PREPARATION & EVALUATION OF ANNONA MURICATA EXTRACT AGAINST CANCER CELLS WITH MODIFIED RELEASE

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About Authors:
*Dilipkumar.J.P, Agliandeshwari.D
Rajiv Gandhi University of Health Sciences
Bangalore, India
*dilipkumar9447@gmail.com

INTRODUCTION
Natural products, especially those derived from plants, have been used to help mankind sustain its health since the dawn of medicine. Over the past century, the phytochemicals in plants have been a pivotal pipeline for pharmaceutical discovery. The importance of the active ingredients of plants in agriculture and medicine has stimulated significant scientific interest in the biological activities of these substances1. Despite these studies, a restricted range of plant species has experienced detailed scientific inspection, and our knowledge is comparatively insufficient concerning their potential role in nature. Hence, the attainment of a reasonable perception of natural products necessitates comprehensive investigations on the biological activities of these plants and their key phytochemicals2. In a pharmaceutical landscape, plants with a long history of use in ethno medicine are a rich source of active phytoconstituents that provide medicinal or health benefits against various ailments and diseases. One such plant with extensive traditional use is Annona muricata. In this review, we describe the botany, distribution and ethnomedicinal uses of this plant, and we summarize the phytochemistry, biological activities and possible mechanisms of A. muricata bioactivities.

Reference Id: PHARMATUTOR-ART-2528

PharmaTutor (Print-ISSN: 2394 - 6679; e-ISSN: 2347 - 7881)

Volume 5, Issue 10

Received On: 14/06/2017; Accepted On: 15/06/2017; Published On: 01/10/2017

How to cite this article: Dilipkumar JP, Agliandeshwari D; Preparation & evaluation of Annona Muricata extract against cancer cells with modified release; PharmaTutor; 2017; 5(10); 63-106

Botanical Description and Distribution
A. muricata L., commonly known as soursop, graviola, guanabana, paw-paw and sirsak, is a member of the Annonaceae family comprising approximately 130 genera and 2300 species3,4. A. muricata is native to the warmest tropical areas in South and North America and is now widely distributed throughout tropical and subtropical parts of the world, including India, Malaysia and Nigeria5. A. muricata is an evergreen, terrestrial, erect tree reaching 5–8 m in height and features an open, roundish canopy with large, glossy, dark green leaves. The edible fruits of the tree are large, heart-shaped and green in color, and the diameter varies between 15 and 20 cm (Figure 1)6.

Figure 1.1: (A) Annona muricata L.; the appearance of the (B) leaves; (C) flowers and (D) fruits.

Ethnomedicinal Uses
All portions of the A. muricata tree, similar to other Annona species, including A. squamosa and A. reticulata are extensively used as traditional medicines against an array of human ailments and diseases, especially cancer and parasitic infections. The fruit is used as natural medicine for arthritic pain, neuralgia, arthritis, diarrhea, dysentery, fever, malaria, parasites, rheumatism, skin rushes and worms, and it is also eaten to elevate a mother’s milk after childbirth. The leaves are employed to treat cystitis, diabetes, headaches and insomnia. Moreover, internal administration of the leaf’s decoction is believed to exhibit anti-rheumatic and neuralgic effects, whereas the cooked leaves are topically used to treat abscesses and rheumatism3,5,7. The crushed seeds are believed to have anthelmintic activities against external and internal worms and parasites. In tropical Africa, the plant is used as an astringent, insecticide and piscicide agent and to treat coughs, pain and skin diseases. In India, the fruit and flower are employed as remedies against catarrh, while the root-bark and leaves are believed to have antiphlogistic and anthelmintic activities8,9. In Malaysia, the crushed leaf mixture of A. muricata together with A. squamosa and Hibiscus rosa-sinensis is used as a juice on the head to protect against fainting10. In South America and tropical Africa, including Nigeria, leaves of A. muricata are deployed as an ethnomedicine against tumors and cancer8. In addition, the anti-inflammatory, hypoglycemic, sedative, smooth muscle relaxant, hypotensive and antispasmodic effects are also attributed to the leaves, barks and roots of A. muricata3,5. In addition to ethnomedicinal uses, the fruits are widely employed for the preparation of beverages, candy, ice creams, shakes and syrups11,12.

Phytochemistry
Extensive phytochemical evaluations on different parts of the A. muricata plant have shown the presence of various phytoconstituents and compounds, including alkaloids (ALKs)4,13, megastigmanes (MGs)14 flavonol triglycosides (FTGs)15, phenolics (PLs)16, cyclopeptides (CPs) and essential oils (Table 1, Figure 2)17,18. However, Annona species, including A. muricata, have been shown to be a generally rich source of annonaceous acetogenin compounds (AGEs)19. The presence of different major minerals such as K, Ca, Na, Cu, Fe and Mg suggest that regular consumption of the A. muricata fruit can help provide essential nutrients and elements to the human body20.

