Argyreia nervosa

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Argyreia nervosa
Elephant creeper (Argyreia nervosa) - 20100808.jpg
Argyreia nervosa flowers (enlarge)
Scientific classification OOjs UI icon edit-ltr.svg
Kingdom: Plantae
Clade: Tracheophytes
Clade: Angiosperms
Clade: Eudicots
Clade: Asterids
Order: Solanales
Family: Convolvulaceae
Genus: Argyreia
Species:
A. nervosa
Binomial name
Argyreia nervosa
Synonyms [1]

Argyreia speciosa(L.f.) Sweet
Convolvulus nervosusBurm.f.
Convolvulus speciosusL.f.
Santaloides minus [2] Lettsomia nervosa(Burm.f.) Roxb.

Contents

Argyreia nervosa is a perennial climbing vine native to the Indian subcontinent and introduced to numerous areas worldwide, including Hawaii, Africa, and the Caribbean. Though it can be invasive, it is often prized for its aesthetic and medicinal value. [3] Common names include Hawaiian baby woodrose, adhoguda अधोगुडा or vidhara विधारा (Sanskrit), elephant creeper and woolly morning glory. Its seeds are known for their powerful entheogenic properties, greater or similar to those of Ipomoea species, with users reporting significant psychedelic and spiritual experiences. [4] [5] The two botanical varieties are Argyreia nervosa var. nervosa described here, and Argyreia nervosa var. speciosa, the roots of which are used in Ayurvedic medicine. [3] [6]

Argyreia nervosa contains various ergoline alkaloids such as ergine. [7] A study reported stereoisomers of ergine to be found in the seeds at a concentration of 0.325% of dry weight. [8] Two modern studies from a team of researchers also revealed lysergic acid, [9] methylergometrine (syn. lysergic acid butanolamide), methysergide, lysergylalanine, and suspected, unidentifed ergopeptines. [10] A study of the related Ipomoea tricolor showed that ergoline concentrations in the leaves are 12-fold lower than that of the seeds. [11]

History

While seeds of other Convolvulaceae, specifically Ipomoea corymbosa (ololiuhqui) and Ipomoea tricolor (tlitliltzin), were used in shamanic rituals of Latin America for centuries, A. nervosa was not traditionally used for this purpose. Its properties were first brought to attention in the 1960s.[ citation needed ]

Cultivation

Where temperatures fall below 13 °C (55 °F), Argyreia nervosa is grown in a warm greenhouse. Elsewhere, it is grown on arbours, pergolas, walls, or trees. It is often grown professionally under glass in a loam-based potting compost (John Innes No. 3) in full light, and watered freely from spring to autumn, with a balanced liquid fertilizer applied monthly and reduced water in winter. It is grown outdoors in moderately fertile, moist but well-drained soil in full sun. Pruning is done in late winter. [12]

Glycosides

Argyroside Argyroside.svg
Argyroside

Ergolines

Ergoline alkaloids of known percentage
Compound namePercentage of dry seed weight constitutedChemical structure
Isoergine 0.188% Ergine.svg
Ergine 0.136%
Ergometrine 0.049% Ergonovine-skeletal.svg
Lysergic acid hydroxyethylamide 0.035% D-lysergic acid methyl carbinolamide.svg
Isolysergic acid hydroxyethylamide 0.024%
Elymoclavine 0.022% Elymoclavine.svg
Ergometrinine 0.011% Ergometrinine.svg
Chanoclavine 0.016% Chanoclavine.svg
Ergoline alkaloids of unknown percentage
Compound nameChemical structure
Agroclavine Agroclavine.svg
Festuclavine Festuclavine.svg
Chanoclavine II Chanoclavine II.svg
Lysergene Lysergene.svg
Lysergol Lysergol.svg
Isolysergol
Setoclavine Setoclavine.svg
Isosetoclavine

Hydroxycinnamic acids

Hydroxycinnamic acids
Compound nameChemical structure
Caffeic acid Kaffeesaure.svg
Ethyl caffeate Ethyl caffeate.svg

Fatty acids

Fatty acids
Compound nameChemical structure
Myristoleic acid Myristoleic acid.png
Myristic acid Myristic acid.svg
Palmitic acid Palmitic acid.svg
Linoleic acid LAnumbering.png
Linolenic acid
Oleic acid Oleic-acid-based-on-xtal-1997-2D-skeletal.png
Stearic acid Stearic acid.svg
Nonadecylic acid Nonadecylic acid.svg
Eicosenoic acid
Heneicosylic acid Heneicosylic acid.png
Behenic acid Behenic Acid.svg
12-methylmyristic acid
15-methylstearic acid
Glycosides of fatty acids
Fatty acidChemical structure
Palmitic acid Palmitic acid.svg
Oleic acid Oleic-acid-based-on-xtal-1997-2D-skeletal.png
Stearic acid Stearic acid.svg
Behenic acid Behenic Acid.svg
Linoleic acid LAnumbering.png
Linolenic acid ALAnumbering.svg

