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Thread: How are terpenoids formed in Cannabis?

  1. #1
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    Question How are terpenoids formed in Cannabis?

    So the title says it all, really. I'll clarify a bit anyway. How does the cannabis plant produce this particular group of chemicals? According to Advanced Nutrition it is at least partly do to nutrients. I am specifically interested to know if there is a particular wavelength of light that might stimulate their production? Perhaps UV? If they are used to protect seeds from UV radiation. Or maybe they are there to lure us humans into fields of cannabis for munching and seed transport. I think this could be a very interesting thread as I haven't seen much dedicated to these chemicals. There should be something as I think they are responsible for smell, taste and may have an affect on the type of high experienced. Any information in this direction would be useful and appreciated.


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    Bump. I'm really surprised that in a forum on advanced cannabis cultivation no one has anything to say about terpenoids. And so few views at that... maybe that is just it, no one bothered to look.

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    Quote Originally Posted by FERMENTATION
    Bump. I'm really surprised that in a forum on advanced cannabis cultivation no one has anything to say about terpenoids. And so few views at that... maybe that is just it, no one bothered to look.
    I saw your thread, but I have no idea whatsoever what are "terpenoids". I have no books...

    But, if anybody knows, please share!

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    Phenolicking hell FERMENTATION your not asking much there!

    UV-B is the wavelength your after, it's a photomorphogenic reaction that spikes after a threshold of 250microwatts per square inch is exceeded. Also at this level of uv-b there should be little smell from the terpinols as most will have been used up in the production of fully realised/developed THC.

    Taste is more down to the glucose content of the plants.

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    Alchemiser: Thankyou. I just went searching for some answers before I saw your comment. I will post links and paste the contents. I did see uv-b mentioned either in one of these or somewhere else. I would like to learn or figure out how to produce specific terpenes for specific odors. It may come down to identifying the terpene that produces a desirable odor them looking up its precursor and adding that to the nutrient mix at the correct time in the plants life cycle.


    http://www.sciencedaily.com/releases...0123223453.htm

    Scientists Find Common Roots For Thousands Of Plant Compounds

    WEST LAFAYETTE, Ind. - Just one cellular pathway produces the raw ingredients plants use to make thousands of compounds, from molecules with anticancer properties to the active ingredient in catnip, according to a team of researchers at Purdue University and the Max Planck Institute for Chemical Ecology.

    These snapdragon flowers helped horticulture professor Natalia Dudareva figure out the first steps plants follow in producing thousands of commercially-important products, such as the essential oils that give flowers their fragrance. Her research challenges long-held assumptions about the production of these compounds, and may have important implications for researchers trying to harness plant pathways to produce these essential oils, often used as flavor additives in food and medicine or as fragrance in body care products. (Purdue News Service photo/David Umberger)

    This finding challenges long-held assumptions about how plants produce these commercially important products. The research also could have important implications for researchers trying to harness plant pathways to produce essential oils, often used as flavor additives in food and medicine or as fragrance in body-care products, said Natalia Dudareva, professor of horticulture and lead researcher of the study.

    "Our research has applications in the future metabolic engineering of essential oil production," Dudareva said. "The yield of these compounds depends on the amount of materials available in the cell, and knowing where these compounds come from and which pathway produces them is the place to start."

    Dudareva and her colleagues report in the current issue (Tuesday, Jan. 18) of Proceedings of the National Academy of Science that the molecular precursors to a group of compounds called terpenoids - the largest and most diverse family of natural products - come from a single plant pathway, located inside the same part of a cell where photosynthesis occurs.

    Terpenoids are made from compounds called precursor molecules, which are a kind of molecular raw material. Just as a potter can transform five identical spheres of clay into five unique pieces of art, identical precursor molecules can transform into unique compounds by following different molecular pathways.

    Scientists previously discovered that two independent pathways, located in different compartments within a plant cell, use these precursor molecules to produce terpenoids. Most scientists assumed that both pathways were capable of producing these precursor molecules as well.

    The discovery that only one pathway produces these precursors is a significant breakthrough, Dudareva said.

    "We never expected to find this," she said. "This is the first time anyone has realized that only one of the two available pathways operates to make the precursor."

    She also found that while some of the precursor molecules remain in the compartment where they are made, some travel through the cell to another compartment, where they enter a second pathway in terpenoid production.

    The process can be likened to a manufacturing plant with an assembly line that makes a car part, such as a steering wheel. Some of those steering wheels remain on-site to be added to cars manufactured at that plant. Additional steering wheels are transported to another plant that, instead of making its own steering wheels, uses those from the first plant to produce its product.

    Just as delivering steering wheels from one manufacturing facility to another requires some kind of transportation, molecules also rely on vehicles to travel around the interior of a cell. Exactly how the precursor molecules in this system travel from one compartment to another, however, remains a mystery.

    "This work hints at the existence of a transporter to carry precursor molecules across the cell," said David Rhodes, Purdue professor of horticulture and a collaborator on the paper. "We already know that plants have a huge number of compartments that exchange materials. Now we need to figure out how these compartments facilitate this one-way flow of precursor molecule."

    Dudareva used snapdragon flowers in this research, a model plant system she also uses in her studies of floral scent regulation.

    While limited to this one species, she suggests similar results might be found in other plants.

    "Others have previously shown indirectly that the same pathway that's not functioning in snapdragons is also blocked in basil plants and in mint," she said. "This opens the question of how widespread is this phenomenon?"

    The finding also raises intriguing questions in plant evolution.

    "We still don't understand why plants have duplicate pathways in different parts of the cell," Rhodes said. "And if one of these pathways is not operating, why haven't plants lost it over the course of evolution?"

    Dudareva's collaborators also include Irina Orlova at Purdue University, as well as Susanna Andersson, Nathalie Gatto, Michael Reichelt, Wilhelm Boland and Jonathan Gershenzon at the Max Planck Institute for Chemical Ecology in Jena, Germany. Funding was provided by The National Science Foundation, Fred Gloeckner Foundation, German Academic Exchange Service and Max Planck Society.

