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Toshihiro Akihisa Toshihiro Motoi Akihito Seki Takashi Kikuchi Makoto Fukatsu Harukuni Tokuda Nobutaka Suzuki Yumiko Kimura 《化学与生物多样性》2012,9(2):318-330
Three prenylated chalcones, 4‐hydroxyderricin ( 1 ), xanthoangelol ( 2 ), and xanthoangelol F ( 3 ), isolated from Angelica keiskei, were transformed by the fungus Aspergillus saitoi. These chalcones were converted to flavanones (i.e., 4, 8 , and 12 ), and prenyl‐chain‐hydrated (i.e., 5, 7, 9 – 11 , and 13 ) and ring‐B‐hydroxylated (i.e., 6 ) chalcones. The structures of three new metabolites, 7, 9 , and 13 , were established as 2″,3″‐dihydro‐4,3″‐dihydroxyderricin, 6″,7″‐dihydro‐7″‐hydroxyxanthoangelol, and 6″,7″‐dihydro‐7″‐hydroxyxanthoangelol F, respectively. Upon evaluation of cytotoxic activities of compounds 1 – 13 , the metabolite 7 exhibited potent cytotoxicity against HL60 cells, and this cell death was revealed to be mostly due to apoptosis. In addition, compounds 1 – 4, 7 – 10, 12 , and 13 were examined for their inhibitory effects on the induction of Epstein? Barr virus early antigen (EBV‐EA) by 12‐O‐tetradecanoylphorbol‐13‐acetate (TPA) in Raji cells. All compounds tested showed inhibitory effects against EBV‐EA activation with potencies higher than that of β‐carotene. Furthermore, the metabolite 13 exhibited inhibitory effect on skin tumor promotion in an in vivo two‐stage mouse skin carcinogenesis test based on 7,12‐dimethylbenz[a]anthracene (DMBA) as initiator, and with TPA as promoter. 相似文献
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Cytotoxic and Melanogenesis‐Inhibitory Activities of Limonoids from the Leaves of Azadirachta indica (Neem)
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Mio Takagi Yosuke Tachi Jie Zhang Takuro Shinozaki Kenta Ishii Takashi Kikuchi Motohiko Ukiya Norihiro Banno Harukuni Tokuda Toshihiro Akihisa 《化学与生物多样性》2014,11(3):451-468
Seventeen limonoids (tetranortriterpenoids), 1 – 17 , including three new compounds, i.e., 17‐defurano‐17‐(2,5‐dihydro‐2‐oxofuran‐3‐yl)‐28‐deoxonimbolide ( 14 ), 17‐defurano‐17‐(2ξ‐2,5‐dihydro‐2‐hydroxy‐5‐oxofuran‐3‐yl)‐28‐deoxonimbolide ( 15 ), and 17‐defurano‐17‐(5ξ‐2,5‐dihydro‐5‐hydroxy‐2‐oxofuran‐3‐yl)‐2′,3′‐dehydrosalannol ( 17 ), were isolated from an EtOH extract of the leaf of neem (Azadirachta indica). The structures of the new compounds were elucidated on the basis of extensive spectroscopic analyses and comparison with literature. Upon evaluation of the cytotoxic activities of these compounds against leukemia (HL60), lung (A549), stomach (AZ521), and breast (SK‐BR‐3) cancer cell lines, seven compounds, i.e., 1 – 3, 12, 13, 15 , and 16 , exhibited potent cytotoxicities with IC50 values in the range of 0.1–9.9 μM against one or more cell lines. Among these compounds, cytotoxicity of nimonol ( 1 ; IC50 2.8 μM ) against HL60 cells was demonstrated to be mainly due to the induction of apoptosis by flow cytometry. Western blot analysis suggested that compound 1 induced apoptosis via both the mitochondrial and death receptor‐mediated pathways in HL60 cells. In addition, when compounds 1 – 17 were evaluated for their inhibitory activities against melanogenesis in B16 melanoma cells, induced with α‐melanocyte‐stimulating hormone (α‐MSH), seven compounds, 1, 2, 4 – 6, 15 , and 16 , exhibited inhibitory activities with 31–94% reduction of melanin content at 10 μM concentration with no or low toxicity to the cells (82–112% of cell viability at 10 μM ). All 17 compounds were further evaluated for their inhibitory effects against the Epstein? Barr virus early antigen (EBV‐EA) activation induced by 12‐O‐tetradecanoylphorbol‐13‐acetate (TPA) in Raji cells. 相似文献
