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Identification and quantification of cannabinol as a biomarker for local hemp retting in an ancient sedimentary record by HPTLC-ESI-MS

Cannabis products have been used in various fields of everyday life for many centuries, and applications in folk medicine and textile production have been well-known for many centuries. For traditional textile production, hemp fibers were extracted from the stems by water retting in stagnant or slow-moving waters. During this procedure, parts of the plant material’ among them phytocannabinoids’ are released into the water. Cannabinol (CBN) is an important degradation product of the predominant…

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. 2020 Apr;412(11):2633-2644.

doi: 10.1007/s00216-020-02492-0. Epub 2020 Feb 14.

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Theresa Schmidt et al. Anal Bioanal Chem. .

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Abstract

Cannabis products have been used in various fields of everyday life for many centuries, and applications in folk medicine and textile production have been well-known for many centuries. For traditional textile production, hemp fibers were extracted from the stems by water retting in stagnant or slow-moving waters. During this procedure, parts of the plant material’ among them phytocannabinoids’ are released into the water. Cannabinol (CBN) is an important degradation product of the predominant phytocannabinoids found in Cannabis species. Thus, it is an excellent indicator for present as well as ancient hemp water retting. In this study, we developed and validated a simple and fast method for the determination of CBN in sediment samples using high-performance thin-layer chromatography (HPTLC) combined with electrospray ionization mass spectrometry (ESI-MS), thereby testing different extraction and cleanup procedures’ as well as various sorbents and solvents for planar chromatography. This method shows a satisfactory overall analytical performance with an average recovery rate of 73%. Our protocol enabled qualitative and quantitative analyses of CBN in samples of a bottom sediment core’ having been obtained from a small lake in Northern India, where intense local retting of hemp was suggested in the past. The analyses showed a maximum CBN content in pollen zone 4 covering a depth range of 262-209 cm, dating from approximately 480 BCE to 1050 CE. These findings correlate with existing records of Cannabis-type pollen. Thus, the method we propose is a helpful tool to track ancient hemp retting activities. Graphical Abstract.

Keywords: Biomarker; Cannabinol; Cannabis; HPTLC; Hemp retting; Sediment.

Conflict of interest statement

The authors declare that they have no conflict of interest.

Figures

None

Graphical Abstract

Fig. 1

Fig. 1

Conversion of CBDA and THCA to CBD and THC as well as the formation of the main degradation product CBN

Fig. 2

Fig. 2

Flow diagram for the extraction of the samples and cleanup protocol. For the quantification of the CBN content, internal standard CBN-d3 was added after sample has been weighed. For the determination of the recovery, CBN-spiked sediment samples (approximately 140, 250, and 330 ng CBN/g sediment) were used, and the residue of the purification with reversed-phase sorbent was solved in a methanolic solution of CBN-d3 (100 μL, 2.5 μg/mL) after having been transferred to a vial and before spotting the solution onto a HPTLC plate

Fig. 3

Fig. 3

MS spectrum of a CBN and b CBN-d3 spotted onto a HPTLC silica gel 60 plate recorded immediately after chromatographic separation using n-heptane/diethyl ether (90:10 v/v) as developing solvent

Fig. 4

Fig. 4

HPTLC silica gel 60 plates developed using an-heptane/diethyl ether/formic acid (75:25:0.3 v/v/v) or bn-heptane/diethyl ether (90:10 v/v) as developing solvent after derivatization with cerium-molybdenum reagent; observed under white light. Tracks 1–7 = CBN standard (from left to right increasing CBN concentration: 7.5, 15, 25, 55, 85, 125, 190 ng CBN/HPTLC zone); 8 = extract (extracting agent: methanol/hexane (10 mL, 9:1 v/v)) of real sample BT-96 spiked with CBN-d3 (62.5 ng CBN-d3/HPTLC zone)

Fig. 5

Fig. 5

HPTLC silica gel 60 plates developed using n-hexane/acetone/triethylamine (40:20:2 v/v/v) as developing solvent after derivatization with FBS reagent; observed under white light. Tracks 1–7 = CBN standard (from left to right increasing CBN concentration: 7.5, 15, 25, 55, 85, 125, 190 ng CBN/HPTLC zone); 8 = extract (extracting agent: methanol/hexane (10 mL, 9:1 v/v)) of real sample BT-96 spiked with CBN-d3 (62.5 ng CBN-d3/HPTLC zone)

Fig. 6

Fig. 6

HPTLC chromatogram of (1) CBN standard (190 ng CBN/HPTLC zone) and (2) an extract of real sample BT-102 spiked with CBN-d3 (62.5 ng CBN-d3/HPTLC zone) as well as a related MS spectrum (HPTLC silica gel 60 plate developed in n-heptane/diethyl ether (90:10 v/v); observed with an UV light source at 254 nm; extracting agent: methanol/hexane (10 mL, 9:1 v/v); after an orthogonal SPE sample preparation)

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References

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    1. Jiang H-E, Li X, Zhao Y-X, Ferguson DK, Hueber F, Bera S, Wang Y-F, Zhao L-C, Liu C-J, Li C-S. A new insight into Cannabis sativa (Cannabaceae) utilization from 2500-year-old Yanghai Tombs, Xinjiang, China. J Ethnopharmacol. 2006;108(3):414–422. doi: 10.1016/j.jep.2006.05.034. – DOI PubMed
    1. Andre CM, Hausman J-F, Guerriero G. Cannabis sativa: The Plant of the Thousand and One Molecules. Front Plant Sci. 2016;7:19. doi: 10.3389/fpls.2016.00019. – DOI PMC PubMed
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Can cbd help prevent hearing loss due to noise?