    Editor's Note: The original news release can be found here.


    More to come...

  7. #6
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    From "Marijuana Botany" by Robert Connell Clarke

    I am sure there are other links to this, but this one will do for now.

    http://www.geocities.com/SunsetStrip...96/botany3.htm

    f) Taste and Aroma - Taste and aroma are closely linked.
    As our senses for differentiating taste and aroma are con-
    nected, so are the sources of taste and aroma in Cannabis.
    Aroma is produced primarily by aromatic terpenes pro-
    duced as components of the resin secreted by glandular
    trichomes on the surface of the calyxes and subtending
    leaflets. When a floral cluster is squeezed, the resinous
    heads of glandular trichomes rupture and the aromatic ter-
    penes are exposed to the air. There is often a large differ-
    ence between the aroma of fresh and dry floral clusters.
    This is explained by the polymerization (joining together in
    a chain) of many of the smaller molecules of aromatic ter-
    penes to form different aromatic and nonaromatic terpene
    polymers. This happens as Cannabis resins age and mature,
    both while the plant is growing and while curing after har-
    vest. Additional aromas may interfere with the primary
    terpenoid components, such as ammonia gas and other
    gaseous products given off by the curing, fermentation or
    spoilage of the tissue (non-resin) portion of the floral
    clusters.
    A combination of at least twenty aromatic terpenes
    (103 are known to occur in Cannabis) and other aromatic
    compounds control the aroma of each plant. The produc-
    tion of each aromatic compound may be influenced by
    many genes; therefore, it is a complex matter to breed
    Cannabis for aroma. Breeders of perfume roses often are
    amazed at the complexity of the genetic control of aroma,
    Each strain, however, has several characteristic aromas, and
    these are occasionally transmitted to hybrid offspring such
    that they resemble one or both parents in aroma. Many
    times breeders complain that their strain has lost the de-
    sired aromatic characteristics of the parental strains. Fixed
    hybrid strains will develop a characteristic aroma that is
    hereditary and often true-breeding. The cultivator with
    preservation of a particular aroma as a goal can clone the
    individual with a desired aroma in addition to breeding it.
    This is good insurance in case the aroma is lost in the off-
    spring by segregation and recombination of genes.
    The aromas of fresh or dried clusters are sampled and
    compared in such a way that they are separated to avoid
    confusion. Each sample is placed in the corner of a twice-
    folded, labeled piece of unscented writing paper at room
    temperature (above 650). A light squeeze will release the
    aromatic principles contained within the resin exuded by
    the ruptured glandular trichome head. When sampling,
    never squeeze a floral cluster directly, as the resins will ad-
    here to the fingers and bias further sampling. The folded
    paper conveniently holds the floral cluster, avoids confu-
    sion during sampling, and contains the aromas as a glass
    does in wine tasting.
    Taste is easily sampled by loosely rolling dried floral
    clusters in a cigarette paper and inhaling to draw a taste
    across the tongue. Samples should be approximately the
    same size.
    Taste in Cannabis is divided into three categories
    according to usage: the taste of the aromatic components
    carried by air that passes over the Cannabis when it is in-
    haled without being lighted; the taste of the smoke from
    burning Cannabis; and the taste of Cannabis when it is con-
    sumed orally. These three are separate entities.
    The terpenes contained in a taste of unlighted Canna-
    bis are the same as those sensed in the aroma, but perceived
    through the sense of taste instead of smell. Orally ingested
    Cannabis generally tastes bitter due to the vegetative plant
    tissues, but the resin is characteristically spicy and hot,
    somewhat like cinnamon or pepper. The taste of Cannabis
    smoke is determined by the burning tissues and vaporizing
    terpenes. These terpenes may not be detected in the aroma
    and unlighted taste.
    Biosynthetic relationships between terpenes and can-
    nabinoids have been firmly established. Indeed, cannabi-
    noids are synthesized within the plant from terpene
    precursors. It is suspected that changes in aromatic ter-
    pene levels parallel changes in cannabinoid levels during
    maturation. As connections between aroma and psycho-
    activity are uncovered, the breeder will be better able to
    make field selections of prospective high-THC parents
    without complicated analysis.


    More to come...

  8. #7
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    This one isn't anything specific to just terpenoids their is also talk about uv-b and it's contribution to the potency as well as some other interesting ideas about cannabis.

    http://www.hempfood.com/IHA/iha01201.html

    Chemical ecology of Cannabis
    David W. Pate
    International Hemp Association, Postbus 75007,
    1070 AA Amsterdam, The Netherlands

    Pate, D.W., 1994. Chemical ecology of Cannabis. Journal of the International Hemp Association 2: 29, 32-37.

    The production of cannabinoids and their associated terpenes in Cannabis is subject to environmental influences as well as hereditary determinants. Their biosynthesis occurs in specialized glands populating the surface of all aerial structures of the plant. These compounds apparently serve as defensive agents in a variety of antidessication, antimicrobial, antifeedant and UV-B pigmentation roles. In addition, the more intense ambient UV-B of the tropics, in combination with the UV-B lability of cannabidiol, may have influenced the evolution of an alternative biogenetic route from cannabigerol to tetrahydrocannabinol in some varieties.


    Figure 1. Resin-producing stalked glandular trichome (Briosi and Tognini 1894).
    Introduction

    Cannabis may have been the first cultivated plant. Records indicate use of this crop for paper, textiles, food and medicine throughout human history (Abel 1980). It is a dioecious annual with rather distinctive palmate leaves, usually composed of an odd number of leaflets. Best growth occurs on recently disturbed sites of high soil nitrogen content, so it is commonly found as a persistent weed at the edge of cultivated fields. Mature height ranges from 1 to 5 meters, according to environmental and hereditary dictates. Typically, the male plant is somewhat taller and more obviously flowered. These flowers have five yellowish tepals, and five anthers that hang pendulously at maturity, dispersing their pollen to the wind. The female plant exhibits a more robust appearance due to its shorter branches and dense growth of leaves and flower-associated bracts. Its double-styled flower possesses only a thin, closely adherent perianth, but is further protected by enclosure in a cuplike bracteole (i.e., perigonal bract), subtended by a usually monophyllous leaflet. A single achene is produced per flower and shed or dispersed as a result of bird predation. The life cycle of the male is completed soon after anthesis, but the female survives until full seed ripeness.

