Antiproliferative Constituents from Umbelliferae Plants. VI. New Ursane-Type Saikosaponin Analogs from the Fruits of Bupleurum rotundifolium.

Fujioka, Toshihiro; Yoshida, Keisuke; Fujii, Hiroko; Nagao, Tsuneatsu; Okabe, Hikaru; Mihashi, Kunihide

doi:10.1248/cpb.51.365

Cited by 24 publications

(17 citation statements)

References 10 publications

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“…[102] Buddlejasaponin I, IV and the sulfated saikosaponin (sandrosaponin I), which were isolated from B. rigidum, exhibited a very potent in-vivo anti-inflammatory effect (1 mg/ear dose) on mouse ear oedema induced by PMA compared with the equivalent dose of indometacin. The effect of these compounds on other inflammatory parameters [109] Rotundioside F (-) Acute inflammation [109] Rotundioside A, H, I, J Cytotoxic against MK-1, HeLa and B16F10 cell lines [30,110] B. salicifolium Polyacetylenes derivatives Antibacterial [111,112] B. scorzonerifolium Acetone extract Cytotoxic against A549 cell line [113][114][115] Wogonin, eugenin, saikochromone A (-) IL-2 [50] Saikosaponin B3, bupleurosides III, VI, IX and XIII and scorzonerosides A, B, C…”

Section: B Rigidummentioning

confidence: 99%

“…[75] The cytotoxic activity of both oleanane-type and ursanetype triterpene saponins isolated from B. rotundifolium by Fujioka and coworkers were examined in human gastric adenocarcinoma (MK-1), human cervical carcinoma (HeLa) and murine melanoma (B16F10) cell lines. [30,110] Among the monodesmosidic ursane-type saponins, rotundifoliosides A, H, I and J exhibited very potent cytotoxic activity with IC50 values in the range 11-71 mm. The highest activity was observed with rotundifolioside J, which had IC50 values of 16, 21 and 11 mm against the aforementioned cell lines, respectively.…”

Section: Cytotoxicity and Anti-tumour Activitymentioning

confidence: 99%

“…The highest activity was observed with rotundifolioside J, which had IC50 values of 16, 21 and 11 mm against the aforementioned cell lines, respectively. [110] The monodesmosidic oleanane saikosaponins also demonstrated different degrees of cytotoxicity but those that contained the epoxy bridge in their skeleton were highly active, with IC50 values in the range 6.6-37.3 mm. [30] This high reactivity is attributed to the presence of the epoxy group which can covalently bond with the SH or amino groups in proteins leading to conformational changes and loss of functionality.…”

Section: Cytotoxicity and Anti-tumour Activitymentioning

confidence: 99%

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Genus Bupleurum: a review of its phytochemistry, pharmacology and modes of action

Ashour

Wink

2011

Journal of Pharmacy and Pharmacology

229

161

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Objectives Radix Bupleuri represents one of the most successful and widely used herbal drugs in Asia for treatment of many diseases over the past 2000 years. Thorough studies have been carried out on many species of this genus and have generated immense data about the chemical composition and corresponding biological activity of extracts and isolated secondary metabolites. In this work, we review the chemistry and pharmacology of the genus Bupleurum and explore the relationships between the pharmacological effects and the chemical composition of these drugs. Key findings Early studies on the genus Bupleurum had focused only on the traditional uses of the plants in the treatment of inflammatory disorders and infectious diseases. After chemical profiling, several groups of secondary metabolites were characterized with relevant biological activity: triterpene saponins (saikosaponins), lignans, essential oils and polysaccharides. As a result, present interest is now focused on the bioactivity of the isolated triterpene saponins acting as immunomodulatory, anti-inflammatory and antiviral agents, as well as on the observed ant-iulcer activity of the polysaccharides and anti-proliferative activity of different lignans. Many saikosaponins exhibited very potent anti-inflammatory, hepatoprotective and immunomodulatory activities both in vivo and in vitro. Conclusions Further investigations and screenings are required to explore other Bupleurum species, to evaluate the clinical safety and possible interactions with other drugs or herbs. Standardization of Bupleuri extracts is crucial for them being integrated into conventional medicine due to large chemical and biological variations between different species and varieties.

