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{{chembox |
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{{Chembox |
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| Verifiedfields = changed |
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| verifiedrevid = 406015131 |
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| Watchedfields = changed |
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| Name=Jatrorrhizine |
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| verifiedrevid = 429924488 |
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| Name = Jatrorrhizine |
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| ImageFile = Jatrorrhizine.svg |
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| ImageFile = Jatrorrhizine.svg |
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| ImageSize = 300px |
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| ImageSize = 200px |
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| IUPACName = 2,9,10-trimethoxy-5,6-dihydroisoquinolinoisoquinolin-7-ium-3-ol |
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| IUPACName = 3-Hydroxy-2,9,10-trimethoxy-7,8,13,13a-tetradehydroberbin-7-ium |
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| SystematicName = 3-Hydroxy-2,9,10-trimethoxy-5,6-dihydro-7λ<sup>5</sup>-isoquinolinoisoquinolin-7-ylium |
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| OtherNames = jateorrhizine, neprotin |
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| OtherNames = {{ubl|Jateorrhizine | Neprotin | Jatrochizine | Jatrorhizine | Yatrorizine}} |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 3621-38-3 |
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| ChEBI = 6087 |
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| ChEMBL = 251055 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = |
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| ChemSpiderID = |
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| ChemSpiderID2_Ref = {{chemspidercite|correct|chemspider}} |
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| InChI = InChI=1S/C20H19NO4/c1-23-18-5-4-12-8-16-14-10-19(24-2)17(22)9-13(14)6-7- |
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| ChemSpiderID2 = 65269 |
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| EINECS = 222-817-3 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = C09553 |
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| PubChem = 72323 |
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| UNII = 091S1F8V5Q |
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| SMILES = COC1=C(C2=C3=C(C=C2C=C1)C4=CC(=C(C=C4CC3)O)OC)OC |
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| InChI = 1S/C20H19NO4/c1-23-18-5-4-12-8-16-14-10-19(24-2)17(22)9-13(14)6-7- |
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21(16)11-15(12)20(18)25-3/h4-5,8-11H,6-7H2,1-3H3/p+1 |
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21(16)11-15(12)20(18)25-3/h4-5,8-11H,6-7H2,1-3H3/p+1 |
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| InChIKey = MXTLAHSTUOXGQF-UHFFFAOYSA-O |
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| InChIKey = MXTLAHSTUOXGQF-UHFFFAOYSA-O |
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| InChI2 = 1/C20H19NO4/c1-23-18-5-4-12-8-16-14-10-19(24-2)17(22)9-13(14)6-7-21(16)11-15(12)20(18)25-3/h4-5,8-11H,6-7H2,1-3H3/p+1 |
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| CASNo_Ref = {{cascite}} |
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| InChIKey2 = MXTLAHSTUOXGQF-IKLDFBCSAC |
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| CASNo = |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| PubChem = 72323 |
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| StdInChI = 1S/C20H19NO4/c1-23-18-5-4-12-8-16-14-10-19(24-2)17(22)9-13(14)6-7-21(16)11-15(12)20(18)25-3/h4-5,8-11H,6-7H2,1-3H3/p+1 |
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| SMILES = COC1=C(C2=C3=C(C=C2C=C1)C4=CC(=C(C=C4CC3)O)OC)OC |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| MeSHName = |
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| StdInChIKey = MXTLAHSTUOXGQF-UHFFFAOYSA-O |
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}} |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=20|H=20|N=1|O=4 |
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| C=20|H=20|N=1|O=4 |
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| Appearance = |
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| Density = |
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| Formula_Charge = +1 |
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| MeltingPt = |
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| Section3 = {{Chembox Hazards |
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| Solubility = |
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|Section3={{Chembox Hazards |
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| MainHazards = |
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| FlashPt = |
