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Michio Takido - One of the best experts on this subject based on the ideXlab platform.
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constituents of compositae plants 2 triterpene diols triols and their 3 o fatty acid esters from edible chrysanthemum flower extract and their anti inflammatory effects
Journal of Agricultural and Food Chemistry, 2001Co-Authors: Motohiko Ukiya, Yoshimasa Kasahara, Yumiko Kimura, Tamotsu Nikaido, Kazuo Koike, Toshihiro Akihisa, Ken Yasukawa, Michio TakidoAbstract:The n-hexane soluble and the nonsaponifiable lipid fractions of the edible flower extract of chrysanthemum (Chrysanthemum morifolium) were investigated for triterpene diol and triol constituents. These Triterpenes occur as the 3-O-fatty acid esters in the n-hexane soluble fraction from which 26 new and 6 known fatty acid esters were isolated and characterized. From the nonsaponifiable lipid fraction, 24 triterpene diols and triols were isolated, of which 3 were new compounds: (24S)-25-methoxycycloartane-3β,24-diol (11), (24S)-25-methoxycycloartane-3β,24,28-triol (22), and 22α-methoxyfaradiol (23). Faradiol (9) and heliantriol C (19), present in the nonsaponifiable lipid fraction and as the 3-O-palmitoyl esters in the n-hexane soluble fraction, were the most predominant triterpene diol and triol constituents. Fourteen triterpene diols and triols and 9 fatty acid esters were evaluated with respect to their anti-inflammatory activity against 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammation in...
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constituents of compositae plants 2 triterpene diols triols and their 3 o fatty acid esters from edible chrysanthemum flower extract and their anti inflammatory effects
Journal of Agricultural and Food Chemistry, 2001Co-Authors: Motohiko Ukiya, Yoshimasa Kasahara, Yumiko Kimura, Tamotsu Nikaido, Kazuo Koike, Toshihiro Akihisa, Ken Yasukawa, Michio TakidoAbstract:The n-hexane soluble and the nonsaponifiable lipid fractions of the edible flower extract of chrysanthemum (Chrysanthemum morifolium) were investigated for triterpene diol and triol constituents. These Triterpenes occur as the 3-O-fatty acid esters in the n-hexane soluble fraction from which 26 new and 6 known fatty acid esters were isolated and characterized. From the nonsaponifiable lipid fraction, 24 triterpene diols and triols were isolated, of which 3 were new compounds: (24S)-25-methoxycycloartane-3beta,24-diol (11), (24S)-25-methoxycycloartane-3beta,24,28-triol (22), and 22alpha-methoxyfaradiol (23). Faradiol (9) and heliantriol C (19), present in the nonsaponifiable lipid fraction and as the 3-O-palmitoyl esters in the n-hexane soluble fraction, were the most predominant triterpene diol and triol constituents. Fourteen triterpene diols and triols and 9 fatty acid esters were evaluated with respect to their anti-inflammatory activity against 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammation in mice. All of the Triterpenes examined showed marked inhibitory activity, with a 50% inhibitory dose (ID50) of 0.03-1.0 mg/ear, which was more inhibitive than quercetin (ID50 = 1.6 mg/ear), a known inhibitor of TPA-induced inflammation in mice.
Masayuki Yoshikawa - One of the best experts on this subject based on the ideXlab platform.