Entheogen

Hawaiian baby woodrose seeds Hawaiian Baby Woodrose Seeds.jpg
Hawaiian baby woodrose seeds

Certain New Age sources claim that, according to 'various oral histories' Huna shamans used the powdered seeds to prepare an entheogenic drink. [14] This is unlikely to reflect an authentic practice having once formed a part of traditional Hawaiian Religion, [15] given that Huna has been widely discredited as a culturally appropriative New Age religion invented by Max Freedom Long. [16] The seeds of Argyreia nervosa can produce psychoactive effects, but it has not yet been demonstrated satisfactorily that their use as an entheogen predates the various countercultural movements of the 1960s. [15] Given that A. nervosa is not native to Hawaii, having been introduced there from India, any Hawaiian practices involving it are unlikely to be of any antiquity. It cannot, however, be ruled out that the plant may have been utilised as an intoxicant in its native India at some time in the past, although evidence for this (if present) has not yet come to light. [15] The seeds of A. nervosa contain ergot alkaloids varying considerably in concentration with LSA weight ranging between exactly similar looking seeds from 3 μg to 34 μg (avg 17 μg). [17] However, in its effects, LSA is about one tenth as potent as its cousin LSD, making a threshold dose level for LSA (D-Lysergic Acid Amide) about 500 μg. [18] The psychoactive effects of the seeds may therefore be due to other alkaloids present in them and the safe and effective dose may be difficult to predict.

Uses in the traditional medicine of India

While he does not claim there to be any evidence for the use of the seeds of A. nervosa as a traditional entheogen in its native India, Christian Rätsch does describe some interesting traditional uses of the root of the plant in Ayurveda somewhat suggestive of effects upon the CNS: [15]

The root is regarded as a tonic for the nerves and brain and is ingested as a rejuvenation tonic and aphrodisiac to increase intelligence. [15]

Other traditional uses are in the treatment of gonorrhea, strangury, chronic ulcers, diabetes, anemia, and cerebral disorders. The plant is also used as appetizer, brain tonic, cardiotonic, and aphrodisiac. It possesses anti-inflammatory, immunomodulatory, antibacterial, antiviral, and antifungal activities [19]

Related Research Articles

<span class="mw-page-title-main">Convolvulaceae</span> Family of flowering plants

Convolvulaceae, commonly called the bindweeds or morning glories, is a family of about 60 genera and more than 1,650 species. These species are primarily herbaceous vines, but also include trees, shrubs and herbs. The tubers of several species are edible, the best known of which is the sweet potato.

<i>Ipomoea corymbosa</i> Species of plant

Ipomoea corymbosa is a species of morning glory, native throughout Latin America from Mexico as far south as Peru and widely naturalised elsewhere. Its common names include Christmasvine, Christmaspops, and snakeplant.

<span class="mw-page-title-main">Ergot</span> Group of fungi of the genus Claviceps

Ergot or ergot fungi refers to a group of fungi of the genus Claviceps.

<span class="mw-page-title-main">Ergine</span> Chemical compound

Ergine, also known as lysergic acid amide and lysergamide, is an ergoline alkaloid that occurs in various species of vines of the Convolvulaceae and some species of fungi. The psychedelic properties in the seeds of ololiuhqui, Hawaiian baby woodrose and morning glories have been linked to ergine and/or isoergine, its epimer, as it is an alkaloid present in the seeds.

<span class="mw-page-title-main">Ergoline</span> Chemical compound

Ergoline is a chemical compound whose structural skeleton is contained in a variety of alkaloids, 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 kg of all ergopeptines and 10,000–15,000 kg of lysergic acid, used primarily in the manufacture of semi-synthetic derivatives.

<span class="mw-page-title-main">Lysergic acid</span> Precursor for a range of ergoline alkaloids produced by the ergot fungus

Lysergic acid, also known as D-lysergic acid and (+)-lysergic acid, is a precursor for a wide range of ergoline alkaloids that are produced by the ergot fungus and found in the seeds of Turbina corymbosa (ololiuhqui), Argyreia nervosa, and Ipomoea tricolor.