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| Autoignition = |
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'''Jatrorrhizine''' is a ] ] found in some plant species, such as '']'' (]).<ref>{{cite web|url=https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=72323&loc=ec_rcs|title=jatrorrhizine - Compound Summary (CID 72323)|publisher=PubChem}}</ref> Synonyms that may be encountered include jateorrhizine, neprotin, jatrochizine, jatrorhizine, and yatrorizine. |
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'''jatrorrhizine''' is a proto] ] isolated from '']'' (]) and other species.<ref>{{cite web|url=http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=72323&loc=ec_rcs|title=jatrorrhizine - Compound Summary (CID 72323)|publisher=PubChem}}</ref> Synonyms that may be encountered include jateorrhizine, neprotin, jatrochizine, jatrorhizine, or yatrorizine. It has been reported to have antiinflammatory effect,<ref>{{cite journal | last1 = Arens | first1 = H | last2 = Fischer | first2 = H | last3 = Leyck | first3 = S | last4 = Römer | first4 = A | last5 = Ulbrich | first5 = B | title = Antiinflammatory Compounds from Plagiorhegma dubium Cell Culture1 | journal = Planta medica | volume = 51 | issue = 1 | pages = 52–6 | year = 1985 | pmid = 17340402 | doi = 10.1055/s-2007-969392 }}</ref> and to improve blood flow and mitotic activity in thioacetamide-traumatized rat livers.<ref>{{cite journal | last1 = Virtanen | first1 = P | last2 = Lassila | first2 = V | last3 = Njimi | first3 = T | last4 = Mengata | first4 = DE | title = Natural protoberberine alkaloids from Enantia chlorantha, palmatine, columbamine and jatrorrhizine for thioacetamide-traumatized rat liver | journal = Acta anatomica | volume = 131 | issue = 2 | pages = 166–70 | year = 1988 | pmid = 3369286 | doi = 10.1159/000146507 }}</ref> It was found to have antimicrobial<ref>{{cite journal | last1 = Moody | first1 = JO | last2 = Bloomfield | first2 = SF | last3 = Hylands | first3 = PJ | title = In-vitro evaluation of the antimicrobial activities of Enantia chlorantha Oliv. Extractives | journal = African journal of medicine and medical sciences | volume = 24 | issue = 3 | pages = 269–73 | year = 1995 | pmid = 8798963 }}</ref> and antifungal<ref>{{cite journal | last1 = Volleková | first1 = A | last2 = Kost'álová | first2 = D | last3 = Kettmann | first3 = V | last4 = Tóth | first4 = J | title = Antifungal activity of Mahonia aquifolium extract and its major protoberberine alkaloids | journal = Phytotherapy research : PTR | volume = 17 | issue = 7 | pages = 834–7 | year = 2003 | pmid = 12916091 | doi = 10.1002/ptr.1256 }}</ref> activity. It binds and noncompetitively inhibits ] (IC<sub>50</sub> 4 ] for MAO-A and 62 for MAO-B)<ref>{{cite journal | last1 = Kong | first1 = LD | last2 = Cheng | first2 = CH | last3 = Tan | first3 = RX | title = Monoamine oxidase inhibitors from rhizoma of Coptis chinensis | journal = Planta medica | volume = 67 | issue = 1 | pages = 74–6 | year = 2001 | pmid = 11270727 | doi = 10.1055/s-2001-10874 }}</ref> It interferes with ] by cancer cells ''in vitro'' when exposed to a chemotherapeutic agent.<ref>{{cite journal | last1 = Zhang | first1 = H | last2 = Yang | first2 = L | last3 = Liu | first3 = S | last4 = Ren | first4 = L | title = Study on active constituents of traditional Chinese medicine reversing multidrug resistance of tumor cells in vitro | journal = Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials | volume = 24 | issue = 9 | pages = 655–7 | year = 2001 | pmid = 11799777 }}</ref> Large doses (50-100 mg/kg) reduced blood sugar levels in mice by increasing aerobic ]. |
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== Bioactive effects == |
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Derivatives of jatrorrhizine (notably 3-alkoxy derivatives, and specifically 3-octyloxy 8-alkyljatrorrhizine derivatives such as 3-octyloxy 8-butyljatrorrhizine) have been synthesized and found to have much stronger antimicrobial effects.<ref>{{cite journal | last1 = Wang | first1 = LJ | last2 = Ye | first2 = XL | last3 = Li | first3 = XG | last4 = Sun | first4 = QL | last5 = Yu | first5 = G | last6 = Cao | first6 = XG | last7 = Liang | first7 = YT | last8 = Zhang | first8 = HS | last9 = Zhou | first9 = JZ | title = Synthesis and antimicrobial activity of 3-alkoxyjatrorrhizine derivatives | journal = Planta medica | volume = 74 | issue = 3 | pages = 290–2 | year = 2008 | pmid = 18300191 | doi = 10.1055/s-2008-1034312 }}</ref><ref>{{cite journal | last1 = Wang | first1 = LJ | last2 = Ye | first2 = XL | last3 = Chen | first3 = Z | last4 = Li | first4 = XG | last5 = Sun | first5 = QL | last6 = Zhang | first6 = BS | last7 = Cao | first7 = XG | last8 = Yu | first8 = G | last9 = Niu | first9 = XH | title = Synthesis and antimicrobial activity of 3-octyloxy-8-alkyljatrorrhizine derivatives | journal = Journal of Asian natural products research | volume = 11 | issue = 4 | pages = 365–70 | year = 2009 | pmid = 19431018 | doi = 10.1080/10286020902727447 }}</ref><ref>{{cite journal | last1 = Bhadra | first1 = K | last2 = Kumar | first2 = GS | title = Therapeutic potential of nucleic acid-binding isoquinoline alkaloids: Binding aspects and implications for drug design | journal = Medicinal research reviews | pages = n/a | year = 2010 | pmid = 20077560 | doi = 10.1002/med.20202 }}</ref> |