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hepatoprotective Triterpenes from traditional tibetan medicine potentilla anserina
Phytochemistry, 2014Co-Authors: Toshio Morikawa, Katsuya Imura, Yoshinori Akagi, Kiyofumi Ninomiya, Takao Hayakawa, Masayuki Yoshikawa, Takahiro Yamaguchi, Osamu MuraokaAbstract:Abstract A methanol extract from the tuberous roots of Potentilla anserina (Rosaceae) exhibited hepatoprotective effects against d -galactosamine ( d -GalN)/lipopolysaccharide-induced liver injuries in mice. Six triterpene 28-O-monoglucopyranosyl esters, potentillanosides A–F, were isolated from the extract along with 32 known compounds, including 15 Triterpenes. The structures of potentillanosides A–F were determined on the basis of spectroscopic properties and chemical evidence. Four ursane-type triterpene 28-O-monoglycosyl esters, potentillanoside A (IC50 = 46.7 μM), 28-O-β- d -glucopyranosyl pomolic acid (IC50 = 9.5 μM), rosamutin (IC50 = 35.5 μM), and kaji-ichigoside F1 (IC50 = 14.1 μM), inhibited d -GalN-induced cytotoxicity in primary cultured mouse hepatocytes. Among these four Triterpenes, potentillanoside A, rosamutin, and kaji-ichigoside F1 exhibited in vivo hepatoprotective effects at doses of 50–100 mg/kg, p.o. The mode of action was ascribable to the reduction in cytotoxicity caused by d -GalN.
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new triterpene constituents foliasalacins a 1 a 4 b 1 b 3 and c from the leaves of salacia chinensis
Chemical & Pharmaceutical Bulletin, 2008Co-Authors: Masayuki Yoshikawa, Seikou Nakamura, Yi Zhang, Tao Wang, Hisashi MatsudaAbstract:Four dammarane-type, three lupane-type, and an oleanane-type Triterpenes named foliasalacins A(1) (1), A(2) (2), A(3) (3), A(4) (4), B(1) (5), B(2) (6), B(3) (7), and C (8) were isolated from the leaves of Salacia chinensis LINN. collected in Thailand. The structures of new triterpene constituents (1-8) were characterized on the basis of chemical and physiochemical evidence.
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structures of new cucurbitane type Triterpenes and glycosides karavilagenins and karavilosides from the dried fruit of momordica charantia l in sri lanka
ChemInform, 2007Co-Authors: Seikou Nakamura, Toshiyuki Murakami, Junko Nakamura, Hisanori Kobayashi, Hisashi Matsuda, Masayuki YoshikawaAbstract:Three new cucurbitane-type triterpene called karavilagenins A, B, and C and five new cucurbitane-type triterpene glycosides called karavilosides I, II, III, IV, and V were isolated from the dried fruit of Sri Lanka Momordica charantia L. (Cucurbitaceae) together with two known cucurbitane-type Triterpenes, 19(R)-methoxy-5beta,19-epoxycucurbita-6,23-dien-3beta,25-diol and 5,19-epoxycucurbita-6,23-diene-3,25-diol, and nine known cucurbitane-type triterpene glycosides, goyaglycosides-b, -c, and -d, and momordicosides F1, F2, G, I, K, and L. The structures of karavilagenins and karavilosides were elucidated on the basis of chemical and physicochemical evidence.
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structures of new cucurbitane type Triterpenes and glycosides karavilagenins d and e and karavilosides vi vii viii ix x and xi from the fruit of momordica charantia
Heterocycles, 2007Co-Authors: Masayuki Yoshikawa, Seikou Nakamura, Hisashi Matsuda, Toshiyuki MurakamiAbstract:Two new cucurbitane-type Triterpenes, karavilagenins D and E, and six new cucurbitane-type triterpene glycosides, karavilosides VI, VII, VIII, IX, X, and XI, were isolated from the fruit of Momordica charantia L. (Cucurbitaceae) cultivated in Sri Lanka. Their structures were elucidated on the basis of chemical and physicochemical evidence.
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structures of new cucurbitane type Triterpenes and glycosides karavilagenins and karavilosides from the dried fruit of momordica charantia l in sri lanka
Chemical & Pharmaceutical Bulletin, 2006Co-Authors: Seikou Nakamura, Toshiyuki Murakami, Junko Nakamura, Hisanori Kobayashi, Hisashi Matsuda, Masayuki YoshikawaAbstract:Three new cucurbitane-type triterpene called karavilagenins A, B, and C and five new cucurbitane-type triterpene glycosides called karavilosides I, II, III, IV, and V were isolated from the dried fruit of Sri Lanka Momordica charantia L. (Cucurbitaceae) together with two known cucurbitane-type Triterpenes, 19(R)-methoxy-5β,19-epoxycucurbita-6,23-dien-3β,25-diol and 5,19-epoxycucurbita-6,23-diene-3,25-diol, and nine known cucurbitane-type triterpene glycosides, goyaglycosides-b, -c, and -d, and momordicosides F1, F2, G, I, K, and L. The structures of karavilagenins and karavilosides were elucidated on the basis of chemical and physicochemical evidence.