    Cannabis seems a virtual factory for the production of secondary metabolic compounds. A variety of alkanes have been identified (Adams, Jr. and Jones 1973, De Zeeuw et al. 1973b, Mobarak et al. 1974a & 1974b), as well as nitrogenous compounds (ElSohly and Turner 1976, Hanus 1975b), flavonoids (Gellert et al. 1974, Paris et al. 1975b, Paris and Paris 1973) and other miscellaneous compounds (Hanus 1976a & 1976b). Terpenes appear in abundance (Hanus 1975a, Hendricks et al. 1975) and contribute to the characteristic odor of the plant (Hood et al. 1973) and some of its crude preparations, such as hashish. The compounds which comprise the active drug ingredients are apparently unique to this genus and are termed cannabinoids. Cannabinoids were originally thought to exist as the phenolic compounds, but later research (Fetterman et al. 1971a, Masoud and Doorenbos 1973, Small and Beckstead 1973, Turner et al. 1973b) has indicated their existence predominantly in the form of carboxylic acids which decarboxylate readily with time (Masoud and Doorenbos 1973, Turner et al. 1973b), upon heating (De Zeeuw et al. 1972a, Kimura and Okamoto 1970) or in alkaline conditions (Grlic and Andrec 1961, Masoud and Doorenboos 1973). There are over 60 of these type compounds present in the plant (Turner et al. 1980).

    Much has been published concerning the influence of heredity on cannabinoid production (e.g., Fetterman et al. 1971b, Small and Beckstead 1973), but ecological factors have long been thought to have an important influence by stressing the Cannabis plant (Bouquet 1950). The resultant increased biosynthesis of the cannabinoid and terpene containing resin, in most cases, seems likely of advantage to the organism in adapting it to a variety of survival-threatening situations. This work reviews these biotic and abiotic challenges and speculates on the utility of Cannabis resin to the plant.
    Anatomical distribution and biogenesis of the cannabinoids

    The major sites of cannabinoid production appear to be epidermal glands (Fairbairn 1972, Hammond and Mahlberg 1973, Lanyon et al. 1981, Malingre et al. 1975) which exhibit a marked variation in size, shape and population density, depending on the anatomical locale examined. While there are no published reports of glands present on root surfaces, most of the aerial parts possess them, along with non-glandular trichomes (De Pasquale et al. 1974). These epidermal glands seem to fall into two broad categories: stalked and sessile. The stalked gland (Fig. 1, front page) can consist of a single cell or small group of cells arranged in a rosette on a single or multicellular pedestal. Lack of thorough ontogenetic study has led to the speculation that some of this variation may be attributable to observation of various developmental stages (Ledbetter and Krikorian 1975). The sessile gland possesses no stalk and has secretory cells located at or below the epidermal surface (Fairbairn 1972). In either case, the glandular cells are covered with a "sheath" under which the resins are secreted via vesicles (Mahlberg and Kim 1992). This sheath consists of a cuticle that coats a polysaccharide layer (presumed cellulose) originating from the primary cell wall (Hammond and Mahlberg 1978). The resins accumulate until the sheath bulges away from the secretory cells, forming a spheroid structure. The resin is then released by rupture of the membrane or through pores in its surface (De Pasquale 1974). The cannabinoid content of each plant part varies, paralleling observable gland distribution (Fetterman et al. 1971, Honma et al. 1971a & 1971b, Kimura and Okamoto 1970, Ohlsson et al. 1971, Ono et al. 1972), although Turner et al. (1978) have disagreed. Roots contain only trace amounts. Stalks, branches and twigs have greater quantities, although not as much as leaf material. Vegetative leaf contains varying quantities depending on its position on the plant: lower leaves possessing less and upper ones more. Leaf glands are most dense on the abaxial (underside) surface. The greatest amount of cannabinoids is found in the new growth near each apical tip (Kimura and Okamoto 1970, Steinberg et al. 1975), although Ono et al. (1972) seem to differ on this point. This variation in leaf gland placement may be due to either loss of glands as the leaf matures or a greater the endowment of glands on leaves successively produced as the plant matures. Additional study on this point is required.

    Once sexual differentiation has occurred, the generation of female reproductive organs and their associated bracts increases total plant cannabinoid content. Bracts subtending the female flowers contain a greater density of glands than the leaves. The small cuplike bracteole (perigonal bract) enclosing the pistil has the highest cannabinoid content of any single plant part (Kimura and Okamoto 1970, Honma et al. 1971a & 1971b). Second only to this is the flower itself (Fetterman et al. 1971b). Since it has no reported epidermal gland structures, the cannabinoids present must be due to either undiscovered production sites or simple adherence of resin from the inner surface of its intimately associated bracteole. This conjecture is supported by the finding that the achenes do not contain substantial amounts of the cannabinoids (Fetterman et al. 1971b, Ono et al. 1972). Reproductive structures of the male plant are also provided with greater concentrations of the cannabinoids (Fetterman et al. 1971b, Ohlsson et al. 1971). Stalked glands have been observed covering the tepal, with massively stalked glands occurring on the stamen filament (Dayanadan and Kaufman 1976). In addition, rows of very large sessile glands are found situated in grooves on the anther itself (Dayanadan and Kaufman 1976, Fairbairn 1972) and apparently provide the pollen with a considerable cannabinoid content (Paris et al. 1975a).