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Jatrorrhizine has been reported to have antiinflammatory effect,<ref>{{cite journal | last1 = Arens | first1 = H | last2 = Fischer | first2 = H | last3 = Leyck | first3 = S | last4 = Römer | first4 = A | last5 = Ulbrich | first5 = B | title = Antiinflammatory Compounds from Plagiorhegma dubium Cell Culture1 | journal = Planta Medica | volume = 51 | issue = 1 | pages = 52–6 | year = 1985 | pmid = 17340402 | doi = 10.1055/s-2007-969392 }}</ref> and to improve blood flow and mitotic activity in thioacetamide-traumatized rat livers.<ref>{{cite journal | last1 = Virtanen | first1 = P | last2 = Lassila | first2 = V | last3 = Njimi | first3 = T | last4 = Mengata | first4 = DE | title = Natural protoberberine alkaloids from Enantia chlorantha, palmatine, columbamine and jatrorrhizine for thioacetamide-traumatized rat liver | journal = Acta Anatomica | volume = 131 | issue = 2 | pages = 166–70 | year = 1988 | pmid = 3369286 | doi = 10.1159/000146507 }}</ref> It was found to have antimicrobial<ref>{{cite journal | last1 = Moody | first1 = JO | last2 = Bloomfield | first2 = SF | last3 = Hylands | first3 = PJ | title = In-vitro evaluation of the antimicrobial activities of Enantia chlorantha Oliv. Extractives | journal = African Journal of Medicine and Medical Sciences | volume = 24 | issue = 3 | pages = 269–73 | year = 1995 | pmid = 8798963 }}</ref> and antifungal<ref>{{cite journal | last1 = Volleková | first1 = A | last2 = Kost'álová | first2 = D | last3 = Kettmann | first3 = V | last4 = Tóth | first4 = J | title = Antifungal activity of Mahonia aquifolium extract and its major protoberberine alkaloids | journal = Phytotherapy Research | volume = 17 | issue = 7 | pages = 834–7 | year = 2003 | pmid = 12916091 | doi = 10.1002/ptr.1256 | s2cid = 33470505 }}</ref> activity. It binds and noncompetitively inhibits ] (IC<sub>50</sub> = 4 ] for ] and 62 μM for ])<ref>{{cite journal | last1 = Kong | first1 = LD | last2 = Cheng | first2 = CH | last3 = Tan | first3 = RX | title = Monoamine oxidase inhibitors from rhizoma of Coptis chinensis | journal = Planta Medica | volume = 67 | issue = 1 | pages = 74–6 | year = 2001 | pmid = 11270727 | doi = 10.1055/s-2001-10874 }}</ref> It interferes with ] by cancer cells ''in vitro'' when exposed to a chemotherapeutic agent.<ref>{{cite journal | last1 = Zhang | first1 = H | last2 = Yang | first2 = L | last3 = Liu | first3 = S | last4 = Ren | first4 = L | title = Study on active constituents of traditional Chinese medicine reversing multidrug resistance of tumor cells in vitro | journal = Zhong Yao Cai | volume = 24 | issue = 9 | pages = 655–7 | year = 2001 | pmid = 11799777 }}</ref> Large doses (50–100 mg/kg) reduced blood sugar levels in mice by increasing aerobic ]. |
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] of jatrorrhizine (notably 3-alkoxy derivatives, and specifically 3-octyloxy 8-alkyljatrorrhizine derivatives such as 3-octyloxy 8-butyljatrorrhizine) have been synthesized and found to have much stronger antimicrobial effects.<ref>{{cite journal | last1 = Wang | first1 = LJ | last2 = Ye | first2 = XL | last3 = Li | first3 = XG | last4 = Sun | first4 = QL | last5 = Yu | first5 = G | last6 = Cao | first6 = XG | last7 = Liang | first7 = YT | last8 = Zhang | first8 = HS | last9 = Zhou | first9 = JZ | title = Synthesis and antimicrobial activity of 3-alkoxyjatrorrhizine derivatives | journal = Planta Medica | volume = 74 | issue = 3 | pages = 290–2 | year = 2008 | pmid = 18300191 | doi = 10.1055/s-2008-1034312 }}</ref><ref>{{cite journal | last1 = Wang | first1 = LJ | last2 = Ye | first2 = XL | last3 = Chen | first3 = Z | last4 = Li | first4 = XG | last5 = Sun | first5 = QL | last6 = Zhang | first6 = BS | last7 = Cao | first7 = XG | last8 = Yu | first8 = G | last9 = Niu | first9 = XH | title = Synthesis and antimicrobial activity of 3-octyloxy-8-alkyljatrorrhizine derivatives | journal = Journal of Asian Natural Products Research | volume = 11 | issue = 4 | pages = 365–70 | year = 2009 | pmid = 19431018 | doi = 10.1080/10286020902727447 | s2cid = 29474375 }}</ref><ref>{{cite journal | last1 = Bhadra | first1 = K | last2 = Kumar | first2 = GS | title = Therapeutic potential of nucleic acid-binding isoquinoline alkaloids: Binding aspects and implications for drug design | journal = Medicinal Research Reviews | pages = 821–862| year = 2010 | pmid = 20077560 | doi = 10.1002/med.20202 | volume = 31 | issue = 6 | s2cid = 206250975 | doi-access = free }}</ref> |
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== References == |
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== References == |
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