<i>Ipomoea</i> Genus of flowering plants

Ipomoea is the largest genus in the plant family Convolvulaceae, with over 600 species. It is a large and diverse group, with common names including morning glory, water convolvulus or water spinach, sweet potato, bindweed, moonflower, etc. The genus occurs throughout the tropical and subtropical regions of the world, and comprises annual and perennial herbaceous plants, lianas, shrubs, and small trees; most of the species are twining climbing plants.

<i>Ipomoea tricolor</i> Species of plant

Ipomoea tricolor, the Mexican morning glory or just morning glory, is a species of flowering plant in the family Convolvulaceae, native to the tropics of the Americas, and widely cultivated and naturalised elsewhere.

<span class="mw-page-title-main">Lysergic acid hydroxyethylamide</span> Chemical compound

D-Lysergic acid α-hydroxyethylamide, also known as D-lysergic acid methyl carbinolamide, is a Lysergamide and alkaloid of the Ergoline family, it is present in higher concentrations in the parasitic fungi species "Claviceps", mainly the Claviceps paspali, also in Claviceps Purpurea. This fungi grows in various species in the Convolvulaceae family like the Ipomoea violacea, the Rivea corymbosa (Ololiuhqui), and the Argyreia nervosa. Heavenly Blue Morning Glory and Hawaiian Baby Woodrose especially contain high amounts of LSH, with content varying between species and by how fresh the seeds are. LSH is a psychoactive Ergoline and has effects similar to LSD due to similarity in the structure and is the main psychoactive compound found in Claviceps Paspali and in (fresh) Heavenly Blue Morning Glory Seeds. LSH is unstable and breaks down into LSA quickly, so old seeds often only contains LSA and iso-LSA. When the seeds are fresh, they contain significantly higher amounts of LSH.

<span class="mw-page-title-main">Methylergometrine</span> Chemical compound

Methylergometrine, also known as methylergonovine and sold under the brand name Methergine, is a medication of the ergoline and lysergamide groups which is used as an oxytocic in obstetrics and as an antimigraine agent in the treatment of migraine headaches. It reportedly produces psychedelic effects similar to those of lysergic acid diethylamide (LSD) at high doses.

<span class="mw-page-title-main">Lysergol</span> Chemical compound

Lysergol is an alkaloid of the ergoline family that occurs as a minor constituent in some species of fungi, and in the morning glory family of plants (Convolvulaceae), including the hallucinogenic seeds of Rivea corymbosa (ololiuhqui), Argyreia nervosa and Ipomoea violacea. Lysergol is not a controlled substance in the USA. Its possession and sale is also legal under the U.S. Federal Analog Act because it does not have a known pharmacological action or a precursor relationship to LSD, which is a controlled substance. However, lysergol is an intermediate in the manufacture of some ergoloid medicines.

<i>Ipomoea violacea</i> Species of flowering plant

Ipomoea violacea is a perennial species of Ipomoea that occurs throughout the world with the exception of the European continent. It is most commonly called beach moonflower or sea moonflower as the flowers open at night.

<span class="mw-page-title-main">Indole alkaloid</span> Class of alkaloids

Indole alkaloids are a class of alkaloids containing a structural moiety of indole; many indole alkaloids also include isoprene groups and are thus called terpene indole or secologanin tryptamine alkaloids. Containing more than 4100 known different compounds, it is one of the largest classes of alkaloids. Many of them possess significant physiological activity and some of them are used in medicine. The amino acid tryptophan is the biochemical precursor of indole alkaloids.

<i>Claviceps purpurea</i> Species of fungus


Claviceps purpurea is an ergot fungus that grows on the ears of rye and related cereal and forage plants. Consumption of grains or seeds contaminated with the survival structure of this fungus, the ergot sclerotium, can cause ergotism in humans and other mammals. C. purpurea most commonly affects outcrossing species such as rye, as well as triticale, wheat and barley. It affects oats only rarely.

<i>Achnatherum robustum</i> Species of flowering plant

Achnatherum robustum, commonly known as sleepy grass, is a perennial plant in the Poaceae or grass family.

<i>Ipomoea hederacea</i> Species of flowering plant

Ipomoea hederacea, the ivy-leaved morning glory or Kaladana, is a flowering plant in the bindweed family. The species is native to tropical parts of the Americas, and has more recently been introduced to North America. It now occurs there from Arizona to Florida and north to Ontario and North Dakota. Like most members of the family, it is a climbing vine with alternate leaves on twining stems. The flowers are blue to rose-purple with a white inner throat and emerge in summer and continue until late fall. The leaves are typically three-lobed, but sometimes may be five-lobed or entire. Flowers occur in clusters of one to three and are 2.5–4.5 cm long and wide. The sepals taper to long, recurved tips and measure 12–24 mm long. The species shares some features with the close relative Ipomoea purpurea, and is almost identical in appearance to wild forms of I. nil.

