New phytoecdysteroids from roots of Ajuga reptans varieties

Calcagno, María Pia; Camps, Francisco; Coll, Josep Pujol i; Melé, Enric; Sánchez‐Baeza, Francisco

doi:10.1016/0040-4020(96)00536-4

Cited by 25 publications

(14 citation statements)

References 7 publications

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“…The known compounds, 22-acetylcasterone (2), 19) ajugalactone (3), 20) cyasterone (4), 21) isocyasterone (5), 21) ajugamacrin B (6), 22) ajugapantin A (7), 23) ajugamarin C1 (8), 15) ajugalide-A (9), 24) -B (10), 24) -C (11), 24) -D (12), 24) pheophytin-a (13), 25) 14) harpagide (18), 26) galiridoside (19), 14) teuhircoside (20), 27) b-sitosterol (21), 28) stigmasterol (22), 28) b-sitosteryl-D-glucoside (23), 28) vanillic acid (24), 28) kaempferol (25) 29) and nicotinic acid (26) 30) were also isolated from Ajuga taiwanensis. Their structures were identified by comparison of their spectroscopic data (UV, IR, NMR and mass spectrometry) with values in the literature.…”

Section: Resultsmentioning

confidence: 99%

A New Phytoecdysteroid from Ajuga taiwanensis

Chan

Kuoh

et al. 2005

Chem. Pharm. Bull.

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Many plants contain ecdysteroids, polyhydroxysteroids with a cis-fused A/B ring junction and 14a-hydroxy-7-ene-6-one system, structurally related with ecdysone, the biosynthetic precursor of the insect moulting hormone.1) These compounds exhibit interesting physiological activities such as regulation of moulting in insects, hormonal functions involve regeneration, metamorphosis, reproduction and differentiation in all arthropods, and antiulcer, antirheumatic, insulin regulation and diuretic or tonic effects in mammals. 2)Among the numerous plants containing phytoecdysteroids, those pertaining to Ajuga genus are unique for the great variety of such compounds produced.3) Species belonging to genus Ajuga have been used as folk medicinal plants as anthelmintic against intestinal disorders, antifungal, hypoglycaemic, antitumor and antimicrobial agents. 4,5) Furthermore, it has also been reported that some species of this genus were especially used as diuretic agents, as a remedy for fever, toothache, dysentery and hypertension. 6) Earlier chemical investigations have led to the isolation of clerodane diterpenoids, 7-9) ecdysteroids, 3,5,10,11) flavonoids, 12) iridoids [13][14][15] and triglycerides.16) The compounds isolated from the genus Ajuga, exert a broad spectrum of biological and pharmacological actions such as cytotoxic, anti-mitotic, anti-bacterial, cardiotonic, vasorelaxing, antifungal and antifeedant and insect growth-inhibitions. These facts encouraged us to investigate the chemical constituents of an Ajuga species A. taiwanensis NAKAI ex MURATA (Labiatae) mainly distributed in the Taiwan, Philippines and Ryukyus which has been often used for the treatment of hepatitis and hepatoma in Taiwanese folk medicine.17) The isolation of ajugalide A to D from title plant has recently been reported from our laboratories. In this paper, we now describe the isolation and structural elucidation of one new phytoecdysteroid, ajugalide-E (1) and twenty five known compounds. Results and DiscussionAjugalide-E (1) was isolated as an optically active, white amorphous solid, mp 210-212°C. The high-resolution fastatom bombardment mass spectrum (HR-FAB-MS) of 1 showed a pseudo molecular ion peak ([MϩH] . These data were consistent with the occurrence of characteristic side chain with g-lactone by similitude with 22-acetylcasterone signals. Additional functionalities included the signal of an olefinic proton at d 6.21 (br s) as well as nine methine protons and seven methylene groups and an acetyl methyl group also supported the basic skeleton of phytoecdysteroid. As shown in Table 1 the 1 H-and 13 C-NMR spectra for compound 1 showed a high analogy with those of 22-acetylcasterone with a cis fused A/B ring junction and 14a-hydroxy-7-ene-6-one skeleton 19) Results of two-dimensional correlation spectroscopy (2D-COSY) and the long-range 13 C-1 H correlation in heteronuclear multiple bond correlation (HMBC) experiments also confirmed that the planar structure of 1 was the same as 22-acetylcasterone (2). But the differences in...

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Section: Resultsmentioning

confidence: 99%

A New Phytoecdysteroid from Ajuga taiwanensis

Chan

Kuoh

et al. 2005

Chem. Pharm. Bull.