    Delta-9-tetrahydrocannabinol (THC) is the cannabinoid responsible for the main psychoactive effects of most Cannabis drug preparations (Mechoulam 1970). In some varieties of Cannabis, additional cannabinoid homologs appear that have the usual pentyl group attached to the aromatic ring, replaced by a propyl (De Zeeuw et al. 1972b & 1973a, Fetterman and Turner 1972, Gill 1971, Gill et al. 1970, Merkus 1971, Vree et al. 1972a, Turner et al. 1973a) or occasionally a methyl group (Vree et al. 1971 & 1972b). Other claims have been made for butyl (Harvey 1976) or heptyl (Isbell 1973) substitutions, but the latter announcement seems particularly tenuous. THC is thought to be produced by the plant (Fig. 2, next page) from cannabidiol (CBD) which, in turn, is derived from cannabigerol (CBG) generated from non-cannabinoid precursors (Hammond and Mahlberg 1994, Shoyama et al. 1984, Turner and Mahlberg 1988). CBG is also the biogenetic precursor of cannabichromene (CBC). Some of the cannabinoids (e.g., cannabielsoin, cannabinol, and cannabicyclol) are probably degradation products of the enzymatically produced cannabinoids (e.g., CBD, THC and CBC, respectively).


    Figure 2. Biosynthesis of cannabinoid acids (redrawn after Shoyama et al. 1975): 1 = cannabigerol (CBG); 2 = cannabidiol (CBD); 3 = cannabichromene (CBC); 4 = delta-9-tetrahydrocannabinol (THC).
    Cannabinoids and environmental stress
    Desiccation

    THC is a viscous hydrophobic oil (Garrett and Hunt 1974) that resists crystallization (Gaoni and Mechoulam 1971) and is of low volatility (Adams et al. 1941). Since the sticky resins produced and exuded on the surface of the plant are varying combinations of THC, other cannabinoids and a variety of terpenes, they can be seen as analogous to the waxy coatings of the cacti and other succulents that serve as a barrier to water loss in dry environments.

    Bouquet (1950) has mentioned that the western side of Lebanon's mountainous Cannabis growing areas is less favorable for resin production because of humid sea winds. De Faubert Maunder (1976) also observed that the copious separable resin needed for hashish production occurs only "in a belt passing from Morocco eastwards, taking in the Mediterranean area, Arabia, the Indian sub-continent and ending in Indo-China." These are mostly areas notable for their sparse rainfall, low humidity and sunny climate. Is it merely coincidence that resin is produced according to this pattern, as well?

    Experimental evidence is accumulating that reinforces these notions. Sharma (1975) reported a greater glandular trichome density on leaves of Cannabis growing in xeric circumstances. Paris et al. (1975a) have demonstrated a marked increase in the cannabinoid content of Cannabis pollen with decreased humidity. Murari et al. (1983) grew a range of Cannabis fiber cultivars in three climatic zones of Italy and found higher THC levels in those plants grown in the drier "continental" (versus "maritime") climate. Hakim et al. (1986) report that CBD-rich English Cannabis devoid of THC produced significant amounts of THC and less CBD, when grown in the Sudan. This trend was accentuated in their next generation of plants.

    Haney and Kutscheid (1973) have shown significant correlations of plant cannabinoid content with factors affecting soil moisture availability: content of clay or sand, percent slope of plot, and competition from surrounding vegetation. In some cases, this last factor was noted to have induced a stunted plant with "disproportionally smaller roots", which would tend to increase both the frequency and severity of desiccation stress.

    In a study of 10 Kansas locations, Latta and Eaton (1975) found wide differences in plant cannabinoid content, observing that "delta-9-THC ranged from 0.012 to 0.49% and generally increased as locations became less favorable for plant growth, suggesting increased plant stress enhanced delta-9-THC production." Mention was also made of a positive correlation between competing vegetation and THC content. Although the sampling area was not considered very moisture deficient, they speculated that "Greater difference among locations might have been observed under drought conditions."
    Temperature

    Temperature may play a role in determining cannabinoid content, but perhaps only through its association with moisture availability. Boucher et al. (1974) reported an increase in cannabinoid content with temperature (32o C. vs. 22o C.), however, some variables such as increased water loss due to accelerated evaporation and plant transpiration at high temperatures were left unaccounted. In contrast, Bazzaz et al. (1975), using 4 Cannabis ecotypes of both tropical and temperate character, demonstrated a definite decrease in cannabinoid production with increased temperature (32o C. vs. 23o C.). Later studies by Braut-Boucher (1980) on clones of 2 strains from South Africa revealed a more complex pattern of biosynthesis according to strain, gender and chemical homologue produced. Clearly, further study of this parameter is needed.
    Soil Nutrients

    Mineral balance seems to influence cannabinoid production. Krejci (1970) found increases related to unspecified "poor soil conditions". Haney and Kutcheid (1973) have shown the influence of soil K, P, Ca and N concentrations on Illinois Cannabis. They report a distinctly negative correlation between soil K and plant delta-9-THC content, although K-P interaction, N and Ca were positively correlated with it. These minerals were also shown to affect the production of CBD, delta-8-THC and cannabinol (CBN), although the latter two compounds are now thought to be spontaneous degradation products of delta-9-THC. Kaneshima et al. (1973) have demonstrated the importance of optimal Fe levels for plant synthesis of THC. Latta and Eaton (1975) reported Mg and Fe to be important for THC production, suggesting that these minerals may serve as enzyme co-factors. Coffman and Gentner (1975) also corroborated the importance of soil type and mineral content, and observed a significant negative correlation between plant height at harvest and THC levels. Interestingly, Marshman et al. (1976) report greater amounts of THC in Jamaican plants growing in "organically" enriched (vs. artificially fertilized) soils.
    Insect predation

    Wounding of the plant has been employed as a method to increase resin production (Emboden 1972). This increase may be a response to desiccation above the point of vascular disruption. Under natural circumstances, wounding most often occurs as a result of insect attack. This is a source of environmental stress which the production of terpenes and cannabinoids may be able to minimize. Cannabis is subject to few predators (Smith and Haney 1973, Stannard et al. 1970) and has even been utilized in powdered or extract form as an insecticide (Bouquet 1950) or repellent (Khare et al. 1974). Its apparent defensive mechanisms include a generous covering of non-glandular trichomes, emission of volatile terpenoid substances, and exudation of the sticky cannabinoids. Cannabis is often noted for its aromatic quality and many of the terpenes produced are known to possess insect-repellent properties. Among these are alpha and beta pinene, limonene, terpineol and borneol. Pinenes and limonene comprise over 75% of the volatiles detected in the surrounding atmosphere, but account for only 7% of the essential oil (Hood et al. 1973). Consistent with glandular trichome density and cannabinoid content, more of these terpenes are produced by the inflorescences than the leaves, and their occurrence is also greater in the female plant (Martin et al. 1961).