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Section: B Rigidummentioning

confidence: 99%

Section: Cytotoxicity and Anti-tumour Activitymentioning

confidence: 99%

Section: Cytotoxicity and Anti-tumour Activitymentioning

confidence: 99%

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Genus Bupleurum: a review of its phytochemistry, pharmacology and modes of action

Ashour

Wink

2011

Journal of Pharmacy and Pharmacology

229

161

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“…8,9) Moreover, agricultural studies of the constituents of the seeds have been begun by Ono et al, 10) and studies of anti-proliferation of tumor cells have been initiated by Mihashi and colleagues. 11,12) In some areas in Kumamoto Prefecture, this plant is cultivated, and its aerial parts are discarded. We investigated the drug's constituents in conjunction with studies of the aerial parts of B. rotundifolium, which is cultivated for cut flowers, and the seeds of B. falcatum.…”

Section: Regular Articlementioning

confidence: 99%

“…HMBC analysis indicated that the sugar chain bonding connected with the C-3 of the sapogenol. Therefore, BFS-14 (11) was characterized as BRA-3 (13), BRA-5 (14), BRA-2 (15), BRA-4 (16), and BRA-7 (17) were identified as rotundifolioside J, 11,12) rotundifolioside I, 11,12) rotundioside E, 15,16) and rotundioside W, 11,12) and rotundioside V, 11,12) respectively. BRA-22 (18) (Table 5) showed a total of 48 carbon signals, of which 18 indicated the presence of a rhamnosyl-(1→2)-glucosyl-(1→2)-fucosyl moiety identical to that of BRA-3 (13).…”

Section: Regular Articlementioning

confidence: 99%

Oleanene Glycosides of the Aerial Parts and Seeds of Bupleurum falcatum and the Aerial Parts of Bupleurum rotundifolium, and Their Evaluation as Anti-hepatitis Agents

Nakahara

Okawa

Kinjo

et al. 2011

CHEMICAL & PHARMACEUTICAL BULLETIN

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To facilitate effective resource utilization, we have investigated triterpene saponins such as saikosaponin from the aerial parts of Bupleurum (B.) falcatum L., which are commonly discarded. Seven oleanene saponins were isolated from this plant; they were classified as the 13,28-epoxy type, 12-ene type, 9(11),12-diene type, and 28-acid type on the basis of their structural characteristics. For comparison, we also examined the oleanene saponins of the seeds of B. falcatum and the aerial parts of B. rotundifolium L. to obtain seven saponins and one sapogenol from the former and thirteen oleanene saponins from the latter. Several compounds obtained from them were investigated for their hepatoprotective activity and hepatotoxicity. The 13,28-epoxy type saponins had hepatoprotectivity. Ursane type showed hepatotoxicity from middle concentration. The 11,13(18)-diene type saponins did not express hepatoprotective activity. The 28-acid type saponin which has a glucosyl carboxy group showed hepatoprotective action.

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Naturally Occurring Triterpenoid Saponins

Dinda

Debnath²,

Mohanta

et al. 2010

Chemistry & Biodiversity

140

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Naturally occurring new triterpenoid saponins reported from mid-1996 to March, 2007 are reviewed including their physical constants and plant sources, and are compiled in Table 1. New saponins are arranged in Table 1 on the basis of the skeletal structures of their aglycones, e.g., oleanane type, ursane type, lupane type, hopane type, taraxastane type, cycloartane type, lanostane type, tirucallane type, dammarane type, cucurbitane type, and holostane type. The known triterpenoid saponins and prosapogenins of the new saponins, the biological and pharmacological activities of which were published during 1996-2007, are also reviewed together with their plant sources listed in Table 2 according to the skeletal structures of their aglycones in the same fashion as in Table 1. The plant and animal sources of both new and known bioactive triterpenoid saponins are collected in Table 3 in alphabetical order. The biological and pharmacological activities such as antiallergic, antiatherosclerosis and antiplatelet, antibacterial, anticomplementary, antidiabetic, contraceptive, antifungal, anti-inflammatory, antileishmanial, antimalarial/antiplasmodial, anti-obesity, anti-proliferative, antipsoriatic, antispasmodic, antisweet, antiviral, cytotoxic/antitumor, detoxication, gastroprotective, haemolytic, hepatoprotective, immunomodulatory, anti-enzyme, anti-osteoporotic, insecticidal, insulin-like, membrane-porosity, molluscicidal, neuropharmacological, anti-endothelial dysfunction, snake venom antidote, and sweet activities of these saponins or derived prosapogenins are discussed briefly after Table 3.

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Antiproliferative Constituents from Umbelliferae Plants. VI. New Ursane-Type Saikosaponin Analogs from the Fruits of Bupleurum rotundifolium.

Cited by 24 publications

References 10 publications

Genus Bupleurum: a review of its phytochemistry, pharmacology and modes of action

Genus Bupleurum: a review of its phytochemistry, pharmacology and modes of action

Oleanene Glycosides of the Aerial Parts and Seeds of Bupleurum falcatum and the Aerial Parts of Bupleurum rotundifolium, and Their Evaluation as Anti-hepatitis Agents

Naturally Occurring Triterpenoid Saponins

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