Armin Scheffler - One of the best experts on this subject based on the ideXlab platform.
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pentacyclic triterpene distribution in various plants rich sources for a new group of multi potent plant extracts
Molecules, 2009Co-Authors: Sebastian Jager, Holger Trojan, Thomas Kopp, Melanie N Laszczyk, Armin SchefflerAbstract:Pentacyclic Triterpenes are secondary plant metabolites widespread in fruit peel, leaves and stem bark. In particular the lupane-, oleanane-, and ursane Triterpenes display various pharmacological effects while being devoid of prominent toxicity. Therefore, these Triterpenes are promising leading compounds for the development of new multi-targeting bioactive agents. Screening of 39 plant materials identified triterpene rich (> 0.1% dry matter) plant parts. Plant materials with high triterpene concentrations were then used to obtain dry extracts by accelerated solvent extraction resulting in a triterpene content of 50 - 90%. Depending on the plant material, betulin (birch bark), betulinic acid (plane bark), oleanolic acid (olive leaves, olive pomace, mistletoe sprouts, clove flowers), ursolic acid (apple pomace) or an equal mixture of the three triterpene acids (rosemary leaves) are the main components of these dry extracts. They are quantitatively characterised plant extracts supplying a high concentration of actives and therefore can be used for development of phytopharmaceutical formulations.
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a preliminary pharmacokinetic study of betulin the main pentacyclic triterpene from extract of outer bark of birch betulae alba cortex
Molecules, 2008Co-Authors: Sebastian Jager, Melanie N Laszczyk, Armin SchefflerAbstract:During the last two decades Triterpenes have attracted attention because of their pharmacological potential. Triterpene extract (TE) from outer bark of birch consisting mainly of betulin is able to form an oleogel which was successfully tested in the treatment of actinic keratosis. Some aspects of TE in vitro pharmacology are already known. Now we show preliminary pharmacokinetics of betulin and results of a subchronic toxicity study of TE in rats and dogs. Because of poor aqueous solubility of the TE-Triterpenes (< 0.1 microg/mL respectively), for pharmacokinetic studies it was suspended in sesame oil (rats, i.p.) and PEG 400 / 0.9 % NaCl (dogs, s.c.). I.p. administered, betulin, the main component of TE, shows time dependency over a period of 4 h and reaches a dose-independent serum level of 0.13 microg/mL. Dose dependency was observed with s.c. administration. At 300 mg/kg a maximum plasma concentration of 0.33 microg/mL betulin was detected after 28 daily applications. The subchronic toxicity study showed no toxicity of TE in rats (i.p.) and dogs (s.c.). In conclusion, triterpene extract from birch bark is safe, its betulin is bioavailable and in addition to published triterpene biological activities TE provides high potential for further pharmaceutical and pharmacological research.
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physical chemical and pharmacological characterization of a new oleogel forming triterpene extract from the outer bark of birch betulae cortex
Planta Medica, 2006Co-Authors: Melanie N Laszczyk, Sebastian Jager, Armin Scheffler, Birgit Simonhaarhaus, Christoph M SchemppAbstract:Triterpenes are biologically active secondary plant substances that display antimicrobial, hepatoprotective and anti-inflammatory effects. However, the poor solubility of Triterpenes in both polar and non-polar solvents as well as expensive purification procedures have prevented the large-scale isolation of these compounds for medicinal purposes. Here, we describe a novel quantitative extraction method of Triterpenes from the outer bark of birch (Betula species) in which betulin, a lupan triterpene, predominates. The resulting highly purified triterpene extract (TE) in the form of a dry powder contains betulin as the major compound, but also betulinic acid, lupeol, erythrodiol and oleanolic acid. We have found that this TE is able to form an oleogel, thus providing an opportunity for the topical application of pharmacologically relevant amounts of Triterpenes. Furthermore, we have investigated the TE in comparison to its major isolated compounds in cell culture experiments with human immortalized keratinocytes and skin cancer cells. We could demonstrate dose-dependent cytotoxic and apoptosis-inducing effects of TE and betulin. These experimental data support the notion from a previous clinical study that TE from the outer bark of birch might represent a new tool for the topical treatment of skin cancer and skin cancer precursors like actinic keratoses.
