Bioactive Triterpenes from the Root of <i>Salvia miltiorrhiza</i> Bunge

Tung, Nguyen Hưu; Nakajima, Kensuke; Uto, Takuhiro; Hải, Nguyễn Thanh; Long, Đinh Đoàn; Ohta, Tomoe; Oiso, Shigeru; Kariyazono, Hiroko; Shoyama, Yukihiro

doi:10.1002/ptr.5877

Cited by 25 publications

(16 citation statements)

References 21 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Both pathways converge to activate caspase‐3. In our researches on anticancer phytotherapy, we reported the induction of apoptosis in human cancer cell lines using natural products such as crocin from saffron (Zhang, Wang, Wen, Shoyama, & Yuan, ), alkanin from Alkanna tinctoria (Tung, Du, Yuan, Shoyama, & Wang, ), corosolic acid from Eriobotrya japonica leaves (Uto et al, ), saikosaponin from Bupleurum falcatum (Tung, Uto, Morinaga, & Shoyama, ), diarylheptanoids from Alnus japonica (Uto et al, ), coumarin derivatives from Mammea siamensis (Uto, Tung, Thongjankaew, Lhieochaiphant, & Shoyama, ), and quassinoid from Eurycoma longifolia (Tung, Nakajima, et al, ).…”

Section: Introductionmentioning

confidence: 99%

Antiproliferative activity and apoptosis induction by trijuganone C isolated from the root of Salvia miltiorrhiza Bunge (Danshen)

Uto

Tung

Ohta

et al. 2018

Phytotherapy Research

Self Cite

View full text Add to dashboard Cite

In this study, we found that the hexane fraction of Danshen, the dried root of Salvia miltiorrhiza (Lamiaceae), exerted antiproliferative effects on human leukemia cells. Phytochemical investigation of the hexane fraction achieved the isolation of the tanshinone diterpenes: dihydrotanshinone I (1), trijuganone C (2), trijuganone B (3), cryptotanshinone (4), tanshinone IIA (5), and tanshinone I (6). Compound 2 showed significant antiproliferative activities against human leukemia cells HL-60, Jurkat, and U937. The antiproliferative activities of 2 against human cancer and normal cells indicated that 2 exhibited potent antiproliferative activities with IC values less than 10 μM against HL-60 and Jurkat cells as well as on the colon cancer cells DLD-1, COLO 205, and Caco-2. Compound 2 induced chromatin condensation, DNA fragmentation, activation of caspase-3, -8, and -9, and the cleavage of poly (ADP-ribose) polymerase (PARP) in HL-60 cells. Moreover, 2 activated Bid and Bax, leading to the loss of mitochondrial membrane potential, and 2 induced the cytochrome c release from mitochondria into cytosol. In contrast, Bcl-2 and Bcl-xL were unaffected by 2. These results suggest that 2 exerts antiproliferative effects via apoptosis induction mediated by mitochondrial dysfunction and caspase activation. Compound 2 may serve as a candidate of potential chemotherapeutic agent for human leukemia.

show abstract

Section: Introductionmentioning

confidence: 99%

Antiproliferative activity and apoptosis induction by trijuganone C isolated from the root of Salvia miltiorrhiza Bunge (Danshen)

Uto

Tung

Ohta

et al. 2018

Phytotherapy Research

Self Cite

View full text Add to dashboard Cite

show abstract

“…Compound 5 (Tung et al, ): Oleanolic acid: White powder, 1 H‐NMR (CDCl 3 ): δ 3.21 (1H, dd, J = 10.8, 5.0 Hz, H‐3), 1.25, 0.98, 0.93, 0.89, 0.88, 0.76, 0.75 (each 3H, s, 7 × CH 3 ). 13 C‐NMR (CDCl 3 ): δ 38.6 (C‐1), 28.9 (C‐2), 79.4 (C‐3), 38.8 (C‐4), 55.4 (C‐5), 18.7 (C‐6), 33.5 (C‐7), 41.2 (C‐8), 47.9 (C‐9), 37.6 (C‐10), 23.3 (C‐11), 122.9 (C‐12), 143.9 (C‐13), 41.9 (C‐14), 27.9 (C‐15), 23.7 (C‐16), 46.8 (C‐17), 41.9 (C‐18), 46.2 (C‐19), 31.0 (C‐20), 34.1 (C‐21), 32.9 (C‐22), 28.6 (C‐23), 17.5 (C‐24), 15.7 (C‐25), 18.7 (C‐26), 26.3 (C‐27), 183.2 (C‐28), 31.9 (C‐29), 23.9(C‐30).…”

Section: Methodsmentioning

confidence: 99%

Chemical components and bioactivity evaluation of extracts from pear (Pyrus UssuriensisMaxim) fruit