 

Table No. 1.1: Chemical compounds isolated from Annona muricata. ALK: alkaloid; AGE: annonaceous acetogenin; MG: megastigmane; FTG: flavonol triglycoside; PL: phenolic; CP: cyclopeptide.

Plant Part

Compound

Class

Biological Activity

References

Fruits

annonaine

ALK

anti-depressive

[21,22]

Fruits

nornuciferine

ALK

anti-depressive

[21,22]

Fruits

asimilobine

ALK

anti-depressive

[21,22]

Fruits

epomusenin-A

AGE

-

[23]

Fruits

epomusenin-B

AGE

-

[23]

Fruits

epomurinin-A

AGE

-

[23]

Fruits

epomurinin-B

AGE

-

[23]

Fruits

cis-annoreticuin

AGE

-

[24]

Fruits

muricin J

AGE

toxicity against prostate PC-3 cancer cells

[25]

Fruits

muricin K

AGE

toxicity against prostate PC-3 cancer cells

[25]

Fruits

muricin L

AGE

toxicity against prostate PC-3 cancer cells

[25]

Fruits

cinnamic acid derivative

PL

-

[16]

Fruits

coumaric acid hexose

PL

-

[16]

Fruits

5-caffeoylquinic acid

PL

-

[16]

Fruits

dihydrokaempferol-hexoside

PL

-

[16]

Fruits

p-coumaric acid

PL

-

[16]

Fruits

caffeic acid derivative

PL

-

[16]

Fruits

dicaffeoylquinic acid

PL

-

[16]

Fruits

feruloylglycoside

PL

-

[16]

Fruits

4-feruloyl-5-caffeoylquinic acid

PL

-

[16]

Fruits

p-coumaric acid methyl ester

PL

-

[16]

Leaves, Pericarp

annomuricin A

AGE

toxicity against brine shrimp, lung A549, breast MCF-7 and colon HT-29 cancer cells

[12,26]

Leaves

annomuricin B

AGE

toxicity against brine shrimp, lung A549, breast MCF-7 and colon HT-29 cancer cells

[12]

Leaves

annomuricin C

AGE

toxicity against brine shrimp, lung A549, breast MCF-7 and colon HT-29 cancer cells

[27]

Leaves

annomuricin E

AGE

toxicity against pancreatic MIA PaCa-2 and colon HT-29 cancer cells

[28]

Leaves

annomutacin

AGE

toxicity against lung A549 cancer cells

[29]

Leaves

(2,4-cis)-10R-annonacin-A-one

AGE

toxicity against lung A549 cancer cells

[29]

Leaves

(2,4-trans)-10R-annonacin-A-one

AGE

toxicity against lung A549 cancer cells

[29]

Leaves

annohexocin

AGE

toxicity against brine shrimp and different cancer cells

[30]

Leaves

muricapentocin

AGE

toxicity against pancreatic MIA PaCa-2 and colon HT-29 cancer cells

[28]

Leaves

(2,4-cis)-isoannonacin

AGE

-

[31]

Leaves, Seeds

(2,4-trans)-isoannonacin

AGE

-

[31,32]

Leaves

muricatocin A

AGE

toxicity against lung A549 cancer cells

[31]

Leaves

muricatocin B

AGE

toxicity against lung A549 cancer cells

[31]

Leaves

muricatocin C

AGE

toxicity against brine shrimp, lung A549, breast MCF-7 and colon HT-29 cancer cells

[27]

Leaves, Seeds

gigantetronenin

AGE

-

[27,32]

Leaves, Seeds, Pericarp

annonacin A

AGE

-

[26,31,33]

Leaves

annopentocin A

AGE

toxicity against pancreatic MIA PaCa-2 cancer cells

[34]

Leaves

annopentocin B

AGE

toxicity against lung A549 cancer cells

[34]

Leaves

annopentocin C

AGE

toxicity against lung A549 cancer cells

[34]

Leaves

cis-annomuricin-D-one

AGE

toxicity against lung A549, colon HT-29 and pancreatic MIA PaCa-2 cancer cells

[34]

Leaves

trans-annomuricin-D-one

AGE

toxicity against lung A549, colon HT-29 and pancreatic MIA PaCa-2 cancer cells

[34]

Leaves

murihexocin A

AGE

toxicity against different cancer cells

[35]

Leaves

murihexocin B

AGE

toxicity against different cancer cells

[35]

