Quassinoids from Eurycoma longifolia

Ang HH, Hitotsuyanagi Y, Takeya K (2000) Eurycolactones A-C, Novel Quassinoids from Eurycoma longifolia. Tetrahedron Lett 41 6849... 

Morita H, Kishi E, Takeya K, Itokawa H, litaka Y (1993) Highly oxygenated quassinoids from Eurycoma longifolia. Phytochemistry 33 691-696... 

Itokawa H, Qin X-R, Morita H, Takeya K, ntaka Y (1993) Novel quassinoids from Eurycoma Longifolia. Chem Pharm Bull 41 403-405... 

Jiwajinda S, Santisopasri V, Murakami A, Hirai N, Ohigashi H (2001) Quassinoids from Eurycoma longifolia as plant growth inhibitors. Phytochtanistry 58 959-962... 

Tada H, Yasuda F, Otani K, Doteuchi M, Ishihara Y, ShiroM (1991) New antiulcer quassinoids from Eurycoma longifolia. Eur J Med Chem 26 345-349... 

Eurycomanol, Quassinoids from Eurycoma Longifolia. Phytochemistry 22,1514 (1983). 

Until 1985 only three quassinoids with Cis skeleton had been isolated from Simaroubaceae species, Samaderine A (5) isolated from Samadera indica [7], and laurycolactone A (6) and B (7) isolated from Eurycoma longifolia Jack [8],... 

Then, two decades passed and only three more quassinoids with Ci8 skeleton were isolated from Eurycoma longifolia, eurycolactone B (8), C (9) [9] and D (10) [10], in a total of six quassinoids with Ci8 skeleton, isolated and identified so far Compound (8) is the first halogenated quassinoid separated from plant sources. 

Only nine quassinoids possessing the C19 basic skeleton were isolated until 1985 samaderins B (11), C (12), D (13), an 3,4-dihydrosamaderin B (14) from the stem and leaves of Samadera indica, cedronin (15) and cedronolin (16) isolated from the fruits of Simaba cedron, eurycomalactone (17) and 5,6-dehydroeurycomalactone (18) from Eurycoma longifolia Jack, and shinjulactone B (19) isolated from Ailanthus altissima Swingle [1],... 

Quassinoid (40) isolated from the roots from Eurycoma longifolia Jack. [14] showed lactonization rarely-occurred C ring with hydroxyl group at C-ll with the carbonyl group at C-13, and eurycolactone A (41) showed a novel carbon framework with ring A contracted [9],... 

Quassinoids, and Linear Triterpene from Eurycoma longifolia... 

Cytotoxic Quassinoids, Linear Triterpenes and Canthin Alkaloids from Eurycoma longifolia [38,39]... 

The novel chloroenone quassinoid eurycolactone B (444) was characterized from the roots of Eurycoma longifolia from Malaysia (629). This is the first halogenated quassinoid discovered in a plant. A series of norditerpene dilactones, including the chlorinated rakanmakilactones E (445), G (446), and 447, were isolated from the leaves of Podocarpus macrophyllus from Japan (630, 631). These represent the first halogenated norditerpene dilactones found in the Podocarpaceae. 

Eurycoma longifolia Jack is one of the most well known folk medicines for intermittent fever (malaria) in Southeast Asia [11]. This plant possesses the largest number of quassinoids with C19 skeleton identified so far. 7a-hydroxyeurycomalactone (20) [12], 6a-hydroxyeurycomalactone (21) [13], eurycolactone E (22) [10], eurycomalide B (23) [14], and quassinoids (24) and (25) [15] isolated from the E. longifolia Jack and cymosanine (26) [16] isolated from... 

Two new quassinoids (34) and (35) with a presence of a 1,2-seco-1 -nor-(5 - 10)-afo o-picrasan-2,5-olide skeleton were isolated from wood Eurycoma longifolia Jack [15]. 

Seven novel highly oxygenated quassinoids were isolated from the leaves of Eurycoma longifolia, 13a(21)-epoxyeurycomanone (127), 15-acetyl- 13a(21)-epoxyeurycomanone (128), 12,15-diacetyl-13a(21)-epoxyeurycomanone (129), 12-acetyl-13,21-... 

Two highly oxygenated quassinoids, (135) and 13P, 18-dihydroeurycomanol (136) were also isolated from the roots of Eurycoma longifolia [57-58],... 

H. Morita, E. Kishi, K. Takeya, H. Itokawa and O. Tanaka, "New Quassinoids from the Roots of Eurycoma longifolia", Chem. Lett., 1990, 749 - 752. 

Itokawa et al. isolated three new quassinoids, 6a-hydroxy-eurycomalactone (63), longilactone (64), and 14.15fi-dihydroxy-klaineanone (65), from the woods of Eurycoma longifolia (Simaroubaceae) along with three known quassinoids, 11-dehydro-klaineanone (66), eurycomalactone (67), and 5,6-dehydro-eurycomalactone (68). All showed potent cytotoxic activity against P-388 and KB cells (see Table 6) [25]. 

Itokawa H, Kishi E, Morita H, Takeya K (1992) Cytotoxic quassinoids and tirucallane-type triterpenes from the woods of Eurycoma longifolia. Chem Pharm Bull 40 1053-1055... 

Samaderine A (1) isolated from Samadera indica 111), laurycolactone A (2) and B (3) isolated from the Vietnamese Simaroubaceae Eurycoma longifolia Jack 67) are the only three Cig-quassinoids so far known. The structures of (1) and (2) were established by X-ray analysis and that of (3) by spectral evidence. 

Eurycomanone (28) and eurycomanol (29) have been isolated from the roots of the Indonesian Eurycoma longifolia (13,14). Both quassinoids do not exhibit inhibitory activity against NIH lymphocytic leukemia. 

Darise, M., H. Kohda, K. Mizutani, and O. Tanaka Eurycomanone and Eurycomanol, Quassinoids from the Roots of Eurycoma Longifolia. Phytochemistry 21, 2091 (1982). 

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