The roots of Buxus papillosa have yielded three new steroidal alkaloids, (+)papillotrienine [1], (+)-Nb-demethylpapillotrienine [2], and (+ )-Nb-demethylharappamine {31• The structures have been determined on the basis of spectroscopic studies.Buxus papillosa C.K. Schneider (Buxaceae) is a shrub widely distributed in the northern regions of Pakistan and locally known as Shamshad (1). Extracts of the shrub find extensive use in the indigenous system of medicine for the treatment of various disorders, especially malaria, rheumatism, and skin infections. We have previously reported a number of new steroidal alkaloids from the leaves of B. papillosa (2-7). We report here the isolation and structure elucidation of three new steroidal alkaloids, papillotrienine [1], Nb-demethylpapillotrienine [2], and Nb-demethylharappamine [3].The structures have been determined through extensive spectroscopic studies. Compounds 1 and 2 are members of a rare group of Buxus bases having conjugated triene chromophores in rings A, B, and C. RESULTS AND DISCUSSION( + )-Papillotrienine [1], C27H44N2, showed a uv absorption maximum at 289 nm, characteristic of a triene system (8). The ir spectrum displayed absorptions at 3300 (N-

A new flavonoid glycoside 1 is isolated from the leaves ofBvurssnnpnvirrnr, and its structure is determined on the basis of spectral studies. It is the first flavonoid glycoside to be isolated from the genus BUXUJ. We also report the isolation of methyl syringate from this plant. The isolation and '3C-nmr spectra of buxpsiine and cyclomicrophylline A are also described.Buxus smpewims L. (Bwaceae) is widely distributed in Eurasia. The H 2 0 extracts of the plant find extensive use in the indigenous system of medicine for the treatment of many diseases (1). Previously, we have reported a number of new steroidal alkaloids and two known flavonoids isolated for the first time from the genus Blrxrrr (2-5). In the present paper, we describe the isolation and structure elucidation of a new flavonoid glycoside, galactobuxin {I], along with methyl syringate 121. The isolation and 13Cnmr spectra of two known bases, bwpsiine 131 and cyclomicrophylline A {4], are also described. RESULTS AND DISCUSSIONGalactobwin 111 was isolated from the EtOH extract of the leaves ofL3.5t~@ervZimu. Uv spectra of the glycoside and aglycone showed a hypsochromic shift between band I of the glycoside (339 nm) and that of the aglycone (350 nm), indicating glycosylation at the 4'-hydroxyl group (6). Confirmation was secured by bathochromic shift of 61 nm for the aglycone in the presence of NaOMe; no such corresponding shift occurred for the glycoside. The presence of a 5-hydroxy-4-keto function was indicated by bathochromic shifts encountered both in the glycoside (30 nm) and in the aglycone (34 nm) when the uv spectrum was recorded with addition of AlCI, (6).The ir spectrum afforded an absorption at 1650 cm-', indicating the presence of a conjugated carbonyl group. Other intense absorptions were observed at 3350 (OH), 1600 (C=C ar.), 1100 (C-0-C) cm-'. Positive fabms showed the molecular ion peak at mlz 536.1527, corresponding to the molecular formula C2,H2,OI3 and indicating 1

No abstract

No abstract