|
|
Practical ecological knowledge for the temperate reader. |
Family: Onagraceae - Evening-Primrose [E-flora]
"Annual to perennial herb, generally from taproot, occasionally rhizomed. Leaf: basal or cauline, alternate, generally pinnately toothed to lobed, generally sessile. Inflorescence: spike, raceme-like, or flowers in axils of distal, reduced leaves. Flower: radial or (sect. Gaura) bilateral, generally opening at dusk; sepals 4, reflexed in flower (sometimes 2–3 remaining adherent); petals 4, yellow, white, rose, or ± purple, generally fading ± orange to ± purple, tip notched or toothed; stamens 8, filaments sometimes (sect. Gaura) with paired teeth at base, anthers attached at middle; ovary chambers 4, stigma generally deeply lobed, generally > anthers and cross-pollinated (or ± = anthers and self-pollinated). Fruit: generally dehiscent, cylindric to ovoid or obovoid, cylindric to 4-winged or -angled, straight to curved, generally sessile (base sometimes seedless, stalk-like). Seed: in generally 2(1–3) rows per chamber, or clustered or reduced to 1–4 per fruit.
145 species: America, some widely naturalized. (Greek: wine-scented) [Wagner et al. 2007 Syst Bot Monogr 83:1–240]
Unabridged references: [Raven & Gregory 1972 Mem Torrey Bot Club 23:1–96; Dietrich & Wagner 1988 Syst Bot Monogr 24:1–91]
Unabridged note: Many species self-pollinated; some of these have chromosome peculiarities (ring of 14 in meiosis) and ± 50% pollen fertility; they yield genetically identical offspring." [Jepson]
Local Species;
"Originating in America (temperate and tropical climate zones), the Oenothera genus (the second largest genus of flowering plants) is currently present in various zones of the planet and include approximately 145 species, which are divided into 18 sections, from which 70 species can be found in Europe [5,6]." [Fecker et al.,2020]
The eastern North American Oenothera biennis is called 'evening-primrose' because its pale yellow. primrose-coloured flowers open in the evening (at sunset). The meaning of Oenothera is not clear. It is probably from the Greek meaning 'wine-scented,' although one source says it means 'wine-catching" (the roots having been taken after a meal to induce further wine-drinking) and another says it means "ass-catcher' (with no explanation why; perhaps it has something to do with people's behaviour after drinking all that wine?). [PCBC2004] "Oenothera is a name that Pliny used for a plant (now unknown) reputed to produce sleep when its juice was drunk in wine." [EWPP]
Cultivation
Large, fragrant, yellow flowers bloom at dusk. In the Tina James strain (O.glaziovinia), the flowers pop open suddenly - great fun to watch. Days to Germination: About 2 weeks at 70 0F to 80 0F (21 0C to 27 0C) Growing Conditions: Any ordinary soil, even poor soil, suits these hardy, drought tolerant plants. The seeds are tiny. Cover them lightly, if temperatures all. Some species are considered biennials, but all reseed freely.[NSSH Bubel] "Propagate from seed, division or soft cutting, they will grow in most soil types, though they prefer light sandy ones for maximum root growth." [Tozer UWP]
References
"Oenothera biennis is a BIENNIAL growing to 1.2 m (4ft).
It is hardy to zone (UK) 4 and is not frost tender. It is in flower from Jun to September, and the seeds ripen from Aug to October. The flowers are hermaphrodite (have both male and female organs) and are pollinated by Lepidoptera, bees, self.The plant is self-fertile. It is noted for attracting wildlife.
Suitable for: light (sandy) and medium (loamy) soils, prefers well-drained soil and can grow in nutritionally poor soil. Suitable pH: acid, neutral and basic (alkaline) soils. It cannot grow in the shade. It prefers dry or moist soil and can tolerate drought." [PFAF]
"Once you learn to recognize them, (the old) dead stalks of evening primrose will tell you where to look for the rosettes. The abundance of the plants varies greatly from year to year in the same place, and so does the proportion of first and second-year plants; there may be many stalks and few rosettes, or vice-versa." [Thayer FH]
"Lowers the threshold for epileptic fits (avoid). Caution if on anticoagulants. Combining with phenothiazines (allopathic medication) can trigger seizures. Adverse effects: may cause headaches and nausea on an empty stomach. Diarrhoea with high doses. Seizures in schizophrenic patients on phenothiazines (allergy antihistamines) [301]." [PFAF] "Although it's contraindicated for epileptics, and it gives sensitive individuals headaches, skin rashes, and nausea, it's not dangerous." [Wildman]
Oleum Oenotherae Biennis [fixed seed oil] may precipitate symptoms of undiagnosed temporal lobe epilepsy, particularly in schizophrenic patients or patients taking epileptogenic drugs such as phenothiazines (70–72).[WHO]
General
Drug interactions
Species Mentioned: Onagra strigosa J Oenothera biennis var. hirsutissima [Harrington] Oenothera species; including O. biennis - Evening Primrose, O. brevipes - Desert Primrose, O. californica - California Evening Primrose O. perennis and O. hookerii - Hooker's Evening Primrose. [Tozer UWP]
All parts of the plant are edible. [mcvicar GH][Tracy HPTCP] Evening primrose was a staple food for many Native American tribes and a famine food for Chinese farmers (3) [Tracy HPTCP]
Flowers of evening primrose (Oenothera biennis) used for hormone imbalances. [Lans et al., 2006]
"Oenothera. Oenothera biennis L. Tree Primrose. Evening Primrose. Onagre, Fr. Nachtkerze, Gr. (Fam. Onagraceae.) —The fleshy root of this plant, before the introduction of the potato, was used as a table vegetable. Many years ago R. E. Griffith commended very highly a strong decoction of the plant frequently applied to eruptive skin diseases. More recently the drug has been commended in whooping cough and spasmodic asthma, and the ointment has been used in prurigo and other cutaneous affections of infants, and as an application to ulcers. Dose, of fluidextract, from a half to one fluidrachm (1.8-3.75 mils). The ointment may be made by incorporating four ounces of the fluidextract in a pound of vaseline or lard." [Remington USD20]
"Oils from borage (Borago officinalis) or from evening primrose (Oenothera biennis) are rich in g-linoleic acid and used for systemic and topical application." [BMBBed]
"Evening primrose oil is extracted from the seeds of Oenothera biennis and is a rich source of omega-6 essential fatty acids, primarily gamma-linolenic acid (GLA) and linoleic acid, both essential components of myelin and the neuronal cell mem- brane. Three trials have examined the effect of GLA in diabetic neuropathy and reported statistically significant improvements in symptom scores (Halat and Dennehy 2003). The side effect profile for evening primrose oil was generally mild and similar to placebo. Evening primrose oil appears to inhibit platelet aggregation by decreasing the formation of thromboxane and increasing the formation of PGE 1 and because of this, patients taking anti-platelet or anticoagulant medications should inform their physician regarding the use of evening primrose oil. The recommended dose is 360–480 mg/day of GLA." [Cho MMVC]
"G02C E Premenstrual syndrome PMS—pre-
menstrual syndrome—appears some days be-
fore the start of menstrual discharge with psychic and somatic symptoms: irritability,
mood changes, headache, breast tenderness,
feeling of bloating.
