C30H48O3；456.68
ursolic acid Constitutional formula
3β－Hydroxyurs －12－en －28－oic acid (I)
ursolic acid Description
Ursolic acid, a carboxylic acid present in a wide variety of plants in the form of a free acid or an aglycone of triterpene saponins.It is also known as urson, prunol, micromerol, and malol, is a pentacyclic triterpenoid compound which naturally occurs in a large number of vegetarian foods, medicinal herbs, and plants1,2. For a long time, it was considered to be pharmacologically inactive3. Thus, ursolic acid and its alkali salts (e.g. potassium or sodium ursolates) were exclusively used as emulsifying agents in pharmaceutical, cosmetic, and food preparations3,4. However, upon closer examination, ursolic acid was found to be medicinally active both topically and internally1. Its anti－inflammatory, antitumor (skin cancer), and antimicrobial properties make it useful in cosmetic applications1.
Ursolic acid [(3b)－3－Hydroxyurs－12－en－28－oic acid] rarely occurs without its isomer oleanolic acid [(3b)－3－Hydroxyolean－12－en－28－oic acid]. They may occur in their free acid form, as shown in Figure 1, or as aglycones for triterpenoid saponins which are comprised of a triterpenoid aglycone linked to one or more sugar moieties. Ursolic and oleanolic acids are similar in pharmacological activity1. Several ursolic acid derivatives, both natural and synthetic, have been reported. Novel ursolic acid derivatives, including ursane－type triterpenoid saponins, naturally occur as secondary metabolites through complex metabolic processes in different parts of the plant5,8－12 Synthetic derivatives obtained from ursolic acid have been reported and evaluated for their pharmacological action3,13－16.
Medicinal plants containing ursolic acid have been used in folk medicine before it was known which constituents were responsible for their therapeutic effectiveness. Contemporary scientific research which led to the isolation and identification of ursolic acid revealed and confirmed that several pharmacological effects, such as antitumor, hepatoprotective, anti－inflammatory (oral and topical), antiulcer, antimicrobial, anti－hyperlipidemic, and antiviral, can be attributed to ursolic acid1. However, its anti－inflammatory (topical), antitumor (skin cancer), and antimicrobial properties are pertinent to the cosmetic industry.
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 tumors more effectively after a single application before initial TPA－treatment as shown in Figure 2. 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 TPA17.
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 carnosol, another constituent of rosemary extract. As shown in Figure 3, twice weekly application of 1 or 2 μmol of ursolic acid along with 5 nmol of TPA for 20 weeks inhibited the formation of skin tumors per mouse by 45 or 61%, respectively. Lower doses (0.1 or 0.3 μmol) of ursolic acid had a similar inhibitory effect as the higher doses. Twice weekly topical application of 0.1, 0.3, 1, or 2 μmol 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%, respectively18.
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 M25.
Ursolic acid and its isomer, oleanolic acid, have been used in tonics to enhance hair growth and prevent scalp irritation26,27. 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 effects27.
b－ursolic acid (triterpenoid sapogenin from the ursan group) inhibited the growth of several strains of stapylococci28. Numerous ursolic acid containing plants from the Lamiaceae family exhibited antibacterial／fungal activity29. The minimal inhibitory concentration of Rosmarinus officinalis, Origanum majorana, and Lavandula officinalis were 500, 250, and 500 μg／cm3, respectively29. Ursolic acid also inhibited the growth of Microsporium lenosum and Candida albicans at 250 μg／mL30
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 fruits6. 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 elasticity31. Concentrations of ursolic acid ranging from 0.01 to 50 mg have been reported for inclusion in skin treatment preparations32－33.C30H48O3；456.68
ursolic acid Constitutional formula
3β－Hydroxyurs －12－en －28－oic acid (I)
ursolic acid Description
Ursolic acid, a carboxylic acid present in a wide variety of plants in the form of a free acid or an aglycone of triterpene saponins.It is also known as urson, prunol, micromerol, and malol, is a pentacyclic triterpenoid compound which naturally occurs in a large number of vegetarian foods, medicinal herbs, and plants1,2. For a long time, it was considered to be pharmacologically inactive3. Thus, ursolic acid and its alkali salts (e.g. potassium or sodium ursolates) were exclusively used as emulsifying agents in pharmaceutical, cosmetic, and food preparations3,4. However, upon closer examination, ursolic acid was found to be medicinally active both topically and internally1. Its anti－inflammatory, antitumor (skin cancer), and antimicrobial properties make it useful in cosmetic applications1.
Ursolic acid [(3b)－3－Hydroxyurs－12－en－28－oic acid] rarely occurs without its isomer oleanolic acid [(3b)－3－Hydroxyolean－12－en－28－oic acid]. They may occur in their free acid form, as shown in Figure 1, or as aglycones for triterpenoid saponins which are comprised of a triterpenoid aglycone linked to one or more sugar moieties. Ursolic and oleanolic acids are similar in pharmacological activity1. Several ursolic acid derivatives, both natural and synthetic, have been reported. Novel ursolic acid derivatives, including ursane－type triterpenoid saponins, naturally occur as secondary metabolites through complex metabolic processes in different parts of the plant5,8－12 Synthetic derivatives obtained from ursolic acid have been reported and evaluated for their pharmacological action3,13－16.