Peng

Xie

et al. 2018

J Food Biochem

View full text Add to dashboard Cite

In order to discover the bioactive metabolites of Pyrus ussuriensis Maxim, the systematic chemical and pharmacological investigations were performed. The ethyl acetate extract of the plant displayed activities against ear edema in mice, with an inhibition rate of 17.1%, at a dose of 400mg/kg in vivo. Meanwhile, the ethyl acetate extract showed the best apophlegmatic (inhibition: 49.9%) and antitussive effects (inhibition: 34%) at 800mg/kg in vivo tests, and inhibition of NO production (IC50=0.06 μg/mL). Subsequently, twelve compounds were isolated from the ethyl acetate extract and identified as friedelin (1), daucosterol (2), β‐sitosterol (3), betulinic acid (4), oleanolic acid (5), ursolic acid (6), 2‐O‐buty‐1‐O’‐(2‐ethylhexyl) benzene‐1,8‐dicarboxylate (7), Narcissin (8), 3‐hydroxy‐3‐carboxyl‐glutaric acid dimethyl ester (9), 2‐hydroxyl ‐butanediol icacid‐4‐methyleste (10), myristic acid (11), and (Z)‐11‐hexadecen‐1‐ol acetate (12). Among them, compounds 1, 2, 4, 5, 6, and 11 exhibited moderate indirect inhibitory effects on lipopolysaccharide‐induced NO and TNF‐α production. Practical applications Pyrus ussuriensis Maxim is an edible and medical fruit with many functional properties. Unfortunately, few literatures about bioactive components of this fruit have been investigated. The result indicated that P. ussuriensis have obvious anti‐inflammatory, antitussive, and apophlegmatic activities, which were associated with the folk uses of this fruit. Furthermore, this work also suggests a potential use of P. ussuriensis as an important source of natural anti‐inflammatory agents and they may also be considered as a functional food.

show abstract

“…The biotransformation experiment was carried out in modified Czapek-Dox medium, which consisted of the following ingredients: glucose (15…”

Section: Biotransformation Mediummentioning

confidence: 99%

The oxygenated products of cryptotanshinone by biotransformation with Cunninghamella elegans exerting anti-neuroinflammatory effects by inhibiting TLR 4-mediated MAPK signaling pathway

Wang¹,

Wu²,

Meng³

et al. 2020

Preprint

View full text Add to dashboard Cite

Background: Neuroinflammatory processes are critical in the development and progression of Alzheimer's disease (AD). The potent anti-neuroinflammatory inhibitors are expected as the candidates to treat AD. Cryptotanshinone (1), a major bioactive constituent in the traditional Chinese medicinal herb Dan-Shen Salvia miltiorrhiza Bunge, has been reported to possess remarkable pharmacological activities, especially anti-oxidation and anti-inflammation. Methods: Cryptotanshinone (1) was biotransformed with the fungus Cunninghamella elegans AS3.2028 to improve its bioactivities and physicochemical properties. The structures of transformed products were elucidated by comprehensive spectroscopic analysis including HRESIMS, NMR and ECD data. Their anti-neuroinflammatory activities were assessed by ELISA, transcriptome analysis, western blot, and immunofluorescence methods. Results: Three oxygenated products (2–4) at C-3 of cryptotanshinone (1) were obtained, among them 2 was a new compound. All of the biotransformed products (2–4) were found to inhibit significantly lipopolysaccharide-induced nitric oxide production in BV2 microglia cells with the IC50 values of 0.16‒1.16 μM, approximately 2‒20 folds stronger than the substrate (1). These biotransformed products also displayed remarkably improved inhibitory effects on the production of inflammatory cytokines (IL-1β, IL-6, TNF-α, COX-2 and iNOS) in BV-2 cells via targeting TLR4 compared to substrate (1). The underlying mechanism of 2 was elucidated by comparative transcriptome analysis, which suggested that it reduced neuroinflammatory mainly through mitogen-activated protein kinase (MAPK) signaling pathway. Western blotting results revealed that 2 downregulated LPS-induced phosphorylation of JNK, ERK, and p38 in MAPK signaling pathway. Conclusion: The biotransformed products of cryptotanshinone exhibit potent anti-neuroinflammatory activities. These findings provide a basal material for the discovery of candidates in treating AD.

show abstract

Bioactive Triterpenes from the Root of Salvia miltiorrhiza Bunge

Cited by 25 publications

References 21 publications

Antiproliferative activity and apoptosis induction by trijuganone C isolated from the root of Salvia miltiorrhiza Bunge (Danshen)

Antiproliferative activity and apoptosis induction by trijuganone C isolated from the root of Salvia miltiorrhiza Bunge (Danshen)

Chemical components and bioactivity evaluation of extracts from pear (Pyrus UssuriensisMaxim) fruit

The oxygenated products of cryptotanshinone by biotransformation with Cunninghamella elegans exerting anti-neuroinflammatory effects by inhibiting TLR 4-mediated MAPK signaling pathway

Contact Info

Product

Resources

About