Low plasma levels of prostaglandins may
be a cause of PMS, whereas women suffering
from dysmenorrhea have a higher content of
PGF2 in the endometrium than normal.
There is also a positive connection be-
tween the degree of pain and the amount of
liberated prostaglandin in individuals, and
the ratio PGF2/PGE is increased; this ratio
correlates best with the occurrence and sever-
ity of dysmenorrhoea.
In therapy three plants are used: Evening
Primrose (Oenothera biennis L., family
Onagraceae), Borage (also known as
Starflower) (Borago officinalis, family
Boraginaceae) and Black currant (Ribes
nigrum, family Grossulariaceae). The seeds of
these three species contain gamma-linolenic
acid (GLA), which, as a precursor to prostag-
landin, leads to increased endogenous produc-
tion, which reduces symptoms of PMS.
Gamma linolenic acid is also used in the treat-
ment of atopic eczema." [Sandberg NR]
The major constituents [of the fixed seed oil are linoleic acid (cis-linoleic acid) (65–80%), g-linolenic acid (cis-g-linolenic acid) (8–14%), oleic acid (6–11%), palmitic acid (7–10%) and stearic acid (1.5–3.5%). Other constituents include sterols and triterpene alcohols (1, 3, 6, 14, 15).[WHO]
Evening primrose oil is extracted from the seeds of Oenothera biennis and is a rich source of omega-6 essential fatty acids, primarily gamma-linolenic acid (GLA) and linoleic acid, both essential components of myelin and the neuronal cell membrane. Three trials have examined the effect of GLA in diabetic neuropathy and reported statistically significant improvements in symptom scores (Halat and Dennehy 2003) . The side effect profile for evening primrose oil was generally mild and similar to placebo. Evening primrose oil appears to inhibit platelet aggregation by decreasing the formation of thromboxane and increasing the formation of PGE1 and because of this, patients taking anti-platelet or anticoagulant medications should inform their physician regarding the use of evening primrose oil. [Cho MMVC]
"Evening primrose.(Oenothera biennis.L.).No available information on salt tolerance of this crop.. Evening primrose is a rich source of polyunsaturated fatty acids that are linked to lowering blood cholesterol levels and reducing the risk of atherosclerosis. As salinity rose from 1 to 3 dS m−1, seed. oil content increased, and the content of palmitic, stearic, and γ-linolenic acids rose. The favorable ratio of omega-6 to omega-3 fatty acids in the oil was also a positive effect of salinity inasmuch as the ratio in human diets plays an essential role in control of membrane polyenoic fatty acids [162]." [Pessarakli HPCS]
Flowers: "The petals of flowers of Oenothera hookeri ssp. venusta contain only carotenoids in the distal ends, but the basal portions contain the chalcone isosalipurposide (16) (Dement and Raven, 1974)." [Seiger PSM]
Leaves: "...in the aqueous extract of the leaves, phenolic compounds (ellagitannins and caffeoyl tartaric acid), flavonoids (quercetin glucuronide; kaempferol glucuronide), carbohydrates (arabinose, glucose, galactose, mannose, glucuronic and galacturonic acid) and tannins (oenothein A; oenothein B) can be detected." [Fecker et al.,2020]
Root: "Timoszuk et al. also described the phytochemical composition of methanolic extracts obtained from the root of evening primrose. They identified sterols (sitosterol, oenothera lanosterol A; oenothera lanosterol), pentacyclic triterpene type maslinic acid and oleanolic acid, carbohydrates, tannins, xanthone and its derivates [5,7]." [Fecker et al.,2020]
[Cheng et al.,2001]
"The seed oil contains an essential fatty acid, "y-linolenic acid (GLA) that is not found in the normal diet, yet it is an essential intermediate in human metabolism." [Cheng et al.,2001]
"Although most plant-derived oils contain high amounts of unsaturated fatty acid glycerides, including those of linoleic and α-linolenic acids, the conversion of linoleic acid into γ-linolenic acid can be blocked or inhibited in certain conditions in humans. This restricts synthesis of prostaglandins. In such cases, the use of food supple- ments, e.g. evening primrose oil from Oenothera bien- nis (Onagraceae) or borage oil from Borago officinalis (Boraginaceae), which are rich in γ-linolenic esters (see Table 3.1), can be valuable and help in the disorder. These plants are somewhat unusual in their ability to desatu- rate linoleic esters towards the carboxyl terminus via a 6-desaturase, rather than towards the methyl terminus as is more common in plants. Expression of 6-desaturase genes, either from plants or suitable fungi, can be used to increase the production of γ-linolenic and stearidonic acids in hosts such as soybeans." [MNP Dewick]
"As GLA is an intermediate in the conversion of linoleic acid to arachidonic
acid, it is not surprising that GLA is found at low levels in many animal fats. It
is present in both cow’s milk fat (~0.1%, w/w of milk) and human milk fat
(0.35–1.0%, w/w of milk fat) and its presence in the latter has often been cited
as an indication of its importance in human nutrition. However, richer sources
of GLA are found in the seed oils of some less common plants and are also
produced by some microorganisms.
