Cleistopholis

S. Liu, B. Oguntimein, C.D. Hufford, and A.M. Clark, 3-Methoxysampangine, a novel antifungal copyrine alkaloid from Cleistopholis patens, Antimicrob. Agents Chemother., 34, 529, 1990. 

Cleistopholis staudtii Chondrofoline, curine, cycleanine, isochondodendrine 541... 

Dielsiquinone (134) is the only Guatteria alkaloid known to possess the 1-azaanthracene ring system (22). This skeleton was found for the first time in the parent compound cleistopholine (154), isolated successively from the An-nonaceae Cleistopholis patens (77) and Meiogyne virgata (78), and later also from Annona cherimolia (79) and A. hayesii (80). The latter species also contains the related annopholine (155). Annona ambotay (81) is the only known... 

Z. Zhang, P. G. Wang, N. Ding, G. Song, and Y. Li, Total synthesis of cleistetroside-2, partially acetylated dodecanyl tetra-rhamnoside derivative isolated from Cleistopholis patens and Cleistopholis glauca, Carbohydr. Res., 342 (2007) 1159-1168. 

Cleistopholine (6), a simple benzoquinoline alkaloid first encountered in Cleistopholis patens (Annonaceae), was isolated from the Sri Lankan Annonaceae Cananga odorata (Lam.) Hook. f. and Thoms. (24). Furoqui-... 

Cleistopholine (2) was first isolated by Waterman and Muhammad in 1985 from the root bark of Cleistopholis patens (Annonaceae) collected in Ghana (5). A petrol (bp 40-50°C) extract of the bark was partitioned through acid-base (pH 10), and the basic fractions were separated by preparative TLC (silica gel toluene-EtOAc-AcOH, 94 6 1) to give cleistopholine as a second fraction (0.006%). 

Four years later, in 1990, 3-methoxysampangine (449) was isolated by Clark et al. from the root bark of Cleistopholis patens (Annonaceae), collected on the University of Ife campus in Ife, Nigeria, along with three known alkaloids eupolauridine (450), liriodenine (451), and eupolauridine A-oxide (452) 194). 

Hufford CD, Liu S, Clark AM, Oguntimein BO. Anticandidal activity of eupolaur-idine and onychine, alkaloids from Cleistopholis patens. J Nat Prod 1987 50 961-4. 

Along with collaborators in Cameroon we decided to investigate Cleistopholis gleuca., No acetogenins were found but six compounds were isolated which turned out to oligosaccharides. On acetylation five of these gave the same peracetate 2 and this simplifies the presentation of the structural elucidation somewhat. 

Returning now to the Cleistopholis compounds, NOE difference experiments where the 1-Hs are irradiated are shown in Fig. 8(i)-(iv). Discrimination between incompletely resolved multiplets, e.g. lb- and Ic-H, is possible by restricting irradiation to only one line of each doublet. Here we see NOEs across the glycosidic links (5%) which confirm the delayed COSY results and also NOEs of the 2-Hs (3%) but not of 3-H or 5-H. Hence we conclude that the glycosidic links are axial (a in the L sugar). 

So far the structure 2 of the peracetate of the Cleistopholis compounds has been deduced. The original compounds are partially... 

Chondrofoline IV.5 1 Uvaria ovata Isolona ghesquieri Uvaria ovata Cleistopholis staudtii... 

Isomoschatoline XI 14 Cleistopholis patens Guatteria blepharophylla Guatteria dielsiana Guatteria melosma Uvaria mocoli... 

Onychine XIV 163 Cleistopholis patens Root bark Nigeria 279... 

Sampangine (XIV. 187) and 3-methoxysampangine (XIV.144) were isolated from Duguetia hadrantha, this is the first report of the cooccurrence of the copyrine-type alkaloids from a Duguetia species. These compounds were isolated previously from C. odorata of Asian and Cleistopholis patens of African origin, respectively. 

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