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Motohiko Ukiya Takashi Kikuchi Harukuni Tokuda Keiichi Tabata Yumiko Kimura Takanari Arai Yoichiro Ezaki Osamu Oseto Takashi Suzuki Toshihiro Akihisa 《化学与生物多样性》2010,7(8):1871-1884
Nineteen known triterpenoids, 1 – 19 , and one known sesquiterpenoid, 20 , were isolated from dammar resin obtained from Shorea javanica K. & V. (Dipterocarpaceae). One of the acidic triterpenoids, dammarenolic acid ( 1 ), was converted to fourteen derivatives, namely, an alcohol, 21 , an aldehyde, 22 , and twelve L ‐amino acid conjugates, 23 – 34 . Compounds 1 – 34 were examined for their inhibitory effects on the induction of Epstein–Barr virus early antigen (EBV‐EA) by 12‐O‐tetradecanoylphorbol 13‐acetate (TPA) in Raji cells, a known primary screening test for antitumor promoters. All of the compounds tested, except for compounds 4, 5, 12 – 14, 16 , and 17 , showed inhibitory effects against EBV‐EA activation with potencies either comparable with or stronger than that of β‐carotene, a known natural antitumor promoter. In addition, (20S)‐20‐hydroxy‐3,4‐secodammara‐4(28),24‐dien‐3‐al ( 22 ) exhibited inhibitory effects on skin tumor promotion in an in vivo two‐stage mouse skin carcinogenesis test based on 7,12‐dimethylbenz[a]anthracene (DMBA) as initiator, and with TPA as promoter. Furthermore, evaluation of the cytotoxic activities of compounds 1 – 34 against human cancer cell lines showed that reduction (i.e., 21 and 22 ) or conjugation with L ‐amino acids (i.e., 23 – 34 ) of compound 1 enhanced the cytotoxicity against human melanoma cell line CRL1579. 相似文献
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Cytotoxic and Nitric Oxide Production‐Inhibitory Activities of Limonoids and Other Compounds from the Leaves and Bark of Melia azedarach
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Xin Pan Masahiro Matsumoto Yuki Nishimoto Eri Ogihara Jie Zhang Motohiko Ukiya Harukuni Tokuda Kazuo Koike Momoko Akihisa Toshihiro Akihisa 《化学与生物多样性》2014,11(8):1121-1139
Nine limonoids, 1 – 9 , one apocarotenoid, 11 , one alkaloid, 12 , and one steroid, 13 , from the leaf extract; and one triterpenoid, 10 , five steroids, 14 – 18 , and two flavonoids, 19 and 20 , from the bark extract of Melia azedarach L. (Chinaberry tree; Meliaceae) were isolated. Among these compounds, three compounds, 4 – 6 , were new, and their structures were established as 3‐deacetyl‐28‐oxosalannolactone, 3‐deacetyl‐28‐oxosalanninolide, and 3‐deacetyl‐17‐defurano‐17,28‐dioxosalannin, respectively, on the basis of extensive spectroscopic analyses and comparison with literature data. All of the isolated compounds were evaluated for their cytotoxic activities against leukemia (HL60), lung (A549), stomach (AZ521), and breast (SK‐BR‐3) cancer cell lines. 3‐Deacetyl‐4′‐demethyl‐28‐oxosalannin ( 3 ) against HL60 and AZ521 cells, and methyl kulonate ( 10 ) against HL60 cells exhibited potent cytotoxicities with IC50 values in the range of 2.8–5.8 μM . In addition, upon evaluation of compounds 1 – 13 against production of nitric oxide (NO) in mouse macrophage RAW 264.7 cells induced by lipopolysaccharide (LPS), seven, i.e., trichilinin B ( 1 ), 4 , ohchinin ( 7 ), 23‐hydroxyohchininolide ( 8 ), 21‐hydroxyisoohchininolide ( 9 ), 10 , and methyl indole 3‐carboxylate ( 12 ), inhibited production of NO with IC50 values in the range of 4.6–87.3 μM with no, or almost no, toxicity to the cells (IC50 93.2–100 μM ). Western blot analysis revealed that compound 7 reduced the expression levels of the inducible NO synthase (iNOS) and COX‐2 proteins in a concentration‐dependent manner. Furthermore, compounds 5, 6, 13 , and 18 – 20 exhibited potent inhibitory effects (IC50 299–381 molar ratio/32 pmol TPA) against Epstein? Barr virus early antigen (EBV‐EA) activation induced by 12‐O‐tetradecanoylphorbol‐13‐acetate (TPA) in Raji cell line. 相似文献
