The Origins of Triterpenoid Skeletal Diversity.

Xu, Ran; Fazio, Gia C.; Matsuda, Seiichi P. T.

doi:10.1002/chin.200422256

Cited by 53 publications

(73 citation statements)

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“…Importantly, the 13 CNMR spectrum exhibited six signals between δ C 70 and 80 for the carbinol carbons out of which the one at δ C 71.32 disappeared in DEPT-135 experiment, suggesting the presence of a quaternary hydroxylated carbon (C-25). These findings and comparison of NMR spectra of 1 with those of known compounds[222324], led us to formulate its structure as 3β, 25-dihydroxy-24-methyl-30-carboxy methyl cucurbita-5-en-3- O -β-d-glucopyranoside and was designated as coccinoside A.…”

Section: Resultsmentioning

confidence: 99%

“…The data were compared with previous reports on cucurbitanes and were found to be in good agreement. [242526] Thus, the structure of 3 was determined as 3β-hydroxy-24-(1-butanol-4-yl)-30-carboxy methyl cucurbita-5, 7, 22-trien-3- O -β-d-glucopyranoside, and was designated as coccinoside C.…”

Section: Resultsmentioning

confidence: 99%

“…Their spectral data were compared with previous reports on cucurbitanes and were found to be in good agreement. [2324252627] This led us to formulate their structures as cucurbit-5, 7-dien-3β-ol ( 4 ), cucurbita-5-en-3β-ol-3- O -β-d-glucopyranoside ( 5 ), and cucurbit-5-en-3β-ol-3- O -β-d-glucopyranosyl-(4′→1′′)- O -β-d-glucopyranoside ( 6 ). This is the first report of these cucurbitacins from these plants.…”

Section: Resultsmentioning

confidence: 99%

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Cucurbitane-type triterpenoids from the blood glucose-lowering extracts of Coccinia indica and Momordica balsamina fruits

et al. 2017

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Context:Few vegetables that are commonly consumed in India as part of diet have been claimed for their antidiabetic potential.Objective:The present study was aimed at evaluating preventive effects of cucurbit vegetables namely, Coccinia indica and Momordica balsamina belonging to family Cucurbitaceae in diabetic hyperglycemia.Materials and Methods:The fruits of M. balsamina and C. indica were extracted with chloroform and fractionated with hexane to prepare an extract rich in moderately polar components. These extracts were used for evaluating the effect of these cucurbits in nicotinamide/streptozotocin-induced type 2 diabetes. Streptozotocin–nicotinamide-induced diabetic animals were orally treated with chloroform extract of fruits (250 mg/kg BW) given daily for a week separately.Results:Both the extracts reduced fasting blood glucose significantly (P < 0.05 versus diabetic control) when estimated on seventh day of treatments. Pretreatment with fruit extracts for 7 days also blunted the OGTT (oral glucose tolerance test) curve. Results indicated that C. indica and M. balsamina fruits possess beneficial effects in diabetes by lowering elevated blood glucose level. Six cucurbitane-type triterpenoids were isolated from bioactive extracts of C. indica ((1-3) and M. balsamina (4-6). The structures of these compounds were elucidated on the basis of spectroscopic data analysis.Conclusion:The study concludes that the inclusion of C. indica and M. balsamina fruits in food can be useful for newly diagnosed diabetic patients or highrisk group of population for glycemic control.SUMMARY“Cucurbitane-type triterpenoids from the blood glucose-lowering extracts of Coccinia indica and M. balsamina fruit” The beneficial effects of chloroform extracts of vegetal cucurbits namely C. indica (Ivy gourd) and M. balsamina (Balsam apple) in streptozotocin-nicotinamide (STZ-NA)-induced diabetic rats has been evaluated.The isolation and characterization of six cucurbitacins from bioactive extracts of C. indica (Coccinoside A, B, and C) and M. balsamina (cucurbit-5, 7-dien-3ß-ol, cucurbita-5-en-3ß-ol-3-O-ß-d-glucopyranoside, and cucurbit-5-en-3ß-ol-3-O-ß-d-glucopyranosyl-(4’→1”)-O-ß-d-glucopyranoside) have been reported for the first time.The study concludes that the inclusion of C. indica and M. balsamina fruits in food can be useful for newly diagnosed diabetic patients or high risk group of population for glycemic control. Abbreviation used: C: indica (Coccinia indica), M: balsamina (Momordica balsamina), Kbr: Potassium bromide, FTIR: Fourier transform infrared spectroscopy, COSY: Corelated Spectroscopy, DEPT: Distortionless Enhancement by Polarization Transfer, DMSO: Dimethyl sulfoxide, TMS: tetramethylsilane, ESI-MS: Electrospray Ionization mass spectrometry, TLC: thin layer chromatography, STZ-NA: Streptozotocin-nicotinamide, CMC: carboxy methyl cellulose, BW: body weight, ANOVA: analysis of variance, AUC: area under curve

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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Cucurbitane-type triterpenoids from the blood glucose-lowering extracts of Coccinia indica and Momordica balsamina fruits

et al. 2017

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“…More than 100 diverse triterpene skeletons are reported from nature (Xu et al, 2004) and are constructed at the cyclization step of oxidosqualene catalyzed by OSC. The different spectra of triterpenes produced by cultured cells and the mother plants can be explained by differential expression of OSCs.…”

Section: Cdna Cloning Of Oscmentioning

confidence: 99%

“…More than 100 triterpene skeletons are constructed at the cyclization step of oxidosqualene catalyzed by OSCs (Xu et al, 2004). So far, more than 30 OSCs with different product specificity have been cloned from higher plants (Phillips et al, 2006).…”

Section: Origin Of Ursane-type Triterpenes In Higher Plantsmentioning

confidence: 99%

Production of Triterpene Acids by Cell-suspension Cultures of Olea europaea

Orihara

Ebizuka

2010

Olives and Olive Oil in Health and Disease Prevention

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Bioactive Usual and Unusual Triterpenoids Derived from Natural Sources Used in Traditional Medicine

Joshi

2023

Chemistry & Biodiversity

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Triterpenoids are accessible in several terrestrial plants as well as marine organisms, including sponges, algae, fungi, and sea cucumbers are examples of marine creatures. So far, more than 20,000 natural triterpenoids have exhibited several varied bioactivities, including anticancer, antimalarial, anti‐HIV, inhibit HIF‐1 activation, antibacterial, chemopreventive, anti‐inflammatory, antioxidant, cardioprotective, antiviral, neuroprotective, hepatoprotective, insecticidal, antidiabetic, cytotoxic. Several plants are used in folklore medicine to treat numerous ailments, and the preparation or uses of traditional practices have been scientifically validated. Although various structural diversity has been observed in the triterpenoids, this review presents the sources and uses of those triterpenoids that showed significant biological activities which could be accessible and promoted to familiar people in the form of traditional medicine or for industrial, or pharmaceutical applications.

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The Origins of Triterpenoid Skeletal Diversity.

Abstract: For Abstract see ChemInform Abstract in Full Text.

Cited by 53 publications

References 1 publication

Cucurbitane-type triterpenoids from the blood glucose-lowering extracts of Coccinia indica and Momordica balsamina fruits

Cucurbitane-type triterpenoids from the blood glucose-lowering extracts of Coccinia indica and Momordica balsamina fruits

Production of Triterpene Acids by Cell-suspension Cultures of Olea europaea

Bioactive Usual and Unusual Triterpenoids Derived from Natural Sources Used in Traditional Medicine

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