    No insect toxicity studies using isolated cannabinoids have been published to date. Rothschild et al. (1977) found THC-rich Mexican (vs. CBD-rich Turkish) Cannabis fatal to tiger moth (Arctia caja) larvae, but not Nigerian grasshopper (Zonocerus elegans) nymphs. Rothschild and Fairbairn (1980) later found that pure THC (vs. CBD) sprayed on cabbage leaves, does repel the large white cabbage butterfly (Pieris brassicae).

    The cannabinoids may also serve as a purely mechanical defense. A tiny creature crossing the leaf surface could rupture the tenuously attached globular resin reservoirs of the glandular trichomes (Ledbetter and Krikorian 1975) and become ensnared in resin. A sizable chewing insect, if able to overcome these defenses, would still have difficulty chewing the gummy resin, along with the cystolithic trichomes and silicified covering trichomes also present on the leaf. The utility of these epidermal features as insect antifeedants is also inferable from their predominant occurrence on the insect-favored abaxial leaf surface. Although the above strategies represent a seemingly sophisticated system, many other plants (Levin 1973) and even arthropods (Eisner 1970) utilize similar defense mechanisms, often employing identical terpenes!
    Competition

    Terpenes may also help to suppress the growth of surrounding vegetation (Muller and Hauge 1967, Muller et al. 1964). Haney and Bazzaz (1970) speculated that such a mechanism may be operative in Cannabis. They further ventured that since the production of terpenes is not fully developed in very young plants, this may explain their inability to compete successfully with other vegetation until more mature. The observation (Latta and Eaton 1975) of increased THC production by plants in competition with surrounding vegetation "at a time in the growing season when moisture was not limiting", may indicate a stimulus for cannabinoid production beyond that of simple water stress.
    Bacteria and fungi

    The cannabinoids may serve as a protectant against microorganisms. Cannabis preparations have long served as medicines (apart from their psychoactive properties) and are effective against a wide variety of infectious diseases (Kabelic et al. 1960, Mikuriya 1969). These antibiotic properties have been demonstrated with both Cannabis extracts (Ferenczy et al. 1958, Kabelic et al. 1960, Radosevic et al. 1962) and a variety of isolated cannabinoids (ElSohly et al. 1982, Farkas and Andrassy 1976, Gal and Vajda 1970, Van Klingeren and Ten Ham 1976). CBG has been compared (Mechoulam and Gaoni 1965) in both "structure and antibacterial properties to grifolin, an antibiotic from the basidiomycete Grifolia conflens." Ferency (1956) has demonstrated the antibiotic properties of Cannabis seed, a factor that may aid its survival when overwintering. Adherent resin on the seed surface, as well as a surrounding mulch of spent Cannabis leaves, may serve in this regard.

    Some of the many fungal pathogens that affect Cannabis include Alternaria alterata (Haney and Kutsheid 1975), Ascochyta prasadii (Shukla and Pathak 1967), Botryosphaeria marconii (Charles and Jenkins 1914), Cercospora cannabina and C. cannabis (Lentz et al. 1974), Fusarium oxysporum (McCain and Noviello 1985), Phoma sp. (Srivastava and Naithani 1979) and Phomopsis ganjae (McPartland 1984).

    While A. alterata attacks Illinois Cannabis and destroys 2.8-45.5% of the seed (Haney and Kutsheid 1975), the balance of these species are leaf spot diseases. McPartland (1984) has demonstrated the inhibitory effects of THC and CBD on Phomopsis ganjae. However, De Meijer et al. (1992), in evaluating a large collection of Cannabis genotypes, did not find a correlation between cannabinoid content and the occurence of Botrytis. Fungal evolution of a mechanism for overcoming the plant's cannabinoid defenses may be responsible for their success as pathogens. Indeed, some have been demonstrated to metabolize THC and other cannabinoids (Binder 1976, Binder and Popp 1980, Robertson et al. 1975).
    Ultraviolet radiation

    Another stress to which plants are subject results from their daily exposure to sunlight. While necessary to sustain photosynthesis, natural light contains biologically destructive ultraviolet radiation. This selective pressure has apparently affected the evolution of certain defenses, among them, a chemical screening functionally analogous to the pigmentation of human skin. A preliminary investigation (Pate 1983) indicated that, in areas of high ultraviolet radiation exposure, the UV-B (280-315 nm) absorption properties of THC may have conferred an evolutionary advantage to Cannabis capable of greater production of this compound from biogenetic precursor CBD. The extent to which this production is also influenced by environmental UV-B induced stress has been experimentally determined by Lydon et al. (1987). Their experiments demonstrate that under conditions of high UV-B exposure, drug-type Cannabis produces significantly greater quantities of THC. They have also demonstrated the chemical lability of CBD upon exposure to UV-B (Lydon and Teramura 1987), in contrast to the stability of THC and CBC. However, studies by Brenneisen (1984) have shown only a minor difference in UV-B absorption between THC and CBD, and the absorptive properties of CBC proved considerably greater than either. Perhaps the relationship between the cannabinoids and UV-B is not so direct as first supposed. Two other explanations must now be considered. Even if CBD absorbs on par with THC, in areas of high ambient UV-B, the former compound may be more rapidly degraded. This could lower the availability of CBD present or render it the less energetically efficient compound to produce by the plant. Alternatively, the greater UV-B absorbency of CBC compared to THC and the relative stability of CBC compared to CBD might nominate this compound as the protective screening substance. The presence of large amounts of THC would then have to be explained as merely an accumulated storage compound at the end of the enzyme-mediated cannabinoid pathway. However, further work is required to resolve the fact that Lydon's (1985) experiments did not show a commensurate increase in CBC production with increased UV-B exposure.