At present there are three commercial sources of GLA from seed oils:
evening primrose (Oenothera biennis and O. lamarckiana), borage (Borago
officinalis), and blackcurrant (Ribes nigrum)." [Gunstone LFFN]
"An alternative source of imported r-linolenic acid (GLA) from Oenothera biennis (evening primrose) has been developed in Japan using strains of Mortierella sp. in a liquid culture medium for the commercial production of a lipid rich in y-linolenic acid (Suzuki, 1988; Subba Rao and Kaushik, 1989; Robbins, 1995)." [Wickens, EB]
"γ-Linolenic acid is an essential ω-6 polyunsaturated fatty acid that also occurs in evening primrose (Oenothera biennis L.) and black currant seed (Ribes nigrum L.)." [Barceloux MTNS]
"... GLA production from Spirulina is more expensive than that from Oenothera biennis (evening primrose)." [Wickens, EB]
"The seed is a good source of gamma-linolenic acid, an unsaturated fatty acid which assists the production of hormone-like substances[222, 238]. This process is commonly blocked in the body, causing disorders that affect the uterine muscles, nervous system and metabolism[238]." [PFAF] Seeds of Oenothera biennis various Ribes species, and borage serve as GLA sources for dietary supplements, borage seed oil having the highest concentration.4 GLA is of potential therapeutic interest in treatments of atopic eczema, premenstrual syndrome, diabetes, alcoholism, inflammation, and prevention of heart disease and stroke. [Leung ENCI]
|
|
|
"As a result of more than two hundred studies conducted since 1970. the effectiveness of evening primrose-derived CLA has been attributed to a regulatory effect on systemic fatty acid imbalances and metabolic functions of the liver." [EMPW]
"...anti-cancer and anti-tumor (extracts/phytocompounds obtained from roots or seeds have shown antiproliferative, antiangiogenic, antimigratory, and antimetastatic effects against prostate, breast, hepatic cancer and leukemia cell lines)..." [Fecker et al.,2020]
"...anti-bacterial (extracts obtained from seed have been shown to have important actions against Pseudomonas aeruginosa, Staphylococcus aureus, Escherichia coli, and Candida albicans)..." [Fecker et al.,2020]
"...anti-fungal(roots–gallic acid)..." [Fecker et al.,2020]
"...anti-viral (topical administration of the oil has been shown to represent a therapeutic alternative for children with Molloscum contagiosum)..." [Fecker et al.,2020]
"The tested extract had a mild bacteriostatic effect on the tested bacterial strains. It was only bactericidal against S. aureus, but fungicidal against all the Candida-tested strains. In the set experimental conditions, the OB extract only manifested significant antiproliferative and pro-apoptotic activity against the A375 human melanoma cell line at the highest tested concentration, namely 60 µg/mL." [Fecker et al.,2020]
"China is now the major producer of evening primrose seed in the world, with an estimated 90% of total supply, which it has been able to achieve through the combination of low-cost hand labor, and growing conditions that are ideally suited to the crop." [Cheng et al.,2001]
"The yield of seeds is generally between 1125 and 1530 kg/ha, and in some better situations, may reach 2700 kg/ha in Jilin.... In 1992, the yield reached 3000 kg/ha in the experimental fields in Qingyuan County. In 1993, in the experimental field of 0.15 ha in Rizhao City of Shandong Province, an even greater yield, equivalent to 3750 kg/ha of seeds, was recorded (Zhang 1994)." [Cheng et al.,2001]
"There are at least 10 factories producing evening primrose oil from seed in China. In 1986, the oil factory of the Institute of Applied Ecology, Academia Sinica (IAE), formerly known as the Institute of Forestry and Soil Science, Academia Sinica, began to extract the oil with mechanical screw presses using the following process (Deng, Hua, and Duan 1993). The seeds are winnowed to remove foreign substances. The seed skins are softened using steam and the oil extracted without additional heat using a spiral oil press. After filtering, the oil is refined by neutralizing with alkali, deodorizing with steam, and decoloring by charcoal filtration. It is then dried, and filtered again to give the final product. Vitamin E is added to the oil. The oil is poured into drums which are purged with nitrogen, sealed, and stored under refrigeration. In China, oil is also extracted by means of solvent (normally hexane) and, to a small extent, with supercritical CO2 (Yu et al. 1992)." [Cheng et al.,2001]
Propagation
Seed - sow in situ from late spring to early summer[200].[PFAF] Sow seeds in either spring or fall. Leave the seed uncovered by substrate and place it in a cold frame. Germination takes three to four weeks. If sowing in fall, pot up and winter the young plants in a cold frame before planting out. Alternatively, sow the seeds directly into prepared open ground in fall. Cover the soil with twigs to prevent birds from eating the seeds. [Mcvicar GH] Days to Germination: About 2 weeks at 700F to 800F (210C to 270C) [NSSH Bubel] "Before sowing, the seeds are normally soaked in water at 40-50oC for 24-48 hours, or put into oven at 25oC to hasten germination (Li et al. 1994). In North-East China the seed may be vernalized by soaking it in water or mixing it with wet soil and then burying it in the frozen soil in early spring.... In some areas, the seed is sown into frozen ground in the Autumn, so that it can become fully vernalized over winter in situ to give an early germination and establishment the following spring." [Cheng et al.,2001]
Cultivation
