Hypericin

Hypericin[1]

Names
Preferred IUPAC name

1,3,4,6,8,13-Hexahydroxy-10,11-dimethylphenanthro[1,10,9,8-opqra]perylene-7,14-dione

Other names

4,5,7,4',5',7'-Hexahydroxy-2,2'-dimethylnaphthodianthrone

Identifiers

CAS Number

* 548-04-9 Y

3D model (JSmol)

* Interactive image

ChEBI |

* CHEBI:5835 Y

ChEMBL |

* ChEMBL286494 Y

ChemSpider |

* 4444511 Y

KEGG |

* D12433
* C07606

PubChem CID

* 5281051

UNII |

* 7V2F1075HD Y

InChI

* InChI=1S/C30H16O8/c1-7-3-9(31)19-23-15(7)16-8(2)4-10(32)20-24(16)28-26-18(12(34)6-14(36)22(26)30(20)38)17-11(33)5-13(35)21(29(19)37)25(17)27(23)28/h3-6,31-36H,1-2H3 Y

Key: BTXNYTINYBABQR-UHFFFAOYSA-N Y

* InChI=1/C30H16O8/c1-7-3-9(31)19-23-15(7)16-8(2)4-10(32)20-24(16)28-26-18(12(34)6-14(36)22(26)30(20)38)17-11(33)5-13(35)21(29(19)37)25(17)27(23)28/h3-6,31-36H,1-2H3

Key: BTXNYTINYBABQR-UHFFFAOYAC

SMILES

* Cc0cc(O)c1C(=O)c2c(O)cc(O)c3c2c4c1c0c5c6c4c7c3c(O)cc(O)c7C(=O)c6c(O)cc5C

Properties

Chemical formula

| C30H16O8
Molar mass | 504.450 g·mol−1

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Y verify (what is YN ?)
Infobox references

Tracking categories (test):

* SizeSet

Hypericin is a naphthodianthrone, an anthraquinone derivative which, together with hyperforin, is one of the principal active constituents of Hypericum (Saint John's wort).[2][3] Hypericin is believed to act as an antibiotic, antiviral[2] and non-specific kinase inhibitor. Hypericin may inhibit the action of the enzyme dopamine β-hydroxylase, leading to increased dopamine levels,[citation needed] although thus possibly decreasing norepinephrine and epinephrine.

It was initially believed[according to whom?] that the anti-depressant pharmacological activity of hypericin was due to inhibition of monoamine oxidase enzyme. The crude extract of Hypericum is a weak inhibitor of MAO-A and MAO-B.[4][5] Isolated hypericin does not display this activity, but does have some affinity for NMDA receptors.[citation needed] This points in the direction that other constituents are responsible for the MAOI effect. The current belief is that the mechanism of antidepressant activity is due to the inhibition of re-uptake of certain neurotransmitters.[2]

The large chromophore system in the molecule means that it can cause photosensitivity when ingested beyond threshold amounts.[citation needed] Photosensitivity is often seen in animals that have been allowed to graze on St. John's Wort.[citation needed] Because hypericin accumulates preferentially in cancerous tissues, it is also used as an indicator of cancerous cells.[citation needed] In addition, hypericin is under research as an agent in photodynamic therapy, whereby a biochemical is absorbed by an organism to be later activated with spectrum-specific light from specialized lamps or laser sources, for therapeutic purposes.[citation needed] The antibacterial and antiviral effects of hypericin are also believed to arise from its ability for photo-oxidation of cells and viral particles.[2]

Hypericin derives from cyclisation of polyketides.[6][7]

The biosynthesis of hypericins is through the polyketide pathway where an octaketide chain goes through successive cyclizations and decarboxylations to form emodin anthrone which is believed to be the precursor of hypericin. Oxidization reactions yield protoforms which then are converted into hypericin and pseudohypericin. These reactions are photosensitive and take place under exposure to light and using the enzyme Hyp-1.[8][9][10][11][12]

