Α-Hederin

α-Hederin (alpha-hederin) is a water-soluble pentacyclic triterpenoid saponin found in the seeds of Nigella sativa and leaves of Hedera helix.^[1][2][3][4]

α-Hederin

Names
IUPAC name 23-Hydroxy-3β-[α-L-rhamnopyranosyl-(2→1)-α-L-arabinopyranosyloxy]olean-12-en-28-oic acid
Systematic IUPAC name (4aS,6aS,4bR,8aR,9R,10S,12aR,12bR,14bS)-10-{[(2S,3R,4S,5S)-4,5-Dihydroxy-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydro-2H-picene-4a-carboxylic acid
Identifiers
CAS Number	27013-91-8 Y
3D model (JSmol)	Interactive image
ChemSpider	66036
ECHA InfoCard	100.043.773
EC Number	248-166-5
PubChem CID	73296
UNII	4H15F0GLV2 Y
CompTox Dashboard (EPA)	DTXSID80909168 DTXSID20949785, DTXSID80909168
InChI InChI=1S/C41H66O12/c1-21-28(44)30(46)31(47)33(51-21)53-32-29(45)24(43)19-50-34(32)52-27-11-12-37(4)25(38(27,5)20-42)10-13-40(7)26(37)9-8-22-23-18-36(2,3)14-16-41(23,35(48)49)17-15-39(22,40)6/h8,21,23-34,42-47H,9-20H2,1-7H3,(H,48,49)/t21-,23-,24-,25+,26+,27-,28-,29-,30+,31+,32+,33-,34-,37-,38-,39+,40+,41-/m0/s1 Key: KEOITPILCOILGM-LLJOFIFVSA-N
SMILES C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@H](CO[C@H]2O[C@H]3CC[C@]4([C@H]([C@]3(C)CO)CC[C@@]5([C@@H]4CC=C6[C@]5(CC[C@@]7([C@H]6CC(CC7)(C)C)C(=O)O)C)C)C)O)O)O)O)O
Properties
Chemical formula	C41H66O12
Molar mass	750.967 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Anticancer studies

α-Hederin and also its derivative, kalopanaxsaponin-I, have been studied for their anticancer activities.^[5][2] α-Hederin has been shown to enhance the cytotoxicity of an established chemotherapeutic agent, 5-fluorouracil, in an animal model of colon carcinoma.^[5]

See also

• Hederagenin
• Thymoquinone

References

1. Evans, William Charles (2009). Trease and Evans' Pharmacognosy (16th ed.). Saunders. p. 322. ISBN 978-0-7020-2933-2.
2. Butt, Masood Sadiq; Sultan, Muhammad Tauseef (2010). "Nigella sativa: Reduces the risk of various maladies". Critical Reviews in Food Science and Nutrition. 50 (7): 654–665. doi:10.1080/10408390902768797. PMID 20694927. S2CID 22905497. N. sativa seeds also contain proteins, alkaloids (nigellicines and nigelledine), and saponins (α-hederin) in substantial amounts ... Some of its components, especially α-Hederin, have shown some significant effects in mitigating the cancerous cell growth (Salem, 2005; Ramadan, 2007).
3. Shafiq, Hammad; Ahmad, Asif; Masud, Tariq; Kaleem, Muhammad (2014). "Cardio-protective and anti-cancer therapeutic potential of Nigella sativa". Iranian Journal of Basic Medical Sciences. 17 (12): 967–979. doi:10.22038/IJBMS.2015.3853. PMC 4387232. PMID 25859300. S2CID 11429394. N. sativa seed composition shows that it is the blessing of nature and it contains and many bioactive compounds like thymoquinone, α-hederin, alkaloids, flavonoids, antioxidants, fatty acids many other compounds that have positive effects on curing of different diseases.
4. Gholamnezhad, Zahra; Havakhah, Shahrzad; Boskabady, Mohammad Hossein (2016). "Preclinical and clinical effects of Nigella sativa and its constituent, thymoquinone: A review". Journal of Ethnopharmacology. 190: 372–386. doi:10.1016/j.jep.2016.06.061. PMID 27364039. S2CID 3109958. The seeds of the plant also contain many non-oily and non-caloric components in trace amounts, including pyrazole alkaloids (nigellidine and nigellicine, Fig. 1d), isoquinoline alkaloids (nigellicimine and nigellicimine-N-oxide, Fig. 1e), alpha-hederin (a water-soluble pentacyclic triterpene, Fig. 1f), saponin (a potential anticancer agent), vitamins (riboflavin, thiamin, niacin, pyridoxine, folic acid, and vitamin E), and minerals (potassium, sodium, calcium, phosphorus, magnesium, copper, and iron) (Nergiz and Ötleş, 1993).
5. Randhawa, Mohammad Akram; Alghamdi, Mastour Safar (2011). "Anticancer activity of Nigella sativa (black seed)—A review". The American Journal of Chinese Medicine. 39 (6): 1075–1091. doi:10.1142/S0192415X1100941X. PMID 22083982. S2CID 28376664. A literature search has revealed that a lot more studies have been recently carried out related to the anticancer activities of N. sativa and some of its active compounds, such as thymoquinone and alpha-hederin ... Another important active compound that has been shown to possess anticancer effects is alpha-hederin, a pentacycline triterpene and a saponin, which is water soluble perhaps the major active component in the aqueous extract of N. sativa ... One of the derivatives of alpha-hederin, kalopanaxsaponin-I, was found to possess anticancer activity ... Alpha-hederin also, in sub-IC₅₀ cytotoxic concentrations, was shown to enhance the cytotoxicity of 5-fluorouracil in a human colon carcinoma model, HT-29 cells, 3.3-fold (Bun et al., 2008) ... Moreover, N. saliva seed, its oil, thymoquinone, alpha-hederin or their analogs could be used in suitable combinations with already established as chemotherapeutic agents.