Crystal Structure of Ipolamiide Monohydrate from Stachytarpheta indica

Roengsumran, Sophon; Sookkongwaree, Kasem; Jaiboon, Nongnuj; Chaichit, Narongsak; Petsom, Amorn

doi:10.2116/analsci.18.1063

Cited by 8 publications

(4 citation statements)

References 3 publications

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“…NOE correlations between H-1, H-9, and 10-CH 3 and that between H-5 and H-6α were consistent with the interatomic distances obtained from the crystal structure. In the present work, we have obtained an X-ray structure of the crystalline ipolamiide ( 9 ) (Figure ), identical to that previously published . Also for this compound clear NOE interactions were evident between H-1/H-9 and H-1/10-CH 3 (see Table S, Supporting Information).…”

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confidence: 83%

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Structural Revision of Some Recently Published Iridoid Glucosides

et al. 2007

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The structures of six different iridoid glucosides have been revised. Three compounds isolated from Eremostachys glabra and designated 6,9-epi-8-O-acetylshanziside (1), 5,9-epi-penstemoside (2), and 5,9-epi-7,8-didehydropenstemoside (3) have been shown to be identical to the known iridoids barlerin (4, 8-O-acetylshanziside), penstemoside (5), and 7,8-didehydropenstemoside (6), respectively. Another compound named harpagoside-B, isolated from Scrophularia deserti and proposed to be 9-epi-6-O-methylharpagoside (11), was demonstrated from the spectroscopic data given to be the known harpagoside (10b). Finally, two alleged iridoid galactosides from Buddleja crispa named buddlejosides A and B (12a and 12b) have been shown to be the corresponding glucosides; the former is identical to agnuside (13a), while the latter is 3,4-dihydroxybenzoylaucubin (13b), an iridoid glucoside not previously published. This clearly showed that care should be taken with the interpretation of NOEs involving bridgehead protons in iridoid structures because they can be capricious and lead to erroneous structural assignments.

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confidence: 83%

“…In the present work, we have obtained an X-ray structure of the crystalline ipolamiide (9) (Figure 1), identical to that previously published. 29 Also for this compound clear NOE interactions were evident between H-1/ H-9 and H-1/10-CH 3 (see Table 1S, Supporting Information). Thus, we have proved that the compound presented as 1 must indeed be barlerin (4).…”

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confidence: 86%

Structural Revision of Some Recently Published Iridoid Glucosides

et al. 2007

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“…Although there is no evidence of antibacterial activity, the anti-inflammatory effects of ipolamiide have been demonstrated in several studies [40,43,46]. Ipolamiide was isolated from S. indica by Tantisewie and Sticher [47] and Roengsumaran et al [48], although there was no indication of biological activities. However, the biosynthesis of ipolamiide has also been reported [49].…”

Section: Discussionmentioning

confidence: 99%

Antibacterial and anti-inflammatory activity of extracts and major constituents derived from Stachytarpheta indica Linn. leaves and their potential implications for wound healing

Agampodi

Katavic

Collet

et al. 2021

Preprint

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Wounds of various types continue to have a severe socioeconomic impact on the cost of health care. Globally, there has been increased interest surrounding the identification of bioactive compounds that promote or modulate the wound healing process. Stachytarpheta indica Linn. is traditionally used to heal wounds and relieve inflammation, however, the theorised pharmacological properties have not yet been scientifically validated. In this study, dried and ground plant leaves were extracted with water and methanol, which were then subjected to various analyses. Antimicrobial activity of the plant extracts and isolated compounds was determined using well diffusion assays, while the minimum inhibitory concentrations were determined with a colorimetric assay. Morphological changes of human keratinocytes in response to plant extracts were observed with differential interference contrast microscope imaging. Cell viability, proliferation and migratory effects post-treatment with the plant extracts were also evaluated via colorimetric cytotoxicity assays and a real-time cell analyser protocol. Anti-inflammatory effects of plant extracts and isolated compounds were evaluated by flow cytometry and cyclooxygenase and lipoxygenase enzyme inhibition assays. Three active compounds i.e. ipolamiide, verbascoside and iso-verbascoside, were isolated from S. indica leaves. Verbascoside demonstrated broad-range antibacterial activity and imposed strong inhibition at 9.77 μg/mL against Staphylococci spp. S. indica extracts (0.1-0.2 mg/mL) were shown to improve human keratinocyte proliferation up to 60 % and induce morphological changes by producing cytoplasmic projections at concentrations higher than 0.4 mg/mL. Plant extracts (6.25-100 μg/mL) and individual compounds (3.125-50 μg/mL) elicited strong anti-inflammatory effects by suppressing the expression of interleukin-8 and inhibiting cyclooxygenase-1 and 5-lipoxygenase enzymes. Collectively, these results indicate that plant extracts and isolated compounds derived from S. indica have the potential to inhibit bacterial growth, promote tissue regeneration and reduce inflammation, hence, potentially providing the basis for a novel therapeutic for the treatment of wounds.

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“…Infusion of bark is used in treating diarrhea and dysentery. Previous investigations of Stachytarpheta species revealed the occurrences of iridoid glycosides, steroids, flavonoids, phenylethanoid and phenylpropanoid glycosides, and some other phenolic and straight-chain aliphatic compounds (Subramanian et al, 1974;Tantisewie & Sticher, 1975;Duret et al, 1976;Lin & Chen, 1976;Garnier, 1977;Akisue et al, 1981;De Luca et al, 1983, 1980Rodriguez & Castro, 1996;Jawad et al, 1997;Futuro & Kaplan, 1998;Ganapaty et al, 1998;Schapoval et al, 1998;Roengsumran et al, 2002). S. urticaefolia growing in Bangladesh has not been studied to date.…”

Section: Introductionmentioning

confidence: 99%

Bioactivity of Extractives fromStachytarpheta urticaefolia

Chowdhury

Rashid

Khan

et al. 2004

Pharmaceutical Biology

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The n-hexane and methanol extracts of Stachytarpheta urticaefolia leaves exhibited significant antinociceptive effects (p < 0.01) in acetic acid-induced writhing model at a dose of 250 mg/kg b.w. Two compounds isolated from the plant, ipolamiide (1) and a-spinasterol (2), were also found to be potent inhibitors of acetic acid-induced writhing on mice at 50 mg/kg b.w. (p < 0.01). Abortifacient activity was demonstrated within 20 h of administration of a methanolic leaf extract at 200 mg/kg b.w. The methanolic leaf extract and compounds 1 and 2 were also tested for in vitro antibacterial activities against 18 bacterial strains. The extract showed mean zones of inhibition ranging from 17 to 30 mm at 500 mg/disk, but the compounds demonstrated only mild or no in vitro antibacterial activity even at 400 mg/disk. Finally, in a cytotoxicity study, the n-hexane and methanol extracts of leaves and root bark of the plant and the purified compounds (1, 2) exhibited LC 50 values of 5. 42, 4.42, 17.15, 5.38, 3.93, and 13.65 mg/ml, respectively, against the brine shrimp nauplii, whereas the positive control, vincristine sulfate, showed an LC 50 of 0.583 mg/ml.

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Crystal Structure of Ipolamiide Monohydrate from Stachytarpheta indica

Cited by 8 publications

References 3 publications

Structural Revision of Some Recently Published Iridoid Glucosides

Structural Revision of Some Recently Published Iridoid Glucosides

Antibacterial and anti-inflammatory activity of extracts and major constituents derived from Stachytarpheta indica Linn. leaves and their potential implications for wound healing

Bioactivity of Extractives fromStachytarpheta urticaefolia

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