GLC analysis (OV-l~l,~loo”, isothermal oronraml indicated 950/, muitv. T’he MS m/e 138 .I, (M+) and UV spectrum t,, 368 nm [14] were consistent with zyxwvutsrqponmlkjihgfedcbaZYXWVUTSRQPONMLKJIHGFEDCBA MQ. zyxwvutsrqponmlkjihgfedcbaZYXWVUTSRQPONMLKJIHGFEDCBA Enzy matic reaction. Reaction mixtures (50 ml) contained 1OmM sodium phosphate, pH 6.5, 10mM H,OI and various cones of phenolic substrates as indicated. Reactions were started by the addition of SOpI peroxidase (50~) and were carried out at 38”. At the end of the incubation, 2 ml 2 N H,SO, were added and the mixture was immediately extracted with EtOAc (2 x 30 ml). The combined organic fractions were dried and evapd to dryness in N,. Trimethylsilanation of enzymatic products and standards was carried out by adding bis-(N,O- trimethylsilyl)trifluoroacetamide-pyridine (1: 1) to the dry residue and heating at 80” for 5 min. Gas chromatography . GLC was carried out with a Varian Model 1700 instrument fitted with a glass column (180 x 0.2 cm i.d.) packed with 3% OV-101 on chromosorb Q 100/120 (Applied Science). The oven temp. was programmed from 100 to 270” at lO’/min unless indicated otherwise. MS was carried out with a DuPont Model 21491B equipped with the same instrument and column for GLC. The spectra were obtained at 70 eV. Acknowledgements-This research was supported by the Crown Zellerbach, International Paper and Weyerhaueser Companies and by the Gottesman Foundation. zyxwvutsrqponmlkjihgfedcbaZYXWVUTSRQPONMLKJIHGFEDCBA REFERENCES 1. Yamazaki, I. (1974) in M olecular M echanisms of O xy gen 2. 3. 4. 5. 6. 7. 8. 9. 10. 11. 12. 13. 14. Activation (Hayaishi, O., ed.) pp. 535-558. Academic Press, New York. Raiha, M. and Sundman, V. (1975) Arch. Microbial. zyxwvutsrqpo 105, 73. Davidson, R. W., Campbell, W. A. and Blaisdell, D. J. (1938) J. Agric. Res. !V, 683. Ander, P. and Eriksson, K. E. (1976) Arch. Microbial. 109,l. Caldwell, E. S. and Steelink, C. (1969) Biochim. Biophys. Acta 184,420. Harkin, J. M. (1967) in Oxidative Coupling of Phenols (Taylor, W. I. and Battersby A. R., eds.) pp. 95-116. Marcel Decker, NY. Freudenberg, K. (1968) in Constifution and Biosynthesis of Lignin (Freudenberg, K. and Neish, A. C., eds.) p. 82. Springer, New York. Kirk, T. K., Harkin, J. M. and Cowling, E. B. (1968) Biochim. Biophys. Acta 165,145. Ishihara, T. and Ishihara, M. (1976) M okuzai Gakkaishi 22,371. Kirk, T. K., Harkin, J. M. and Cowling, E. B. (1968) Biochim. Biophys. Acra 165, 134. Ishikawa, H, Schubert, W. J. and Nord, F. F. (1963) Arch. Biochem. Biophys. 100,131. Katagiri, M., Yamamoto, S. and Hayaishi, 0. (1962) J. Biol. Chem. 237, PC 2413. Taniuchi, H., Hatanaka, M., Kuno, S., Hayaishi, O., Nakajima, M. and Kurihara, N. (1964) J. Biol. Chem. 239,2204. Westermark, U. and Eriksson, K. E. (1974) Acta Chem. Stand. Ser. B 28,209. zyxwvutsrqponmlkjihgfedcbaZYXWVUT Phyr ochemist r y, 1979, Vol. 18, pp. 2021-2022. Q Pergamoa Press Ltd. Printed in England. 0031-9422/79J1201-2022 $02/00/O OVALIN, A NEW PIPECOLIC ACID FROM MILLETIA O~ALIFOLIA SEEDS RAJINDER KUMAR GUPTA and M. KRISHNAMURTI Chemistry Department, University of Delhi, Delhi-l 10007, India (Received 14 May 1979) Key W ord Index- M illetia ooalifolia; Leguminosae; ovalin. In continuation of our earlier work [ 11, further examina- tion of M illetia oualifolia seeds led to the isolation of a new pipecolic acid, ovalin, from the methanol extract. Ovalin was obtained chromatographically pure as colourless needles from EtOH-Me&O; mp 280-281” (decomp.); R, 0.36 (PC n-BuOH-HCO,H-H,O, 15: 3:2). It analysed for C,H,,NO,; M+ 159; [a];’ -41.2” (H,O) was chemically neutral and insoluble in all organic solvents except alcohol in which it was partially soluble, but was readily soluble in H,O. There was no UV absorption in the range 200-3OOnm. The IR spec- trum (KBr) indicated an -OH group (v 3350cm-‘), \ ,=0 of carboxylate (1630 cm- ‘) and a quaternary ammonium group (=N+=) (14OOcm-‘). It did not respond to tests for amino acids, peptides and alkaloids. The inertness towards most of the reagents and the presence of nitrogen suggested it to be a pipecolic acid derivative, some of which are known to occur in the seeds of leguminous plants [Z]. The ‘H NMR spectrum (6OMHg solvent D,O, values) indicated the presence of \ N-Me group, methine and methylene protons. / The spectrum closely resembled that of Chydroxypipecolic acid recorded in D,O [3-51. A quintet centred at 4.3 (J, = J, = 3.5 Hz, 1H) was assigned to an equatorial C-4 proton. A pair of doublets centred at 3.85 (J,, = 5; J, = 11 Hz, 1H) was assigned to an axial C-2 proton because of the large coupling constant, characteristic of axial-axial neigh-