Prefers a dryish well-drained sandy loam and a warm sunny position[1, 4, 200], though it is tolerant of most soils[4]. Heavy clay soils may induce winter rots[200]. Grows well on very poor soils[160, 238]. Established plants are drought resistant[160]. Formerly cultivated for its edible roots, the evening primrose is being increasingly cultivated for the oil contained in its seed which contains certain essential fatty acids and is a very valuable addition to the diet[66]. See the notes on medicinal uses for more details. The flowers open in the evening and are strongly scented with a delicious sweet perfume[245], attracting pollinating moths[4]. The seeds are a good food source for birds[200]. Plants usually self-sow freely if they are growing in a suitable position, they can naturalize in the wild garden[4, K].[PFAF] "The evening primrose that has formed the shape of lotus throne (rosette) by autumn can survive through the winter even with temperatures as low as -22oC It has strong resistance to drought, diseases, and insect pests. On the other hand, wet and hot conditions in the rainy (summer) season, long-term accumulation of water, and overcrowded plants may bring about root rot, leaf blight, and loss of leaves. Sometimes insect pests appear...." [Cheng et al.,2001]
Plant in well-drained soil in a dry, sunny position. Oenothera biennis is not suited to growing in containers because it is too tall.[Mcvicar GH]
Wildlife: "The flowers are adapted for moth pollination: These insects' long mouth parts can reach down the tube. Moths are active at night, when pale yellow is the easiest color to detect." [Wildman]
"LESSER EVENING PRIMROSE (Oenothera biennis) The tap roots have been used as a vegetable, boiled, which makes them quite nutritious, but they were little used after the introduction of the potato (C P Johnson). The taste is not unlike parsnips (Loewenfeld), or even salsify, so it is claimed (Kearney). There are a few medicinal uses. The American Indians, or at any rate the Ojibwe, used to soak the whole plant in warm water to make a poultice that would heal bruises (H H Smith. 1945). But there are recognized herbal remedies involving the bark and leaves, which are known to be sedative and astringent, so they have been used for gastro-intestinal disorders in particular, and also for asthma and whooping cough (Grieve. 1931). More recently, the seeds have been successfully used to treat eczema (T Walker). Oil of Evening Primrose helps menopausal changes and pre-menstrual problems, and it has been recommended to help arthritis, and even to slow down changes in multiple sclerosis (M Evans)." [DPL Watts]
"Oenothera biennis Linn. Onagraceae. EVENING PRIMROSE. GERMAN RAMPION. Northeastern America. This plant was formerly cultivated in English gardens for its edible roots, which, when boiled, are wholesome and nutritious. In Germany the roots are used as scorzonera and the young shoots in salads. The roots are sweet to the taste, somewhat resembling parsnips. The roots may be used as scorzonera, but the plant is cultivated in France only as a curiosity. It is said by Loudon to be cultivated in Germany, and, in Carniola, the roots are eaten in salad. It first reached Europe in 1614. It is given by Burr for American gardens in 1863, under the name German Rampion." [Sturtevant EPW]
"Oenothera biennis, also called evening-primrose, is a plant, that comes from North America. It was brought to Europe as an ornamental plant in the 17th century. Currently, this plant has spread to all continents in except Antarctica (Fleischhauer et al., 2013)." [Sadowska et al, 2018]
"Its advantage is that it blooms even in adverse climatic conditions and on poorly fertilized areas. It is grown commercially in over 30 countries around the world, mainly in Canada, the United States and China (Eskin, 2008). Although the whole plant is edible, the oil obtained from its seeds is the most important." [Sadowska et al, 2018]
"Oenothera biennis oil is obtained in industry, as a result of cold pressing of seeds or solvent extraction with n - hexane. The largest producer of evening primrose oil is China. Over 90% of the world production of this raw material is obtained there (Eskin, 2008). Oenothera biennis seed oil is characterized by a high content of polyunsaturated fatty acids. First of all, it is one of the few natural sources of gamma-linolenic acid (GLA) (Ghasemnezhad and Honermeier, 2007, 2008). Polyunsaturated fatty acids contained in Oenothera biennis oil have antioxidant and anti-inflammatory effects. Therefore, it is used primarily in the food industry as a dietary supplement, that supports the treatment of such diseases as hypertension, allergy, psoriasis or cancer (Barre, 2001; Białek and Rutkowska, 2015), also in the cosmetics industry, as an ingredient of soaps and body lotions (Muggli, 2007). In comparison with the most popular oils, such as rapeseed, soybean, linseed, palm etc., the content of unsaturated fatty acids in this oil is much higher (over 90% of all fatty acids) (Paciorek-Sadowska et al., 2018). In fact, Oenothera biennis oil is a future raw material for the oleochemical industry, including for the production of bio-polyols for the synthesis of PU materials." [Sadowska et al, 2018]
"The most popular methods for the synthesis of bio-polyols based on vegetable oils include: transesterification of fatty acid triglycerides with glycerol or triethanolamine (Veronese et al., 2011; Badri, 2012; Fridrihsone-Girone and Stirna, 2014), epoxidation of double bonds with opening of epoxide rings by diols (Noreen et al., 2016; Garrison et al., 2014), hydroformylation using synthesis gas (Guo et al., 2000; Petrović et al., 2010; Vanbesien et al., 2013), the addition of halogen or hydrogen halide to unsaturated double bonds in the reaction with secondary amine (Garrett and Du, 2010, 2014). Apart from the methods of obtaining polyols from vegetable oils, there are many other technologies based on these methods and their combinations. The choice of synthesis method depends on: scale of production, the type of final products, its usage and the availability of oil raw materials (Prociak et al., 2014)." [Sadowska et al, 2018]
