Picrasma ailanthoides

H NMR parameters for 1 -hydroxymethyl-/ -carboline from Picrasma ailanthoides PLANCHON (212) are shown in [332]. 

Nigaki alcohol (18) has been identified by spectroscopic and chemical means as a constituent of Picrasma ailanthoides Planchon. Latia luciferin (19) has been synthesized in a stereoselective manner. A key step in this synthesis involves the addition of lithium dimethylcuprate to an enol phosphate derived from a 8-keto-ester to form an a,/3-unsaturated ester. Dehydro-/8-ionilideneacetic acid (20), an important intermediate in the synthesis of abscisic acid, has been prepared, as have the two nor-abscisic acid derivatives (21). The metabolite (22) of abscisic acid has been identified in the seeds of Robinia pseudacacia... 

Quassinoids.— The full paper on the structural elucidation of picrasins A—G has been published. Two new compounds, nigakihemiacetals E (79) and F (80), have been isolated from Picrasma ailanthoides. 

Quassinoids of the Japanese Picrasma ailanthoides Planchon (= P. quassioides Bennett) have been investigated in detail and more than twenty quassinoids have been obtained until 1984. However, very few reports for quassinoid glycosides have been found [63]. Eight quassinoids glycosides, picrasinoside A (141), B (142), C (143), D (144), E (145), F (146), G (147), H (148), and quassinoids hemiacetals, picrasinol A (149), B (150), C (151), and D (152) were isolated from Picrasma ailanthoides the last two decades [63-66]. 

Forty-five quassinoids isolated from the three Simaroubaceous plants, Brucea javanica, Brucea antidysenterica and Picrasma ailanthoides, and fourteen isolated from Ailanthus altissima were tested for Okano et al. [106-108] for their inhibitory activities using a short-term in vitro assay of the EBV-EA activation induced by TP A in Raji cells. 

Non-isoprenoid Tryptamines. The stems of Picrasma ailanthoides, from which plant canthine derivatives had previously been obtained, has now yielded 1-methoxycarbonyl- and l-hydroxymethyl-j5-carboline. The molecular shape of eserine (= physostigmine) in the crystal has been determined. The new evidence fits in well with information, summarized previously, from n.m.r. NOE measurements. More alkylations at the C-1 methyl of harmaline have been reported.The A -methyl derivative of 1,2,3,4,6,7,12,12b-octahydro-indolo[2,3-a]quinolizine has been isolated from cranberries. 

Picrasma ailanthoides (Simarouhaceae) is a deciduous tree that grows wild in the mountains and plains of Japan. The dried wood without the bark is called Nigaki in Japan, and is used for the treatment of gastrointestinal... 

Matsuzaki T, Fukamiya N, Okano M, Fujita T (1991) Pitaasinoside H, a new quassinoid glucoside, and related compounds from the stem wood of Picrasma ailanthoides. J Nat Prod 54 844-848... 

Inamoto N, Masuda S, Shimamura O, Tsuyuki T 1961 4,5-Dimethoxycanthin-6-one and 2,6-di-methoxy-p-benzoquinone from Picrasma ailanthoides Planchon. Bull Chem Soc Japan 34 888-889... 

Okano M, Fukamiya N, Kondo K, Fujita T et al. 1982 Picrasinoside-A, a novel quassinoid glucoside from Picrasma ailanthoides. Chem Lett pp. 1425-1426... 

Investigation of the minor bitter constituents of Picrasma ailanthoides Planchon led to the isolation and structural elucidation of the following new quassinoids Nigakilactone K (8), L (9), M (10) and N (11) (62). Quite recently two quassinoids hemiacetals, picrasinol-A (12) and -B (13) have been isolated from the bark of the same plant (77) they all have a methyl group at C-8. 

Okano, M., N. Fukamiya, K. Kondo, T. Fujita, and T. Aratani Picrasinoside-A, A Novel Quassinoid Glucoside from Picrasma Ailanthoides Planchon. Chemistry Lett. 1425 (1982). 

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