Ergoline: Difference between revisions

{{Short description|Chemical compound}}

{{Drugbox

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| type =

| IUPAC_name = (6a''R'')-4,6,6a,7,8,9,10,10a-Octahydroindolo[4,3-''fg'']quinoline

| image = Ergoline Structural Formulae V.1.svg

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| image2 = 3D ergoline molecule animation.gif

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| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 478-88-6

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<!--Chemical data-->| C = 14

| H = 16

| N = 2

| smiles = [H][C@@]34Cc1c[nH]c2cccc(c12)[C@@]3([H])CCCN4

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| StdInChIKey = RHGUXDUPXYFCTE-ZWNOBZJWSA-N

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'''Ergoline''' is a chemical compound whose structural skeleton is contained in a variety of [[alkaloid]]s, referred to as ergoline derivatives or ergoline alkaloids. Ergoline alkaloids, one being [[ergine]], were initially characterized in [[ergot]]. Some of these are implicated in the condition [[ergotism]], which can take a convulsive form or a gangrenous form. Even so, many ergoline alkaloids have been found to be clinically useful. Annual world production of ergot alkaloids has been estimated at 5,000–8,000&nbsp;kg of all ergopeptines and 10,000–15,000&nbsp;kg of [[lysergic acid]], used primarily in the manufacture of semi-synthetic derivatives.<ref name=":02">{{cite journal | vauthors = Schiff PL | title = Ergot and its alkaloids | journal = American Journal of Pharmaceutical Education | volume = 70 | issue = 5 | pages = 98 | date = October 2006 | pmid = 17149427 | pmc = 1637017 | doi = 10.5688/aj700598 }}</ref>

Others, such as [[lysergic acid diethylamide]], better known as LSD, a [[Semisynthesis|semi-synthetic]] derivative, and [[ergine]], a natural derivative found in ''[[Argyreia nervosa]]'', ''[[Ipomoea tricolor]]'' and related species, are known [[Psychedelic drug|psychedelic]] substances.<ref>{{cite journal | vauthors = Juszczak GR, Swiergiel AH | title = Recreational use of D-lysergamide from the seeds of Argyreia nervosa, Ipomoea tricolor, Ipomoea violacea, and Ipomoea purpurea in Poland | journal = Journal of Psychoactive Drugs | volume = 45 | issue = 1 | pages = 79–93 | year = 2013 | pmid = 23662334 | doi = 10.1080/02791072.2013.763570 | s2cid = 22086799 }}</ref>

==Natural occurrence==

Ergoline alkaloids are found in lower [[fungi]] and some species of [[flowering plant]]s: the [[Mexico|Mexican]] species ''[[Turbina corymbosa]]'' and ''[[Ipomoea tricolor]]'' of the [[Convolvulaceae]] (morning glory) family, the seeds of which were identified as the psychedelic plant drugs known as "ololiuhqui" and "tlitliltzin", respectively.<ref name="Schardl20063">{{cite book|vauthors=Schardl CL, Panaccione DG, Tudzynski P|year=2006|title=Ergot alkaloids&nbsp;– biology and molecular biology|series=The Alkaloids: Chemistry and Biology|volume=63|pages=45–86|doi=10.1016/S1099-4831(06)63002-2|isbn=978-0-12-469563-4|pmid=17133714}}</ref><ref>{{cite journal | vauthors = Carod-Artal FJ | title = Hallucinogenic drugs in pre-Columbian Mesoamerican cultures | journal = Neurologia | volume = 30 | issue = 1 | pages = 42–49 | year = 2015 | pmid = 21893367 | doi = 10.1016/j.nrl.2011.07.003 | doi-access = free }}</ref> The principal alkaloids in the seeds are ergine and its [[optical isomer]] isoergine, with several other lysergic acid derivatives and clavines present in lesser amounts. The [[Hawaii]]an species ''[[Argyreia nervosa]]'' includes similar alkaloids. It is possible, though not proven, that [[ergine]] or isoergine are responsible for the [[Psychedelic drug|psychedelic]] effects. There may be a fungal origin of the ergoline alkaloids also in the Convolvulaceae. Like the ergot alkaloids in some monocot plants, the ergoline alkaloids found in the plant ''[[Ipomoea asarifolia]]'' (Convolvulaceae) are produced by a seed-transmitted [[Endophyte|endophytic]] [[Clavicipitaceae|clavicipitaceous]] [[fungus]].<ref>{{cite journal | vauthors = Steiner U, Ahimsa-Müller MA, Markert A, Kucht S, Gross J, Kauf N, Kuzma M, Zych M, Lamshöft M, Furmanowa M, Knoop V, Drewke C, Leistner E | display-authors = 6 | title = Molecular characterization of a seed transmitted clavicipitaceous fungus occurring on dicotyledoneous plants (Convolvulaceae) | journal = Planta | volume = 224 | issue = 3 | pages = 533–544 | date = August 2006 | pmid = 16525783 | doi = 10.1007/s00425-006-0241-0 | s2cid = 25682792 }}</ref>