    This CBC pigmentation hypothesis would imply the development of an alternative to the accepted biochemical pathway from CBG to THC via CBD. Until 1973 (Turner and Hadley 1973), separation of CBD and CBC by gas chromatography was difficult to accomplish, so that many peaks identified as CBD in the preceding literature may in fact have been CBC. Indeed, it has been noted (De Faubert Maunder 1970) and corroborated by GC/MS (Turner and Hadley 1973) that some tropical drug strains of Cannabis do not contain any CBD at all, yet have an abundance of THC. This phenomenon has not been observed for northern temperate varieties of Cannabis. Absence of CBD has led some authors (De Faubert Maunder 1970, Turner and Hadley 1973) to speculate that another biogenetic route to THC is involved. Facts scattered through the literature do indeed indicate a possible alternative. Holley et al. (1975) have shown that Mississippi-grown plants contain a considerable content of CBC, often in excess of the CBD present. In some examples, either CBD or CBC was absent, but in no case were plants devoid of both. Their analysis of material grown in Mexico and Costa Rica served to accentuate this trend. Only one example actually grown in their respective countries revealed the presence of any CBD, although appreciable quantities of CBC were found. The reverse seemed true as well. Seed from Mexican material devoid of CBD was planted in Mississippi and produced plants containing CBD.

    Could CBC be involved in an alternate biogenetic route to THC? Yagen and Mechoulam (1969) have synthesized THC (albeit in low yield) directly from CBC. The method used was similar to the acid catalyzed cyclization of CBD to THC (Gaoni and Mechoulam 1966). Reaction by-products included cannabicyclol, delta-8-THC and delta-4,8-iso-THC, all products which have been found in analyses of Cannabis (e.g., Novotny et al. 1976). Finally, radioisotope tracer studies (Shoyama et al. 1975) have uncovered the intriguing fact that radiolabeled CBG fed to a very low THC-producing strain of Cannabis is found as CBD, but when fed to high THC-producing plants, appeared only as CBC and THC. Labeled CBD fed to a Mexican example of these latter plants likewise appeared as THC. Unfortunately, radiolabeled CBC was not fed to their plants, apparently in the belief that CBC branched off the biogenetic pathway at CBD and dead ended. Their research indicated that incorporation of labeled CBG into CBD or CBC was age dependent. Vogelman et al. (1988) likewise report that the developmental stage of seedlings, as well as their exposure to light, affects the occurrence of CBG, CBC or THC in Mexican Cannabis. No CBD was reported.
    Conclusions

    Although the chemistry of Cannabis has come under extensive investigation, more work is needed to probe the relationship of its resin to biotic and abiotic factors in the environment. Glandular trichomes are production sites for the bulk of secondary compounds present. It is probable that the cannabinoids and associated terpenes serve as defensive agents in a variety of antidessication, antimicrobial, antifeedant and UV-B pigmentation roles. UV-B selection pressures seem responsible for the distribution of THC-rich Cannabis varieties in areas of high ambient radiation, and may have influenced the evolution of an alternate biogenetic pathway from CBG to THC in some of these strains. Though environmental stresses appear to be a direct stimulus for enhanced chemical production by individual plants, it must be cautioned that such stresses may also skew data by hastening development of the highly glandular flowering structures. Future studies will require careful and representative sampling to assure meaningful results.

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    Thats all for now folks.

    FERMENT Nw
    Last edited by FERMENTATION; Mar-22-2006 at 19:18.

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    Quote Originally Posted by FERMENTATION
    Alchemiser: Thankyou. I just went searching for some answers before I saw your comment. I will post links and paste the contents. I did see uv-b mentioned either in one of these or somewhere else. I would like to learn or figure out how to produce specific terpenes for specific odors. It may come down to identifying the terpene that produces a desirable odor them looking up its precursor and adding that to the nutrient mix at the correct time in the plants life cycle.
    Hiya FERMENTATION
    You've definitely been looking along the right lines of research, just wish it wasn't so long since i had to think about these things
    First things first the second Glucose pathway is only activated when Mycorrhizal fungi forms a symbiotic relationship with the plant, UV-B is needed to activate the top part of the pathway thus doubling the number of trichs
    The odors from the girls is something we've worked hard to get rid of, probably best if you stick with pre-cursor formed thc by not using to much uv-b to have more pre-cursors left.
    Did lookup changing the taste of the girls with fruit juice etc, then tried feeding just a bit of glucose once a week during flowering & couldn't be bothered with trying anything else. Real Fruity everytime now
    Quote Originally Posted by FERMENTATION
    This one isn't anything specific to just terpenoids their is also talk about uv-b and it's contribution to the potency as well as some other interesting ideas about cannabis.

    http://www.hempfood.com/IHA/iha01201.html
    Good but still missing far to much as to uv-b's effects on the trichs, more interesting is the feeding of CBG & CBD resulting in an increase of THC!
    Unfortunately getting hold of CBG & CBD was the hard thing to do, along with all the other fun chemicals
    We did try an experiment feeding phenylalanine recently with some very positive results, though being quite so constantly stoned nowadays makes it hard to keep going with the extra work
    Will go through me bookmarks to see what's there, finding links that still work is the prob.
    Hope i've made enough sense to give you something to think about FERMENTATION

  10. #9
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    The odors from the girls is something we've worked hard to get rid of, probably best if you stick with pre-cursor formed thc by not using to much uv-b to have more pre-cursors left.

    UV-B if converted into the visible spectrum is 5150K about which is the sun. Alot depends on the CRI

    The odors our in the fat and amino acids get rid of the fat (oil) so I hear. Not sure if it is healthy, but it is sold by some fertilizer companies

  11. #10
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    UV-b cannot be converted to the visable spectrum karmaxul, the CRI is a complete waste of time when it comes to uv.
    Wavelength in nanometers
    Frequency in hertz
    Intensity in microwatts

    FAT i can honestly say i've no idea what your on about in the second statement
    In the Terpenes is where the aramatic hydro-carbons are found, the amino acid we added didn't increase smell at all

  12. #11
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    Nor should the amino acids increase the smell. It is used in burning fats and would decrease it.