## References

1. ↑ Merck Index, 11th Edition, 4799
2. ↑ 2.0 2.1 2.2 2.3 Mehta, Sweety (2012-12-18). "Pharmacognosy of St. John's Wort". Pharmaxchange.info. http://pharmaxchange.info/press/2012/12/pharmacognosy-of-st-johns-wort/.
3. ↑ Oubre, Alondra (1991). "Hypericin: the active ingredient in Saint John's Wort". http://www.delano.com/ReferenceArticles/Hypericin-Active.html.
4. ↑ Thiede, H. M.; Walper, A. (October 1994). "Inhibition of MAO and COMT by hypericum extracts and hypericin". Journal of Geriatric Psychiatry and Neurology 7 (Suppl 1): S54–56. doi:10.1177/089198879400700114. ISSN 0891-9887. PMID 7857510.
5. ↑ Bladt, S.; Wagner, H. (October 1994). "Inhibition of MAO by fractions and constituents of hypericum extract". Journal of Geriatric Psychiatry and Neurology 7 (Suppl 1): S57–59. doi:10.1177/089198879400700115. ISSN 0891-9887. PMID 7857511.
6. ↑ Loren W. Walker (1999). A Review of the Hypothetical Biogenesis and Regulation of Hypericin synthesis via the Polyketide Pathway in Hypericum perforatum and Experimental Methods Proposed to Evaluate the Hypothesis. http://www.l2w.cc/pages/HYPE/index.htm. Retrieved 2011-01-04.
7. ↑ Christian Hertweck (2009). "Polyketide Biosynthesis". Angew. Chem. Int. Ed. 48 (26): 4688–4716. doi:10.1002/anie.200806121. PMID 19514004.
8. ↑ "Hypericins as potential leads for new therapeutics". Int J Mol Sci 11 (2): 562–594. 2010. doi:10.3390/ijms11020562. PMID 20386655.
9. ↑ "From the Photosensitizer Hypericin to the Photoreceptor Stentorin- The Chemistry of Phenanthroperylene Quinones". Angew. Chem. Int. Ed. Engl. 38 (21): 3116–3136. 1999. doi:10.1002/(SICI)1521-3773(19991102)38:21<3116::AID-ANIE3116>3.0.CO;2-S. PMID 10556884.
10. ↑ "Molecular and biochemical characterization of an enzyme responsible for the formation of hypericin in St. John's wort (Hypericum perforatum L.)". J. Biol. Chem. 278 (34): 32413–32422. 2003. doi:10.1074/jbc.M301681200. PMID 12799379.
11. ↑ "Crystal structure of Hyp-1, a St. John's wort protein implicated in the biosynthesis of hypericin". J. Struct. Biol. 169 (2): 161–171. 2010. doi:10.1016/j.jsb.2009.10.008. PMID 19853038.
12. ↑ "Hypericins: biotechnological production from cell and organ cultures". Appl. Microbiol. Biotechnol. 98 (22): 9187–9198. 2014. doi:10.1007/s00253-014-6119-3. PMID 25301586.

Glutamate receptor modulators

* v
* t
* e

Ionotropic glutamate receptor modulators

AMPAR|

* Agonists: Main site agonists: 5-Fluorowillardiine
* Acromelic acid (acromelate)
* AMPA
* BOAA
* Domoic acid
* Glutamate
* Ibotenic acid
* Proline
* Quisqualic acid
* Willardiine; Positive allosteric modulators: Aniracetam
* BIIB-104 (PF-04958242)
* Cyclothiazide
* CX-516
* CX-546
* CX-614
* Farampator (CX-691, ORG-24448)
* CX-717
* CX-1739
* CX-1942
* Diazoxide
* Hydrochlorothiazide (HCTZ)
* IDRA-21
* LY-392098
* LY-395153
* LY-404187
* LY-451646
* LY-503430
* Mibampator (LY-451395)
* Nooglutyl
* ORG-26576
* Oxiracetam
* PEPA
* Piracetam
* Pramiracetam
* S-18986
* Tulrampator (S-47445, CX-1632)

* Antagonists: ACEA-1011
* ATPO
* Becampanel
* Caroverine
* CNQX
* Dasolampanel
* DNQX
* Fanapanel (MPQX)
* GAMS
* Kaitocephalin
* Kynurenic acid
* Kynurenine
* Licostinel (ACEA-1021)
* NBQX
* PNQX
* Selurampanel
* Tezampanel
* Theanine
* Topiramate
* YM90K
* Zonampanel; Negative allosteric modulators: Barbiturates (e.g., pentobarbital, sodium thiopental)
* Cyclopropane
* Enflurane
* Ethanol (alcohol)
* Evans blue
* GYKI-52466
* GYKI-53655
* Halothane
* Irampanel
* Isoflurane
* Perampanel
* Pregnenolone sulfate
* Sevoflurane
* Talampanel; Unknown/unsorted antagonists: Minocycline

