Auxins Alkaloids of Genus Heimia Page

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This page is updated as new information is evaluated.
Page Last Updated
22 December 2003
The latest update was in "Medical properties of the alkaloids"

DISCLAIMER AND LAW:
The information in this page is intended for educational purposes only and it is not intended to be used to treat or diagnose any disease, nor is it meant to be a guide for drug use or manufacture. The information put forth in this document has been collected from various sources and I give no warranty expessed or implied as to the accuracy of any data provided by this document. Also, all the images herein are my creations and I retain all rights to them- they may not be altered, uploaded, posted, or otherwise used anywhere on the internet or in any printed or electronic document without my written consent.

Index:
1: Structures of selected biphenylquinolizidine lactone alkaloids of Heimia salicifolia, H. myrtifolia, and H. montana
2: Structures of selected phenylquinolizidinol and phenylquinolizidine ester alkaloids of Heimia salicifolia, H. myrtifolia, and H. montana
3: Medical properties of the alkaloids
4: Concentration of alkaloids in the Heimias
5: Biosynthesis Notes
6: Chemical properties of selected alkaloids
7: Identification of TLC spots
8: References


Structures

Structures of selected biphenylquinolizidine lactone alkaloids of Heimia salicifolia, H. myrtifolia, and H. montana:






Structures of selected phenylquinolizidinol and phenylquinolizidine ester alkaloids of Heimia salicifolia, H. myrtifolia, and H. montana:




Medical properties of the alkaloids:
The biphenylquinolizidine lactone alkaloids are considered the primary biologically active components of mature Heimia. The pharmacological properties of these alkaloids are not fully known, but some of their properties have been clinically studied. The most concentrated alkaloid in H. salicifolia is vertine (cryogenine) [1] and it is this alkaloid most often considered as being the primary source for the effects of the traditional Heimia salicifolia brew. Clinically observed effects of vertine include Anticholinergic [10], Antiinflammatory [11], Antispasmodic [10], Hyperglycemic, Hypotensive, Sedative [11], Tranquilizer, and Vasodilator [10] activity. Lythrine is considered to be the most effective diuretic, it and the mixed alkaloidal extract are considered to be relatively free of toxicity [9]. Nesodine has been shown to produce an antiinflammatory effect [12], and sinicuichine is known to act as a tranquilizer [10]. My research to date has not uncovered the source of any hallucinogenic effect observed in Heimia preperations.
The phenylquinolizidinols and phenylquinolizidine esters are seemingly only found in young Heimia seedlings [3], so their biological effects are probably irrelevant in the subject of traditional Heimia medicines and sacraments.

Concentration of Alkaloids in the Heimias:

Heimia salicifolia, 5 Month Old Plants- Dry Weight
Lyfoline 0.739% Lythrine 0.145%
Nesodine 0.003% Sinicuichine 0.113%
Vertine 1.060%

[1]


Heimia salicifolia, Adult Plants of Unknown Age- Dry Weight
Lyfoline 1.08% Lythridine 0.005%
Lythrine 0.21% Nesodine 0.0025%
Vertine 1.21%

*No heimidine detected* [2]


Heimia myrtifolia, Adult Plants of Unknown Age- Dry Weight
Heimidine 0.009% Lyfoline 1.08%
Lythridine 0.26% Lythrine 0.005%
Nesodine 0.78% Vertine 1.20%

[2]


Heimia montana, Adult Plants of Unknown Age- Dry Weight
Heimidine 0.03% Lythridine 0.18%
Lythrine 0.78% Nesodine 0.002%
Vertine 0.40%

*No lyfoline detected* [2]


Biosynthesis Notes:

Where do the atoms in the Heimia alkaloids come from, you ask?:



(These biosynthetic origin pictures were constructed from data obtained from [5,6, and 8])
It has been found that the alkaloids of heimia are formed from biosynthesis starting with phenylalanine, lysine, and acetate [5,6,8]. In one study the radiolabled phenylalanine used to prove the biosynthetic importance of phenylalanine was actually administered by feeding it to the roots of intact plants [8]. As opposed to the cell culture biosynthetic research this root feeding of phenylalanine proved that if a plant is given this precursor in its water supply it can absorb it and incorporate it into the quinolizidine alkaloids. This will undoubtably be of interest to those interested in 'doping' their plants with the precursors to the alkaloids they desire in order to obtain plants of higher alkaloidal content. But before you get too excited, the best plant 'doping' effect that could be hoped for is allowing the plant to optimize its alkaloid production and in optimal conditions the plants may already be at their peak production level. In the biosynthesis of the quinolizidine alkaloids one of the enzymes that has been found to be essential is lysine decarboxylase (LDC) and there is evidence that the activity of the LDC in Heimia may be mediated by the quinolizidine alkaloids. In that study it was determined that the activity of lysine decarboxylase was reduced to 16% productivity in the presence of 5 mM vertine, a concentration which may be acheived (or at least approached) in the zone of the LDC controled portion of vertine biosynthesis [6]. If vertine does infact control its own biosynthesis rate by a end-product feedback mechanism then 'doping' a plant with exogenous feeding of precursors may not increase alkaloid production to any worth-while degree. It could, however, provide an interesting insight into the reason Heimia evolved to contain quinolizidine alkaloids. Generally by default it is assumed that alkaloids are in plants to protect the plant from attack by predators, but given the strong possibility of the quinolizidine alkaloids actively controling the activity of LDC in vivo it is conceivable that the quinolizidine alkaloids are being produced to control other LDC mediated biosynthetic pathways, like the biosynthesis of chlorophyll for instance. Perhaps they even serve a dual role of protection and biochemical mediation, if this is the case the question that naturally follows is 'which came first- quinolizidine based Heimia defence mechanisms, or quinolizidine based biochemical control mechanisms?' We may never know the answer to that.

