Phytochemistry

Phytochemistry and pharmacology (consolidated from pharmacological reviews)

P. incarnata:

Primary Active Constituents:

Flavonoids – Apigenin, luteloin, quercetin, kaempferol, 6-β-d-allopyranosyl-8-β-xylopyranosyl-apigenin, C-glycosyl flavonoids vitexin, isovitexin, orientin, isoorientin, schaftoside, isoschaftoside, isovitexin-2″-O-glucopyranoside, isoorientin-2″-O-gluco-pyranoside, 2-glucosylapigenin, isoscoparin-2″-O-glucoside, 2″-O-glucosyl-6-C-glucosylapigenin, 6-β-d-glucopyranosyl-8-β-d-ribopyranosyl apigenin and swertisin. The greatest accumulation of these flavonoids is in the leaves and the highest concentration of isovitexin was found to be between the pre-flowering and flowering stages. The ethanol free liquid extract contains higher contents of flavonoids as compared to commercial preparations. P. incarnata has the highest content of isovitexin among various other species.

Alkaloids – simple indole alkaloids based on β-carboline ring system (harman, harmol, harmine, harmalol, and harmaline)

Miscellaneous phyto-constituents – maltol, carbohydrates (raffinose, sucrose, D-glucose, and D-fructose; essential oil contains hexanol, benzyl alcohol, linalool, 2-phenylethyl alcohol, 2-hydroxy benzoic acid methyl ester, carvone, trans-anethol, eugenol, isoeugenol, β-ionone, α-bergamotol, and phytol; odor constituents are limonene, cumene, α-pinene, perzizaene, zizaene, and zizanene; twenty one amino acids; and a cyanogenic glycoside gynocardin.

 

Pharmacological Research Summaries:

Cannabinoids Reversal – The benzoflavone moiety significantly prevented the development of tolerance and dependence of cannabinoids in mice treated with delta9-THC.

Nicotine Reversal – The benzoflavone moiety (BZF) extracted from aerial parts significantly reduced the number of withdrawal jumps in mice relative to the group treated with nicotine alone. BZF treatment also prevented weight loss and resulted in normal performance in the swimming endurance test, which may be a measure of stress and/or depression. The effects were dose dependents with higher doses preventing some of the nicotine-withdrawal effects.

Alcohol Withdrawal – Chronic administration of P. incarnata with alcohol had better preventative effects than a single acute treatment in alcohol-dependent mice. The results showed that treatment of P. incarnata extract could be used as a safe and alternative drug for alcohol withdrawal.

Anti-convulsant – There is evidence for anticonvulsant activity in clonic seizure of pentylenetetrazole model tested in mice suggesting use for treatment of absence seizure.

Antianxiety – A fraction derived from the methanol extract has been observed to exhibit significant anxiolytic activity in mice using elevated plus-maze model of anxiety.

Aphrodisiac – BZF has been found to speed up the restoration of sexuality in rats upon cessation of the administration of substances like alcohol, nicotine, and alcohol-nicotine combinations. The aphrodisiac properties of the methanol extract of leaves of P. incarnata has been evaluated in mice by observing mounting behavior suggesting that it may cause sexual desire in humans as well.

Antitussive – The methanolic extract of leaves (100 and 200 mg/kg) exhibited significant antitussive activity on sulfur dioxide-induced cough in mice comparable to codeine phosphate.

 

P. edulis:

Primary Active Constituents:

Glycosides – A cyclopropane triterpene glycoside named Passiflorine [(22R),(24S)-22,28-epoxy-24-methyl-1α,3β,24,28-tetrahydroxy-9,19-cyclo-9β-lanostan-4-oic acid β-d-glucosyl ester] was isolated from the methanol extract of air dried leaves. Flavonoid glycosides (luteolin-6-C-chinovoside, luteolin-6-C-fucoside), Cyanogenic glycosides (passicoriacin, epipassicoriacin, epitetraphyllin B, cyanogenic-β-rutinoside, amygdalin, prunasin, mandelonitrile rhamnopyranosyl-β-D-glucopyranoside, sambunigrin), 6-O-α-l-arabinopyranosyl-β-d-glucopyranosides of linalool (benzyl alcohol and 3 methyl-but-2en-1-ol), β-d-glucopyranoside and 6-O-α-l-rhamnopyranosyl-β-d-glucopyranoside of methyl salicylate, and β-d-glucopyranoside of eugenol.