KAR|

* Agonists: Main site agonists: 5-Bromowillardiine
* 5-Iodowillardiine
* Acromelic acid (acromelate)
* AMPA
* ATPA
* Domoic acid
* Glutamate
* Ibotenic acid
* Kainic acid
* LY-339434
* Proline
* Quisqualic acid
* SYM-2081; Positive allosteric modulators: Cyclothiazide
* Diazoxide
* Enflurane
* Halothane
* Isoflurane

* Antagonists: ACEA-1011
* CNQX
* Dasolampanel
* DNQX
* GAMS
* Kaitocephalin
* Kynurenic acid
* Licostinel (ACEA-1021)
* LY-382884
* NBQX
* NS102
* Selurampanel
* Tezampanel
* Theanine
* Topiramate
* UBP-302; Negative allosteric modulators: Barbiturates (e.g., pentobarbital, sodium thiopental)
* Enflurane
* Ethanol (alcohol)
* Evans blue
* NS-3763
* Pregnenolone sulfate

NMDAR|

* Agonists: Main site agonists: AMAA
* Aspartate
* Glutamate
* Homocysteic acid (L-HCA)
* Homoquinolinic acid
* Ibotenic acid
* NMDA
* Proline
* Quinolinic acid
* Tetrazolylglycine
* Theanine; Glycine site agonists: β-Fluoro-D-alanine
* ACBD
* ACC (ACPC)
* ACPD
* AK-51
* Apimostinel (NRX-1074)
* B6B21
* CCG
* D-Alanine
* D-Cycloserine
* D-Serine
* DHPG
* Dimethylglycine
* Glycine
* HA-966
* L-687414
* L-Alanine
* L-Serine
* Milacemide
* Neboglamine (nebostinel)
* Rapastinel (GLYX-13)
* Sarcosine; Polyamine site agonists: Neomycin
* Spermidine
* Spermine; Other positive allosteric modulators: 24S-Hydroxycholesterol
* DHEA (prasterone)
* DHEA sulfate (prasterone sulfate)
* Epipregnanolone sulfate
* Pregnenolone sulfate
* SAGE-201
* SAGE-301
* SAGE-718