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Jie Zhang Yuki Nishimoto Harukuni Tokuda Nobutaka Suzuki Ken Yasukawa Worapong Kitdamrongtham Hiroyuki Akazawa Aranya Manosroi Jiradej Manosroi Toshihiro Akihisa 《化学与生物多样性》2013,10(10):1866-1875
The aqueous extract of Peltophorum pterocarpum (Fabaceae) wood exhibited potent inhibitory effects against Epstein? Barr virus early antigen (EBV‐EA) activation induced with 12‐O‐tetradecanoylphorbol‐13‐acetate (TPA) in Raji cells and against melanogenesis in α‐melanocyte‐stimulating hormone (α‐MSH)‐stimulated B16 melanoma cells, as well as potent 1,1‐diphenyl‐2‐picrylhydrazyl (DPPH) free radical‐scavenging activity. Two phenolic acid derivatives, bergenin ( 1 ) and gallic acid ( 2 ), were isolated from the ethyl acetate (AcOEt)‐soluble fraction obtained from the extract. Compound 1 exhibited potent inhibitory effect against EBV‐EA activation and against skin tumor promotion in an in vivo two‐stage mouse skin carcinogenesis test based on 7,12‐dimethylbenz[a]anthracene (DMBA) as initiator, and with TPA as promoter. Both compounds 1 and 2 exhibited melanogenesis‐inhibitory activities in α‐MSH‐stimulated B16 melanoma cells, and, in addition, compound 2 showed strong DPPH radical‐scavenging activity. 相似文献
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Cytotoxic and Apoptosis‐Inducing Activities,and Anti‐Tumor‐Promoting Effects of Cyanogenated and Oxygenated Triterpenes
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Takashi Kikuchi Kenta Ishii Eri Ogihara Jie Zhang Motohiko Ukiya Harukuni Tokuda Takashi Iida Reiko Tanaka Toshihiro Akihisa 《化学与生物多样性》2014,11(4):491-504
Two of each semisynthetic lanostane‐ and cycloartane‐type triterpenes with a cyano‐enone functionality, i.e., 13 and 18 , and 23 and 28 , respectively, sixteen of their synthetic intermediates, 9 – 12, 14 – 17, 19 – 22 , and 24 – 27 , along with seven semisynthetic oxygenated triterpene acetates, 29 – 35 , and eight natural hydroxy triterpenes, 1 – 8 , were evaluated for their cytotoxic activities against leukemia (HL60), lung (A549), stomach (AZ521), and breast (SK‐BR‐3) cancer cell lines. One natural triterpene, 8 , and ten semisynthetic triterpenes, 9, 13, 15, 18, 23, 25, 28, 29, 32 , and 33 , exhibited potent cytotoxicities against one or more cell lines with IC50 values in the range of 1.4–9.9 μM . Two lanostane‐type triterpenes with a cyano‐enone functionality, 3‐oxolanosta‐1,8,24‐triene‐2‐carbonitrile ( 13 ) and 3‐oxolanosta‐1,8‐diene‐2‐carbonitrile ( 18 ), induced apoptosis in HL60 cells, as observed by membrane phospholipid exposure in flow cytometry. Western blot analysis showed that 13 and 18 significantly reduced procaspases‐3, ‐8, and ‐9, and increased cleaved caspases‐3, ‐8, and ‐9. These findings indicated that compounds 13 and 18 induced apoptosis in HL60 cells via both the mitochondrial and the death receptor‐mediated pathways. In addition, upon evaluation of the inhibitory effects on Epstein? Barr virus early antigen (EBV‐EA) activation induced with 12‐O‐tetradecanoylphorbol‐13‐acetate (TPA) in Raji cells, seven natural triterpenes, 1 – 6 and 8 , and ten semisynthetic triterpenes, 9, 10, 14, 15, 19, 20, 24, 25, 29 , and 30 , exhibited inhibitory effects which were higher than that of β‐carotene, a vitamin A precursor studied widely in cancer‐chemoprevention animal models. 相似文献
