Chemical Constituents of the Roots and Rhizomes of Saposhnikovia divaricata and their Cytotoxic Activity

Phytochemical investigation of the MeOH extract of the roots and rhizomes of Saposhnikovia divaricata (Umbelliferae) resulted in the isolation of six chromons (1-6) and five polyacetylene derivatives (7-11). Compounds 9 and 11 were isolated from S. divaricate for the first time. The chromon derivatives (1-6) were evaluated for their cytotoxic activity against HL-60 human promyelocytic leukemia cells. Compound 1 (3′- O-angeloylhamaudol) showed the most potent cytotoxic activity with an IC50 value of 4.41 μM and was found to induce apoptotic cell death in HL-60 cells. The loss of mitochondrial membrane potential, release of cytochrome c into the cytoplasm, and activation of caspase-9 in the 1-treated HL-60 cells suggests that 1 induces apoptosis through the mitochondrial-dependent apoptotic pathway.

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Chemical Constituents of the Underground Parts of Iris florentina and their Cytotoxic Activity

Natural Product Communications ◽

10.1177/1934578x1501000641 ◽

2015 ◽

Vol 10 (6) ◽

pp. 1934578X1501000 ◽

Cited By ~ 2

Author(s):

Akihito Yokosuka ◽

Yoshikazu Koyama ◽

Yoshihiro Mimaki

Keyword(s):

Cell Death ◽

Cytotoxic Activity ◽

Spectroscopic Data ◽

Apoptotic Cell ◽

Chemical Constituents ◽

Promyelocytic Leukemia ◽

Apoptotic Cell Death ◽

Leukemia Cells ◽

Hydrolytic Cleavage ◽

New Compounds

Three new isoflavonoid glycosides (1, 5, and 9) and 10 known compounds (2–4, 6–8, and 10–13) were isolated from the underground parts of Iris florentina (Iridaceae). The structures of the new compounds were determined based on extensive spectroscopic data and the results of hydrolytic cleavage. The isolated compounds and the aglycones were evaluated for cytotoxic activity against HL-60 human promyelocytic leukemia cells. Compound 12 induced apoptotic cell death in the HL-60 cells.

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Chemical Constituents of the Leaves of Dracaena thalioides

Natural Product Communications ◽

10.1177/1934578x1300800309 ◽

2013 ◽

Vol 8 (3) ◽

pp. 1934578X1300800 ◽

Cited By ~ 1

Author(s):

Akihito Yokosuka ◽

Atsushi Sekiguchi ◽

Yoshihiro Mimaki

Keyword(s):

Cell Death ◽

Cytotoxic Activity ◽

Related Compound ◽

Spectroscopic Data ◽

Apoptotic Cell ◽

Chemical Constituents ◽

Promyelocytic Leukemia ◽

Leukemia Cells ◽

Hydrolytic Cleavage ◽

New Compounds

Two new furostanol bisdesmosides (1 and 2) and seven known compounds (3-9) were isolated from the leaves of Dracaena thalioides (Agavaceae). The structures of the new compounds were determined on the basis of spectroscopic data and the results of hydrolytic cleavage. The isolated compounds were evaluated for cytotoxic activity against HL-60 human promyelocytic leukemia cells. Compound 5, a glyceroglycolipid-related compound assigned as (2 S)-1- O-linoleoyl-3- O-β-D-galactopyranosylglycerol, was found to induce apoptotic cell death in HL-60 cells with an IC50 value of 25.8 μM.

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Phytochemical Constituents of Annona reticulata and their Cytotoxic Activity

Letters in Organic Chemistry ◽

10.2174/1570178616666190724123004 ◽

2020 ◽

Vol 17 (3) ◽

pp. 206-210

Author(s):

Ty Viet Pham ◽

Thang Quoc Le ◽

Anh Tuan Le ◽

Hung Quoc Vo ◽

Duc Viet Ho

Keyword(s):

Cytotoxic Activity ◽

Cell Lines ◽

Structural Determination ◽

Phytochemical Investigation ◽

Ic50 Values ◽

Phytochemical Constituents ◽

First Time ◽

Annona Reticulata

A phytochemical investigation of the leaves of Annona reticulata led to the isolation and structural determination of β-sitosterol (1), ent-pimara-8(14),15-dien-19-oic acid (2), ent-pimara- 8(14),15-dien-19-ol (3), quercetin (4), quercetin 3-O-α-L-arabinopyranoside (5), and a mixture of quercetin 3-O-β-D-galactopyranoside (6a) and quercetin 3-O-β-D-glucopyranoside (6b). Of these, compounds 2 and 3 were isolated from the genus Annona for the first time. Compound 3 showed strong cytotoxicity against SK-LU-1 and SW626 cell lines with IC50 values of 17.64 ± 1.07 and 19.79 ± 1.41 μg mL-1, respectively.

