Ursolic acid:Actions,Commonly Known Benefit and Research.
Article Content:
- .Basic Chemical Info.
- .Basic Introduction and Botanical Info.
- .Actions and Chemistry of Ursolic Acid.
- .Commonly Known Benefit of Ursolic Acid.
- .Pentacyclic Triterpenes (PCTs) as Inhibitors of Inflammation.
- .Safety and Toxicity for Ursolic Acid.
- .Administration and Dosage.
- .Research Update of Ursolic acid.
Commonly Known Benefit of Ursolic Acid.
1.Inhibition of Tumor Promotion in skin:
Ursolic acid (UA) and oleanolic acid (OA), isolated from Glechoma hederacea, inhibited Epstein-Barr virus activation induced by 12-O-tetradecanoylphorbol 13-acetate (TPA) in mouse skin. The inhibitory effects were evaluated for 20 weeks. Continuous application of UA and OA (41 nmol of each) before TPA-treatment (4.1 nmol) delayed the formation of papillomas in mouse skin and reduced the rate (%) of papilloma bearing mice. Both UA and OA exhibited remarkable inhibitory activity against tumor promotion, which is comparable to the known tumor inhibitor, retinoic acid (RA). Compared to either RA or OA, ursolic acid inhibited tumor more effectively after a single application before initial TPA-treatment as shown in Figure 1. This suggests that the role of tumor inhibition by UA differs from that of either RA or OA. It is suggested that pretreatment of skin with UA may inhibit the first dramatic cellular event in tumor promotion caused by TPA.
Topical application of ursolic acid derived from rosemary extract inhibited TPA-induced tumor initiation and promotion, inflammation, and ornithine decarboxylase activity in mouse skin. Ursolic acid exhibited strong anti-inflammatory activity. It is even more active than of 1 or 2 mmol of ursolic acid along with 5 nmol of TPA for TPA for 20 weeks inhibited the formation of skin tumors per mouse by 45 or 61% respectively.
Lower doses (0.1 or 0.3 mmol) of ursolic acid had a similar inhibitory effect as the higher doses. Twice weekly topical application of 0.1, 0.3, 1, or 2 mmol of ursolic acid along with 5 nmol TPA for 8,12, and 18 weeks reduced the number of skin tumors per mouse by 52-86%, 49-63%, and 44-61%, respectively.
Ursolic acid and its isomer, oleanolic acid have been recommended for skin cancer therapy in China. Topical cosmetic preparations containing ursolic acid/ oleanolic acid have been patented in China for the prevention of topical skin cancer. An ursolic acid/ oleanolic acid ointment inhibited 7,12-dimethylbenz [alpha] anthracene (DMBA)-induced skin cancer in mice. Reportedly, 0% and 3% of mice developed cancer in 15 weeks and 30 weeks, respectively compared to 50% and 90% for the control mice.
Iridoids are common components of plants, but the iridoid glycosides are important active components of only certain Chinese herbs, particularly rehmannia, with which cornus is frequently combined. It is thought that the glucose molecule is cleaved in the digestive system to yield the aglycone as the active compound that has anti-inflammatory actions.
Oleanolic acid (OA) and ursolic acid (UA) are isomers; they have the same chemical formula. These two pentacyclic triterpenes are of interest to scientists because of their numerous biological activities. OA can lower blood sugar, a property attributed to cornus, which is listed among the Chinese herbs used for treating diabetes. UA and OA have liver-protecting and anti-inflammatory effects; cornus is used in some herb formulas for viral hepatitis and the anti-inflammatory effects may be one reason that cornus can be recommended for low back and knee pain associated with aging.
2.Hair Growth Stimulant:
Ursolic acid and its isomer, oleanolic acid, have been used in to nics to enhance hair growth and prevent scalp irritation. Both triterpenoid compounds encourage hair growth by stimulating the peripheral blood flow in the scalp and activating the hair mother cells. They also furnish alopecia-preventing and dandruff-preventing effects.
