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Meroterpenoids
A meroterpene (or meroterpenoid) is a chemical compound having a partial terpenoid structure. Examples Terpenophenolics Terpenophenolics are compounds that are part terpenes, part natural phenols. Plants in the genus '' Humulus'' and '' Cannabis'' produce terpenophenolic metabolites, such as humulone and tetrahydrocannabinol respectively. Other examples of terpenophenolics from plants include bakuchiol and lapachol. The antibiotic marinone produced by marine bacteria Bacteria (; : bacterium) are ubiquitous, mostly free-living organisms often consisting of one Cell (biology), biological cell. They constitute a large domain (biology), domain of Prokaryote, prokaryotic microorganisms. Typically a few micr ... is another example. Terpenophenolics can also be isolated from animals. The terpenophenolics methoxyconidiol, epiconicol and didehydroconicol, isolated from the ascidian '' Aplidium aff. densum'', show antiproliferative activity. References
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Meroterpenes
A meroterpene (or meroterpenoid) is a chemical compound having a partial terpenoid structure. Examples Terpenophenolics Terpenophenolics are compounds that are part terpenes, part natural phenols. Plants in the genus ''Humulus'' and ''Cannabis'' produce terpenophenolic metabolites, such as humulone and tetrahydrocannabinol respectively. Other examples of terpenophenolics from plants include bakuchiol and lapachol. The antibiotic marinone produced by marine bacteria is another example. Terpenophenolics can also be isolated from animals. The terpenophenolics methoxyconidiol, epiconicol and didehydroconicol, isolated from the ascidian Ascidiacea, commonly known as the ascidians or sea squirts, is a paraphyletic class in the subphylum Tunicata of sac-like marine invertebrate filter feeders. Ascidians are characterized by a tough outer test or "tunic" made of the polysaccharid ... '' Aplidium aff. densum'', show antiproliferative activity. References {{ ...
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Bakuchiol
Bakuchiol is a meroterpenoid (a chemical compound having a partial terpenoid structure) in the class terpenophenol. It was first isolated in 1966 by Mehta et al. from ''Psoralea corylifolia'' seed and was called Bakuchiol based on the Sanskrit name of the plant, Bakuchi. Bakuchiol is a meroterpene phenol abundant in and mainly obtained from the seeds of the Psoralea corylifolia plant, which is widely used in Indian Ayurveda to treat a variety of diseases. It has also been isolated from other plants, such as P. grandulosa, P. drupaceae, Ulmus davidiana, Otholobium pubescens, Long pepper, Piper longum and Aerva sangulnolenta Blum. Even though the first complete synthesis of Bakuchiol was described in 1973, its first commercial use in topical applications did not occur until 2007 when it was introduced to the market under the trade name Sytenol A by Sytheon Ltd. It has been reported to have anticancer activity in preclinical models, possibly due to its structural similarity with res ...
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Marinone
Marinone is an antibiotic made by marine actinomycetes. Biosynthesis The proposed biosynthesis of marinone was first reported by Murray ''et al.'' in 2018. The biosynthesis of marinone begins with 1,3,6,8-tetrahydroxynaphthalene (THN), which is known to be biosynthesized via the condensation of five malonyl-coenzyme A units followed by the aromatization of the resulting pentaketide using a type III polyketide synthase. Next, THN undergoes geranylation or farnesylation Prenylation (also known as isoprenylation or lipidation) is the addition of hydrophobic molecules to a protein or a biomolecule. It is usually assumed that prenyl groups (3-methylbut-2-en-1-yl) facilitate attachment to cell membranes, similar to ... at the C-4 position, yielding 1 (Fig. 1). This transformation is catalyzed in vivo by NphB aromatic prenyltransferase in naphterpin biosynthesis or by CnqP3 or CnqP4 in marinone biosynthesis. Then, 1 undergoes oxidative dearomatization which is catalyzed by VCPO, ...
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Cannabis
''Cannabis'' () is a genus of flowering plants in the family Cannabaceae that is widely accepted as being indigenous to and originating from the continent of Asia. However, the number of species is disputed, with as many as three species being recognized: '' Cannabis sativa'', '' C. indica'', and '' C. ruderalis''. Alternatively, ''C. ruderalis'' may be included within ''C. sativa'', or all three may be treated as subspecies of ''C. sativa'', or ''C. sativa'' may be accepted as a single undivided species. The plant is also known as hemp, although this term is usually used to refer only to varieties cultivated for non-drug use. Hemp has long been used for fibre, seeds and their oils, leaves for use as vegetables, and juice. Industrial hemp textile products are made from cannabis plants selected to produce an abundance of fibre. ''Cannabis'' also has a long history of being used for medicinal purposes, and as a recreational drug known by ...