"Noteworthy research on using bio-polyols based on soybean oil was conducted by Miao et al. The authors used soy polyols obtained from two methods (transesterification of triglycerides to monoglycerides and the opening of oxirane rings of epoxidized soybean oil) for the production of various PU materials. On the basis of first polyol raw material, they obtained PU elastomer characterized by very good mechanical properties and high cellular biocompatibility. The last parameter has particular importance in biomedical applications, eg in production of bio-implants. The second polyol was used to obtain oil-based materials with "shape memory". The research results proved that use of soybean bio-polyol improves the performance and creates new applications for this material, for example in biomedical engineering (Miao et al., 2012, 2013a; Miao et al., 2013b). Veronese et al. used a mixture of petrochemical and soybean polyol, synthesized in transesterification of hydroxylated oil with triethanolamine, in production of rigid polyurethane foams (RPUF). Obtained bio-based foams had better mechanical properties than their counterparts obtained from petrochemical raw materials (Veronese et al., 2011). Bhoyate et al. used bio-polyols based on soybean, castor and orange peel oils in a mixture with phosphorus and sulfur containing polyol to obtaining polyurethane foams. The presence of flame retardant elements has significantly reduced the self-extinguish time and weight loss after combustion. The authors showed that the improvement of fire resistance was caused by the formation of a protective layer on the foam surface resulting from the decomposition of phosphorus compounds (Bhoyate et al., 2018)." [Sadowska et al, 2018]
"Bio-polyol based on rapeseed oil has gained a significant value in recent years. It is used to obtain all types of PU foams, elastomers and adhesives (Prociak, 2008a, b). Prociak et al. developed and patented methods for obtaining polyols based on rapeseed oil for synthesis of rigid and flexible PU foams. They consisted of epoxidation reaction of double bonds of fatty acids and opening of epoxy rings with diethylene glycol (Pielichowski et al., 2010a, b). During the research, they used the obtained bio-polyol raw material in a mixture with petrochemical raw material. Foams based on bio-polyol were characterized by higher content of closed cells and lower thermal conductivity (Prociak, 2008a,b; Rojek and Prociak, 2012). Prociak et al. also analyzed the influence of the chemical structure of bio-polyols from rapeseed oil on the foaming process of RPUF. They showed that the method of synthesis of bio-polyol raw material, which affects the reactivity of polyurethane systems, has a significant influence on the chemical structure. Polyols obtained by the transesterification method are more reactive than those obtained by the method of opening the epoxide ring. In addition, the introduction of the amino group into the molecule significantly increases the reactivity of the bio-polyol (Prociak et al., 2018). Kurańska et al. did research on the replacement of petrochemical polyol for a bio-polyol based on rapeseed oil. The works pertained to the production of rigid polyurethane and polyurethane-polyisocyanurate (PUR-PIR) foams. Obtained materials had similar properties (such as: thermal conductivity coefficient, water absorption, closed cell contents) like unmodified foams (Kurańska and Prociak, 2014; Prociak et al., 2017; Kurańska and Prociak, 2016). Kirpluks et al. conducted research on obtaining of highly reactive bio-polyols from rapeseed oil for the synthesis of RPUF intended for thermal insulation. For this purpose, they used two methods of synthesis: ring opening of the appropriate epoxidized oil and transesterification of glyceryl backbone with different polyfunctional alcohols. The obtained bio-polyols were characterized by high functionality and reactivity. RPUF obtained on the basis of them had a low thermal conductivity coefficient and a high content of closed cells (Kirpluks et al., 2018)." [Sadowska et al, 2018]
"The article raises the issue of the research on obtaining a new bio-polyol based on Oenothera biennis seed oil and 2,2′-mercaptodiethanol (2,2′-MDE) and its use to produce rigid polyurethane-polyisocyanurate foams." [Sadowska et al, 2018]
Seed Viability "Buried seeds play an important role in the propa- gation and recruitment of weeds (Harper 1977, Chapter 4). The longevity of buried weed seeds has been documented by a number of workers (e.g., Sarukhan 1974; Burnside et al. 1977). Kivilaan and Bandurski (1973) reported that out of 23 species whose seeds had been buried in moist sand by Dr. Beal, Rumex crispus and Oenothera biennis remain- ed alive over 80 years, and Verbascum blattaria over 90 years." [Holzner BEW]
| Oenothera albinervis R.R. Gates Oenothera angustissima R.R. Gates Oenothera biennis subsp. caeciarum Munz, subsp. centralis Munz, var. canescens Torr. & A. Gray, var. hookeri (Torr. & A. Gray) B. Boivin, var. oakesiana A. Gray, var. pycnocarpa (Atk. & Bartlett) Wiegand Oenothera canovirens Steele Oenothera cruciata var. stenopetala (E.P. Bicknell) Fernald |
Oenothera depressa Greene Oenothera hookeri Torr. & A. Gray, subsp. montereyensis Munz Oenothera muricata L. Oenothera parviflora subsp. angustissima (R.R. Gates) Munz, var. angustissima (R.R. Gates) Wiegand, var. oakesiana (A. Gray) Fernald Oenothera pycnocarpa Atk. & Bartlett Oenothera strigosa subsp. canovirens (Steele) Munz Oenothera villosa subsp. canovirens (Steele) W. Dietr. & P.H. Raven [E-flora] |
"Oenothera glazioviana is a BIENNIAL growing to 1.5 m (5ft).