3.Antimicrobial Activity:
Beta ursolic acid (triterpenoid sapogenin from the ursan group) inhibited the growth of several strains of staphylococci. Numerous ursolic acid containing plants from the Lamiaceae family exhibited antibacterial/ fungal activity. The minimal inhibitory concentration of Rosmarinus officinalis, Origanum majorana, and Lavandula officinalis were 500, 250, and 500 mg/cm3, respectively. Ursolic acid also inhibited the growth of Microsporium lenosum and Candida albicans at 250 mg/mL.
4.Anti-Aging Agent:
Ursolic acid treatment improves the health of skin and hair. Ursolic acid and its derivatives form oil-resistant barriers on the skin and hair as they do in the waxy coating of fruits. Ursolic acid has been used to treat photoaged skin because it prevents and improves the appearance of wrinkles and age spots by restoring the skin's collagen bundle structures and its elasticity. Concentrations of ursolic acid ranging from 0.01 to 50 mg have been reported for inclusion in skin treatment preparations
5.Anti-Inflammatory Activity:
Ursolic acid is a potent anti-inflammatory agent. Thus, it has been recommended for use in burn ointments. It not only inhibits human leucocyte elastase(HLE), but also 5-lipoxygenase and cyclooxygenase activity. Ursolic acid (1.0 mg/ear) inhibited TPA-induced mouse ear edema by 72.4%23. Hirota and coworkers24 determined that 200 mg and 50 mg applications of ursolic acid inhibited 12-O-hexadecanoyl-16-hydroxyphorbol-13-acetate (HPPA) - induced inflammation by 49% and 33%, respectively. In addition, it inhibited concanavalin A (Con A) induced histamine release, which can cause severe inflammation, by 95% at a concentration of 0.001 M.
6.Remembrance and acetylcholinesterase inhibitor:
Soundbite Molecules: Rosemary and Ursolic acid for Remembrance
Simon Cotton, teacher at Uppingham School, takes a look at those compounds that find themselves in the news or relate to our everyday lives.
That's from a Shakespeare play, isn't it?
Yes, in act IV scene v of Hamlet, Ophelia says to Hamlet,,'There's rosemary, that's for remembrance, pray you, love, remember'.
And is there any connection?
One link is that the plant symbolises remembering the dead. In act IV scene v of Romeo and Juliet, rosemary was placed on Juliet's body for her burial ('Stick your rosemary on this fair cor[p]se'). Australians wear a sprig of rosemary on Anzac day to honour the dead soldiers of World War I. The herb grows wild on the Gallipoli peninsula, Turkey, where many Anzacs died during the ill-fated Allied campaign of 1915.
Is there any evidence that rosemary helps memory?
Recent research by Dr Mark Moss and his colleagues at Northumbria University in Newcastle suggests that exposure to rosemary oil can enhance long-term memory by ca 15 per cent.
Which chemicals might be responsible for this effect?
Rosemary contains hundreds of different chemicals. The herb has been used in medicine as a stimulant, possibly owing to its camphor (1) content, while cineole (eucalyptol, 2) and camphor are among the molecules that give the plant microbiocidal properties. Rosemary has long been used as a food preservative. The plant contains antioxidants such as rosemarinic acid (3) and carnosic acid (4). But possibly the most interesting chemical component that affects memory is ursolic acid (5).
How so?
Ursolic acid inhibits acetylcholinesterase. This the enzyme catalyses the breakdown of the neurotransmitter chemical acetylcholine, which is important for effective cognition and reasoning. The degeneration of acetylcholine-producing neurons in the brains of people with Alzheimer's disease (AD) has been blamed for the symptom of memory loss associated with AD. Thus, sustaining acetylcholine levels may help delay this memory loss. Ursolic acid has also been shown to slow skin tumour development.
Reference:
1.Ursolic acid:Actions,Commonly Known Benefit and Research.
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