Motohiko Ukiya - One of the best experts on this subject based on the ideXlab platform.
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constituents of compositae plants 2 triterpene diols triols and their 3 o fatty acid esters from edible chrysanthemum flower extract and their anti inflammatory effects
Journal of Agricultural and Food Chemistry, 2001Co-Authors: Motohiko Ukiya, Yoshimasa Kasahara, Yumiko Kimura, Tamotsu Nikaido, Kazuo Koike, Toshihiro Akihisa, Ken Yasukawa, Michio TakidoAbstract:The n-hexane soluble and the nonsaponifiable lipid fractions of the edible flower extract of chrysanthemum (Chrysanthemum morifolium) were investigated for triterpene diol and triol constituents. These Triterpenes occur as the 3-O-fatty acid esters in the n-hexane soluble fraction from which 26 new and 6 known fatty acid esters were isolated and characterized. From the nonsaponifiable lipid fraction, 24 triterpene diols and triols were isolated, of which 3 were new compounds: (24S)-25-methoxycycloartane-3β,24-diol (11), (24S)-25-methoxycycloartane-3β,24,28-triol (22), and 22α-methoxyfaradiol (23). Faradiol (9) and heliantriol C (19), present in the nonsaponifiable lipid fraction and as the 3-O-palmitoyl esters in the n-hexane soluble fraction, were the most predominant triterpene diol and triol constituents. Fourteen triterpene diols and triols and 9 fatty acid esters were evaluated with respect to their anti-inflammatory activity against 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammation in...
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constituents of compositae plants 2 triterpene diols triols and their 3 o fatty acid esters from edible chrysanthemum flower extract and their anti inflammatory effects
Journal of Agricultural and Food Chemistry, 2001Co-Authors: Motohiko Ukiya, Yoshimasa Kasahara, Yumiko Kimura, Tamotsu Nikaido, Kazuo Koike, Toshihiro Akihisa, Ken Yasukawa, Michio TakidoAbstract:The n-hexane soluble and the nonsaponifiable lipid fractions of the edible flower extract of chrysanthemum (Chrysanthemum morifolium) were investigated for triterpene diol and triol constituents. These Triterpenes occur as the 3-O-fatty acid esters in the n-hexane soluble fraction from which 26 new and 6 known fatty acid esters were isolated and characterized. From the nonsaponifiable lipid fraction, 24 triterpene diols and triols were isolated, of which 3 were new compounds: (24S)-25-methoxycycloartane-3beta,24-diol (11), (24S)-25-methoxycycloartane-3beta,24,28-triol (22), and 22alpha-methoxyfaradiol (23). Faradiol (9) and heliantriol C (19), present in the nonsaponifiable lipid fraction and as the 3-O-palmitoyl esters in the n-hexane soluble fraction, were the most predominant triterpene diol and triol constituents. Fourteen triterpene diols and triols and 9 fatty acid esters were evaluated with respect to their anti-inflammatory activity against 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammation in mice. All of the Triterpenes examined showed marked inhibitory activity, with a 50% inhibitory dose (ID50) of 0.03-1.0 mg/ear, which was more inhibitive than quercetin (ID50 = 1.6 mg/ear), a known inhibitor of TPA-induced inflammation in mice.
Sebastian Jager - One of the best experts on this subject based on the ideXlab platform.