It is hardy to zone (UK) 3 and is not frost tender. It is in flower from Jul to October, and the seeds ripen from Aug to October. The flowers are hermaphrodite (have both male and female organs) and are pollinated by Lepidoptera, bees, self.The plant is self-fertile.
It is noted for attracting wildlife.
Suitable for: light (sandy) and medium (loamy) soils and prefers well-drained soil. Suitable pH: acid, neutral and basic (alkaline) soils. It cannot grow in the shade. It prefers dry or moist soil" [PFAF]
General: Biennial herb from a taproot; forming rosette in first year and erect stem in second; densely minutely-stiff-hairy, with spreading hairs from red blister-like bases, glandular in inflorescence; stems 50-150 cm tall. [IFBC-E-flora]
Leaves: Stem leaves alternate, elliptic to lanceolate, 5-15 cm long, nearly entire to toothed, crinkled, hairy. [IFBC-E-flora]
Flowers: Inflorescence a spike, the buds erect, opening in the evening, subtended by large bracts or reduced leaves; hypanthium 3.5-5 cm long; petals yellow, fading reddish-orange, 3.5-5 cm long; sepals 2.8-4.5 cm long, lobes 4, bent back in flower, the free tips in bud 5-8 mm long; stigmas deeply 4-lobed [IFBC-E-flora]
Fruits: Capsules, erect, narrowly lanceolate, 2-3.5 cm long, 5-6 mm wide, more or less straight, 4-chambered, hairy; seeds 1.3-2 mm long, angled, irregularly pitted, about half sterile. [IFBC-E-flora]
Habitat/Range
Mesic to dry roadsides and waste places in the lowland and steppe zones; infrequent garden escape in S BC, especially along the coast; thought to be originally of garden origin in Eurasia. [IFBC-E-flora]
Origin Status: Exotic [E-flora]
| Root |
|---|
"Root - cooked. Boiled and eaten like salsify[144]. Fleshy and succulent." [PFAF]
| Young Shoots |
|---|
"Young shoots - raw or cooked[144]. Mild and inoffensive[144]" [PFAF]
| Seed |
|---|
Oil: "Seed contains 28% of a drying oil[114]. It is edible and a very good source of gammalinolenic acid[141], an essential fatty acid that is not found in many plant sources and has numerous vital functions in the body. Difficult to harvest, it has to be done by hand[160]." [PFAF]
| Oil |
|---|
"The oil in the seeds is anticholesterolemic, astringent, hypotensive, sedative[4, 21]. Reduces cholesterol levels[66]. Research suggests that the oil is potentially very valuable in the treatment of multiple sclerosis, pre-menstrual tension, hyperactivity etc[66]." [PFAF]
"Evening primrose oil (Oenothera glazioviana Family- onagraceae) Evening primrose oil is the oil from the seeds of the oenothera glazioviana plant. The flower of many species open in the evening, hence the name evening primrose is used commonly [10]. Evening primrose oil is marketed in U.V.radiations induced cancer therapy. It contains γ linolenic acid which shows antioxidant property [38]" [Kulkarni, 2014]
Propagation
"Seed - sow in situ from late spring to early summer." [PFAF]
Cultivation
"Prefers a dryish well-drained sandy loam and full sun[1, 200]. Heavy clay soils may induce winter rots[200]. Succeeds on poor soils[200]. The flowers open in the evening, they are richly scented and are very attractive to moths[4]. The seeds are a good food source for birds, especially finches[200]. The plants of this species are of hybrid origin and usually mutate freely[1]. Usually self-sows freely if in a suitable position[K]." [PFAF]
[Granica et al.,2013]
Synonyms
SUBTAXA PRESENT IN BC
Oenothera villosa ssp. strigosa - Native [E-flora]
Oenothera villosa ssp. villosa - Exotic [E-flora]
"General: Biennial herb from a stout taproot; forming rosette in first year and an erect, stiff stem in second; greyish stiff-hairy, also with spreading hairs from red blister-like bases; stems 50-200 cm tall, simple or branched." [E-flora]
"Leaves: Stem leaves alternate, ascending or spreading, lanceolate or elliptic, 10-30 cm long, entire to minutely-toothed, hairy." [E-flora]
"Flowers: Inflorescence a few-flowered, open spike, glandular, buds erect, opening in the evening, subtended by large bracts or reduced leaves; hypanthium 2.5-4 cm long; petals yellow, fading duller or pale orange, 0.7-2 cm long; sepals 0.9-1.8 cm long, often marked reddish, bent back when in flower, the free tips in bud 0.5-2.5 mm long." [E-flora]
"Fruits: Capsules, erect, narrowly lanceolate, 2-3.5 cm long, 4-7 mm wide, more or less straight, 4-chambered, hairy; seeds 1-2 mm long, angled, irregularly pitted." [E-flora]
"Habitat / Range: Dry shrubland, roadsides and disturbed areas in the lowland and steppe zones; infrequent in C and S BC east of the Coast-Cascade Mountains, rare along the coast, where probably introduced; E to ON and S to MI, WI, NE, NM, AZ and CA." [E-flora]
"Evening primrose or sundrops (Oenothera spp.)—used as a diet aid and panacea for general strengthening."[NAH Orr]
"We would guess that all the related species of this large group of plants would stand a trial; as far as we know none are poisonous." [Harrington]
Oenothera hookeri; "It has been tried by us and appeared to be of about the same value as [O. biennis]. ...O. albicaulis, has podlike fruits that were eaten by the Indians (Cas tetter & Gpler, 45). We have tried eating the cooked young pods of several species of evening primrose and found them acceptable. Even the older (but still unripe) pods, although rather tough, can be cooked and eaten." [Harrington]
" Oenothera hookeri and O. biennis; "Preparation and Uses: The root is good when cooked at the right time of year, usually early spring. At other times it may have a peppery taste. O. biennis is a native species that was introduced into Europe and cultivated for its root. Other species in this genus are also known to be edible but the genus is so varied, and hybridizes so readily that it is impossible to say whether or not all of the species are edible." [Kirk WEP]