    Volatile oils:
    1). Another name for essential oils, volatile oils are responsible for producing the aroma in certain plants and flowers. Volatile oils stimulate the tissue they come in contact with and can arouse or soothe, depending on their source and concentration.
    2). These are easily evaporated terpene derivitives found in plants which impart taste and aroma

    Terpene:
    1). Naturally occurring hydrocarbons, emitted by many trees and plants. They mostly have very strong smells and are responsible for the aromas of the vegetation in which they are found. Terpenes can be thought of as being built from units of isoprene, C 5 H 8 , joined together into chains and rings. Monoterpenes, formula C 10 H 16 , constitute the major emissions from conifers and fruit trees. Sesquiterpenes, formula C 15 H 24 , are commonly found in citrus trees.
    2). Monoterpenes and triterpenes comprise the terpenes under investigation. Most of the attention is focused on two monoterpenes: limonene and perillyl alcohol


    As far as saying, "UV-b cannot be converted to the visable spectrum karmaxul, the CRI is a complete waste of time when it comes to uv."

    The rainbow goes in cycles if you will and the sun in our gravity produces light from 375 Nm to 750Nm which is the pure light specturm.

    The UV spectrum goes from 0 - 375 Nm

    The sun gives
    5.3% red light 723.18 nanometers
    36.3% blue light 508.7 nanometers
    58.3% yellow light 616 nanometers

    5.3% x 723.18 = 38.32
    36.3% x 508.7 = 184.6
    58.3% x 616.0 = 359.1
    (38.32 + 184.6 + 359.1 = 582)

    582.1 Nm = 5153.6 K (3,000,000/Nm(582.1 in pure light spectrum)=K(5153.6))
    Also the suns degree K

    “When considering the effect of UV radiation on human health and the environment, the range of UV wavelengths is often subdivided into UVA (380–315 nm), also called Long Wave or "blacklight"; UVB (315–280 nm), also called Medium Wave; and UVC (< 280 nm), also called Short Wave or "germicidal". “
    http://en.wikipedia.org/wiki/Ultraviolet

    750 (Nm) End of pure light / beginning of Infrared spectrum
    723 Red
    669 Orange
    616 Yellow
    562 Green
    508 Blue
    455 Indigo
    401 Violet
    375 (Nm) End of pure light / beginning of Ultra violet spectrum


    UV colors not visible to human eye:
    375 (Nm) End of pure light / beginning of Ultra violet spectrum
    348 UV Red
    294 UV Orange
    241 UV Yellow
    187 UV Green
    134 UV Blue
    80 UV Indigo
    27 UV Violet
    0 (Nm) End of UV

    UV is radiation as it is not stable in the gravity of the earth. The gravity of the earth dictates the length of the light cycles which is why they are 375 space gaps.

    Notice that UV Green is 187 Nm. This is also the exact frequency which we produce ozone at. It is actually exactly 187.5 but we can call it 187 just to make it a bit easier.

    Plants use again
    5.3% red light 723.18 nanometers
    36.3% blue light 508.7 nanometers
    58.3% yellow light 616 nanometers

    Which if converted into the UV realm is:
    5.3% UV red light 348 nanometers
    36.3% UV blue light 134 nanometers
    58.3% UV yellow light 241 nanometers

    Light frequency under 187.5 is straight up deadly.

    Plants can use a bit of 200 - 375 Nm but not much.
    The UV-B is really just a cheap but some what usable version of yellow light of the pure non radioactive spectrum which plants use the most of anyways.

    Now for frequency.

    Hz is opposite Nm in that 375 Hz = 750 Nm and 375 Nm = 750 Hz

    I suspect human voice as in a mother talking to a child is healthy and nurturing.

    I know different vitamins are built up and broken down at different wavelengths or frequencies of light. I once found a chart showing the different spectrums of vitamin formation, but it is on my crashed pc which I need to get fixed before I can access it.

    From previous research I found that the Hz is the opposite of the nanometer

    375Nm = 750Hz and 375Hz = 750Nm

    # Frequency Range of the Human Voice
    * Voice range covers 300 Hz to 3500 Hz
    * Most energy concentrated below 1000 Hz
    http://www.kodachrome.org/salt/sunderst.htm

    Since plants need:
    5.3% red light 723.18 nanometers
    36.3% blue light 508.7 nanometers
    58.3% yellow light 616 nanometers

    So in Hz that would be

    401.78 Hz at 5.3%
    669.9 Hz at 36.3%
    508.7 Hz at 58.3% as vitamins can also be built up and broken down at this end of the spherical spectrum that makes up earth.

  13. #12
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    Quote Originally Posted by karmaxul


    UV is radiation as it is not stable in the gravity of the earth. The gravity of the earth dictates the length of the light cycles which is why they are 375 space gaps.
    Please explain, how does gravity dictate the length of the light cycle? what do you mean 375 space gaps?


    Quote Originally Posted by karmaxul
    Now for frequency.

    Hz is opposite Nm in that 375 Hz = 750 Nm and 375 Nm = 750 Hz

    From previous research I found that the Hz is the opposite of the nanometer

    375Nm = 750Hz and 375Hz = 750Nm
    That is utterly WRONG. 375hz isnt anywhere near the visible spectrum!
    Anyone who knows anything about physics will know Speed of light (c) = Wavelength (lambda) x frequency (f). Therefore
    375nm light = speed of light (299,792,000 m/s) divided by wavelength (375 x 10e9) = 7.99 x 10^14Hz or 799445333333333Hz, no where near 750!

    Please stop spreading wrong information karmaxul, I argue with you on a weekly basis about it. If you want more evidence that you're wrong in this case, I can provide it.

  14. #13
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    Thanks Bluefunk
    It's amazing just how much gibberish 1 human can come out with in just 1 post!