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Toshihiro Akihisa Shun Tochizawa Nami Takahashi Ayako Yamamoto Jie Zhang Takashi Kikuchi Makoto Fukatsu Harukuni Tokuda Nobutaka Suzuki 《化学与生物多样性》2012,9(6):1172-1187
Five new saccharide fatty acid esters, named nonioside P ( 3 ), nonioside Q ( 4 ), nonioside R ( 8 ), nonioside S ( 10 ), and nonioside T ( 14 ), and one new succinic acid ester, butyl 2‐hydroxysuccinate (=4‐butoxy‐3‐hydroxy‐4‐oxobutanoic acid) ( 31 ), were isolated, along with 26 known compounds, including eight saccharide fatty acid esters, 1, 2, 5, 6, 7, 9, 12 , and 13 , three hemiterpene glycosides, 15, 17 , and 18 , six iridoid glycosides, 21 – 25 , and 27 , and nine other compounds, 20, 28, 29 , and 32 – 37 , from a MeOH extract of the fruit of Morinda citrifolia (noni). Upon evaluation of these and five other glycosidic compounds, 11, 16, 19, 26 , and 30 , from M. citrifolia fruit extract for their inhibitory activities against melanogenesis in B16 melanoma cells induced with α‐melanocyte‐stimulating hormone (α‐MSH), most of the saccharide fatty acid esters, hemiterpene glycosides, and iridoid glycosides showed inhibitory effects with no or almost no toxicity to the cells. These compounds were further evaluated with respect to their cytotoxic activities against two human cancer cell lines (HL‐60 and AZ521) and their inhibitory effects on Epstein? Barr virus early antigen (EBV‐EA) activation induced with 12‐O‐tetradecanoylphorbol‐13‐acetate (TPA) in Raji cells. 相似文献
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Melanogenesis‐Inhibitory Activities of Isomeric C‐seco Limonoids and Deesterified Limonoids
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Toshihiro Akihisa Maiko Horiuchi Masahiro Matsumoto Eri Ogihara Kenta Ishii Jie Zhang 《化学与生物多样性》2016,13(10):1410-1421
Treatment of eight C‐seco limonoids including six of salannin‐type, 1 – 6 , and two of nimbin‐type, 7 and 8 , with a combination of BF3 · Et2O and iodide ion yielded the isomeric C‐seco derivatives, i.e., six isosalannins, 1a – 6a , and two isonimbins, 7a and 8a , respectively. Ohchinin ( 1 ) was further subjected to LiAlH4 reduction which yielded a deesterified trihydroxy limonoid, nimbidinol ( 9 ). In addition, ten limonoids including seven of azadirone‐type, 10 – 16 , and three of gedunin‐type, 17 – 19 , all of which possess no ester functionality in the molecule, were obtained from the neutral fraction of Azadirachta indica seed extract after alkaline hydrolysis. Among the above, twelve compounds, i.e., 1a – 4a , 6a , 9 , 13 – 16 , 18 , and 19 , were new compounds, and their structures were elucidated on the basis of extensive spectroscopic analysis and comparison with literature data. Upon evaluation of all these limonoids for their inhibitory activities against melanogenesis in B16 melanoma cells induced with α‐melanocyte‐stimulating hormone (α‐MSH), five structurally modified limonoids, 3‐deacetyl‐28‐oxosalannin ( 6a ), 9 , 17‐epi‐17‐hydroxynimbocinol ( 14 ), 17‐epi‐17‐hydroxy‐15‐methoxynimbocinol ( 15 ), and 7‐deacetyl‐17‐epinimolicinol ( 18 ), in addition to a natural limonoid, 1 , exhibited potent inhibitory activities with 26 – 66% reduction of melanin content at 100 μm concentration with almost no or low toxicity to the B16 melanoma cells (70 – 99% cell viability at 100 μm ). 相似文献
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An Unusual Tetrahydrofuran Lignan from the Roots of Zanthoxylum planispinum and the Potential Anti‐inflammatory Effects
