Eurycoma

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. 

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

Both 10-hydroxy- (20) and lO-methoxycanthin-6-one (21) have been isolated from the wood of 5. multiflora (42), and 20 has also been isolated from the root of Eurycoma longifolia (43). The UV spectrum of 20 shows a large bathochromic shift (76 nm) on alkali addition. Both the UV and IR spectra of 20 resemble those of 18. Acetylation and methylation of 20 produce the monoacetate and monomethyl ether, respectively. In the H-NMR spectrum of 20, two isolated pairs of vicinal protons in rings C and D and 1, 2, 4-trisubstituted aromatic protons are observed. From these observations Arisawa et al. (42) concluded that the hydroxyl function should associate with position 9 or 10. The position was fixed by the interlocking evidence, and structure 20 was determined. There was an increase in the molecular ion of 14 mass units in the mass spectrum of 21 as compared to 20 and the appearance of a new signal (8 3.91, 3H, s)... 

A full paper on eurycomalactone(147)from Eurycoma /ongi/o/ia, has appeared. Eurycomalactone is at present the only example of this type of C19 compound. 

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],... 

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]. 

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],... 

Eurycoma harmandiana Pierre is a small Simaroubaceae plant (Thai name Ian-don) distributed in the border regions between Thailand and Laos. Three new unusual 15a-0H quassinoids named iandonosides A (124), B (125), and iandonone (126) were isolated from the roots of Eurycoma harmandiana [55],... 

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 quassinoids with Cu> skeleton identified so far. 

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-... 

The new 2-epi- 1-dehydroklaineanone (134) isolated from the leaves Eurycoma longifolia showed moderate activity (plant growth inhibitor) against cucumber seedling [56]. 

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

Six quassinoids isolated from Eurycoma tongifolia Jack, were subjected to in vitro tests on anti-tumor promoting. The most active compound for inhibition of tumor promoter-induced Epstein-Barr virus activation was 14,15 p-dihydroklaineanone (136, ICso= 5pM) [109]. This inhibitory potential was much higher than quercetin (IC50" 23 pM) and p-carotene (ICjo- 30 pM), two common antitumor promoting natural agents [110],... 

Seven quassinoids isolated from the leaves of Eurycoma longtfolia showed as plant growth inhibitors [117]. Taking into account the tested compounds, the activities of 150-hydroxyklaineanone (133) and 14,150-dihydroxyklaineanone (136) were significantly higher than the others. 

Examination of the extracts of Eurycoma longifolia Jack., a slender small tree indigenous to Southeast Asia which has played a major role in folk medicine, led to the isolation and the characterization via spectral methods of a new quassinoid, 14p,15P-dihydroxyklaineanone (136) [143],... 

Quassinoids, and Linear Triterpene from Eurycoma longifolia... 

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

Eurycoma longifolia Jack (Simaroubaceae), a famous folk medicine known as "Pasak Bumi" in Southeast Asia, has been used as an antimalaria and tonic etc. The roots of E. longifolia collected in Indonesia were treated with 50% aqueous methanol, TTie extract was partitioned between water and ether, then n-butanol successively. The chromatographic purification of ether and n-butanol soluble fractions furnished canthin alkaloids (34 -36) and quassinoids (37 - 42), respectively. Their structures were coiifirmed as shown in Fig. 5 by various spect data or comparison with... 

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

H. Itokawa, E. Kishi, H. Morita, K. Takeya and Y. litaka, "Eurylene, A New Squalene-Type Triterpene from Eurycoma longifolia . Tetrahedron Lett., 1991, 32, 1803 - 1804. 

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]. 

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