==History==

Ergoline [[alkaloid]]s were first isolated from [[ergot]], a fungus that infects rye and causes [[ergotism]] or St. Anthony's fire.<ref>{{cite journal | vauthors = Gerhards N, Neubauer L, Tudzynski P, Li SM | title = Biosynthetic pathways of ergot alkaloids | journal = Toxins | volume = 6 | issue = 12 | pages = 3281–3295 | date = December 2014 | pmid = 25513893 | pmc = 4280535 | doi = 10.3390/toxins6123281 | doi-access = free }}</ref> Reports of the toxic effects due to ergoline alkaloids date back to the 12th century.<ref name=":12">{{cite journal | vauthors = de Groot AN, van Dongen PW, Vree TB, Hekster YA, van Roosmalen J | title = Ergot alkaloids. Current status and review of clinical pharmacology and therapeutic use compared with other oxytocics in obstetrics and gynaecology | journal = Drugs | volume = 56 | issue = 4 | pages = 523–535 | date = October 1998 | pmid = 9806101 | doi = 10.2165/00003495-199856040-00002 | s2cid = 46971443 }}</ref> Ergot also has a long history of medicinal use, which led to attempts to characterize its activity chemically. First reports of its use date back to 1582, where preparations of ergot were used in small doses by midwives to induce strong uterine contractions.<ref name=":02"/><ref name=":12"/> The first use of ergoline alkaloids in modern medicine was described in 1808 by John Stearns, an American physician, who had reported on the uterine contractile actions of a preparation of ergot as a remedy for "quickening birth".<ref name=":02" />

Attempts to characterize the activity of ergoline alkaloids began in 1907, with the isolation of ergotoxine by G. Barger and F. H. Carrin.<ref name=":2">{{Cite book| vauthors = Sfetcu N |title=Health & Drugs - Disease, Prescription & Medication|publisher=Lulu.com|year=2014|isbn=9781312039995}}</ref> However, the industrial production of ergot alkaloids didn't begin until 1918, when [[Arthur Stoll]] patented the isolation of [[ergotamine tartrate]], which was marketed by [[Sandoz]] in 1921. Following the determination of the basic [[chemical structure]] of the ergot alkaloids in 1930, an era of intensive exploration of synthetic derivatives began and industrial production of ergoline alkaloids exploded, with Sandoz continuing to be the leading company in their production worldwide, up until 1950 when other competitors arose.<ref name=":02" /><ref name=":2" /> The company, now renamed [[Novartis]], still retains its leadership in the product of ergot alkaloids. In 1943, Arthur Stoll and [[Albert Hofmann]] reported the first total synthesis of an ergot alkaloid, ergometrine.<ref>{{cite book | vauthors = Stoll A, Hofmann A | chapter = Chapter 21 The Ergot Alkaloids|date=1965| title = The Alkaloids: Chemistry and Physiology |volume=8 |pages=725–783 |publisher=Elsevier |language=en |doi=10.1016/s1876-0813(08)60060-3 |isbn=978-0-12-469508-5 }}</ref> Though the synthesis found no industrial application, this was a huge leap forward in the industry.

