Über die Konstitution von Loroglossin. Vorläufige Mitteilung

A perennial glabrous herb with two entire, ovoid or subglobose tubers. Roots short and relatively thick. Stem (10 -) 20 -70 (-115) cm, pale green, sometimes faintly marbled with purple, solid, cylindrical, smooth, and obscurely angled above. Leaves pale to dark green; the lower 4-10, 5-20 × 3.5-6 cm, elliptical-oblong to oblong-lanceolate, obtuse to acute at apex, entire, keeled and erect or spreading, many-veined; the upper smaller, tapering to an acute apex, clasping the stem. Inflorescence a spike 1-25 (-50) × 4-12 cm, rather lax, and cylindrical. Bracts 0.5-5 × 0.1-0.2 cm, pale green or white, often tinged with rose, narrow linear, tapering to an acute apex, more or less membranous, often with in-rolled edges, with a green central vein and about three others on either side. Flowers greenish-white with a very long, ribbon-like and white, green and purple or brownish twisted labellum hanging obliquely downwards (on small spikes with few scattered flowers the labella often appear horizontal), and a strong smell of billy goats. Outer perianth segments 0.7-1 cm, forming a helmet or hood, cohering at the base, free or not at the tip, whitish-green often flushed with purple spots or streaks inside and out, ovate, rounded at apex, concave, 3-or 4-veined (often green), the upper arched forward and rather boat-shaped. Inner perianth segments slightly shorter than the outer, very narrow, linear spotted, and 1-veined. Labellum 2-6 cm, linear, wedge-shaped and broader at the base, with (approximately) 12 purple spots around the junction where the three lobes meet; the edges are crimped. Side lobes 0.5-2 cm, purple brownish, curled and ribbon-like. Middle lobe white on top near its base, becomes purple light brownish for the 80% nearest the tip, and is curled. Spur short, conical, sock-like, rounded at the apex and directed downwards. Column rather short and erect. Single anther greenish-white and pyriform. There are two olive-green, pyriform pollinia. Caudicles thick, yellow, longer than the pollinia and bent at the apex. Viscidium elliptical or quadrangular, enclosed in a bursicle and very sticky. Stigma obtusely 4-cornered or ovatecordate and bordered by a dark line. Rostellum beaklike, projecting beyond the stigma. Ovary about 1 cm, pale green, spindle-shaped, twisted, pedicellate, with 3 slight, longitudinal ridges. Capsule long, tapering at the base, with marked ridges, 0.5-1.5 cm long and about 0.25-0.75 cm in diameter and contains 0-2000 seeds. Seeds 340 µ m in length by 120 µ m in diameter with the embryo measuring 100 µ m in length and 70 µ m in diameter. Seed mass > 0.01 µ g.A species of calcareous grasslands, sand dunes and occasionally woodland edges. It often appears sporadically as individuals or small colonies in new sites where it may last 20 years. In England larger colonies appeared only in the latter part of the 20th century and their persistence is not known.

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“…(1975). In addition, Gray et al . (1976, 1977) showed that the configurations at C‐2 and C‐3 were ( R ) and ( S ), respectively.…”

Section: Structure and Physiologymentioning

confidence: 99%

“…The structure of loroglossin (shown in Pridgeon et al 2001) was determined to be bis[4-( β-glucopyranosyloxy)benzyl] erythroisobutyltartrate by Aasen et al (1975). In addition, Gray et al (1976Gray et al ( , 1977 showed that the configurations at C-2 and C-3 were (R) and (S), respectively.…”

Section: ⁽  ⁾   mentioning

confidence: 99%

Himantoglossum hircinum(L.) Sprengel

Carey

Farrell

2002

Journal of Ecology

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“…6S (Supporting Information). According to the above information and after comparison with the previous literature [5][6][7][8][9][10][11], the two compounds were identified as bis [4-(β-D-O-glucopyranosyloxy)-benzyl] (S)-2-isopropylmalate (compound 1) and bis 4-[β-D-O-glucopyrnosyloxy)-benzyl]-(2R,3S)-2-isopropyl tartrate (compound 2), commonly known as vanilla glucoside A. (▶ Fig.…”

Section: Resultsmentioning

confidence: 99%

“…6S (Supporting Information). According to the above information and after comparison with the previous literature [5][6][7][8][9][10][11], the two compounds were identified as bis The potential biological activities of VPCE and compounds 1 and 2 were investigated through a series of biological activity experiments. Elastase is a serine protease that plays a crucial role in the wrinkling or sagging of the skin through the degradation of the elastic fibres of the dermis (elastin), causing the skin to lose its elasticity.…”

Section: Vanilla Pompona Leaves and Stems As New Sources Of Bioactive...mentioning

confidence: 99%

Vanilla pompona Leaves and Stems as New Sources of Bioactive Compounds: The Therapeutic Potential for Skin Senescence

et al. 2023

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A large variety of natural plants are widely produced and utilised because of their remarkable pharmacological effects. In this study, two phenolic glycosides were isolated for the first time from Vanilla pompona Schiede (Orchidaceae) from Kyushu, Japan: bis [4-(β-D – O-glucopyranosyloxy)-benzyl] (S)-2-isopropylmalate (1) and bis 4-[β-D-O-glucopyranosyloxy)-benzyl]-(2R,3S)-2-isopropyl tartrate (2). We have discovered that the crude extract of V. pompona leaves and stems and its two phenolic glycosides (compounds 1 – 2) are highly effective in reversing skin senescence. V. pompona and compounds 1 – 2 were found to promote the synthesis of collagen, hyaluronic acid, and elastin in skin fibroblasts in a normal skin cell model; in a replicative senescence model, V. pompona and compounds 1 – 2 significantly reduced the ageing phenotype in skin fibroblasts. These compounds also demonstrated a significant protective effect in a UV-induced photo-senescence model; the possible mechanisms of this effect were investigated in this study. To the best of our knowledge, this study is the first to develop V. pompona leaves and stems as new sources of bioactive compounds and to examine their therapeutic potential for skin senescence. The development potential of V. pompona leaves and stems for use in the cosmetics, cosmeceutical, and pharmaceutical industries remains to be investigated.

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“…3 4 -O-Methylpiscidic acid dimethyl ester 2 has been isolated from Narcissus poeticus L. 1,2 and the glucoside loroglossin 4 is a characteristic constituent of orchids. 4 Structurally related eucomic acid 5 has been isolated from the bulbs of Eucomis punctata L'Hérit. Most of these structures can be seen basically as alkylated tartaric acid derivatives and although several syntheses of these compounds have been reported, 1,2,4 the work of Seebach 5 is notable for its concise approach.…”

mentioning

confidence: 99%