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An unusual tetrahydrofuran lignin, zanthplanispine ( 1 ), together with 14 known lignans ( 2 – 15 ) were isolated from the AcOEt‐soluble fraction from the MeOH extract of Z. planispinum roots. The structures of 1 was elucidated on the basis of 1D‐ and 2D‐NMR experiments as well as HR‐ESI‐MS analysis. The known compounds were identified by the comparison of their NMR data with previously reported in the literatures. Bioassay showed that compounds 1 – 4 could inhibit nitric oxide (NO) production in lipopolysaccharide (LPS) stimulated RAW 264.7 cells. In particular, compound 1 showed significant inhibitory activity with an IC50 value of 36.8 μm . 相似文献
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Toshihiro Akihisa Ayano Takeda Hiroyuki Akazawa Takashi Kikuchi Satoru Yokokawa Motohiko Ukiya Makoto Fukatsu Kensuke Watanabe 《化学与生物多样性》2012,9(8):1475-1489
Nine cyclic diarylheptanoids, 1 – 9 , including two new compounds, i.e., 9‐oxoacerogenin A ( 8 ) and 9‐O‐β‐D ‐glucopyranosylacerogenin K ( 9 ), along with three acyclic diarylheptanoids, 10 – 12 , and four phenolic compounds, 13 – 16 , were isolated from a MeOH extract of the bark of Acer nikoense (Aceraceae). Acid hydrolysis of 9 yielded acerogenin K ( 17 ) and D ‐glucose. Two of the cyclic diarylheptanoids, acerogenin A ( 1 ) and (R)‐acerogenin B ( 5 ), were converted to their ether and ester derivatives, 18 – 24 and 27 – 33 , respectively, and to the dehydrated derivatives, 25, 26, 34 , and 35 . Upon evaluation of compounds 1 – 16 and 18 – 35 for their inhibitory activities against melanogenesis in B16 melanoma cells, induced with α‐melanocyte‐stimulating hormone (α‐MSH), eight natural glycosides, i.e., six diarylheptanoid glycosides, 2 – 4, 6, 9 , and 12 , and two phenolic glycosides, 15 and 16 , exhibited inhibitory activities with 24–61% reduction of melanin content at 100 μM concentration with no or almost no toxicity to the cells (88–106% of cell viability at 100 μM ). In addition, when compounds 1 – 16 and 18 – 35 were evaluated for cytotoxic activity against human cancer cell lines, two natural acyclic diarylheptanoids, 10 and 11 , ten ether and ester derivatives, 18 – 22 and 27 – 31 , and two dehydrated derivatives, 34 and 35 , exhibited potent cytotoxicities against HL60 human leukemia cell line (IC50 8.1–19.3 μM ), and five compounds, 10, 11, 20, 29 , and 30 , against CRL1579 human melanoma cell line (IC50 10.1–18.4 μM ). 相似文献
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Jie Zhang Ryosuke Koike Ayako Yamamoto Motohiko Ukiya Makoto Fukatsu Norihiro Banno Motofumi Miura Shigeyasu Motohashi Harukuni Tokuda Toshihiro Akihisa 《化学与生物多样性》2013,10(10):1851-1865
A new flavonoid glycoside, chrysin 6‐C‐β‐rutinoside (chrysin α‐L ‐rhamnopyranosyl‐(1→6)‐C‐β‐glucopyranoside; 2 ), and two new triterpene glycosides, (31R)‐31‐O‐methylpassiflorine ( 7 ) and (31S)‐31‐O‐methylpassiflorine ( 8 ), along with 14 known glycosides, including three flavonoid glycosides, 1, 3 , and 4 , six triterpene glycosides, 5, 6 , and 9 – 12 , three cyano glycosides, 13 – 15 , and two other glycosides, 16 and 17 , were isolated from a MeOH extract of the leaves of Passiflora edulis (passion flower; Passifloraceae). The structures of new compounds were elucidated on the basis of extensive spectroscopic analysis and comparison with literature data. Upon evaluation of compounds 1 – 17 against the melanogenesis in the B16 melanoma cells induced with α‐melanocyte‐stimulating hormone (α‐MSH), three compounds, isoorientin ( 1 ), 2 , and (6S,9R)‐roseoside ( 17 ), exhibited inhibitory effects with 37.3–47.2% reduction of melanin content with no, or almost