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“…2 and CCDC 235748). Table 4 Another compound 1A should be an isomer of cyasterone based on comparison of its NMR data with those data previously reported as shown in Tables 1-3 [3,4]. Only the 1 H and 13 C NMR data of the side chain were different in 1A and 1B except for C-21 and C-26 (Table 1).…”

Section: ) N-[2-hydroxy-(nonadecanoyl-tricosanoyl)]-4-hydroxytrans-8mentioning

confidence: 99%

“…5). The known compounds ajuforrestins A (3) and B (4) [8], 20-hydroxyecdysone (5) [9][10][11], polypodin B (6) [9,12], ajugalactone (7) [4], 8-O-acetylharpagid (8) [13,14], and N- [2-hydroxy-(nonadecanoyl-tricosanoyl)]-4-hydroxytrans-8-sphingenine (10) [5] were identified by their spectral data and by comparison with previously reported data. Apigenin (9), ␤-sitosterol (11), and daucosterol (12) were identified by their spectral data and by co-TLC with authentic samples.…”

Section: O-␤-d-glucopyranosyl-(2s3s4r 8e)-2-[(2r)-2-hydroxyh-mentioning

confidence: 99%

Phytoecdysteroids and glycoceramides from Eriophyton wallchii

Luo

et al. 2004

Steroids

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“…1) This plant has been reported to contain iridoids, 1,2) diterpenoids, [3][4][5][6][7] ecdysteroids, [8][9][10] and anthocyanins.…”

Section: Notementioning

confidence: 99%

“…

Compounds 5-13 were identified as reptoside (5), 12) harpagide (6), 12) 6-epi-acetyl harpagide (7), 13) acetyl harpagide (8), 12) ajugaside A (9), 15) ajugalactone (11), 9) 20-hydroxyecdysone (12), 16) and 20-hydroxyecdysone 3-acetate (13), 16) respectively, based on their physical and spectral data ( Fig.

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mentioning

confidence: 99%

Four New Iridoid Glucosides from Ajuga reptans

Ono

Furusawa

Ozono

et al. 2011

CHEMICAL & PHARMACEUTICAL BULLETIN

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NoteAjuga reptans L. (Labiatae) is native to Europe, and has been used as a traditional vulnerary.1) This plant has been reported to contain iridoids, 1,2) diterpenoids, [3][4][5][6][7] ecdysteroids, [8][9][10] and anthocyanins.11) The present paper describes the isolation and structural elucidation of four new iridoid glucosides (1-4) along with four known iridoid glucosides (5-8), one known diterpenoid glycoside (9), one known aliphatic alcohol glycoside (10), and three known ecdysteroids (11-13), as well as the antioxidative activities of 9.Dried whole plants of A. reptans were extracted with methanol (MeOH). This extract was successively subjected to Diaion HP20, silica gel, and Chromatorex octadecyl silica (ODS) column chromatography as well as HPLC using ODS to yield 13 compounds (1-13).Compounds 5-13 were identified as reptoside (5), 12) harpagide (6), 12) 6-epi-acetyl harpagide (7), 13) acetyl harpagide (8), 12) ajugaside A (9), 15) ajugalactone (11), 9) 20-hydroxyecdysone (12), 16) and 20-hydroxyecdysone 3-acetate (13), 16) respectively, based on their physical and spectral data ( Fig. 1).Compound 1, tentatively named ajureptaside A, was obtained as a syrup, and exhibited an [MϩNa] ϩ ion peak at m/z 477 in the positive-ion FAB-MS. (d 99.9, 74.6, 78.0, 71.8, 77.8, 63.0). These 1 H-and 13 C-NMR signals (Tables 1 and 2, respectively) were assigned with the aid of 1 H-1 H correlation spectroscopy (COSY), heteronuclear multiple quantum coherence (HMQC), and heteronuclear multiple bond correlation (HMBC) spectra. The planar structure of 1, which was an iridoid glucopyranoside whose aglycone moiety (Agl) possessed three hydroxyl groups at C-4, C-5, and C-6, one methoxy group at C-3, and one acetoxy group at C-8, could be determined as illustrated in Fig. 2. The relative configurations at C-1, C-3, C-4, C-5, C-6, C-8, and C-9 of Agl were concluded to be S*, R*, R*, S*, R*, S*, and S*, respectively, on the basis of the nuclear Overhauser and exchange spectroscopy (NOESY) spectrum, in which key correlations were observed between H-1 of Agl and H 3 -10 of Agl; H-4 of Agl and H-6 of Agl; and H-4 of Agl and H 3 -10 of Agl, as shown in Fig. 3, and by analysis of the coupling constants (J H-1-H-9 0 Hz; J H-3-H-4 8.0 Hz) between H-1 and H-9; and H-3 and H-4 in the 1 H-NMR spectrum. Acidic hydrolysis of 1 gave D-glucose, which was confirmed by optical rotation using chiral detection in HPLC analysis, and the coupling constant of the signal due to the anomeric proton [d 4.73 (d, Jϭ8.0 Hz)] indicated the mode of glycosidic linkage of the glucopyranosyl group to be b. Consequently, the structure of 1 was concluded to be 8-Oacetyl-4b-hydroxy-3a-methoxy-dihydroharpagide. Four new iridoid glucosides were isolated from the whole plant of Ajuga reptans L. (Labiatae) along with four known iridoid glucosides, one known diterpenoid glycoside, one known aliphatic alcohol glycoside, and three known ecdysteroids. Their chemical structures were determined on the basis of spectroscopic data and chemical evidence. The diterpenoid gl...

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New phytoecdysteroids from roots of Ajuga reptans varieties

Cited by 25 publications

References 7 publications

A New Phytoecdysteroid from Ajuga taiwanensis

A New Phytoecdysteroid from Ajuga taiwanensis

Phytoecdysteroids and glycoceramides from Eriophyton wallchii

Four New Iridoid Glucosides from Ajuga reptans

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