Chemical Properties of Selected Alkaloids

Lythridine mp 218-219 C Sol. in CHCl3, CH2Cl2, dioxane, acetone, methanol, etc. Insol. in pet. ether. = -153.4 (conc. = 0.37% in CHCl3).
Lythridine hydrochloride mp >320 C Sol. in methanol.
Lythrine mp 241-242 C Sol. in CHCl3, CH2Cl2, dioxane, acetone, etc. Insol. in water, cold methanol, pet. ether. = +40.6 (conc. = 0.3% in CHCl3)
Lythrine acetate ester mp 172-173 C = +33.1 (conc. = 0.75% in CHCl3)
Lythrine hydrochloride mp > 300 C
Vertine (Cryogenine) mp 250-251 C Sol. in CHCl3, CH2Cl2, benzene, methanol, etc. Insol. in water, pet. ether. [9]

Identification of TLC spots

1: By Developing with Diazotized p-Nitroaniline Spray

Dehydrodecodine produces a fuchsia spot.
Heimidine produces a orange spot.
Lyfoline produces a grey spot.
Lythridine produces a orange spot.
Lythrine produces a grey-lavender spot.
Nesodine produces a grey-lavender spot.
Sinicuichine produces a purple spot.
Vertine (Cryogenine) produces a purple spot. [1]

2: By TLC Mobility Ratio with Chlorpromazine as the Reference Compound

The Rcp value is the ratio of the movement of the alkaloid to that of chlorpromazine on a silica gel G thin layer plate using a chloroform methanol eluent under standard conditions.
Lythridine was found to have a Rcp value of 1.12 +/- 0.06
Lythrine was found to have a Rcp value of 2.01 +/- 0.09 [9]


This page has been accessed times since 5 August 2003.



__________________THANKS__________________

I would like to extend my thanks to Shaman Australis Botanicals and the members of the Shaman Australis Botanicals forums for their support in my research.
I would also like to thank the following scientists for their work on the alkaloids of genus Heimia:
A. E. SCHWARTING
ANA ROTHER
J. MICHAEL EDWARDS
JERRY A. WELSBACH
JORGE MARROQUIN
LENORE A. PELOSI
R. H. DOBBERSTEIN
SERGIO QUINTERO B. BEATRIZ VARGAS S.
XORGE ALEJANDRO DOMINGUEZ


References:
[1] THE SEQUENTIAL APPEARANCE AND METABOLISM OF ALKALOIDS IN HEIMIA SALICIFOLIA: Phytochemistry, 1975, Vol. 14, pp. 1769-1775.
[2] ALKALOIDS OF HEIMIA MONTANA: Phytochemistry, Vol. 29, No. 5, pp. 1683-1686, 1990.
[3] DESMETHOXYABRESOLINE AND 10-EPI-DESMETHOXYABRESOLINE, NEW ESTER ALKALOIDS IN HEIMIA SALICIFOLIA: Phytochemistry, 1978, Vol 17, pp 305-309.
[4] THE EFFECT OF LIGHT ON THE PRODUCTION OF HEIMIA ALKALOIDS: Phytochemistry, Vol. 24, No. 10, pp. 2215-2218, 1985.
[5] BIOSYNTHESIS OF PHENYLQUINOLIZIDINE ALKALOIDS BY HEIMIA SALICIFOLLA: Phytochemistry. Vol 36. No. 4. pp. 91 l-914 1994
[6] LYSINE DECARBOXYLASE ACTIVITY AND ALKALOID PRODUCTION IN HEIMIA SALICIFOLIA CULTURES: Phytochemistry, Vol. 25, No. 10. pp. 2315-2319, 1986.
[7] TWO NEW QUINOLIZIDINE ALKALOIDS FROM HEIMIA SALICIFOLIA: Phytochemistry. 1975, Vol. 14, pp. 1883-1884.
[8] PHENYLALANINE AS A PRECURSOR FOR CRYOGENINE BIOSYNTHESIS IN HEIMIA SALICIFOLIA: Phytochemistry, 1972, Vol. 11, PP. 2475 to 2480.
[9] HEIMIA ALKALOIDS: US Patent 3,184,446 (1965)
[10] CRC Handbook of Medicinal Herbs and/or CRC Handbook of Proximate Analyses
[11] Phytochemical Dictionary. A Handbook of Bioactive Compounds from Plants. 1983 Edition. Taylor & Frost, London. 791 pp.
[12] Handbook of biologically active phytochemicals and their activities. Duke, James A. 1992. Boca Raton, FL. CRC Press.
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