<span class="mw-page-title-main">Ergocryptine</span> Chemical compound

Ergocryptine is an ergopeptine and one of the ergoline alkaloids. It is isolated from ergot or fermentation broth and it serves as starting material for the production of bromocriptine. Two isomers of ergocryptine exist, α-ergocryptine and β-ergocryptine. The beta differs from the alpha form only in the position of a single methyl group, which is a consequence of the biosynthesis in which the proteinogenic amino acid leucine is replaced by isoleucine. β-Ergocryptine was first identified in 1967 by Albert Hofmann. Ergot from different sources have different ratios of the two isomers.

<span class="mw-page-title-main">LSD-Pip</span> Compound related to LSD

LSD-Pip is a compound from the ergoline family, related to LSD but with the N,N-diethyl substitution replaced by a piperidine group. It is more potent than the corresponding pyrrolidine and morpholine analogues, but is still several times less potent than LSD as a 5-HT2A agonist. Early studies suggested this compound to be inactive as a psychedelic in humans, though this does not seem to have been confirmed by any more recent work.

Periglandula are a genus of fungi in the family Clavicipitaceae. They live as epibionts, in a symbiotic relationship with two species of plant, Ipomoea asarifolia and Ipomoea corymbosa. They are known to produce ergot alkaloids related to lysergic acid.

<span class="mw-page-title-main">Lysergine</span> Ergot alkaloid and serotonin receptor agonist

Lysergine, also known as 9,10-didehydro-6,8β-dimethylergoline, is an ergot alkaloid and serotonin receptor agonist of the ergoline family. It is a minor constituent of ergot.

