Quassinoids isolation

Ailantinol G (43) a quassinoid isolated from Ailanthus altissima was evaluated for its antitumor effects promotion against Epstein-Barr virus early antigen activation introduced by 12-0-tetradecanoylphorbol-13-acetate in Raji cells [25],... 

Eighteen quassinoids glycosides and nine known quassinoids isolated from Brucea javanica, Brucea cmtidysenterica and Ailanthus altissima were tested for inhibitory activity against HIV replication in H9 lymphocytic cells [103],... 

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. 

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],... 

Some quassinoids isolated from the leaves of Evrycoma longifotia Jack, were subjected to in vitro antischistosomal activities [109],... 

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. 

In a previous paper [1], we reviewed the isolation of quassinoids, alkaloids, and fatty acids from Simaroubaceous plants during the period 1972-1988 and discussed their biological activities, such as antitumor, antimalarial, and anti-inflammatory agents as well as insect antifeedants, amoebicides, and herbicides. This review will add new quassinoids isolated from Simaroubaceous plants from 1988 onwards and their biological activities, for example, antitumor, anti-tumor-promotor (= inhibitor against TPA-induced EBV-EA activation), anti-HIV, anti-tuberculosis, and insect antifeedant activities. Furthermore, the stability of quassinoids, lower activities of degradation products, and the synthesis of fluorinated quassinoids are also described. 

Short-term in vitro assays for tumor-promoters and anti-tumor-promoters (Epstein-Barr virus activation test) were carried out for 14 quassinoids isolated from A. altissima, as shown in Table 12. Some quassinoids, including ailantinol-B (41), ailantinol-C (42), ailanthone (80) and shijulactone-A (116), showed moderate activity at a molar ratio of 1 100 (TPA/quassinoids), and the results led to the following structure-activity relationships (1) an epoxy group enhances the activity (2) an OH group at C-6 and/or at C-11 enhances the activity (3) an OH group at C-13 and/or C-15 weakens the activity and esterification of the OH oup at C-15 may enhance the activity [35]. 

In vitro evaluation of anti-tuberculosis activity was conducted for fifty-six quassinoids isolated in our laboratory from the Simaroubaceous plants A. altissima (10 compounds), B. antidysenterica (16 compounds), P. ailanthoides (14 compounds), and B.javanica (16 compounds), as shown in Table 15. Of the compounds tested, shinjulactone-K (119)... 

A series of six quassinoids isolated from Simaba multiflora and Soulamea soulameoides were shown to be active as growth inhibitors and as antifeedants against Heliothis virescens (cotton budworm) and Spodoptera frugiperda (fall armyworm) (Klocke et al., 1985). 

Polonsky J, Maivantri, Varon Z, Prange T et al. 1980 Quassinoids. Isolation from Soulamea muelleri and structures of 1,12-di-O- acetyl soulameanone and -2-picrasin B. X-Ray analysis of soulameanone. Tetrahedron 36 2983-2988... 

Structure (e) has so far been found only in certain quassinoids isolated from the genus Brucea whilst structure (f) occurs so far only in two quassinoids, sergeolide (62) and 15-deacetylsergeolide (63) (see below). 

Polonsky, J., Mai Van Tri, Z. Varon, T. Prange, C. Pascard, T. Sevenet, and J. Pusset Quassinoids. Isolation from Soulamea muelleri and Structures of 1,12-Di-0-Acetyl Soulameanone and A -Picrasin B, X-Ray Analysis of Soulameanone. Tetrahedron 36, 2983 (1980). 

Isolation of two quassinoids (quassin and simalikalactone D) from root bark of Quassia africana Baill... 

Quassinoids —The antileukaemic activity of some quassinoids has revived interest in this group. Three new biologically active compounds have been isolated. Quassimarin (118) occurs in Quassia amara with the inactive simalikalactone D (129) 86 Bruceoside A, from Brucea javanica, is the glucoside (120). The third... 

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. 

From the seeds and bark of Samadera indica (Simaroubaceae), indaquassin C (296) was isolated together with three additional quassinoids. Only 296, present in 0.006% in seed kernels, exhibited moderate antifeedant activity toward S. litura, with 1 pg leafcm 2, resulting in 48.9% feeding inhibition.128... 

Lin, L. Z. Zhang, J. S. Chen, Z. L. Xu, R. S. Studies on chemical constituents of Brucea javanica (L.) Merr.l. Isolation and identification of bruceaketolic acid and other four quassinoids. Huaxue Xuebao, 1982, 40 73-7. ... 

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.—2 -AcetylgIaucarubine (98) and a new antineoplastic quassinoid, 13,18-dehydroglaucarubinone (99), have been isolated from Simarouba amara. The related 13,18-dehydroglaucarubol-15-isovalerate (100) has been reported from Ailanthus excelsa. The details of the crystal structural analyses of samaderin 7A (101), from Samadera indica, and 6-hydroxypicrasin B (102), from Soulamea species, have appeared. 

For such review the collected data are from 1985 up to 2004 focusing on all the isolated and identified quassinoids, as well as, the main biological activities and some synthetic processes. 

The review containing structural data, biological activities and chemical modifications of quassinoids was published last decade with references up to September 1984 by Polonsky [1]. According to Simao et al. [2] more than two hundred quassinoids were isolated and identified until December 1984. 

All isolated quassinoids he has only a group methyl in the carbon C-4 so far. 

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

Support for this biogenetic picture has also come from the isolation of compounds representing the various stages and structural variations among quassinoids. 

To follow what has been described, all quassinoids (divided by basic skeletons) were isolated and identified since 1985 to June 2004. 

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],... 

Two decades passed and twenty-three more quassinoids were isolated from Simaroubaceae species in a total of thirty-two quassinoids with C19 skeleton identified so far. 

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... 

The eight new quassinoids C19 type shinjulactone B (19) with a presence of a l,2-seco-l-nor-(5->10)-a >eo-picrasan-2,5-olide skeleton have been isolated from Simaroubaceae species. 

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],... 

Chemical examination of Ailanthus excelsa has been carried out by several workers resulting in the isolation of quassinoids, alkaloids and... 

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