* Antagonists: Competitive antagonists: AP5 (APV)
* AP7
* CGP-37849
* CGP-39551
* CGP-39653
* CGP-40116
* CGS-19755
* CPP
* Kaitocephalin
* LY-233053
* LY-235959
* LY-274614
* MDL-100453
* Midafotel (d-CPPene)
* NPC-12626
* NPC-17742
* PBPD
* PEAQX
* Perzinfotel
* PPDA
* SDZ-220581
* Selfotel; Glycine site antagonists: 4-Cl-KYN (AV-101)
* 5,7-DCKA
* 7-CKA
* ACC
* ACEA-1011
* ACEA-1328
* Apimostinel (NRX-1074)
* AV-101
* Carisoprodol
* CGP-39653
* CNQX
* D-Cycloserine
* DNQX
* Felbamate
* Gavestinel
* GV-196771
* Harkoseride
* Kynurenic acid
* Kynurenine
* L-689560
* L-701324
* Licostinel (ACEA-1021)
* LU-73068
* MDL-105519
* Meprobamate
* MRZ 2/576
* PNQX
* Rapastinel (GLYX-13)
* ZD-9379; Polyamine site antagonists: Arcaine
* Co 101676
* Diaminopropane
* Diethylenetriamine
* Huperzine A
* Putrescine; Uncompetitive pore blockers (mostly dizocilpine site): 2-MDP
* 3-HO-PCP
* 3-MeO-PCE
* 3-MeO-PCMo
* 3-MeO-PCP
* 4-MeO-PCP
* 8A-PDHQ
* 18-MC
* α-Endopsychosin
* Alaproclate
* Alazocine (SKF-10047)
* Amantadine
* Aptiganel
* Argiotoxin-636
* Arketamine
* ARL-12495
* ARL-15896-AR
* ARL-16247
* Budipine
* Coronaridine
* Delucemine (NPS-1506)
* Dexoxadrol
* Dextrallorphan
* Dextromethadone
* Dextromethorphan
* Dextrorphan
* Dieticyclidine
* Diphenidine
* Dizocilpine
* Ephenidine
* Esketamine
* Etoxadrol
* Eticyclidine
* Fluorolintane
* Gacyclidine
* Ibogaine
* Ibogamine
* Indantadol
* Ketamine
* Ketobemidone
* Lanicemine
* Levomethadone
* Levomethorphan
* Levomilnacipran
* Levorphanol
* Loperamide
* Memantine
* Methadone
* Methorphan
* Methoxetamine
* Methoxphenidine
* Milnacipran
* Morphanol
* NEFA
* Neramexane
* Nitromemantine
* Noribogaine
* Norketamine
* Orphenadrine
* PCPr
* PD-137889
* Pethidine (meperidine)
* Phencyclamine
* Phencyclidine
* Propoxyphene
* Remacemide
* Rhynchophylline
* Rimantadine
* Rolicyclidine
* Sabeluzole
* Tabernanthine
* Tenocyclidine
* Tiletamine
* Tramadol; Ifenprodil (NR2B) site antagonists:
* Besonprodil
* Buphenine (nylidrin)
* CO-101244 (PD-174494)
* Eliprodil
* Haloperidol
* Isoxsuprine
* Radiprodil (RGH-896)
* Rislenemdaz (CERC-301, MK-0657)
* Ro 8-4304
* Ro 25-6981
* Safaprodil
* Traxoprodil (CP-101606); NR2A-selective antagonists: MPX-004
* MPX-007
* TCN-201
* TCN-213; Cations: Hydrogen
* Magnesium
* Zinc; Alcohols/volatile anesthetics/related: Benzene
* Butane
* Chloroform
* Cyclopropane
* Desflurane
* Diethyl ether
* Enflurane
* Ethanol (alcohol)
* Halothane
* Hexanol
* Isoflurane
* Methoxyflurane
* Nitrous oxide
* Octanol
* Sevoflurane
* Toluene
* Trichloroethane
* Trichloroethanol
* Trichloroethylene
* Urethane
* Xenon
* Xylene; Unknown/unsorted antagonists: ARR-15896
* Bumetanide
* Caroverine
* Conantokin
* D-αAA
* Dexanabinol
* Flufenamic acid
* Flupirtine
* FPL-12495
* FR-115427
* Furosemide
* Hodgkinsine
* Ipenoxazone (MLV-6976)
* MDL-27266
* Metaphit
* Minocycline
* MPEP
* Niflumic acid
* Pentamidine
* Pentamidine isethionate
* Piretanide
* Psychotridine
* Transcrocetin (saffron)

* Unsorted: Allosteric modulators: AGN-241751

* See also: Receptor/signaling modulators
* Metabotropic glutamate receptor modulators
* Glutamate metabolism/transport modulators

* v
* t
* e

Metabotropic glutamate receptor modulators

Group I|

| mGluR1|

* Agonists: ACPD
* DHPG
* Glutamate
* Ibotenic acid
* Quisqualic acid
* Ro01-6128
* Ro67-4853
* Ro67-7476
* VU-71
* Theanine

* Antagonists: BAY 36-7620
* CPCCOEt
* Cyclothiazide
* LY-367,385
* LY-456,236
* MCPG
* NPS-2390

|

mGluR5|

* Agonists: ACPD
* ADX-47273
* CDPPB
* CHPG
* DFB
* DHPG
* Glutamate
* Ibotenic acid
* Quisqualic acid
* VU-1545

* Antagonists: CTEP
* DMeOB
* LY-344,545
* Mavoglurant
* MCPG
* NPS-2390
* Remeglurant
* SIB-1757
* SIB-1893; Negative allosteric modulators: Basimglurant
* Dipraglurant
* Fenobam
* GRN-529
* MPEP
* MTEP
* Raseglurant