There are a variety of clinically useful ergoline derivatives for the purpose of [[vasoconstriction]], the treatment of [[migraine]]s, and treatment of [[Parkinson's disease]]. Ergoline alkaloids found their place in pharmacology long before modern medicine as preparations of ergot were often used by midwives in the 12th century to stimulate childbirth.<ref>{{Cite book|last=European Commission. Joint Research Centre.|title=Report on the 2017 proficiency test of the European Union reference laboratory for mycotoxins determination of ergot alkaloids in rye.|oclc=1060942360}}</ref> Following Arthur Stoll's isolation of ergometrine, the therapeutic use of ergoline derivatives became well explored.

The induction of uterine contractions via the preparation of ergot was attributed to [[ergonovine]], an ergoline derivative found in ergot, which is a powerful [[oxytocic]]. From this, [[methergine]], a synthetic derivative, was elucidated.<ref name=":12"/> While used to facilitate child birth, ergoline derivatives can pass into [[breast milk]] and should not be used during breastfeeding.<ref name="kidsgrowth2">[http://www.kidsgrowth.org/resources/articledetail.cfm?id=471 kidsgrowth.org --> Drugs and Other Substances in Breast Milk] {{webarchive|url=https://archive.today/20070623011707/http://www.kidsgrowth.org/resources/articledetail.cfm?id=471|date=2007-06-23}} Retrieved on June 19, 2009.</ref> They are uterine contractors that can increase the risk of miscarriage during pregnancy.<ref name="Schardl20063"/>

Another example of medically relevant ergoline alkaloids is [[ergotamine]], an alkaloid also found in ergot. It acts as a [[Vasoconstriction|vasoconstrictor]] and has been reported to control [[migraine]]s. From ergotamine, the [[anti-migraine]] drugs [[dihydroergotamine]] and [[methysergide]] were developed by Albert Hofmann.<ref>{{Cite book| vauthors = Winkelman M, Roberts TB |title=Psychedelic medicine : new evidence for hallucinogenic substances as treatments|date=2007|publisher=Praeger Publishers|isbn=978-0-275-99023-7|oclc=85813998}}</ref>

Ergoline derivatives, such as [[hydergine]], a mixture of dihydroergotoxine mesylates or ergoline mesylates, have also been used in the treatment of dementia. The use of these alkaloids in the treatment of [[Parkinson's disease]] has also been prominent. Drugs such as [[bromocriptine]] act as a dopamine receptor [[agonist]], stimulating the nerves that control movement.<ref name=":3">{{cite journal | vauthors = Lataste X | title = The history and pharmacology of dopamine agonists | journal = The Canadian Journal of Neurological Sciences. Le Journal Canadien des Sciences Neurologiques | volume = 11 | issue = 1 Suppl | pages = 118–123 | date = February 1984 | pmid = 6713309 | doi = 10.1017/S0317167100046266 | doi-access = free }}</ref> Newer synthetic ergoline derivatives that have been synthesized for the treatment of Parkinson's disease include [[pergolide]] and [[lisuride]], which both act as dopamine agonists as well.<ref name=":3" />

A famous ergoline derivative is the [[psychedelic drug]] [[LSD]], a [[Semisynthesis|semi-synthetic]] ergoline alkaloid that was discovered by Albert Hofmann. LSD is considered a [[Schedule I controlled substance]]. [[Ergometrine]] and [[ergotamine]] are included as schedule I precursors in the [[United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances]].<ref name="http://www.incb.org/pdf/e/list/red.pdf2">{{cite web | title = List of Precursors and Chemicals Frequently Used in the Illicit Manufacture of Narcotic Drugs and Psychotropic Substances Under International Control | edition = Eleventh | date = January 2007 | work = International Narcotics Control Board | location = Vienna, Austria | url = http://www.incb.org/pdf/e/list/red.pdf | archive-url = https://web.archive.org/web/20080227224025/http://www.incb.org/pdf/e/list/red.pdf | archive-date=2008-02-27}}.</ref>

== Mechanism of action ==

The mechanism of ergoline alkaloids varies for each derivative. A variety of modifications can be made to the ergoline skeleton to produce medically relevant derivatives. Types of potential ergoline-based drugs include [[dopaminergic]], [[antidopaminergic]], [[Serotonin|serotonergic]], and [[antiserotonergic]].<ref name=":4">{{cite journal | vauthors = Mantegani S, Brambilla E, Varasi M | title = Ergoline derivatives: receptor affinity and selectivity | journal = Farmaco | volume = 54 | issue = 5 | pages = 288–296 | date = May 1999 | pmid = 10418123 | doi = 10.1016/s0014-827x(99)00028-2 }}</ref> Ergoline alkaloids often interfere with multiple receptor sites, leading to negative side effects and adding to the challenge of drug development.

