From Punica granatum

Sudheesh S and Vijayalakshmi NR. 2005. Flavonoids from Punica granatum—potential antiperoxidative agents. Fitoterapia 76(2) 181—186. 

Chauhan, D. and Chauhan, J.S., Flavonoid diglycoside from Punica granatum, Pharm. Biol, 39, 155, 2001. 

The simple piperidine pelletierine from Punica granatum (pomegranate) (Punicaceae) and Duboisia myoporoides (Solanaceae) is an anthelmintic. The simple piperidine derivatives deoxy-mannojirimycin (DMJ) and deoxynojirimycin (DNJ) from Lonchocarpus species (Fabaceae) are glycosidase inhibitors because they are structurally similar to the pyranose (six-membered ring) sugar moieties of the glycosidase disaccharide substrates. 

Reddy, M.K. Gupta S.K. Jacob, M.R. Khan, S.I. Ferreira, D. 2007. Antioxidant, antimalaria, and antimicrobial activity of ellagitannins and phenolic acids from punica granatum. Planta Med. 73 461 67. 

Pseudopelletierine (331) was isolated from Punica granatum bark [440], and was synthesized by mercuric acetate oxidation of A-methylpelletierine (170) [696]. Pseudopelletierine oxime was found to be asymmetric, and the (+)-oxime was resolved [697]. 

Fatope, M.O., S.K. Al Burtomani, and Y. Takeda. 2002. Monoacylglycerol from Punica granatum seed oil. /. Agric. Food Chem. 50 357-360. 

In 1963, Beyerman and Maat [6] already described the synthesis and absolute configuration of Tanret s (-)-pelletierine. The synthesis is described of (-)-pelletierine picrate as identical with Tanret s pelletierine picrate from Punica granatum L. and its antipode by oxidation, respectively, of (-)- and of (+)-sedridine. The sedridines are alkaloids with known absolute configuration of the piperidine asymmetric carbon atom. From this follows the Ds-configuration of (-)-pelletierine. 

Pseudopelletierine has been obtained from the bark of the pomegranate tree (Punica granatum L.).2-5 The synthesis of the alkaloid from glutaraldehyde, methylamine, and calcium acetonedicarboxylate was first achieved by Menzies and Robinson.6 The synthetic method subsequently was improved by Schopf and Lehmann,7 and others.8 9 The condensation of a dialdehyde with an amine and acetonedicar-boxylic acid to form a heterobicyclic compound (an alkaloid or alkaloid analog, usually employing mild or so-called physiological conditions) is sometimes referred to as a Robinson-Schopf synthesis. 

Seeram, N.P., Lee, R., and Heber, D., Bioavailabihty of ellagic acid in human plasma after consumption of ellagitannins from pomegranate (Punica granatum L.) juice, Clin. Chim. Acta, 348, 63, 2004. 

The fruits of pomegranate (Punica granatum, L. Punicaceae) are popular in the East and far East countries. The dried pericarp has been utilized in folk medicine for colic, colitis, diarrhea, dysentery, leucorrhea, menorrhagia, oxyuriasis, paralysis and rectocele. The flavonoid extract from cold pressed seed oil showed 31-44% inhibition of sheep COX-1 enzyme and 69-81% inhibition of soybean lipoxygenase [181]. 

Fischer, U.A. Carle R. Kammerer, D.R. 2011. Identification and quantification of phenolic compounds from pomegranate (Punica granatum L.) peel, mesocarp, aril and differently produced juices by HPLC-DAD-ESI/MSn. Food Chem. 127 807-821. 

The tracer results thus indicate a similar pathway to the piperidine rings of pipecolic acid (12) and iV-methylpelletierine (13) (Scheme 2), and the latter may be derived plausibly from A -piperideine (11) by condensation with acetoacetate. The possibility that acetoacetate is a precursor is supported by the finding that the side chain of iV-methylpelletierine is synthesized from acetate in Punica granatum. Attempts to show the involvement of acetoacetate using [3- C]-and [4- " C]-j -hydroxybutyrate, considered to be more easily manipulated than acetoacetate, were unsuccessful as the derived N-methylpelletierine showed a labelling pattern very similar to that found with acetate, to which presumably the j -hydroxybutyrate is first degraded. ... 

V-(2, 5 -Dihydroxyphenyl)pyridinium chloride (116) was isolated from leaf extract of Punica granatum[333]. Its structure was established with UV, FABMS. one- and two-dimensional H and 13C NMR, formation of a precipitate with aqueous AgNQ3, and alkaline fusion to give hydroquinone [333]. 

A recent synthesis of (+)-sedridine (167) was reported in which a key step was the asymmetric cycloaddition of the nitrone 2,3,4,5-tetrahydropyridine A-oxide with an asymmetric crotonic acid derivative containing a chiral auxilliary [439], Sedridine has recently been isolated from the bark of Punica granatum [440],... 

N-Methylpelletierine was recently isolated from the spruce Picea breweriana [441] and both 169 and 170 were isolated from the bark of Punica granatum [440]. In a synthesis of 170, the side chain was introduced by alkynylation of an 5-methylthioamidium salt generated from N-methylpiperidine-2-thione [444],... 

The alkaloids Af-methylpelletierine (90) and pseudopelletierine (91) of Punica granatum and also anaferine (92) of Withania somnifera are probably related in biosynthesis to sedamine and anabasine. The proposed biosynthesis (Scheme 17) has received support from recent tracer studies.57... 

Galinovsky and his co-workers have re-examined the alkaloids of the bark of Punica granatum L. In a sample, labeled pelletierine hydrobromide, that they obtained from Merck (Darmstadt), the only secondary base present was not j3-(2-pelletierine) but isopelletierine identical with a synthetic sample (12). They further found that methylisopelletierine and isopelletierine retain their optical activity in the presence of acid, but racemize in contact with alkali, and the former racemizes appreciably faster than the latter. If the bases were optically active in the plant they would racemize during the process of extraction and isolation unless the work is done rapidly (13). 

The bark of the pomegranate tree (Punica granatum L.) was first investigated by C. Tanret who isolated from it four alkaloids which he named pelletierine (204), isopelletierine, methylpelletierine, and pseudo-pelletierine (205, 206). Methylpelletierine and pelletierine were observed to be optically active while isopelletierine and pseudopelletierine were inactive. Later, Piccinini (207) found a fifth alkaloid, isomethylpelletierine in the mother liquors obtained from the preparation of pseudopelletierine. Eventually, however, Hess (208) while reinvestigating the bark obtained pseudopelletierine, Piccinini s isomethylpelletierine and a third, optically inactive base, but found no trace of Tanret s optically active methylpelletierine. He could not find any optically active alkaloids and, considering his third base identical with Tanret s isopelletierine (185) renamed the latter base pelletierine. Further, Hess and Eichel (209) considered Tanret s methylpelletierine and Piccinini s isomethylpelletierine as identical but different from methylated pelletierine and named it methyliso-pelletierine (185). 

---