    So karmaxul UV-B has now become just a cheap form of visable yellow light...RALMAO
    Remembering this is going to have me giggling for ages to come

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    Quote Originally Posted by karmaxul
    375Nm = 750Hz and 375Hz = 750Nm

    # Frequency Range of the Human Voice
    * Voice range covers 300 Hz to 3500 Hz
    * Most energy concentrated below 1000 Hz
    http://www.kodachrome.org/salt/sunderst.htm
    This is also wrong, 300 - 3500 hz is the frequency range of a telephone.. not a human voice. The voiced speech of a typical adult male will have a fundamental frequency of from 85 to 155 Hz.

    Baken, R. J. (1987). Clinical Measurement of Speech and Voice. London: Taylor and Francis Ltd. - read up on it. Dont trust kiddie science webpages.

    Also why is energy concentrated below 1000hz? the amount of energy in a wave is directly proportional to the frequency ie high frequency, high energy.


    Thanks alchemiser, too right!

  16. #15
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    So, you two (Einstein and Feyman) can't even ASK him for his numbers... the why's... and the how's....

    No... you just ride in here, as cowboys, shoot the idea down, some shit thrown around,... and that's it?

    Look, fine... I see your points in clearing up the Hz = nm thing and others... but, CAN YOU ASK IN A POLITE FUCKING WAY?

    There are actual people at the other sides of these computers... not to get mushy mushy, but you can ruin a person's day/week with a post.

    I've seen Karmaxul post those numbers two or three times before, and I want to know the WHY he has them... what's his reasoning for getting them...

    I'm open to possibilities... peace IN,

    -turtle420
    .

  17. #16
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    Quote Originally Posted by Bluefunk
    wavelength (375 x 10e9)
    You sure about this number?

    I'm about to make a joke on it... but I want to give you a chance to correct your equations...

  18. #17
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    turtle I see you point but.. the first, second and even third time I've corrected karmaxel for saying things that are wrong, I did it in a police way. Each time I asked him not to try to explain things he does not fully understand but he carries on.

    I'm sorry (to you for being unpleasant on your board) but people like this are the source of so much misinformation which is spread about boards like this and I'm sure you'll agree. Especially if he's posting these numbers over and over again, and he is infact wrong.

    Your opinion turtle?

  19. #18
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    Quote Originally Posted by turtle420
    You sure about this number?

    I'm about to make a joke on it... but I want to give you a chance to correct your equations...
    Sorry 10 x 10e-9 if that's what you mean.

    a number like 10 x 10e9 means to the power of, it's easier than doing superscript on these boards. no error... programs such as excel do this with large numbers as they cannot format superscript. Type "999999999999999" in a cell on excel if you want to check.




  20. #19
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    Quote Originally Posted by Bluefunk
    turtle I see you point but.. the first, second and even third time I've corrected karmaxel for saying things that are wrong, I did it in a police way. Each time I asked him not to try to explain things he does not fully understand but he carries on.

    I'm sorry (to you for being unpleasant on your board) but people like this are the source of so much misinformation which is spread about boards like this and I'm sure you'll agree. Especially if he's posting these numbers over and over again, and he is infact wrong.

    Your opinion turtle?
    Thanks for the kind reply...

    1st, I hope these where "my" boards... I'm just another member man...

    Like you say :::: Misinformation is bad. No doubt.

    Let me re-read Karmaxul's information, and think about it a little bit.

    Thanks for the "cool" reply... I thought this was going to turn into a shit-slinging fest... I'm happy to know we can discuss stuff

    (BTW: Shouldn't it had been 10e-9 instead of 10e9?)

    I'll be re-loading and digesting the info... I'll post in a couple of minutes.

    Peace and love... and more joints to you Bluefunk (and alchemiser!),

    -turtle420
    .

  21. #20
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    Sorry you beat me to it before I could edit it. fair cop - my bad

  22. #21
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    Quote Originally Posted by Bluefunk
    Sorry you beat me to it before I could edit it. fair cop - my bad
    Ahahha.... we're all good man... we're all good

    My joke was:
    That's the longest wave I've ever come across in my life!

    lol....

    But, once (during college), I did some studying for HOURS... and, in the wee hours of the morning, I came out with the answer... a temperature...
    It was like -3,000 degrees Celcius!!! Colder than the start of the universe! Colder than cold!

    I was all happy and dandy, wrote everything down, closed my books, went out for a smoke (3/4AM)... in the middle of smoking, it hits me:
    There's no temperature under 0 Kelvin... WTF turtle????
    Ahahhaa! Funny shit.

    <><><>
    I'm still reading Karmaxul's information man... still trying to "get it in".

  23. #22
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    Quote Originally Posted by Bluefunk
    Sorry 10 x 10e-9 if that's what you mean.

    a number like 10 x 10e9 means to the power of, it's easier than doing superscript on these boards. no error... programs such as excel do this with large numbers as they cannot format superscript. Type "999999999999999" in a cell on excel if you want to check.
    Ahhh.... I enjoyed the "nitpicking" line....

    Arghh... I'll be waiting 5 minutes between replies... lol !

  24. #23
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    """UV is radiation as it is not stable in the gravity of the earth. The gravity of the earth dictates the length of the light cycles which is why they are 375 space gaps."""

    Hmmm.... could it be 365 space gaps? The same # as days in a year?

    And the gaps, I'm unsure where they're at...
    KARMAXUL, are these gaps in the spectrum? Visible part? UV part? Both parts?

    And, I'm unsure about the gravity of the Earth having effects... BUT I want to know what Karmaxul means before making a decision...

    Hmm... I'm still re-reading.

  25. #24
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    alchemiser: Thank you. I am looking forward to any links you can provide. If you kept notes while you were experimenting it would be cool if you could find them for show and tell. I'm to tired for a proper response so maybe tomorrow.

    Bluefunk & alchemiser: You have both done a great good by pointing out Karmaxul's errors. This is not the first time I have seen that nonesense posted.

    Goodnight.


    FERMENT. It is good for you.

  26. #25
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    Turtle: You are very entertianing when you get excited. At least you seem excited to my sleepy head.

    Can we please keep this on topic. As fun as it is to rip Karmaxul new orifices(pl) and laugh at mumbo jumbo.

    Topic: How are terpenoids formed in cannabis? (and other CLOSELY related thoughts.)

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