"Experimental work with Oenothera (Robberecht and Caldwell, 1983) and Arabidopsis (Li et aI., 1993; Lois, 1994; Lois and Buchanan, 1994), for example, has clearly established that flavonoids do provide a significant measure of pro- tection against shorter wavelength UV radiation. A useful overview of UV- acclimation in higher plants was published by Caldwell et al. (1983)." [Bohm FSF]
"Oenothein B (11) and related oligomers with a macrocyclic structure have been found in the genera Oenothera and Epilobium of Onagraceae (fig. 7). Woodfordin C (12) and cuphiin Dl (13), which were characterized as gallates of 11, were also obtained from species of Lythraceae.3 These dimers were shown to possess in vivo antitumor activity or to have an in vitro inhibitory effect on DNA-topoisomerase II as described earlier. Accordingly, these compounds might be potential" [Gross, PP2]
Oenothera cespitosa;Oenothera cespitosa - Ceremonial aid,gynecological aid,unspecified: Dermatological aid - O. cespitosa contains antineoplas agents [Heaton, 2004]
Oenothera erythrosepala;"Oenothein B (45), the main tannin component of Oenothera erythrosepala (Onagraceae),42 was the first isolated macrocyclic dimer of this type." [Chu PP] "Oenthein-B is hydrolysable tannin is found in Oenothera erythrosepala." [HPEP]
Oenothera erythrosepala;"Oenothein B, a macrocyclic ellagitannin from Oenothera erythrosepala Bordes, induced cytostatic macrophages to release interleukin I (IL-I)-like activity and IL-Ib. It is sug- gested that oenothein B exerts its anti- tumor effect through potentiation of the host immune defense via activation of macroph- ages.179"[Chung,1998]
Oenothera erythrosepala;Oenothein B was first isolated from Oenothera erythrosepala and then from the flower of Woodfordia fruticosa. [Gross, PP2]
"Some of the other medicinal plants produced in Jilin Province include evening primrose (Oenothera odorata Jaeq.) (Yue Jian Cao), used for cardiovascular diseases". [FCTM USDA]
"In this study, we found that whole-plant O.odorata extract inhibited the growth of cancer cells In Vitro and In Vivo. Moreover, the butanol-soluble (OOB) and water-soluble (OOW) fractions showed similar anti-proliferative effects. Interestingly, the anti-proliferative effect of both fractions was limited to cancer cells, with no effects on normal cells. Metabolic alternations in cancer cells may in part underlie the anti-tumor properties of O. odorata extract. Thus, O. odorata extract shows promise as a novel anti-tumor therapy through its control of cancer cell metabolism." [Lee et al.,2020]
"...we demonstrated that the water-soluble fraction of O. odorata extract was significantly cytotoxic to A549 lung carcinoma cells but not immortalized cell lines BEAS-2B and NIH/3T3.... In addition, the anti-proliferative effects of O. odorata extract were further verified by measuring the inhibition of B16-F10 melanoma cell growth In Vivo. Considering that body weight and neutrophil population in peripheral blood were not significantly altered by treatment, it is suggested that O. odorata extract or its fractions including OOB and OOW are not toxic or do not induce inflammation (26,27). Taken together, the anti-proliferative effect of OOB and OOW is most likely specific for cancer cells" [Lee et al.,2020]
Oenothera ovata;"Oenothera ovata Nutt. in T. & G. Lechuguilla. Foliage eaten, either raw, or boiled or steamed. (3)" [Bocek]
"Among edible flowers with potential anticancer effects, which modulates oxidative stress, the extract of Oenothera paradoxa Hudziok at 5–200 lg/mL enhanced ROS production and GSH level in human skin melanoma cells (Jaszewska et al. 2009). Flavanols and other polyphenols extracted from O. paradoxa lead to a decrease in the level of MMP9, VEGF, c-Jun, c-Fos in breast cancer cells (Lewandowska et al. 2013; Lewandowska et al. 2014)." [Fakhri et al.,2021]
"Polyphenols extracted from evening primrose seeds (industrial waste product) were studied as apoptosis inducers in human colorectal adenocarcinoma Caco-2 and HT-29 cell lines and in rat normal intestinal IEC-6 cells. The extract dose- dependently inhibited the growth of Caco-2, HT-29, and IEC-6 cells. However, nuclear DNA fragmentation characteristic of apoptosis was observed only in Caco-2. After 72 h of incubation with the extract at 150 μM gallic acid equivalents (44.1 μg extract/mL), Caco-2 cell numbers decreased to 19% of control and 48.8% of the cells were identified by flow cytometry as apoptotic." [Gorlach et al.,2011]
"Cytotoxic Action on HTB-140 [Human melanoma cells, line Hs 294T] Cells and NHDFs [Human skin fibroblast cells]. As shown by the conducted MTT [3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide] test, the viability of both cellular lines is closely dependent on the type and concentration of the adminis- tered extract. At 24 h of incubation of HTB-140 cells, IC50 values (50% growth inhibition concentration) of 169.7 ( 5.9 μg/mL, 72.4 ( 3.8 μg/mL, and 155.3 ( 6.3 μg/mL were obtained for the aqueous extract, 60% ethanolic extract, and 30% isopropanolic extract at the tested concentrations (5-200 μg/mL), respectively, while IC50 was not attained for the NHDF cells. (Figure 1) At 72 h of incubation, IC50 for the HTB-140 cells was 69.6 (5.8 μg/mL; 17.1 (2.6 μg/mL and 34.8 (4.3 μg/mL for the aqueous extract, 60% ethanolic extract, and 30% isopropanolic extract, respectively, while for NHDFs, the IC50 values were significantly higher and were 81.7 ( 6.9 μg/mL; 43.3 ( 4.8 μg/mL and 62.7 ( 6.4 μg/mL, respectively." [Jaszewska et al.,2009]
