Acylated pregnane glycosides from Caralluma tuberculata and their antiparasitic activity

Abdel‐Sattar, Essam; Harraz, Fathalla M.; Al-ansari, Soliman Mohammed Abdullah; El‐Mekkawy, Sahar; Ichino, Chikara; Kiyohara, Hiroaki; Ishiyama, Aki; Otoguro, Kazuhiko; Ōmura, Satoshi; Yamada, Hideaki

doi:10.1016/j.phytochem.2008.05.017

Cited by 66 publications

(42 citation statements)

References 25 publications

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“…This was confirmed by the results of HMBC experiments which showed clear long-range correlation peaks between the carbonyl carbon (C-1) and H-12 of the aglycone. Moreover, the data from 12 H, 13 C-NMR and 2D NMR (Table 1 and 2) were also confirmed the two tigloyl groups and confirmed by the carbon signals due to the acyl groups at δ165.80 and 166.94 which located at C-8 and C-11. The HMBC was exhibited obvious correlation peak between the two carbonyl (C- [14] and about coupling constants of H-11 and H-12, the conclusion was drawn that the orientation of the two protons had shown in the structure.…”

Section: Discussionmentioning

confidence: 55%

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A New Polyoxypregnane Glycoside from the Roots of Dregea volubilis (L.f) Benth. ex Hook. f and its Chondroprotective Effect

Sanyacharernkul¹,

Itghiarbha²,

Kongtawelert³

et al. 2009

American J. of Biochemistry and Biotechnology

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Problem statement: Dregea genus (Asclepiadaceae) is well known for the rich of steroid pregnane contents and these plants are famous for the potential to be applied as alternative biological activities. Dregea volubilis is the only species of Dregea genus in Thailand. The chemical and biological investigations of this plant are interesting to bioassay-guided fractionation, particularly chondroprotective effect. Approach: The research was carried out to extract, isolate, purify and elucidate structure of the active compound from the roots Dregea volubilis. Both of the solvent extracts and isolated compound were evaluated with kinds of chondroprotection. i.e., S-GAG), HA, UA and production of matrix metalloproteinase-2 (MMP-2). Results: Polyoxypregnane glycoside (PGG) or 12-0-benzoyl-8, 11-ditigloyl-3β, 8β, 11α, 12β, 14β-pentahydroxy-pregn-14-ol, 20-one,-3-0-methyl-β-D-allopyranosyl (1→4)-β-D-thevetopyranoside was isolated from the active ethyl acetate extract of the roots Dregea volubilis. The spectroscopic techniques were provided for success in structure determination. In addition, a new compound was the most powerful to biological activities. Chondroprotective effect of PPG on the degradation of sulfated glycosaminoglycan (S-GAG), hyaluronan (HA), uronic acid (UA) and production of matrix metalloproteinase-2 (MMP-2) in interleukin-1β (IL-1β)-stimulated porcine articular cartilage were also assessed. PGG was interestingly effective in reducing IL-1β induced S-GAG, HA release from cartilage explant and MMP-2 activity. Furthermore, PPG can reverse effect of IL-1β-reduced the levels of uronic acid remaining in cartilage tissue. Conclusion: The PGG was possessed a potent chondroprotective activity using the IL-1β stimulated cartilage explant model. Therefore, it is possible to use this compound as a new pharmacological agent for the management of degenerative joint diseases.

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Section: Discussionmentioning

confidence: 55%

“…All these data indicated that this compound had two sugars at position-6 deoxy. From the ESIMS, COSY, HMQC and HMBC experiments showed the presence of one β-thevetopyranosyl unit linked to C-3 of the aglycone and one terminal β-allopyranosyl [12] moiety. The conformation of the two sugars was exhibited by the 1 H NMR spectrum signals.…”

Section: Discussionmentioning

confidence: 99%

A New Polyoxypregnane Glycoside from the Roots of Dregea volubilis (L.f) Benth. ex Hook. f and its Chondroprotective Effect