Group II|

| mGluR2|

* Agonists: BINA
* CBiPES
* DCG-IV
* Eglumegad
* Glutamate
* Ibotenic acid
* LY-379,268
* LY-404,039 (pomaglumetad)
* LY-487,379
* LY-566,332
* MGS-0028
* Pomaglumetad methionil (LY-2140023)
* Talaglumetad; Positive allosteric modulators: JNJ-40411813 (ADX-71149)

* Antagonists: APICA
* CECXG
* EGLU
* HYDIA
* LY-307,452
* LY-341,495
* MCPG
* MGS-0039
* PCCG-4; Negative allosteric modulators: Decoglurant
* RO4491533

|

mGluR3|

* Agonists: CBiPES
* DCG-IV
* Eglumegad
* Glutamate
* Ibotenic acid
* LY-379,268
* LY-404,039 (pomaglumetad)
* LY-487,379
* MGS-0028
* Pomaglumetad methionil (LY-2140023)
* Talaglumetad

* Antagonists: APICA
* CECXG
* EGLU
* HYDIA
* LY-307,452
* LY-341,495
* MCPG
* MGS-0039; Negative allosteric modulators: Decoglurant
* RO4491533

Group III|

| mGluR4|

* Agonists: Glutamate
* L-AP4
* PHCCC
* VU-001,171
* VU-0155,041; Positive allosteric modulators: Foliglurax
* MPEP

* Antagonists: CPPG
* MAP4
* MPPG
* MSOP
* MTPG
* UBP-1112

|

mGluR6|

* Agonists: Glutamate
* L-AP4

* Antagonists: CPPG
* MAP4
* MPPG
* MSOP
* MTPG
* UBP-1112

mGluR7|

* Agonists: AMN082
* Glutamate
* L-AP4

* Antagonists: CPPG
* MAP4
* MMPIP
* MPPG
* MSOP
* MTPG
* UBP-1112

mGluR8|

* Agonists: DCPG
* Glutamate
* L-AP4

* Antagonists: CPPG
* MAP4
* MPPG
* MSOP
* MTPG
* UBP-1112

See also: Receptor/signaling modulators • Ionotropic glutamate receptor modulators • Glutamate metabolism/transport modulators

* v
* t
* e

Sigma receptor modulators

σ1|

* Agonists: 3-PPP
* 4-PPBP
* 5-MeO-DMT
* Alazocine (SKF-10047)
* Amantadine
* ANAVEX2-73
* Arketamine
* BD-737
* BD-1052
* Captodiame
* Citalopram
* CGRP
* Cloperastine
* Cocaine
* Cutamesine (SA-4503)
* Cyclazocine
* Dehydroepiandrosterone (DHEA) (prasterone)
* Dehydroepiandrosterone sulfate (DHEA-S) (prasterone sulfate)
* Dextrallorphan
* Dextromethorphan (DXM)
* Dextrorphan (DXO)
* Dimemorfan
* Dimethyltryptamine (DMT)
* Ditolylguanidine (DTG)
* Donepezil
* Eliprodil
* Escitalopram
* Fabomotizole (afobazole)
* Fluoxetine
* Fluvoxamine
* Ifenprodil
* Igmesine (JO-1784)
* IPAB
* Ketamine
* L-687384
* MDMA (midomafetamine)
* Memantine
* Methamphetamine
* Methoxetamine
* Methylphenidate
* Nepinalone
* Neuropeptide Y
* Noscapine
* OPC-14523
* Opipramol
* Pentazocine
* Pentoxyverine (carbetapentane)
* PRE-084
* Pregnenolone
* Pregnenolone sulfate
* Pridopidine
* Racemethorphan (methorphan)
* Racemorphan (morphanol)
* UMB-23
* UMB-82

* Antagonists: 3-PPP
* AC-927
* BD-1008
* BD-1031
* BD-1047
* BD-1060
* BD-1063
* BD-1067
* BMY-14802 (BMS-181100)
* CM-156
* Dup-734
* E-5842
* E-52862 (S1RA)
* Haloperidol
* LR-132
* LR-172
* MS-377
* NE-100
* NPC-16377
* Panamesine (EMD-57455)
* PD-144418
* Pentazocine
* Progesterone
* Rimcazole (BW-234U)
* Sertraline
* SR-31742A