=== Dopaminergic/antidopaminergic ===

Ergolines, such as ergotoxin, have been reported to inhibit the deciduoma reaction, which is reversed through injection of progesterone. Thus, it was concluded that ergotoxin, and related ergolines, act via the [[hypothalamus]] and [[pituitary gland]] to inhibit the [[secretion]] of [[prolactin]].<ref name=":4" /> Drugs such as [[bromocriptine]] interact with the dopaminergic receptor sites as agonists with selectivity for D₂ receptors, making them effective in treating Parkinson's disease. While the part of the ergoline alkaloid structure responsible for dopaminergic properties has yet to be identified, some reason that it is due to the pyroleethylamine moiety while others assert that it is due to the indoleethylamine partial structure.<ref name=":4" />

Antidopaminergic ergolines have found use in [[antiemetic]]s and in the treatment of [[schizophrenia]]. These substances are [[neuroleptic]] and are either an antagonist of dopamine at the postsynaptic level at the D₂ receptor site or an agonist of dopamine at the presynaptic level at the D₁ receptor site.<ref name=":4" /> The antagonist or agonist behavior of the ergolines are substrate dependent and mixed agonist/antagonist behaviors of ergoline derivatives have been reported.<ref name=":4" />

=== Serotonergic/antiserotonergic ===

The primary challenges of developing serotonergic/antiserotonergic ergolines is attributed to [[serotonin]], or 5-HT, acting on various distinct receptor sites. Similarly, ergoline alkaloids have been shown to exhibit both 5-HT agonist and antagonist behaviors for multiple receptors, such as [[metergoline]], a 5-HT_1A agonist/5-HT_2A antagonist, and [[mesulergine]], a 5-HT_2A/2C antagonist.<ref name=":4" /> The selectivity and affinity of ergolines for certain 5-HT receptors can be improved by introducing a bulky group on the phenyl ring of the ergoline skeleton, which would prevent the interaction of ergoline derivatives with receptors.<ref name=":4" /> This methodology has been used to develop selective 5-HT_1A and 5-HT_2A ergolines in particular.

There are 3 main classes of ergoline derivatives, the water-soluble [[amide]]s of ''[[lysergic acid]]'', the water-insoluble ''ergopeptines'' (i.e., ''ergo[[peptides]]''), and the ''clavine'' group.<ref name="Schardl2006">{{cite book|vauthors=Schardl CL, Panaccione DG, Tudzynski P |year=2006|title=Ergot alkaloids&nbsp;– biology and molecular biology|volume=63|pages=45–86|pmid=17133714|doi=10.1016/S1099-4831(06)63002-2|series=The Alkaloids: Chemistry and Biology|isbn=978-0-12-469563-4}}</ref>

===Lysergic acid amides===

** [[CAS number]]: {{CAS|478-94-4}}

** IUPAC name: (8beta(S))-9,10-didehydro-N-(2-hydroxy-1-methylethyl)-6-methyl-ergoline-8-carboxamide

** CAS number: {{CAS|60-79-7}}

** INN: methylergometrine

** IUPAC name: (8beta(S))-9,10-didehydro-N-(1-(hydroxymethyl)propyl)-6-methyl-ergoline-8-carboxamide

** CAS number: {{CAS|113-42-8}}

** INN: methysergide

** IUPAC name: (8''beta'')-9,10-didehydro-''N''-(1-(hydroxymethyl)propyl)-1,6-dimethyl-ergoline-8-carboxamide

** CAS number: {{CAS|361-37-5}}

** INN: lysergide

** IUPAC name: (8beta)-9,10-didehydro-N,N-diethyl-6-methyl-ergoline-8-carboxamide

** CAS number: {{CAS|50-37-3}}

** IUPAC name: 9,10-didehydro-N-(1-hydroxyethyl)-6-methylergoline-8-carboxamide

** CAS number: {{CAS|3343-15-5}}

[[File:Ergine - Ergines.svg|left|Substituted ergine (structural formula)]]