Sanyacharernkul¹,

Itghiarbha²,

Kongtawelert³

et al. 2009

American J. of Biochemistry and Biotechnology

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“…Accordingly, the CHCl3 soluble fraction was chosen for isolating the bioactive compounds. Compounds 1-6 were isolated from this fraction and their antimalarial and antitrypanosomal activity were evaluated [28]. Other members of this genus like Caralluma fimbriata and Caralluma siniaca were considered to reduce body weight and blood glucose level respectively [49,54].…”

Section: Introductionmentioning

confidence: 99%

A mini review on a Caralluma tuberculata N. E. Br. uncommon and wild succulents but having exciting pharmacological attributes

Noreen

2017

PAB

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Caralluma tuberculata belongs to milky weed family Apocynaceae which upholds 424 genera. This natural medicinal plant is widely distributed in South Asia, Africa, Middle East, and Spain etc. Overall phytochemistry of Caralluma tuberculata is endowed with flurry of pharmacologically active constituents like pregnane glycosides and aglycones, flavanoid, saponins and titerpenes etc. Caralluma tuberculata and its various other species of this genus have been explored for their anti-inflammatory action, strong hypoglycemic and weight reduction effect, quite effective for rheumatoid arthritis, paralysis stomach disorders, abdominal pain, migraine, fever wound healing and cardiac problems. Present review focuses on the comprehensive profile of Caralluma tuberculata with respect to its highly valuable phytoconstituent along with their available pharmacological characteristics and therapeutic prospective.

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“…Several pregnane glycosides isolated from organic extracts of Caralluma tuberculata showed cytotoxicity against the MRC5 human diploid embryonic cell line (Abdel-Sattar et al 2008. Pregnanes are C 21 steroids and often found in nature conjugated as glycosides.…”

Section: Introductionmentioning

confidence: 99%

Novel acylated steroidal glycosides from Caralluma tuberculata induce caspase-dependent apoptosis in cancer cells

Waheed

Barker

Barton

et al. 2011

Journal of Ethnopharmacology

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Aim of the study: Pregnane glycosides are potent cytotoxic agents which may represent new leads in the development of anti-tumour drugs, particularly in the treatment of breast cancer, because of the structural similarity to estrogenic agonists. Caralluma species are natural sources of a wide variety of pregnane glycosides. The aim of the study was to isolate, using an activity-guided fractionation approach, novel pregnane glycosides for testing on breast cancer and other tumour lines. Materials and Methods:The effect of crude extracts, specific organic fractions and isolated compounds from Caralluma tuberculata was tested on the growth and viability of MCF-7 oestrogen-dependent, and MDA-MB-468 oestrogen-independent breast cancer cells, Caco-2 human colonic cells, HUVECs and U937 cells. Neutral red uptake and MTT assays were used. Apoptosis was detected by Western blot of poly-(ADP ribose) polymerase (PARP) as were other markers of nuclear fragmentation (DNA ladder assay, staining of cells with nuclear dye DAPI). The involvement of caspases was investigated using the pan-caspase inhibitor Z-VAD-FMK. Results:The ethyl acetate fraction of Caralluma tuberculata was found to be the most potent antiproliferative fraction against all three cancer cell lines. Two novel steroidal glycosides were isolated from the active fraction after a series of chromatographic experiments. The structure of the isolated

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Acylated pregnane glycosides from Caralluma tuberculata and their antiparasitic activity

Cited by 66 publications

References 25 publications

A New Polyoxypregnane Glycoside from the Roots of Dregea volubilis (L.f) Benth. ex Hook. f and its Chondroprotective Effect

A New Polyoxypregnane Glycoside from the Roots of Dregea volubilis (L.f) Benth. ex Hook. f and its Chondroprotective Effect

A mini review on a Caralluma tuberculata N. E. Br. uncommon and wild succulents but having exciting pharmacological attributes

Novel acylated steroidal glycosides from Caralluma tuberculata induce caspase-dependent apoptosis in cancer cells

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