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pentacyclic triterpene distribution in various plants rich sources for a new group of multi potent plant extracts
Molecules, 2009Co-Authors: Sebastian Jager, Holger Trojan, Thomas Kopp, Melanie N Laszczyk, Armin SchefflerAbstract:Pentacyclic Triterpenes are secondary plant metabolites widespread in fruit peel, leaves and stem bark. In particular the lupane-, oleanane-, and ursane Triterpenes display various pharmacological effects while being devoid of prominent toxicity. Therefore, these Triterpenes are promising leading compounds for the development of new multi-targeting bioactive agents. Screening of 39 plant materials identified triterpene rich (> 0.1% dry matter) plant parts. Plant materials with high triterpene concentrations were then used to obtain dry extracts by accelerated solvent extraction resulting in a triterpene content of 50 - 90%. Depending on the plant material, betulin (birch bark), betulinic acid (plane bark), oleanolic acid (olive leaves, olive pomace, mistletoe sprouts, clove flowers), ursolic acid (apple pomace) or an equal mixture of the three triterpene acids (rosemary leaves) are the main components of these dry extracts. They are quantitatively characterised plant extracts supplying a high concentration of actives and therefore can be used for development of phytopharmaceutical formulations.
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a preliminary pharmacokinetic study of betulin the main pentacyclic triterpene from extract of outer bark of birch betulae alba cortex
Molecules, 2008Co-Authors: Sebastian Jager, Melanie N Laszczyk, Armin SchefflerAbstract:During the last two decades Triterpenes have attracted attention because of their pharmacological potential. Triterpene extract (TE) from outer bark of birch consisting mainly of betulin is able to form an oleogel which was successfully tested in the treatment of actinic keratosis. Some aspects of TE in vitro pharmacology are already known. Now we show preliminary pharmacokinetics of betulin and results of a subchronic toxicity study of TE in rats and dogs. Because of poor aqueous solubility of the TE-Triterpenes (< 0.1 microg/mL respectively), for pharmacokinetic studies it was suspended in sesame oil (rats, i.p.) and PEG 400 / 0.9 % NaCl (dogs, s.c.). I.p. administered, betulin, the main component of TE, shows time dependency over a period of 4 h and reaches a dose-independent serum level of 0.13 microg/mL. Dose dependency was observed with s.c. administration. At 300 mg/kg a maximum plasma concentration of 0.33 microg/mL betulin was detected after 28 daily applications. The subchronic toxicity study showed no toxicity of TE in rats (i.p.) and dogs (s.c.). In conclusion, triterpene extract from birch bark is safe, its betulin is bioavailable and in addition to published triterpene biological activities TE provides high potential for further pharmaceutical and pharmacological research.
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physical chemical and pharmacological characterization of a new oleogel forming triterpene extract from the outer bark of birch betulae cortex
Planta Medica, 2006Co-Authors: Melanie N Laszczyk, Sebastian Jager, Armin Scheffler, Birgit Simonhaarhaus, Christoph M SchemppAbstract:Triterpenes are biologically active secondary plant substances that display antimicrobial, hepatoprotective and anti-inflammatory effects. However, the poor solubility of Triterpenes in both polar and non-polar solvents as well as expensive purification procedures have prevented the large-scale isolation of these compounds for medicinal purposes. Here, we describe a novel quantitative extraction method of Triterpenes from the outer bark of birch (Betula species) in which betulin, a lupan triterpene, predominates. The resulting highly purified triterpene extract (TE) in the form of a dry powder contains betulin as the major compound, but also betulinic acid, lupeol, erythrodiol and oleanolic acid. We have found that this TE is able to form an oleogel, thus providing an opportunity for the topical application of pharmacologically relevant amounts of Triterpenes. Furthermore, we have investigated the TE in comparison to its major isolated compounds in cell culture experiments with human immortalized keratinocytes and skin cancer cells. We could demonstrate dose-dependent cytotoxic and apoptosis-inducing effects of TE and betulin. These experimental data support the notion from a previous clinical study that TE from the outer bark of birch might represent a new tool for the topical treatment of skin cancer and skin cancer precursors like actinic keratoses.
