• Natural Product Sciences
• /
• 제24권1호
• /
• pp.54-58
• /
• 2018

A phytochemical investigation of Allium macrostemon Bunge (Liliaceae) afforded the new pregnane steroidal glycoside, named allimacroside F (1), along with three known glycosides, benzyl-O-${\alpha}-{\text\tiny{L}}$-rhamnopyranosyl-($1{\rightarrow}6$)-${\beta}-{\text\tiny{D}}$-glucopyranoside (2), phenylethyl-O-${\alpha}-{\text\tiny{L}}$-rhamnopyranosyl-($1{\rightarrow}6$)-${\beta}-{\text\tiny{D}}$-glucopyranoside (3), (Z)-3-hexenyl-O-${\alpha}-{\text\tiny{L}}$-rhamnopyranosyl-($1{\rightarrow}6$)-${\beta}-{\text\tiny{D}}$-glucopyranoside (4). The identification and structural elucidation of a new compound (1) was carried out based on spectral data analyses ($^1H-NMR$, $^{13}C-NMR$, $^1H-^1H$ COSY, HSQC, HMBC, and NOESY) and HR-FAB-MS.

• 생약학회지
• /
• 제9권2호
• /
• pp.57-72
• /
• 1978

The constituents of Ranunculaceae plants are summerized from more than one hundred of papers. Fifteen steroidal alkaloids, thirty two of terpenoids (diterpenes and triterpenes), fifty four isoquinoline alkaloids are recorded. Thirty three papaverines, eighteen berberines, and three hydrastines belong to isoquinoline group. Besides, of alkaloids a number of glycosides are also found. Adonis glycoside, famous cardiotonics, from Adonis and cyanogenin glycoside and calthoside D were identified from the leaves of Thalictrum aquilegifolium and Caltha silvestris. Anemonin, the irritating substance, found in Pulsatilla grandiz $W_{ENDER}$. Kaempf-erol and dihydrokaempferol were isolated and identified from the leaves of Clematis brachyura ^M_{AXIMOWICZ}$ by author in 1968.

• Natural Product Sciences
• /
• 제12권1호
• /
• pp.62-66
• /
• 2006

A steroidal saponin, $3-O-{\alpha}-L-rhamnopyranosyl-(1{\rightarrow}2)-[{\alpha}-L-rhamnopyranosyl-(1{\rightarrow}3)]-{\beta}-D-glucopyranosylpennogenin$ ;(1, spiroconazole A) was isolated from the tubers of Dioscorea bulbifera L. var sativa and $^1H-and\;^{13}C-NMR$ assignment was completed using HMBC correlation. In addition, four phenolic substances, 2,7-dihydroxy-4-methoxyphenanthrene (2), quercetin (3), $quercetin-3-O-{\beta}-D-glucopyranoside$ (4), and $quercetin-3-O-{\beta}-D-galactopyranoside$ (5) were also isolated.

• Journal of Microbiology and Biotechnology
• /
• 제33권6호
• /
• pp.797-805
• /
• 2023

Species belonging to the Vernonia (Asteraceae), the largest genus in the tribe Vernonieae (consisting of about 1,000 species), are widely used in food and medicine. These plants are rich sources of bioactive sesquiterpene lactones and steroid saponins, likely including many as yet undiscovered chemical components. A phytochemical investigation resulted in the separation of three new stigmastane-type steroidal saponins (1 - 3), designated as vernogratiosides A-C, from whole plants of V. gratiosa. Their structures were elucidated based on infrared spectroscopy (IR), one-dimensional (1D) and two-dimensional nuclear magnetic resonance (2D NMR), high-resolution electrospray ionization mass spectrometry (HR-ESI-MS), and electronic circular dichroism analyses (ECD), as well as chemical reactivity. Molecular docking analysis of representative saponins with α-glucosidase inhibitory activity was performed. Additionally, the intended substances were tested for their ability to inhibit α-glucosidase activity in a laboratory setting. The results suggested that stigmastane-type steroidal saponins from V. gratiosa are promising candidate antidiabetic agents.

• International Journal of Oral Biology
• /
• 제49권2호
• /
• pp.42-47
• /
• 2024

Ophiopogonin D (OPD) is a steroidal glycoside derived from Ophiopogon japonicus, a traditional Chinese medicine with diverse biological activities, including antithrombosis, anti-inflammation, and antitussive effects. To investigate the cellular effects and mechanisms of OPD on oral squamous cell carcinoma, cell viability was explored, and the effects of OPD on cell cycle regulators, apoptotic marker proteins, and key proteins involved in metastasis and signaling pathways were examined by MTT assay and Western blotting in YD38 cells. OPD strongly inhibited cell proliferation and induced caspase-dependent apoptosis of YD38 cells by suppressing the cell cycle and activating caspase-3 and poly ADP ribose polymerase. Additionally, OPD suppressed the expression of vital proteins regulating metastasis and proliferation within the integrin/matrix metalloproteinases/FAK and AKT/PI3K/mTor pathways. Thus, OPD can be a potential treatment candidate for gingival cancer.

• Archives of Pharmacal Research
• /
• 제24권1호
• /
• pp.44-50
• /
• 2001

To search for cytotoxic components from Allium victoriallis , MTT assays on each extract and an isolated component, gitogenin 3-O-lycotetroside, were performed against cancer cell lines. Cytotoxicities of most extract were shown to be comparatively weak, though $IC_50$ values of $CHCl_3$fraction was found to be <31.3-368.4 $\mu\textrm{g}/ml$. From the incubated methanol extract at $36^{\circ}C, eleven kinds of organosulfuric flavours were predictable by CG-MS performance. The most abundant peak was revealed to be 2-vinyl-4H-1,3-dithiin(1) by its mass spectrum. Further, this extract showed significant cytotoxicities toward cancer cell lies. Silica gel column chromatography of the n-butanol fraction led to the isolation of gitogenin 3-O-lycotetroside (3) along with astragalin (4) and kaempferol 3, 4'-di-O-$\beta$-D-glycoside (5). This steroidal saponin exhibited significant cytotoxic activities ($IC_50$, 6.51-36.5 $\mu\textrm{g}/ml$) over several cancer cell lines. When compound 3 was incubated for 24 h with human intestinal bacteria, a major metabolite was produced and then isolated by silica gel column chromatography. By examining parent and prominent ion peak in FAB-MS spectrum of the metabolite, the structure was speculated not to be any of prosapogenins of 3, suggesting that spiroketal ring were labile to the bacterial reaction. These suggest that disulfides produced secondarily are the antitumor principles.