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Cucurbitacins - An insight into medicinal leads from nature.

Kaushik U, Aeri V, Mir SR - Pharmacogn Rev (2015 Jan-Jun)

Bottom Line: Cucurbitacins which are structurally diverse triterpenes found in the members of Cucurbitaceae and several other plant families possess immense pharmacological potential.Research focused on these unattended medicinal leads from the nature can prove to be of immense significance in generating scientifically validated data with regard to their efficacy and possible role in various diseases.This review is aimed to provide an insight into the chemical nature and medicinal potential of these compounds exploring their proposed mode of action, probable molecular targets and to have an outlook on future directions of their use as medicinal agents.

View Article: PubMed Central - PubMed

Affiliation: Department of Pharmacognosy and Phytochemistry, Phytochemistry Research Laboratory, Faculty of Pharmacy, New Delhi, India.

ABSTRACT
Cucurbitacins which are structurally diverse triterpenes found in the members of Cucurbitaceae and several other plant families possess immense pharmacological potential. This diverse group of compounds may prove to be important lead molecules for future research. Research focused on these unattended medicinal leads from the nature can prove to be of immense significance in generating scientifically validated data with regard to their efficacy and possible role in various diseases. This review is aimed to provide an insight into the chemical nature and medicinal potential of these compounds exploring their proposed mode of action, probable molecular targets and to have an outlook on future directions of their use as medicinal agents.

No MeSH data available.


Chemical structures of cucurbitacin analogs
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Figure 2: Chemical structures of cucurbitacin analogs

Mentions: All cucurbitacins contain a basic 19-(10→9β)–abeo--10α–lanost–5--ene ring skeleton. A common feature among all compounds in the category of Cucurbitacins is the presence of 5,(6)--double bond. The difference of Cucurbitacins from steroidal nucleus lies in the fact that in basic structure of Cucurbitacins a methyl group is located at C-9 rather than C-10.[6] Most of the Cucurbitacins are tetracyclic, but some representatives have an extra ring due to formal cyclization between C--16 and C--24 as in cucurbitacins S and T.[7] The Cucurbitacins differ from most of the other tetracyclic triterpenes by being highly unsaturated and contains numerous keto--, hydroxyl--, and acetoxy--groups.[8] Certain Cucurbitacins have been discovered in the form of glycosides and some of them lack C--11 carbonyl function.[9] Chemically, Cucurbitacins are ranked according to presence of various functional groups on rings A and C, diversity in side chain and stereochemical considerations.[10] The structural composition of following Cucurbitacins are known and have been designated by the letters: A, B, C, D, E, F, G, H, I, J, K, L, O, P, Q, R and S [Figure 2]. The term --““Cucurbitacin””-- refers to group of Cucurbitacins along with their glycosidic forms mentioned above, including those forms listed before.[11] Cucurbitacin G and H have same structures but differ from each other in the configuration of the hydroxyl group at position 24 which is not yet established.[12] Cucurbitacin R was demonstrated to be 23, 24-dihydrocucurbitacin D (DHCD) hence, its description has been moved to the group of Cucurbitacin D.[13] Similarly Cucurbitacin J and K differ from each other only in the configuration of hydroxyl group at position 24 which is yet to be determined.[14] A special group of Cucurbitacins are called as momordicosides, named after their occurrence in Momordica charantia. Momordicosides have never been identified in any other plant species. The common feature of momordicosides is that C19 has been oxidized to an aldehyde group.


Cucurbitacins - An insight into medicinal leads from nature.

Kaushik U, Aeri V, Mir SR - Pharmacogn Rev (2015 Jan-Jun)

Chemical structures of cucurbitacin analogs
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4441156&req=5

Figure 2: Chemical structures of cucurbitacin analogs
Mentions: All cucurbitacins contain a basic 19-(10→9β)–abeo--10α–lanost–5--ene ring skeleton. A common feature among all compounds in the category of Cucurbitacins is the presence of 5,(6)--double bond. The difference of Cucurbitacins from steroidal nucleus lies in the fact that in basic structure of Cucurbitacins a methyl group is located at C-9 rather than C-10.[6] Most of the Cucurbitacins are tetracyclic, but some representatives have an extra ring due to formal cyclization between C--16 and C--24 as in cucurbitacins S and T.[7] The Cucurbitacins differ from most of the other tetracyclic triterpenes by being highly unsaturated and contains numerous keto--, hydroxyl--, and acetoxy--groups.[8] Certain Cucurbitacins have been discovered in the form of glycosides and some of them lack C--11 carbonyl function.[9] Chemically, Cucurbitacins are ranked according to presence of various functional groups on rings A and C, diversity in side chain and stereochemical considerations.[10] The structural composition of following Cucurbitacins are known and have been designated by the letters: A, B, C, D, E, F, G, H, I, J, K, L, O, P, Q, R and S [Figure 2]. The term --““Cucurbitacin””-- refers to group of Cucurbitacins along with their glycosidic forms mentioned above, including those forms listed before.[11] Cucurbitacin G and H have same structures but differ from each other in the configuration of the hydroxyl group at position 24 which is not yet established.[12] Cucurbitacin R was demonstrated to be 23, 24-dihydrocucurbitacin D (DHCD) hence, its description has been moved to the group of Cucurbitacin D.[13] Similarly Cucurbitacin J and K differ from each other only in the configuration of hydroxyl group at position 24 which is yet to be determined.[14] A special group of Cucurbitacins are called as momordicosides, named after their occurrence in Momordica charantia. Momordicosides have never been identified in any other plant species. The common feature of momordicosides is that C19 has been oxidized to an aldehyde group.

Bottom Line: Cucurbitacins which are structurally diverse triterpenes found in the members of Cucurbitaceae and several other plant families possess immense pharmacological potential.Research focused on these unattended medicinal leads from the nature can prove to be of immense significance in generating scientifically validated data with regard to their efficacy and possible role in various diseases.This review is aimed to provide an insight into the chemical nature and medicinal potential of these compounds exploring their proposed mode of action, probable molecular targets and to have an outlook on future directions of their use as medicinal agents.

View Article: PubMed Central - PubMed

Affiliation: Department of Pharmacognosy and Phytochemistry, Phytochemistry Research Laboratory, Faculty of Pharmacy, New Delhi, India.

ABSTRACT
Cucurbitacins which are structurally diverse triterpenes found in the members of Cucurbitaceae and several other plant families possess immense pharmacological potential. This diverse group of compounds may prove to be important lead molecules for future research. Research focused on these unattended medicinal leads from the nature can prove to be of immense significance in generating scientifically validated data with regard to their efficacy and possible role in various diseases. This review is aimed to provide an insight into the chemical nature and medicinal potential of these compounds exploring their proposed mode of action, probable molecular targets and to have an outlook on future directions of their use as medicinal agents.

No MeSH data available.