* Allosteric modulators: Phenytoin; Positive: Methylphenylpiracetam
* SOMCL-668

* Unknown/unsorted: 3-Methoxydextrallorphan
* 3-MeO-PCP
* 4C-T-2
* 4-IBP
* 4-IPBS
* 4-MeO-PCP
* 5-MeO-DALT
* 5-MeO-DiPT
* Amitriptyline
* Azidopamil
* Chlorpromazine
* Clemastine
* Clomipramine
* Clorgiline
* D-Deprenyl
* DiPT
* DPT
* Ibogaine
* Imipramine
* KCR-12-83.1
* Nemonapride
* Noribogaine
* RHL-033
* RS-67,333
* RTI-55
* Saffron
* Safinamide
* Selegiline
* Spipethiane
* Trifluoperazine
* W-18
* YKP10A

σ2|

* Agonists: 3-PPP
* Arketamine
* BD-1047
* BD1063
* Ditolylguanidine (DTG)
* DKR-1005
* DKR-1051
* Haloperidol
* Ifenprodil
* Ketamine
* MDMA (midomafetamine)
* Methamphetamine
* OPC-14523
* Opipramol
* PB-28
* Phencyclidine
* Siramesine (Lu 28-179)
* UKH-1114

* Antagonists: AC-927
* BD-1008
* BD-1067
* CM-156
* CT-1812
* LR-172
* MIN-101
* Panamesine (EMD-57455)
* SAS-0132

* Unknown/unsorted: 3-Methoxydextrallorphan
* 3-MeO-PCE
* 4-MeO-PCP
* 5-MeO-DALT
* 5-MeO-DiPT
* Clemastine
* DiPT
* DPT
* Ibogaine
* Nemonapride
* Nepinalone
* Noribogaine
* Pentazocine
* RS-67,333
* Safinamide
* TMA
* UMB-23
* UMB-82
* W-18

Unsorted|

* Agonists: Berberine
* Ethylketazocine
* Fourphit
* Metaphit
* Naluzotan
* Tapentadol
* Tenocyclidine

* Antagonists: AHD1
* AZ66
* Lamotrigine
* Naloxone
* SM-21
* UMB-100
* UMB-101
* UMB-103
* UMB-116
* YZ-011
* YZ-069
* YZ-185

* Allosteric modulators: SKF-83959

* Unknown/unsorted: 18-Methoxycoronaridine
* BMY-13980
* Butaclamol
* Caramiphen
* Carvotroline
* Chlorphenamine (chlorpheniramine)
* Chlorpromazine
* Cinnarizine
* Cinuperone
* Clocapramine
* Dezocine
* EMD-59983
* Hypericin (St. John's wort)
* Fluphenazine
* Gevotroline (WY-47384)
* Mepyramine (pyrilamine)
* Molindone
* Perphenazine
* Pimozide
* Proadifen
* Promethazine
* Propranolol
* Quinidine
* Remoxipride
* SL 82.0715
* SR-31747A
* Tiospirone (BMY-13859)
* Venlafaxine

See also: Receptor/signaling modulators

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Original source: https://en.wikipedia.org/wiki/Hypericin. Read more

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Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:Hypericin&oldid=489200"
*[CID]: Compound ID
*[v]: View this template
*[t]: Discuss this template
*[e]: Edit this template
*[AMPAR]: α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptor
*[KAR]: Kainate receptor
*[NMDAR]: N-Methyl-D-aspartate receptor
*[DHEA]: Dehydroepiandrosterone
*[mGluR1]: Metabotropic glutamate receptor 1
*[mGluR5]: Metabotropic glutamate receptor 5
*[mGluR2]: Metabotropic glutamate receptor 2
*[mGluR3]: Metabotropic glutamate receptor 3
*[mGluR4]: Metabotropic glutamate receptor 4
*[mGluR6]: Metabotropic glutamate receptor 6
*[mGluR7]: Metabotropic glutamate receptor 7
*[mGluR8]: Metabotropic glutamate receptor 8
*[CGRP]: Calcitonin gene-related peptide
*[MDMA]: Methylenedioxymethamphetamine
*[DiPT]: N,N-Diisopropyltryptamine
*[DPT]: N,N-Dipropyltryptamine
*[TMA]: 3,4,5-Trimethoxyamphetamine