Phenols - 4-Hydroxy-β-ionol, 4-oxo-β-ionol, 4-hydroxy-7,8-dihydro-β-ionol, 4-oxo-7,8-dihydro-β-ionol, 3-oxo-α-ionol, isomeric 3-oxo retro-α-ionols, 3-oxo-7,8-dihydro-α-ionol, 3-hydroxy-1,1,6-trimethyl-1,2,3,4-tetrahydronaphthalene vomifoliol and dehydrovomifoliol, terpene alcohols linalool and α-terpeneol, terpene diols (E) and (Z)-2,6-dimethyl-octa-2,7-diene-1,6-diol, 2,6-dimethyl-octa-3,7-dien-2,6-diol, 2,6-dimethyl-1,8-octanediol, 2,6-dimethyl-octa-1,7-diene-3,6-diol, ionol derivatives oxygenated in position 3, and 2,5-dimethyl-4-hydroxy-3-(2H)-furanone (furaneol)

Alkaloids – harman, harmine, harmaline, and harmalol with the highest concentration of harman alkaloids present in the leaves

Miscellaneous phyto-constituents – Carotenoids, L-ascorbic acid, Anthocyanins, y-Lactones, Flavor components (esters, 3-methyl-thiohexan-1-ol, 2-methyl-4-propyl-1, 3-oxathione enantiomers, edulans I and II), volatile oil constituents (hexyl caproate and butyrate, and ethyl caproate and butyrate, limonene, 2-tridecanone, (9Z)-octadecenoic acid, 2-pentadecanone, hexadecenoic acid, 2-tridecanol, octadecanoic acid and caryophyllene oxide), amino acids (proline, aspartic acid, glutamic acid, serine, alanine), carbohydrates (fructose, glucose, sucrose, maltose, lactose, and pectin), Minerals (Na, K, Mg, Ca, Zn, Mn, Fe), enzyme cytoplasmic pyruvate kinase, cycloartane triterpenes, cyclopassifloic acids A-D, and their saponins, cyclopassiflosides I-VI.

 

Pharmacological Research Summaries:

Anti-inflammatory – The aqueous leaves extract possess a significant anti-inflammatory activity in mice characterized by inhibition of leukocyte influx to the pleural cavity and associated with marked blockade of myeloperoxidase, nitric oxide, TNFa and IL-1a levels in the acute model of inflammation caused by intra pleural injection of carrageenan. This extract was also effective in inhibiting leukocytes in the pleurisy induced by bradykinin, histamine, and substance-P with the extract showing similar effects to dexamethasone.

Anti-anxiety – In a study on mice performance in elevated plus maze, open-field, and horizontal-wire tests, the aqueous extract presented an anxiolytic-like activity without any significant effect upon the motor activity while the total flavonoid fraction presented an anxiolytic-like activity but compromised motor activity.

Antihypertensive – The orally administered methanol extract of rind or luteloin (one of consistent polyphenols of the extract) significantly lowered systolic blood pressure in spontaneously hypertensive rats. The extract contained a relatively high concentration of GABA which may be the main mechanism of action along with the vasodilatory effect of polyphenols such as luteolin.

Cholesterol and lipid lowering effects – The insoluble fiber-rich fraction prepared from the defatted passion fruit seed had cholesterol and lipid-lowering effects as compared to cellulose the mechanism was determined to be in part due to the enhanced excretion of lipids and bile acids via feces.

Antioxidant – The antioxidant activity of P. edulis leaves extract was significantly correlated with polyphenol contents. The extract attenuated ex vivo iron-induced cell death, quantified by lactate dehydrogenase leakage, and effectively protected against protein damage induced by iron and glucose.

Anti-tumor – The fruit’s decoction has been evaluated for the inhibition of activity of gelatinase matrix metalloproteinases (MMP-2 and MMP-9) involved in tumor invasion, metastasis and angiogenesis. Results showed that the water extract at different concentrations inhibited the enzymes.

Antifungal – A novel plant peptide of 5.0kDa, Pe-AFP-1 purified from the seeds of passion fruit demonstrated inhibition of the development of filamentous fungi Trichoderma harzianum, Fusarium oxysporum, and Asperfillus fumigatus in in vitro assays. This indicates potential use in antifungal drugs.