no, toxicity to the cells (90.8–100.2% cell viability) at 100 μM . Western blot analysis showed that compound 2 reduced the protein levels of MITF, TRP‐1, and tyrosinase, in a concentration‐dependent manner while exerted almost no influence on the level of TRP‐2, suggesting that this compound inhibits melanogenesis on the α‐MSH‐stimulated B16 melanoma cells by, at least in part, inhibiting the expression of MITF, followed by decreasing the expression of TRP‐1 and tyrosinase. In addition, compounds 1 – 17 were evaluated for their inhibitory effects against the Epstein? Barr virus early antigen (EBV‐EA) activation induced by 12‐O‐tetradecanoylphorbol‐13‐acetate (TPA) in Raji cells. 相似文献
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Nitric Oxide Production‐Inhibitory Activity of Limonoids from Azadirachta indica and Melia azedarach
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Toshihiro Akihisa Yuki Nishimoto Eri Ogihara Masahiro Matsumoto Jie Zhang Masahiko Abe 《化学与生物多样性》2017,14(6)
Seventy‐three limonoids isolated from three Meliaceae plants, Azadirachta indica, A. indica var. siamensis, and Melia azedarach, or semi‐synthesized from the Meliaceae limonoids, were evaluated for their inhibitory activity against nitric oxide (NO) production in mouse macrophage RAW 264.7 cells induced by lipopolysaccharide (LPS), as a primary screening test for anti‐inflammatory agents. Of the compounds tested, 21 compounds exhibited inhibitory activity (IC50 4.6 – 58.6 μm ) without any significant toxicity (IC50 > 100 μm ) which were more potent than l ‐NMMA (NO‐production inhibitory activity, IC50 65.6 μm ; cytotoxicity, IC50 > 100 μm ), and among which, nine compounds, i.e., 17‐hydroxy‐15‐methoxynimbocinol ( 6 ), ohchinin ( 20 ), 1‐cis‐cinnamoyl‐1‐decinnamoylohchinin ( 24 ), salannin ( 27 ), methyl nimbidate ( 32 ), isosalannin ( 55 ), nimbolinin D ( 58 ), mesendanin E ( 69 ), and 7‐deacetylgedunin ( 73 ) exhibited potent inhibitory activity (IC50 4.6 – 29.3 μm ). In particular, compounds 6 (IC50 7.3 μm ), an azadirone‐type limonoid, and 73 (IC50 4.6 μm ), a gedunin‐type limonoid, exhibited remarkable activity. Western blot analysis revealed that 27 and 73 reduced the expression levels of the inducible NO synthase and cyclooxygenase‐2 proteins in a concentration‐dependent manner. These findings suggest that limonoids of A. indica, A. indica var. siamensis, and M. azedarach, and their semi‐synthetic derivatives may be effective against inflammation. 相似文献
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Wannapha Molee Anuchit Phanumartwiwath Chatchai Kesornpun Sanya Sureram Nattaya Ngamrojanavanich Kornkanok Ingkaninan Chulabhorn Mahidol Somsak Ruchirawat Prasat Kittakoop 《化学与生物多样性》2018,15(3)
New naphthalene derivatives ( 1 and 2 ) and a new isomer ( 3 ) of ventilagolin, together with known anthraquinones, chrysophanol ( 4 ), physcion or emodin 3‐methyl ether ( 5 ), and emodin ( 6 ), were isolated from vines of Ventilago denticulata. The isolated compounds exhibited cytotoxic activity with IC50 values of 1.15 – 40.54 μg/ml. Compounds 1 – 3 selectively exhibited weak antibacterial activity (MIC values of 200.0 – 400.0 μg/ml), while emodin ( 6 ) displayed moderate antibacterial activity with MIC value of 25.0 μg/ml. The isolated compounds showed nitric oxide and DPPH radical scavenging activities. Compounds 1 – 3 and 6 exhibited weak xanthine oxidase inhibitory activity, while emodin ( 6 ) acted as an aromatase inhibitor with the IC50 value of 10.1 μm . Compounds 1 and 2 exhibited phosphodiesterase 5 inhibitory activity with IC50 values of 8.28 μm and 6.48 μm , respectively. 相似文献
