From Annona muricata

Muricatacin 19 (5-hydroxyheptadecan-4-olide) was isolated from Annona muricata (11) as a mixture of (+) and (-) muricatacin with a slight excess of the (-)-enantiomer (4R, 5R) and it is supposed to be a natural (or unnatural) metabolite of acetogenins. It has been shown tha this hydroxy-butyrolactone presents some in vitro cytotoxicity (11). Since its isolation in 1991, many syntheses have been reported in the literature and are discussed herein. 

Corrossolone 161 was isolated from Annona muricata (48). Gromek et al. (9) reported its hemi-synthesis as an diastereomeric mixture at C-15/16/19/20, starting from corepoxylone 5, after treatment with 70 % perchloric acid in acetone. Indeed it has been shown by HPLC that two products, 161 and 162, were obtained, having identical spectroscopic data ( H NMR, 13C NMR, MS). These two compounds arise from the opening of the oxiranes at either C-15 or at C-20 position (Fig. 27). 

The known atherosperminine and thallglucinone have been retsolated from Annona muricata and Thalictrum minus var. microphyllum, respectively. ... 

Although xyloglucans from various plants possess common structural features, the degree and type of side-chain substitution may differ considerably. Xyloglucans isolated from Annona muricata seeds have a (1—>4)- to (1 4,6)-linked glucose ratio of 1.0 0.3, and the polymer is soluble only in... 

Twenty-six benzyltetrahydroisoquinolines were isolated from some species of Annona and Xylopia and from Monodorajunodii and Monodora grandidiera. The most frequently occurring benzyltetrahydroisoquinoline is reticuHne (11.27). Anomuricine (II.2) and anomurine (II.3) from Annona muricata° are special at that they are substituted in C-5. 

Liaw C, Chang F, Lin C, Chou C, Chiu H, Wu M, Wu Y (2002) New cytotoxic monotetra-hydrofuran annonaceous acetogenins from Annona muricata. J Nat Prod 65 470-475. 

Hasrat JA, De Bruyne T, De Backer JP, Vauquelin G, Vlietinck AJ. Isoquinoline derivatives isolated from the fruit of Annona muricata as 5-HTergic 5-HT1A receptor agonists in rats unexploited antidepressive (lead) products. J Pharm Pharmacol 1997 49 1145-1149. 

Treatment of an alkali-soluble xyloglucan from the seed of Annona muricata with cellulase liberated tetra- and penta-saccharides, together with D-glucose, cellobiose, and a small proportion of a D-xylosylcellobiose.25 From the molar amounts of these products, it may be postulated that the... 

The y-lactone natural product muricatacin 1 is a member of the class of biologically active Annonaceous acetogenin family. Muricatacin was isolated from the seeds of Annona muricata L., a variety of apple trees grown commercially in the Caribbean and Central America, by McLaughlin and co-workers in 1991 [1, 2]. Muricatacin exists namrally as a mixture of syn enantiomers in an approximate ratio of 62 38 ( 24 % ee) of (-)-muricatacin (41 , 5R) versus (+)-muricatacin (45, 55) (Fig. 3.1). These 5-hydroxy-y-lactones are comprised of adjacent chiral centres, one of which is incorporated into the lactone framework, with a dodecyl alkyl chain extending from the hydroxy bearing carbon atom. 

Isol. from the seeds of Annona muricata. Precursor of annonaceous acetogenins. Obt. as a mixt. with Epomuricenin A (see Epoxymurin A, E-30092). Roblot, F. et al. Phytochemistry, 1993, 34, 281. 

Isol. from the bark of Annona muricata. Precursor of annonaceous acetogenins. 

Soursop Annona muricata L.) is among the four best known species of the genus Annona. It is being processed and marketed in the United States, Cuba, Philippines, Brazil and Venezuela. Soursop fruits are grown in the eastern and south-eastern parts of Nigeria. A palatable drink with good keeping qualities can be produced from the local fruits. The seed of the fruit contains 22.1% pale yellow oil and 21.4% protein. Since the oil was reported to be toxic and some studies have shown it to have insecticidal properties, further work is deemed necessary before it can be exploited for culinary purposes (Awan et al., 1980). 

NRIC 0313 ), isolated from fruit of zirzak (Annona muricata) in Indonesia. The DNA G+C content of the type strain is 53.7 mol%. 

Application of ATH in Stereoselective Synthesis Murlcatacln can be isolated as a scalemic mixture from the seeds of Annona muricata Muricatacin and epi-muricata-cin showed anti-proliferative activity against certain cell Unes. The enantioselective total synthesis of a potent cytotoxic agent (- -)- p/-muricatacin was reported by Kumarasw-amy et employing Noyori catalytic asymmetric transfer hydrogenation of benzyl 128 to (15,25)-1,2-diphenylethane-1,2-diol, which subsequently reacted with 129 to produce a key chiral intermediate 130 (Scheme 30.26). 

Folkloric medicine has led many scientists to discover important plant-derived medicines. It has been known for some time that the seeds of several Annonaceous species have an emetic property (Morton, 1987). Eli Lilly, Inc. in 1898 sold a fluid extract made from paw paw seeds A. triloba) for inducing emesis (Anonymous, 1898). Folkloric uses of Annonaceous species also suggest pesticidal properties. The Thai people use extracts of Annona squamosa, A. muricata,A. cherimolia, and A. reticulata for the treatment of head lice (Chumsri, 1995). For this, 10 to 15 fresh leaves of A. squamosa L. are finely crushed and mixed with coconut oil, and the mixture is applied uniformly onto the head and washed off after 30 min. 

A series of acetate-derived compounds have been reported from plants of the family Annonaceae (Annona cherimolia, A. muricata, A. squamosa, and oth r Annona species Asim-ina triloba, pawpaw Goniothalamus giganteus , and several Rollinia and Uvaria species) (Fig. 5.20) (Alkofahi et al., 1989 Lieb et al., 1990 Nahrstedt, 1985 Rupprecht et al., 1986). Most of these compounds exhibit potent antimicrobial, antiparasitic, cytotoxic, and antitumor activity (Bories et al., 1991). For example, asimicin (36), from the bark of Asimina triloba, is extremely cytotoxic (ED50 <10 p-/ml with several cell cultures) fractionation of the plant material was monitored by the brine shrimp bioassay (Alkofahi et al., 1989). This compound also is toxic to the striped cucumber beetle, Mexican bean beetle, mosquito larvae, blowfly larvae, melon aphid, two spotted spider mite, and the free-living nematode, Caenorabditis elegans (Rupprecht et al., 1986). 

---