Leaves

murihexocin C

AGE

toxicity against different cancer cells

[36]

Leaves

muricoreacin

AGE

toxicity against different cancer cells

[36]

Leaves

cis-corossolone

AGE

toxicity against human hepatoma cells

[37]

Leaves

annocatalin

AGE

toxicity against human hepatoma cells

[37]

Leaves

annocatacin B

AGE

toxicity against human hepatoma cells

[38]

Leaves

anonaine

ALK

neurotoxic

[39,40]

Leaves

isolaureline

ALK

-

[39]

Leaves

xylopine

ALK

-

[39]

Leaves

Quercetin 3-O-α-rhamnosyl-(1→6)-β-sophoroside

FTG

-

[15]

Leaves

gallic acid

FTG

-

[15]

Leaves

epicatechine

FTG

-

[15]

Leaves

quercetin 3-O-rutinosid

FTG

-

[15]

Leaves

quercetin 3-O-neohispredoside

FTG

-

[15]

Leaves

quercetin 3-O-robinoside

FTG

-

[15]

Leaves

catechine

FTG

-

[15]

Leaves

chlorogenic acid

FTG

-

[15]

Leaves

argentinine (1-N,N-dimethylethanyl-4,6-dimethoxy-3,8-dihydroxy-phenanthrene)

FTG

-

[15]

Leaves

kaempferol 3-O-rutinoside

FTG

-

[15]

Leaves

quercetin 3-O-glucoside

FTG

-

[15]

Leaves

quercetin

FTG

-

[15]

Leaves

kaempferol

FTG

-

[15]

Leaves

annonamine

ALK

-

[40]

Leaves

(S)-norcorydine

ALK

-

[40]

Leaves

(R)-4′-O-methylcoclaurine

ALK

-

[40]

Leaves

(R)-O,O-dimethylcoclaurine

ALK

-

[40]

Leaves

annoionol A

MG

-

[14]

Leaves

annoionol B

MG

-

[14]

Leaves

annoionol C

MG

-

[14]

Leaves

annoionoside

MG

-

[14]

Leaves

vomifoliol

MG

-

[14]

Leaves

roseoside

MG

-

[14]

Leaves

turpinionoside A

MG

-

[14]

Leaves

citroside A

MG

-

[14]

Leaves

blumenol C

MG

-

[14]

Leaves

(+)-epiloliolide

MG

-

[14]

Leaves

loliolide

MG

-

[14]

Leaves

(1S,2S,4R)-trans-2-hydroxy-1,8-cineole β-d-glucopyranoside

MG

-

[14]

Leaves

(Z)-3-hexenyl β-d-glucopyranoside

MG

-

[14]

Leaves

rutin

MG

-

[14]

Leaves

kaempferol 3-O-rutinoside

MG

-

[14]

Leaves

kaempferol 3-O-robinobioside

MG

-

[14]

Leaves

kaempferol 3-O-β-d-(2′′-O-β-d-glucopyranosyl,6′′-O-α-l-rhamnopyranosyl)glucopyranoside

MG

-

[14]

Roots

montecristin

AGE

-

[41]

Roots

cohibin A

AGE

-

[42]

Roots

cohibin B

AGE

-

[42]

Roots

cis-solamin

AGE

-

[43]

Roots

cis-panatellin

AGE

-

[43]

Roots

cis-uvariamicin IV

AGE

-

[43]

Roots

cis-uvariamicin I

AGE

-

[43]

Roots

cis-reticulatacin

AGE

-

[43]

Roots

cis-reticulatacin-10-one

AGE

-

[43]

Roots

chatenaytrienin 1

AGE

-

[44]

Roots

chatenaytrienin 2

AGE

-

[44]

Roots

chatenaytrienin 3

AGE

-

[44]

Roots

muridienin 3

AGE

-

[44]

Roots

muridienin 4

AGE

-

[44]

Roots

muricadienin

AGE

-

[44]

Roots

coronin

AGE

-

[45]

Roots, Fruits

sabadelin

AGE

-

[24,46]

Seeds

murisolin

AGE

-

[47]

Seeds

muricatacin

AGE

toxicity against lung A549, breast MCF7, colon HT-29 cancer cells

[48]

Seeds, Leaves, Pericarp

annonacin

AGE

neurotoxic, molluscicidal, inhibitor of mitochondrial complex I

[12,26,48,49,50,51]

Seeds, Leaves

corossolone

AGE

toxicity against oral KB cancer cells and brine shrimp larva, antileishmanial

[37,52,53,54]

Seeds

corossolin

AGE

toxicity against oral KB cancer cells and brine shrimp larva

[52]