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Biological Activities of Phenolics from the Fruits of Phyllanthus emblica L. (Euphorbiaceae)
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Jie Zhang Dan Miao Wan‐Fang Zhu Jian Xu Wen‐Yuan Liu Worapong Kitdamrongtham Jiradej Manosroi Masahiko Abe Toshihiro Akihisa Feng Feng 《化学与生物多样性》2017,14(12)
Seven phenolic compounds, 1 – 7 , including a new organic acid gallate, mucic acid 1‐ethyl 6‐methyl ester 2‐O‐gallate ( 7 ), were isolated from the MeOH extract of the fruits of Phyllanthus emblica L. (Euphorbiaceae). The structures were elucidated on the basis of extensive spectroscopic analysis and comparison with literature data. Upon evaluated for their antioxidant abilities by 1,1‐diphenyl‐2‐picrylhydrazyl (DPPH), 2,2′‐azinobis(3‐ethylbenzthiazoline‐6‐sulfonic acid) (ABTS), and ferric reducing antioxidant power (FRAP) assays. The inhibitory activities against melanogenesis in B16 melanoma cells induced by α‐MSH, as well as cytotoxic activities against four human cancer cell lines were also evaluated. All phenolic compounds, 1 – 7 , exhibited potent antioxidant abilities (DPPH: IC50 5.6 – 12.9 μm ; ABTS: 0.87 – 8.43 μm Trolox/μm ; FRAP: 1.01 – 5.79 μm Fe2+/μm , respectively). Besides, 5 – 7 , also exhibited moderate inhibitory activities against melanogenesis (80.7 – 86.8% melanin content), even with no or low toxicity to the cells (93.5 – 101.6% cell viability) at a high concentration of 100 μm . Compounds 1 – 3 exhibited cytotoxic activity against one or more cell lines (IC50 13.9 – 68.4%), and compound 1 with high tumor selectivity for A549 (SI 3.2). 相似文献
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Limonoids from Azadirachta indica var. siamensis Extracts and Their Cytotoxic and Melanogenesis‐Inhibitory Activities
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Aranya Manosroi Worapong Kitdamrongtham Kenta Ishii Takuro Shinozaki Yosuke Tachi Mio Takagi Kodai Ebina Jie Zhang Jiradej Manosroi Rima Akihisa Toshihiro Akihisa 《化学与生物多样性》2014,11(4):505-531
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Jia‐Qing Cao Yan Wu Yuan‐Lin Zhong Ni‐Ping Li Mu Chen Man‐Mei Li Wen‐Cai Ye Lei Wang 《化学与生物多样性》2018,15(7)
Callistrilones F – K ( 1 – 6 ), six new triketone‐phloroglucinol‐monoterpene hybrids were isolated from the twigs and leaves of Callistemon rigidus. Their structures with absolute configurations were established by a combination analysis of NMR spectra, X‐ray diffraction, and electronic circular dichroism (ECD) calculations. Compounds 3 and 4 exhibited moderate inhibitory activities against herpes simplex virus (HSV‐1) with IC50 values of 10.00 ± 2.50 and 12.50 ± 1.30 μm , respectively. 相似文献
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Zha‐Jun Zhan Yan‐Tao Wen Feng‐Yun Ren Gui‐Wei Rao Wei‐Guang Shan Cheng‐Ping Li 《化学与生物多样性》2012,9(12):2754-2760
Two new labdane diterpenoids, namely hedycoronals A and B ( 1 and 2 , resp.), were isolated from the rhizomes of Hedychium coronarium, together with eight known diterpenoids, 4 – 11 , and a known diarylheptanoid, 3 . The structures of 1 and 2 were established by detailed interpretation of their 1D‐ and 2D‐NMR spectra and HR‐ESI‐MS data. Inhibitory activities against human umbilical vein endothelial cells (HUMECs) proliferation and cytotoxic activities against four cancer cell lines were assessed for all the isolates. Most of these metabolites showed moderate or potent cytotoxic activities against four cancer cell lines. Moreover, compounds 3 and 8 exhibited promising inhibitory activities against HUMECs with the IC50 values of 6.4 to 3.3 μM . 相似文献