Medicinal plants containing ursolic acid have been used in folk medicine before it was known which constituents were responsible for their therapeutic effectiveness. Contemporary scientific research which led to the isolation and identification of ursolic acid revealed and confirmed that several pharmacological effects, such as antitumor, hepatoprotective, anti－inflammatory (oral and topical), antiulcer, antimicrobial, anti－hyperlipidemic, and antiviral, can be attributed to ursolic acid1. However, its anti－inflammatory (topical), antitumor (skin cancer), and antimicrobial properties are pertinent to the cosmetic industry.
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 tumors more effectively after a single application before initial TPA－treatment as shown in Figure 2. 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 TPA17.
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 carnosol, another constituent of rosemary extract. As shown in Figure 3, twice weekly application of 1 or 2 μmol of ursolic acid along with 5 nmol of TPA for 20 weeks inhibited the formation of skin tumors per mouse by 45 or 61%, respectively. Lower doses (0.1 or 0.3 μmol) of ursolic acid had a similar inhibitory effect as the higher doses. Twice weekly topical application of 0.1, 0.3, 1, or 2 μmol 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%, respectively18.
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 M25.
Ursolic acid and its isomer, oleanolic acid, have been used in tonics to enhance hair growth and prevent scalp irritation26,27. 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 effects27.
b－ursolic acid (triterpenoid sapogenin from the ursan group) inhibited the growth of several strains of stapylococci28. Numerous ursolic acid containing plants from the Lamiaceae family exhibited antibacterial／fungal activity29. The minimal inhibitory concentration of Rosmarinus officinalis, Origanum majorana, and Lavandula officinalis were 500, 250, and 500 μg／cm3, respectively29. Ursolic acid also inhibited the growth of Microsporium lenosum and Candida albicans at 250 μg／mL30
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 fruits6. 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 elasticity31. Concentrations of ursolic acid ranging from 0.01 to 50 mg have been reported for inclusion in skin treatment preparations32－33.C30H48O3；456.68
ursolic acid Constitutional formula
3β－Hydroxyurs －12－en －28－oic acid (I)
ursolic acid Description
Ursolic acid, a carboxylic acid present in a wide variety of plants in the form of a free acid or an aglycone of triterpene saponins.It is also known as urson, prunol, micromerol, and malol, is a pentacyclic triterpenoid compound which naturally occurs in a large number of vegetarian foods, medicinal herbs, and plants1,2. For a long time, it was considered to be pharmacologically inactive3. Thus, ursolic acid and its alkali salts (e.g. potassium or sodium ursolates) were exclusively used as emulsifying agents in pharmaceutical, cosmetic, and food preparations3,4. However, upon closer examination, ursolic acid was found to be medicinally active both topically and internally1. Its anti－inflammatory, antitumor (skin cancer), and antimicrobial properties make it useful in cosmetic applications1.
Ursolic acid [(3b)－3－Hydroxyurs－12－en－28－oic acid] rarely occurs without its isomer oleanolic acid [(3b)－3－Hydroxyolean－12－en－28－oic acid]. They may occur in their free acid form, as shown in Figure 1, or as aglycones for triterpenoid saponins which are comprised of a triterpenoid aglycone linked to one or more sugar moieties. Ursolic and oleanolic acids are similar in pharmacological activity1. Several ursolic acid derivatives, both natural and synthetic, have been reported. Novel ursolic acid derivatives, including ursane－type triterpenoid saponins, naturally occur as secondary metabolites through complex metabolic processes in different parts of the plant5,8－12 Synthetic derivatives obtained from ursolic acid have been reported and evaluated for their pharmacological action3,13－16.
Medicinal plants containing ursolic acid have been used in folk medicine before it was known which constituents were responsible for their therapeutic effectiveness. Contemporary scientific research which led to the isolation and identification of ursolic acid revealed and confirmed that several pharmacological effects, such as antitumor, hepatoprotective, anti－inflammatory (oral and topical), antiulcer, antimicrobial, anti－hyperlipidemic, and antiviral, can be attributed to ursolic acid1. However, its anti－inflammatory (topical), antitumor (skin cancer), and antimicrobial properties are pertinent to the cosmetic industry.
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 tumors more effectively after a single application before initial TPA－treatment as shown in Figure 2. 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 TPA17.
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 carnosol, another constituent of rosemary extract. As shown in Figure 3, twice weekly application of 1 or 2 μmol of ursolic acid along with 5 nmol of TPA for 20 weeks inhibited the formation of skin tumors per mouse by 45 or 61%, respectively. Lower doses (0.1 or 0.3 μmol) of ursolic acid had a similar inhibitory effect as the higher doses. Twice weekly topical application of 0.1, 0.3, 1, or 2 μmol 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%, respectively18.
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 M25.
Ursolic acid and its isomer, oleanolic acid, have been used in tonics to enhance hair growth and prevent scalp irritation26,27. 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 effects27.
b－ursolic acid (triterpenoid sapogenin from the ursan group) inhibited the growth of several strains of stapylococci28. Numerous ursolic acid containing plants from the Lamiaceae family exhibited antibacterial／fungal activity29. The minimal inhibitory concentration of Rosmarinus officinalis, Origanum majorana, and Lavandula officinalis were 500, 250, and 500 μg／cm3, respectively29. Ursolic acid also inhibited the growth of Microsporium lenosum and Candida albicans at 250 μg／mL30
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 fruits6. 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 elasticity31. Concentrations of ursolic acid ranging from 0.01 to 50 mg have been reported for inclusion in skin treatment preparations32－33.
Ursolic acid SH3-C30H48O3