{| class="wikitable" style="float:right"

| [[LSD]] || H || [[Ethyl group|CH₂CH₃]] || CH₂CH₃

{{clear}}

===Peptide alkaloids===<!-- Ergotoxine, Ergopeptine and other titles redirect here -->

Peptide ergot alkaloids or '''[[ergopeptines]]''' (also known as ''ergopeptides'') are ergoline derivatives that contain a tri[[peptide]] structure attached to the basic ergoline ring in the same location as the [[amide]] group of the lysergic acid derivatives. This structure consists of [[proline]] and two other α-amino acids, linked in an unusual [[cyclol]] formation >N-C(OH)< with the carboxyl carbon of proline, at the juncture between the two [[lactam]] rings.<ref>{{cite journal| vauthors = Floss HG |title=Biosynthesis of Ergot Alkaloids and Related Compounds|journal=Tetrahedron Report|date= January 1976 |volume=32|issue=14|pages=873–912|doi=10.1016/0040-4020(76)85047-8}}</ref> Some of the important ergopeptines are summarized below.<ref>{{Cite journal| vauthors = Yates SG, Plattner RD, Garner GB |doi=10.1021/jf00064a038 |title=Detection of ergopeptine alkaloids in endophyte-infected, toxic Ky-31 tall fescue by mass spectrometry/mass spectrometry |journal=Journal of Agricultural and Food Chemistry |volume=33 |issue=4 |pages=719–722 |date = July 1985 |url=http://ddr.nal.usda.gov/bitstream/10113/23986/1/IND86034816.pdf }}{{dead link|date=December 2016 |bot=InternetArchiveBot |fix-attempted=yes }}</ref> In addition to the following ergopeptines, a commonly encountered term is '''ergotoxine''', which refers to a mixture of equal proportions of [[ergocristine]], [[ergocornine]] and ergocryptine, the latter being a 2:1 mixture of ''[[Ergocryptine|alpha]]''- and [[Beta-Ergocryptine|''beta''-ergocryptine]].

* Ergotoxine group ([[valine]] as the amino acid attached to the ergoline moiety, at R² below)

** [[Ergocristine]]

*** [[IUPAC name]]: Ergotaman-3',6',18-trione, 12'-hydroxy-2'-(1-methylethyl)-5'-(phenylmethyl)-, (5'-alpha)-

*** [[CAS number]]: {{CAS|511-08-0}}

** [[Ergocornine]]

*** IUPAC name: Ergotaman-3',6',18-trione, 12'-hydroxy-2',5'-bis(1-methylethyl)-, (5'-alpha)-

*** CAS number: {{CAS|564-36-3}}

** ''alpha''-[[Ergocryptine]]

*** IUPAC name: Ergotaman-3',6',18-trione, 12'-hydroxy-2'-(1-methylethyl)-5'-(2-methylpropyl)-, (5'alpha)-

*** CAS number: {{CAS|511-09-1}}

** [[beta-Ergocryptine|''beta''-Ergocryptine]]

*** IUPAC name: Ergotaman-3',6',18-trione, 12'-hydroxy-2'-(1-methylethyl)-5'-(1-methylpropyl)-, (5'alpha(''S''))-

*** CAS number: {{CAS|20315-46-2}}

* Ergotamine group ([[alanine]] at R²)

** [[Ergotamine]]

*** IUPAC name: Ergotaman-3',6',18-trione, 12'-hydroxy-2'-methyl-5'-(phenylmethyl)-, (5'-alpha)-

*** CAS number: {{CAS|113-15-5}}

** [[Ergovaline]]

*** IUPAC name: Ergotaman-3',6',18-trione, 12'-hydroxy-2'-methyl-5'-(1-methylethyl)-, (5'alpha)-

*** CAS number: {{CAS|2873-38-3}}

** ''alpha''-[[Ergosine]]

*** IUPAC name: Ergotaman-3',6',18-trione, 12'-hydroxy-2'-methyl-5'-(2-methylpropyl)-, (5'-alpha)-

*** CAS number: {{CAS|561-94-4}}

** [[beta-Ergosine|''beta''-Ergosine]]

*** IUPAC name: Ergotaman-3',6',18-trione, 12'-hydroxy-2'-methyl-5'-(1-methylpropyl)-, (5'-alpha(''S''))-

*** CAS number: {{CAS|60192-59-8}}

[[File:Ergopeptine - Ergopeptines.svg|left|Ergopeptides (structural formula)]]