References

  1. "Argyreia nervosa". Germplasm Resources Information Network . Agricultural Research Service, United States Department of Agriculture . Retrieved 2010-11-10.
  2. Glossary Of Indian Medicinal Plants
  3. 1 2 "Medicinal uses and biological activities of Argyreia speciosa Sweet (Hawaiian Baby Woodrose) An Overview". Indian Journal of Natural Products and Resources: 286–291. September 2011.
  4. E. Al-Assmar, Sami (1999). "The Seeds of the Hawaiian Baby Woodrose Are a Powerful Hallucinogen". Arch Intern Med. 159 (17): 2090. doi:10.1001/archinte.159.17.2090 (inactive 2024-11-13). PMID   10510998.{{cite journal}}: CS1 maint: DOI inactive as of November 2024 (link)
  5. Paulke, Alexander; et al. (2015). "Studies on the alkaloid composition of the Hawaiian Baby Woodrose Argyreia nervosa, a common legal high". Forensic Science International. 249: 281–293. doi:10.1016/j.forsciint.2015.02.011. PMID   25747328.
  6. The Ayurvedic Pharmacopoeia of India, part 1, vol. 5. Government of India, Ministry of Health and Family Welfare, Department of Ayush. http://www.ayurveda.hu/api/API-Vol-5.pdf
    A. nervosa entry: page 16
    “T.L.C. of methanolic extract of the roots on precoated silica gel G plate using methanol - chloroform (20 : 80) showed a blue fluorescent spot under UV (365nm) along with number of other spots of very weak intensity. Due to the presence of very negligible amount of alkaloids in the roots these could not be isolated.” (p. 17)
  7. Halpern, J.H. (2004). "Hallucinogens and dissociative agents naturally growing in the United States". Pharmacology & Therapeutics. 102 (2): 131–138. doi:10.1016/j.pharmthera.2004.03.003. PMID   15163594. S2CID   30734515. Although LSD does not occur in nature, a close analogue, lysergic acid amide (LSA, ergine) is found in the seeds of Argyreia nervosa (Hawaiian baby woodrose)
  8. Chao JM, Der Marderosian AH (1973). "Ergoline alkaloidal constituents of Hawaiian baby wood rose, Argyreia nervosa (Burmf) Bojer". J. Pharm. Sci. 62 (4): 588–91. doi:10.1002/jps.2600620409. PMID   4698977.
  9. Paulke, Alexander; Kremer, Christian; Wunder, Cora; Wurglics, Mario; Schubert-Zsilavecz, Manfred; Toennes, Stefan W. (2014-09-01). "Identification of legal highs – Ergot alkaloid patterns in two Argyreia nervosa products". Forensic Science International. 242: 62–71. doi:10.1016/j.forsciint.2014.06.025. ISSN   0379-0738. PMID   25036782
    “Additionally the presence of the ergot alkaloid diastereomers chanoclavine I and II was assumed in DF (cf. Fig. 6) together with traces of lysergic acid and the isobars lysergol, isolysergol, elymoclavine, molliclavine, setoclavine, or isosetoclavine.” (3.1. Mass spectrometry data, p. 65)
    “Indications of traces of [M+H]+ = 255.15 0.01 corresponding to lysergol/isolysergol, elymoclavine, setoclavine/isosetoclavine or molliclavine as well as [M+H]+ = 269.13 0.01 corresponding to lysergic acid were only obtained in the DF extracts and the resolution and the quality of the EICs and product spectra was poor. Therefore, the presence of lysergol/isolysergol, elymoclavine, setoclavine/isosetoclavine, molliclavine or lysergic acid cannot be excluded, but proof cannot be provided and additional research will be necessary.” (3.1. Mass spectrometry data, pages 65 & 68)
    {{cite journal}}: CS1 maint: postscript (link)
  10. Paulke, Alexander; et al. (2015). "Studies on the alkaloid composition of the Hawaiian Baby Woodrose Argyreia nervosa, a common legal high". Forensic Science International. 249: 281–293. doi:10.1016/j.forsciint.2015.02.011. PMID   25747328
    “On the other hand, methylergometrine, methysergide, and lysergylalanine were detected, which have not yet been reported as compounds of Argyreia nervosa seeds. Furthermore, some high molecular weight ergot alkaloid derivatives and hydroxyalanine derived ergopeptide fragments could be observed at various retention times (c.f. chapter 3.1). Altogether, lysergylalanine, the high molecular weight ergot alkaloids and the hydroxyalanine derived ergopeptide fragments strongly suggest the presence of ergopeptides in Argyreia nervosa. However, due to the disadvantage of the applied APCI technique for peptide analysis (c.f. chapter 3.1) additional research (e.g. ESI-HRMS/MS) will be necessary to verify this assumption and to elucidate the structure of the ergopeptides.” (3. Results and discussion, p. 283)
    {{cite journal}}: CS1 maint: postscript (link)
  11. Nowak, Julia; Woźniakiewicz, Michał; Klepacki, Piotr; Sowa, Anna; Kościelniak, Paweł (May 2016). "Identification and determination of ergot alkaloids in Morning Glory cultivars". Analytical and Bioanalytical Chemistry. 408 (12): 3093–3102. doi:10.1007/s00216-016-9322-5. ISSN   1618-2642. PMC   4830885 . PMID   26873205"ergine and ergometrine concentration is 12-fold lower in plant samples than in seeds." Analysis of IP-HB2 young plants{{cite journal}}: CS1 maint: postscript (link)
  12. Brickell, Christopher (2016). Royal Horticultural Society: A-Z Encyclopedia Of Garden Plants. Great Britain: Dorling Kindersley. p. 110. ISBN   9780241239124.
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  14. "Entheology.org - Preserving Ancient Knowledge". www.entheology.org. Archived from the original on 2006-05-02. Retrieved 2017-10-24.
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  16. Chai, Makana Risser (2011). "Huna, Max Freedom Long, and the Idealization of William Brigham" (PDF). The Hawaiian Journal of History. 45. Archived from the original (PDF) on 2021-01-18.
  17. Paulke, Alexander; Kremer, Christian; Wunder, Cora; Wurglics, Mario; Schubert-Zsilavecz, Manfred; Toennes, Stefan W. (2014). "Identification of legal highs--ergot alkaloid patterns in two Argyreia nervosa products". Forensic Science International. 242: 62–71. doi:10.1016/j.forsciint.2014.06.025. ISSN   1872-6283. PMID   25036782.
  18. Wasson RG, Hofmann A, Ruck CA, Webster P (2008-11-25). The Road to Eleusis: Unveiling the Secret of the Mysteries. Berkley, California: North Atlantic Books. ISBN   9781556437526.
    “The effective dose of lysergic acid amide is 1 to 2 mg by oral application.” Albert Hofmann. 2. A Challenging Question and My Answer, p. 40
  19. Bharati, A. J.; Bansal, Y. K. (2014). "Phytochemical investigation of natural and in vitro raised Vṛddhadāruka plants". Ancient Science of Life. 34 (2): 80–84. doi: 10.4103/0257-7941.153463 . PMC   4389397 . PMID   25861141.