Picrasma quassinoides

Small amounts (0.33%) of quassins are produced by callus and suspension cultures of Picrasma quassinoides (Chari wood and Chari wood, 1991). 

Hikino, H., T. Ohta, and T. Takemoto Picrasins, Simaroubolides of Japanese Quassia Tree Picrasma Quassinoides. Phythochemistry 14, 2473 (1975). 

N.A. Picrasma exeelsa (Sw.) Planch. Quassinoid (quassin), alkaloids, coumarin (scopoletin), vitamin B,.09 Strengthen digestive systems, increase bile flow, secretion of salivary juices, and stomach acid production. 

Quassin is a bitter-tasting substance that can be extracted from the quassia tree (bitter tree, Picrasma quassioides Benn).156 It is said to be the most bitter substance found in nature. Quassin is used in traditional Chinese medicine. Besides quassin, modified triterpenes, the so-called quassinoid, are the principal component of the bitter taste. 

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.—Simarolide (136) had previously been the only substance providing a structural link between limonoids and quassinoids. The related picrasin A (137) has now been isolated from Picrasma quassioides P. ailan-thoides). It was accompanied in the extract by picrasin B (138) which was converted to quassin (139) by bismuth oxide oxidation and methylation. A series of closely related quassin derivatives, nigakilactones A (140), B (141), C (142), E (143), and F (144) occur with quassin in P. ailanthoides. - The structure of amarolide has been revised to (145). Observation of a large coupling between H-9 and H-11 in the n.m.r. spectrum makes the previous... 

Quassinoids O-glycosylated were isolated from species of genera Brucea and Picrasma. 

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]. 

Picrasma crenata (Veil.) Engler is a Brazilian tree, which is used in traditional medicine to treat Diabetes mellitus, gastric disturbance and hypertension [67], Three quassinoids quassin type, 3-dihydronomeoquassin (153), 16-P-O-methylneoquassin (154), and 16-3-O-ethylneoquassin (155) were isolated from Picrasma crenata [67-68],... 

Until 1985, only six quassinoids possessing the C25 basic skeleton were known simarolide (209) from the bark of Simarouba amara, picrasin A (210) isolated from Picrasma quassioides, soulameolide (211) from Soulamea tomentosa, simarinolide (212) and guanepolide (213) from the root bark of the Simaba cf. orinocencis, and deacetylsimarolide (214) isolated from the fruits of Simaba moretii [1]. 

Since then, seven more C25 quassinoids have been discovered Odyendane (215) and odyendene (216) from the Odyendea gabonensis [90], klaineanolide A (217) and B (218) from the Hannoa klaineana [61], indaquassin F (219) from the Quassia indica [80], javanicinoside E (220) isolated from the Picrasma javanica [76] and the new epimer from simarolide (221) [91],... 

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. 

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... 

Koike K, Yokoh M, Furukaw M, Ishil S, Ohmoto T (1995) Picrasane quassinoids from Picrasma javanica. Phytochemistry 40 233-238... 

Yang S-P, Yue J-M (2004) Five new quassinoids from the bark of Picrasma quassioides. Helv Chim Acta 87 1591-1600... 

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. 

Nestler, T., G. Tittel, and H. Wagner Quantitative Bestimmung der Bitter Quassinoide von Quassia amara und Picrasma excelsa. Planta Medica 38, 204 (1980). 

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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