! Name !! R¹ !! R² !! R³ !! Amino acid at R² !! Amino acid at R³

| [[Ergocristine]] || || [[Isopropyl|CH(CH₃)₂]] || [[benzyl]] || Valine || [[Phenylalanine]]

| [[Ergocornine]] || || CH(CH₃)₂ || CH(CH₃)₂ || Valine || [[Valine]]

| ''alpha''-[[Ergocryptine]] || || CH(CH₃)₂ || CH₂CH(CH₃)₂ || Valine || [[Leucine]]

| [[beta-Ergocryptine|''beta''-Ergocryptine]] || || CH(CH₃)₂ || CH(CH₃)CH₂CH₃ (''S'') || Valine || [[Isoleucine]]

| [[Ergotamine]] || || [[Methyl|CH₃]] || benzyl || [[Alanine]] || Phenylalanine

| [[Ergovaline]] || || CH₃ || CH(CH₃)₂ || Alanine || Valine

|-

| ''alpha''-[[Ergosine]] || || CH₃ || CH₂CH(CH₃)₂ || Alanine || Leucine

|-

| [[beta-Ergosine|''beta''-Ergosine]] || || CH₃ || CH(CH₃)CH₂CH₃ (''S'') || Alanine || Isoleucine

|-

| [[Bromocriptine]] ([[semisynthetic]]) || [[Bromine|Br]] || CH(CH₃)₂ || CH₂CH(CH₃)₂ || Valine || Leucine

{{clear}}

===Clavines===

A variety of modifications to the basic ergoline are seen in nature, for example [[agroclavine]], [[elymoclavine]], [[lysergol]]. Those deriving from [[dimethylergoline]] are referred to as clavines. Examples of clavines, include [[festuclavine]], [[fumigaclavine A]], [[fumigaclavine B]] and [[fumigaclavine C]].

===Others===

* [[Cabergoline]] ([[International Nonproprietary Name|INN]])

** [[IUPAC name]]: 1-[(6-Allylergolin-8β-yl)-carbonyl]-1-[3-(dimethylamino)propyl]-3-ethylurea

** [[CAS number]]: {{CAS|81409-90-7}}

* [[Pergolide]] (INN)

** IUPAC name: (8β)-8-((methylthio)methyl)-6-propyl-ergoline

** CAS number: {{CAS|66104-22-1}}

* [[Lisuride]] (INN)

** IUPAC name: 3-(9,10-didehydro-6-methylergolin-8α-yl)-1,1-diethylurea

** CAS number: {{CAS|18016-80-3}}

== See also ==

== References ==

== External links ==

* [https://web.archive.org/web/20040411102155/http://www.people.vcu.edu/~asneden/The%20Ergot%20Alkaloids.pdf The Ergot Alkaloids (A. T. Sneden)]

* [https://web.archive.org/web/20040720041016/http://www.world-of-fungi.org/Mostly_Medical/Ziad_Madlom/Ergot_alkaloids.htm The Ergot Alkaloids Story (Z. Madlom)]

* [http://www.tacethno.com/info/claviceps/ergotalkfungi.txt The Psychoactive Ergot Alkaloids and their occurrence in the Microfungi&nbsp;— M. P. Bock and D. G. Parbery]

* [http://www.erowid.org/plants/mushrooms/references/other/1971_hofmann_bulletin-narcotics.shtml Hofmann, A. ''Teonanácatl and Ololiuqui, two ancient magic drugs of Mexico'' Bulletin on Narcotics 1971 1 3]

{{Hallucinogens}}

{{Adrenergics}}

{{TAAR ligands}}

[[Category:Tryptamine alkaloids]]

[[Category:Quinoline alkaloids]]

[[Category:Alkaloids found in fungi]]