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Humulone
Humulone (α-lupulic acid), a Vinylogy, vinylogous type of organic acid, is a Bitterness (taste), bitter-tasting chemical compound found in the resin of mature hops (''Humulus lupulus''). Humulone is a prevalent member of the class of compounds known as alpha acids, which collectively give hopped beer its characteristic bitter flavor. Chemistry In terms of structure, humulone is a phloroglucinol Derivative (chemistry), derivative with three isoprenoid side-chains. Two side-chains are prenyl groups and one is an isovaleryl group. The acidity of the ring enol moieties that give rise to its designation as an acid lie in their Vinylogy, vinylogous relationship with the ring and side chain carbonyl functional groups. Isohumulone During the brewing process, humulone degrades to ''cis-'' and ''trans-''isohumulone. These “alpha acids” survive the boiling process, although numerous oxidized derivatives are produced. The iso-alpha acids are significantly more soluble than humul ...
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Tetrahydrocannabinol
Tetrahydrocannabinol (THC) is a cannabinoid found in cannabis. It is the principal psychoactive constituent of ''Cannabis'' and one of at least 113 total cannabinoids identified on the plant. Although the chemical formula for THC (C21H30O2) describes multiple isomers, the term ''THC'' usually refers to the delta-9-THC isomer with chemical name (−)-''trans''-Δ9-tetrahydrocannabinol. It is a colorless oil. Medical uses THC, referred to as dronabinol in the pharmaceutical context, is approved in the United States as a capsule or solution to relieve chemotherapy-induced nausea and vomiting and HIV/AIDS-induced anorexia. THC is an active ingredient in nabiximols, a specific extract of ''Cannabis'' that was approved as a botanical drug in the United Kingdom in 2010 as a mouth spray for people with multiple sclerosis to alleviate neuropathic pain, spasticity, overactive bladder, and other symptoms. Nabiximols (as Sativex) is available as a prescription drug in Canada. In 20 ...
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Humulus
''Humulus'', or hop, is a small genus of flowering plants in the family Cannabaceae. The hop is native to temperate regions of the Northern Hemisphere. Hops are the female flowers (seed cones, strobiles) of the hop species '' H. lupulus''; as a main flavor and aroma ingredient in many beer styles, ''H. lupulus'' is widely cultivated for use by the brewing industry. Description Although frequently referred to in American literature as the hops "vine", it is technically a bine; unlike vines, which use tendrils, suckers, and other appendages for attaching themselves, bines have stout stems with stiff hairs to aid in climbing. In British literature the term "vine" is generally reserved for the grape genus ''Vitis''. ''Humulus'' is described as a twining perennial herbaceous plant which sends up new shoots in early spring and dies back to the cold-hardy rhizome in autumn. Hop shoots grow very rapidly, and at the peak of growth can grow per week. Hop bines climb by wrapping clockwise ...
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Lapachol
Lapachol is a natural phenolic compound isolated from the bark of the lapacho tree.Record, Samuel J.. "Lapachol" pages 17-19. In: ''Tropical Woods'' (1925). This tree is known botanically as '' Handroanthus impetiginosus'', but was formerly known by various other botanical names such as ''Tabebuia avellanedae''. Lapachol is also found in other species of ''Handroanthus''. Lapachol is usually encountered as a yellow, skin-irritating powder from wood. Chemically, it is a derivative of vitamin K Vitamin K is a family of structurally similar, fat-soluble vitamers found in foods and marketed as dietary supplements. The human body requires vitamin K for post-translational modification, post-synthesis modification of certain proteins ....Louis F.Fieser. ''The Scientific Method'' pages 163-191. Reinhold Publishing Corporation, New York, 1964 Once studied as a possible treatment for some types of cancer, the levels of lapachol required for cancer treatment are considered too ...
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Natural Phenol
In biochemistry, naturally occurring phenols are natural products containing at least one phenol functional group. Phenolic compounds are produced by plants and microorganisms. Organisms sometimes synthesize phenolic compounds in response to ecological pressures such as pathogen and insect attack, UV radiation and wounding. As they are present in food consumed in human diets and in plants used in traditional medicine of several cultures, their role in human health and disease is a subject of research. Some phenols are germicidal and are used in formulating disinfectants. Classification Various classification schemes can be applied. A commonly used scheme is based on the number of carbons and was devised by Jeffrey Harborne and Simmonds in 1964 and published in 1980: C6-C7-C6 Diarylheptanoids are not included in this Harborne classification. They can also be classified on the basis of their number of phenol groups. They can therefore be called ''simple phenols'' or ...
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Bacteria
Bacteria (; : bacterium) are ubiquitous, mostly free-living organisms often consisting of one Cell (biology), biological cell. They constitute a large domain (biology), domain of Prokaryote, prokaryotic microorganisms. Typically a few micrometres in length, bacteria were among the first life forms to appear on Earth, and are present in most of its habitats. Bacteria inhabit the air, soil, water, Hot spring, acidic hot springs, radioactive waste, and the deep biosphere of Earth's crust. Bacteria play a vital role in many stages of the nutrient cycle by recycling nutrients and the nitrogen fixation, fixation of nitrogen from the Earth's atmosphere, atmosphere. The nutrient cycle includes the decomposition of cadaver, dead bodies; bacteria are responsible for the putrefaction stage in this process. In the biological communities surrounding hydrothermal vents and cold seeps, extremophile bacteria provide the nutrients needed to sustain life by converting dissolved compounds, suc ...
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