"In both tests (MTT [[3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide]]and LDH [lactate dehydrogenase]release), the 60% ethanolic extract displayed a significantly more potent action than the aqueous extract (p < 0.05)." [Jaszewska et al.,2009]
"In conclusion, EPE [defatted seeds extract], PGG [pentagalloylglucose] and the procyanidin fraction exhibited potent cytotoxic effect against human melanoma cells. Incubation of HTB-140 [metastatic melanoma] cells with EPE and VCR [vincristine] reduced the viability, increased mortality and limited the synthesis of intracellular ATP, while addition of an MRP1 [indomethacin] inhibitor did not produce any further cytotoxicity changes. HepG2 [hepatoma] cells were much less sensitive to both EPE alone and EPE with VCR. In future, EPE might prove a component increasing the effectiveness of therapy for certain types of cancer, including melanoma, but further studies on cell lines resistant to cytostatics as well as in vivo studies are still needed." [Jaszewska et al.,2010]Oenothera picensis;"Gonza´lez et al. (2011) evaluated the effects of MGDA [a biodegradable chelate] on Cu increase phytoextraction by Oenothera picensis and the minimal leaching of Cu through the soil." [Bini PHE]
Oenothera rosea;Oenothera rosea L’Her. ex Aiton - Leaves - Colic complaints - Bhatia et al., 2014 [Pugnaire FPE]
Oenothera rosea Ait. - Tender shoots - Carbuncles - Shah et al., 2008 [Pugnaire FPE]
Oenothera rosea;"Oenothera rosea Ait., yawarchunka, has a high repute in folk medicine of the valley. It grows wild on hillsides in the upper valley. The leaves are used as poul- tices for bruises, and they are also taken internally for such maladies as pneumonia and changes in the blood." [Gade PMLP]
Oenothera sinuata;"Another herb was ‘called tuesten [Tarascan tarepeni, or Oenothera sinuata] which is similar to salvia. If a wound is bloodied or cancerous, they apply the leaves… and it makes it better… it does not ache..." [Williams AAM]
Oenothera speciosa; "In summary, a novel biflavonol, named speciin, and two new flavonol glycosides, myricetin 4'-O-α- L-rhamnopyranoside and quercetin 3'-O-α-L-rhamnopyranoside have been isolated from the 80 % aqueous methanol extract of the aerial parts of Oenothera speciosa Nutt. (Onagraceae). In addition, fourteen known phenolic metabolites: myricitrin, europetin 3-O-α-L-1C4-rhamnopyranoside, quercitrin, hyperin, rhamnetin 3-O-β-galactopyranoside, caffeic acid, caffeic acid methyl ester, chlorogenic acid, chlorogenic acid methyl ester, gallic acid, gallic acid methyl ester, myricetin, quercetin and ellagic acid have been identified from the plant under investigation. The 80 % aqueous methanol extract exhibited significant antihyperglycaemic and anti-inflammatory activities in dose dependant manner. The investigated extract, myricitrin and hyperin also showed potent in vitro antioxidant activity using the DPPH free radical method." [Marzouk et al.,2009]
Oenothera tanacetifolia;"Oenothera tanacetifolia T. & G. Tansy-leaved Evening Primrose. 'Azee' pixe'tshiin xaltchiihikiih (medicine, its base, red ; i. e. medicine [plant which is] red [at] its base). It is used as a remedy for boils in the form of a liniment (24:115)."[Elmore EON]
Oenothera trichocalyx;"Oenothera trichocalyx Nutt. Evening- primrose. Used as a potherb (6, 39)." [Krochmal&Paur]
"...plants that make flowers that produce linalool (a monoterpene) often attract moth pollinators during the night, while species that may look similar and live in the same area, but do not produce linalool, do not attract moths (Raguso et al., 1996). They are pollinated by other insects, usually bees or butterflies, during the daytime. Thus, the components of a floral scent have important implications for the pollination success of the plants that produce them (Dodson, 1993; Galen and Kevan, 1983; MacSwain et al., 1973; Pellmyr, 1986)." [T&F NPP]
"Oenothera and Clarkia are in the same family (Onagraceae) and are thus closely related. Most Oenothera produce scent, including linalool; yet only two species within the Clarkia genus, C. concinna and C. breweri, produce linalool (Pichersky et al., 1994, 1995; Raguso and Pichersky, 1995). Flowers of C. concinna, like those of all other Clarkia species, are odorless to the human nose. However, linalool and its pyranoid and furanoid oxides were detected in C. concinna stigmas using gas chromatography/mass spectrometry (GC-MS), but at levels 1000-fold less than in C. breweri." [T&F NPP]
"It is generally accepted that Oenothera and Clarkia species share a common ancestor; yet, they show a surprising diversity in the ability to produce linalool. By characterizing the expression and regulation of genes that encode enzymes, such as linalool synthase, researchers can uncover how scented species, such as Oenothera, evolve into non-scented species, such as most Clarkia species, and yet retain the ability to evolve into scented species again — as C. breweri has done." [T&F NPP]
Oenothera missouriensis; "The secondary compounds produced by herbaceous perennials can also contribute to their ability to resist deer browsing and insect infestation. In our roadside trials, we observed that Missouri primrose (Oenothera missouriensis) and other Onoethera spp. were attractive to browsing deer, whereas catmint, lady’s mantle, and creeping phlox were never disturbed (Weston 2005)." [Zeng ASA]
References