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Visit our community site for vetted suppliers at http://theCBD.place. It’s time that this subject was given more internet exposure. We are here to discuss topics related to medical marijuana and our experiences using CBD. Please do not assume that anyone here is a medical professional.

Source: https://www.reddit.com/r/CBD/comments/l5b0ik/can_cbd_help_prevent_hearing_loss_due_to_noise/

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Europe – Where to incorporate CBD affiliate company

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I’m looking for advice. I have been working on CBD affiliate sites for the last few months, the sites are starting to have a decent amount of traffic and I need to incorporate a company.

The question is; where should I incorporate it? I’m not looking for massive tax breaks, but rather a country where the banking isn’t a massive headache and a place where I don’t have to be personally present.

Source: https://www.reddit.com/r/CBD/comments/l59wcr/europe_where_to_incorporate_cbd_affiliate_company/

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Plant Power: Everyday Plants That Activate the Endocannabinoid System

When people hear about cannabinoids, they automatically think of cannabis (which makes sense, given the name). What most have yet to realize is that many other plants make cannabinoids too – a lot of everyday flowers, vegetables, and spices that you probably wouldn’t expect. This train of thought was not exclusive to consumers though; until […]

The post Plant Power: Everyday Plants That Activate the Endocannabinoid System appeared first on CBD Testers.

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When people hear about cannabinoids, they automatically think of cannabis (which makes sense, given the name). What most have yet to realize is that many other plants make cannabinoids too – a lot of everyday flowers, vegetables, and spices that you probably wouldn’t expect.

This train of thought was not exclusive to consumers though; until recently, even scientists had only been able to identify cannabinoids in the cannabis plant. But current studies have found these compounds in a handful of common, day-to-day plants, including clove, black pepper, cocoa, echinacea, broccoli, ginseng, hops, and even carrots.

But no matter how much of these plants you consume, they won’t feel any type of psychedelic effects. This is because they don’t have the cannabinoids we’re all familiar with, like tetrahydrocannabinol (THC), cannabidiol (CBD), or cannabigerol (CBN). Rather, they have their own compounds that directly engage our Endocannabinoid Systems (ECS).

The ECS is itself only recently discovered, and understanding how different phytocannabinoids interact with this network of neurotransmitters in our bodies can lead to important medical innovations in the future. Ones that are natural, safer for patients, and more focused on plant-based healthcare.

To learn more about cannabis, and for exclusive deals on flowers and other products, subscribe to The CBD Flowers Weekly Newsletter


Pain-relieving drugs made from plants

­Chronic pain affects at least 10 percent of the global population, which is approximately 60 million people. However, experts estimate that figure to be closer to 20-25 percent on some countries and regions. Finding a solution that doesn’t put patients at risk for addiction and addition problems, is paramount.

As we humans have done since the dawn of time, we continue looking to the plant world for ways to improve our health and wellbeing. Cannabinoids might be the trendiest at the moment, but they’re certainly not the only plant-based compound that’s been utilized to help fight pain.

Opiates

Opiates get a bad rap because of their high rate for addiction and abuse, but they do have an important place in the world of medicine. Very intense pain, post-surgical or from a broken bone for example, typically won’t respond to cannabinoids. Something stronger like morphine, codeine, and other opiate drugs are sometimes necessary. They have many added ingredients these days, but believe-it-or-not, these medicates have a natural element to them. Opiates are made from opium, which comes from the poppy plant. Just like cannabinoids, these pharmaceutical drugs interact with opiate receptors in the human brain, which is why they can be incredibly effective when used responsibly.

Aspirin

Dating back to ancient Egypt, tea made from the willow tree was used to manage pain and reduce fever. Fast forward a few centuries and scientists are looking at the willow tree yet again, this time isolating the active compound used in that ancient tea – salicylic acid – and used it to formulate numerous medications used to treat pain and inflammation; most notably, aspirin. Salicylic acid is also a very common active ingredient in acne medication.

Anesthetics

Common anesthetics like lidocaine, used routinely by dentists to numb the mouth before initializing treatment, are also distantly related to wild plant – Coca. The leaves of the coca plant were used in the ancient Incan Empire in South America to treat many different levels of pain, from headaches to fractures. Eventually, the coca plant gave way to the drug cocaine, which is an illegal drug of abuse but also a very effective anesthetic.   

Plant cannabinoids and the endocannabinoid system

Cannabis has been used medicinally for centuries, but it wasn’t until recently that science started to catch up with what our ancestors have been telling us. Ancient texts from China, Egypt, Tibet, and many other parts of the world hail cannabis as a natural remedy for numerous ailments including pain, inflammation, nausea, anxiety, epilepsy, and even sexual dysfunction. But how can one plant serve so many different functions in the human body? It all boils down to a network of receptors and neurotransmitters known as the Endocannabinoid System (ECS).