Seeds, Roots, Leaves

solamin

AGE

toxicity against oral KB cancer and normal kidney VERO cells

[37,43,55]

Seeds

corepoxylone

AGE

-

[56]

Seeds, Leaves

annonacin-10-one

AGE

-

[12,57]

Seeds

isoannonacin

AGE

molluscicidal, anticancer

[49,57]

Seeds

isoannonacin-10-one

AGE

-

[57]

Seeds, Leaves

goniothalamicin

AGE

molluscicidal

[12,49,57]

Seeds

gigantetrocin

AGE

-

[57]

Seeds, Leaves

gigantetrocin A

AGE

toxicity against colon HT-29 cancer cells

[12,32,58]

Seeds

gigantetrocin B

AGE

toxicity against colon HT-29 cancer cells

[12,32,58]

Seeds, Leaves

muricatetrocin A

AGE

toxicity against colon HT-29 cancer cells

[58]

Seeds, Leaves

muricatetrocin B

AGE

toxicity against colon HT-29 cancer cells

[58]

Seeds, Leaves

epomuricenin A

AGE

-

[23,59]

Seeds, Leaves

epomuricenin B

AGE

-

[23,59]

Seeds

annomuricatin A

CP

-

[60,61]

Seeds

annocatacin A

AGE

toxicity against human hepatoma cells

[38]

Seeds

annomuricatin C

CP

-

[62]

Seeds

cis-annonacin

AGE

crown gall tumor inhibition, toxicity against brine shrimp, lung A549, breast MCF-7 and colon HT-29 cancer cells

[63]

Seeds

cis-annonacin-10-one

AGE

crown gall tumor inhibition, toxicity against brine shrimp, lung A549, breast MCF-7 and colon HT-29 cancer cells

[63]

Seeds

cis-goniothalamicin

AGE

crown gall tumor inhibition, toxicity against brine shrimp, lung A549, breast MCF-7 and colon HT-29 cancer cells

[63]

Seeds

arianacin

AGE

crown gall tumor inhibition, toxicity against brine shrimp, lung A549, breast MCF-7 and colon HT-29 cancer cells

[63]

Seeds

javoricin

AGE

crown gall tumor inhibition, toxicity against brine shrimp, A549, breast MCF-7 and colon HT-29 cancer cells

[63]

Seeds

murihexol

AGE

-

[33]

Seeds

donhexocin

AGE

-

[33]

Seeds

cohibin C

AGE

-

[64]

Seeds

cohibin D

AGE

-

[64]

Seeds

muricatenol

AGE

-

[32,65]

Seeds

2,4-cis-gigantetrocinone

AGE

-

[32]

Seeds

2,4-trans-gigantetrocinone

AGE

-

[32]

Seeds

2,4-trans-isoannonacin-10-one

AGE

-

[32]

Seeds

annomontacin

AGE

-

[32]

Seeds

longifolicin

AGE

toxicity against human hepatoma cells

[66]

Seeds

muricin A

AGE

toxicity against human hepatoma cells

[66]

Seeds

muricin B

AGE

toxicity against human hepatoma cells

[66]

Seeds

muricin C

AGE

toxicity against human hepatoma cells

[66]

Seeds

muricin D

AGE

toxicity against human hepatoma cells

[66]

Seeds

muricin E

AGE

toxicity against human hepatoma cells

[66]

Seeds

muricin F

AGE

toxicity against human hepatoma cells

[66]

Seeds

muricin G

AGE

toxicity against human hepatoma cells

[66]

Seeds

muricin H

AGE

toxicity against human hepatoma cells

[37]

Seeds

muricin I

AGE

toxicity against human hepatoma cells

[37]

Seeds

cis-annomontacin

AGE

toxicity against human hepatoma cells

[37]

Seeds, Leaves

annonacinone

AGE

-

[37]

Seeds

xylomaticin

AGE

-

[37]

Seeds

N-fatty acyl tryptamines

ALK

-

[32]

Seeds

annoreticuin-9-one

AGE

-

[24]

Stem barks

epoxymurin A

AGE

-

[67]

Stem barks

epoxymurin B

AGE

-

[67]

Leaves, Roots, Stems, Barks

reticuline

ALK

-

[68]

Leaves, Roots, Stems, Barks

coclaurine

ALK

-

[68]

Leaves, Roots, Stems, Barks

coreximine

ALK

-

[68]

Leaves, Roots, Stems, Barks

atherosperminine

ALK

-

[68]

Leaves, Roots, Stems, Barks

stepharine

ALK

-

[68]

Leaves, Roots, Stems, Barks

anomurine

ALK

-

[68]

Leaves, Roots, Stems, Barks

anomuricine

ALK

-

[68]

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