Unfortunately, the federally illegal status of cannabis and its use as a recreational drug has been a major hinderance on the ability of researchers to study the full capabilities of this plant. Until recently, most of the information we had came from scientists in Israel, where they had less restrictions when it came to using the plant compounds medicinally.

The Endocannabinoid System (ECS) is involved in multiple physiological processes including appetite regulation, pain threshold, sleep/wake cycles, memory, and mood. It plays a major role in allowing our bodies to achieve homeostasis, or internal balance. The discovery of the ECS shed new light on how and why plant-based cannabinoids, or phytocannabinoids, affect humans in the way they do. In cannabis alone, over 80 phytocannabinoids have been indexed and these compounds exist in many, many plants we consume regularly.

Other plants that engage the ECS

Like cannabis, many other plants have compounds that engage the endocannabinoid system, and with growing attention on this newly-discovered system, the more sources of phytocannabinoids we have the better. While these other plants don’t have cannabinoids as we know them, many of them contains Alkylamides, compounds that are structurally similar to endocannabinoids, and terpenes, that give plants their unique aromas – both of which effectively activate the ECS.

Plants of interest include (but not limited to):

  • Black pepper
  • Hops
  • Helichrysum
  • Oregano
  • Cinnamon
  • Carrots
  • Basil
  • Cloves
  • Lavender
  • Rosemary
  • Cocoa
  • Echinacea
  • Black truffles
  • Electric daisies
  • Liverwort
  • Kava

More about plant terpenes

Worth an additional mention since they often work synergistically with cannabinoids, in addition to activating the endocannabinoid system indirectly. Terpenes are a very large and diverse class of organic compounds that are produced by a wide variety of plants, including the ones listed above. In cannabis, they are secreted by the same glands that produce some of the more dominant cannabinoids including THC and CBD. Their role and effects are quite different, however.

Terpenes are aromatic plant oils that, when combined with other plant compounds, create a never-ending palate of scents and flavors. In nature, terps serve as a defense mechanism by deterring herbivores and by attracting predators and parasites that attack herbivores.

Chemically, terpenes are hydrocarbons, and they differ from terpenoids, which typically have added functional groups such as oxygen. The words “terpenes” and “terpenoids” are often used interchangeably but this is incorrect. Terpenes are also the major component of rosin, which a sap/waxy-like substance that is produced when cannabis buds are placed under high heat and pressure. Climate, weather, age and maturation, fertilizers, soil type, and light cycles can have an impact on the development of terpenes.

As far as cannabis goes, terpenes are the key to differentiating the effects and flavor of a strain. Some terpenes are relaxing, like those found in lavender, while others are energizing, like citrus. Some smell fruity, some are piney, others are musky, or even floral. There really is no limit to the variation. So far, over 100 different terpenes have been discovered in cannabis plants alone, and each strain typically has its own unique blend and composition of terps.

Terpenes have long been known to hold great therapeutic value, and some of the more common ones have been studied more extensively, considering they’re found in many different types of legal plants. More research is needed to determine the extent of their medicinal effects when combined with other cannabis plant compounds.

Conclusion

No matter how many veggies you munch on, or how many spices you add to your dish, you won’t get high from it like you would with actual cannabis. Our everyday plants don’t have THC, CBD, or any of the other major cannabinoids, but they have their own structurally similar compounds that engage with our Endocannabinoid Systems and can offer us natural, medicinal possibilities well beyond what science ever believed would be possible.

Thank you for visiting CBDtesters.co, your #1 spot for all cannabis-related news and information. Join us regularly to keep up with the world of legal cannabis, and sign up to our newsletter so you’re always in the know!


RESOURCES:

It Was Just a Matter of Time: GMO Cannabis on Its Way
Compared to Prescription Medication, Medical Cannabis Not Always Affordable Alternative
A Brief History Of CBD The Week in Review: Canadian Cannabis, Antibiotic Resistance, Father’s Day Gift Ideas, and more
Can You Treat COVID-19 With CBD and Reduce Mortality Rates? A New Israeli Research Believes You Can!

Not Just for Getting High – The Underreported Medical Uses of THC
In a world plagued with antibiotic resistance, look to cannabis as a natural alternative
The CBD Flowers Weekly newsletter (your top resource for all things smokable hemp flowers)
The Medical Cannabis Weekly newsletter (International medical cannabis business report)
Cannabis Heroes of History: How Robert Randall Beat the U.S.

The Delta 8 Weekly Newsletter (All you need to know about Delta 8 thc) and the Best Black Friday Delta 8 THC Deals 2020.  The best delta-8 THC deals, coupons and discounts.
The Medical Cannabis Weekly Review: Antibiotic Resistance, Cannabis in Italy, CBD for Weight Loss, and more Argentina Allows Cannabis Self-Cultivation
CBG Study Shows Antimicrobial Properties of Cannabis

Source: https://cbdtesters.co/2021/01/26/plants-cannabinoids-endocannabinoid-system/

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