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Chemical Constituents of the Marine Sponge Aaptos aaptos (Schmidt, 1864) and Their Cytotoxic Activity

Natural Product Communications ◽

10.1177/1934578x21993345 ◽

2021 ◽

Vol 16 (2) ◽

pp. 1934578X2199334

Author(s):

Do Thi Trang ◽

Bui Huu Tai ◽

Dan Thuy Hang ◽

Pham Hai Yen ◽

Phan Thi Thanh Huong ◽

...

Keyword(s):

Cytotoxic Activity ◽

Spectral Data ◽

Absolute Configuration ◽

Marine Sponge ◽

Chemical Constituents ◽

2D Nmr ◽

Extensive Analysis ◽

First Time ◽

Tddft Method ◽

Mcf 7

Seven compounds (1-7) were isolated from the marine sponge Aaptos aaptos living in the Vietnamese sea. Their structures were determined as 2 hours, 5 H,7 H,9 H-9 S-hydroxy-imidazo[1,5- α]pyridine-1,3-dione (1), 3-([9-methylhexadecyl]oxy)propane-1,2-diol 2, 2,3-dihydro-2,3-dioxoaaptamine (3), indol-3-aldehyde (4), methyl indole-3-carboxylate (5) 4-hydroxy-5-(indole-3-yl)−5-oxo-pentan-2-one (6), and thymidine (7) by extensive analysis of HR-ESI-MS, 1D, and 2D NMR spectral data, as well as by comparison of the spectral data with those reported in the literature. In addition, the absolute configuration of 1 was determined from the experimental ECD spectrum and comparison of this with the theoretical ECD calculations using the TDDFT method. Compounds 1 and 2 were isolated from nature for the first time. Compound 3 induced cytotoxic activity against SK-LU-1, MCF-7, HepG2, and SK-Mel-2 cell lines with IC50 values of 41.27 ± 2.63, 40.70 ± 2.65, 34.31 ± 3.43, and 36.63 ± 1.40 µM, respectively.

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CONTRIBUTE TO STUDY ON CHEMICAL CONSTITUENTS OF URENA LOBATA (L.) OF VIETNAM

Vietnam Journal of Science and Technology ◽

10.15625/2525-2518/57/2/13019 ◽

2019 ◽

Vol 57 (2) ◽

pp. 162

Author(s):

Quan Minh Pham ◽

Hoai Van Thi Tran ◽

Lam Tien Do ◽

Phuong Lan Doan ◽

Inh Thi Cam ◽

...

Keyword(s):

Mental Disorders ◽

Ethyl Acetate ◽

Ethyl Acetate Extract ◽

Chemical Constituents ◽

2D Nmr ◽

Spectroscopic Methods ◽

Tree Roots ◽

Chemical Structures ◽

Phytochemical Investigation ◽

First Time

Urena lobata L. is used in Vietnamese traditional medicine for the treatment of several diseases. Tree roots are used to treat rheumatism, dysentery, poor digestion, flu, tonsils, malaria, asthma, goiter. Flowers are used to treat chickenpox, fever, and mental disorders. Branches, leaves or whole trees used to treat injuries bruises, rheumatism, mastitis, bites. Phytochemical investigation of the n-hexan and ethyl acetate extract of Urena lobata L. led to the isolation of β-sitosterol (1), β-sitosterol-3-O-β-D-glucopyranoside (2), a-acetylamino-phenylpropyl a-benzoylamino-phenylpropanoate (3), quercetin (4), and trans-tiliroside (5). Their chemical structures were determined by spectroscopic methods including MS, 1D, 2D NMR and comparing with those reported in previous papers. Two compounds 3, 5 were isolated for the first time from Urena lobata plant.

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New Chromone and Triglyceride from Cucumis melo Seeds

Natural Product Communications ◽

10.1177/1934578x1400900217 ◽

2014 ◽

Vol 9 (2) ◽

pp. 1934578X1400900

Author(s):

Sabrin R. M. Ibrahim

Keyword(s):

Antioxidant Activity ◽

Cytotoxic Activity ◽

Cucumis Melo ◽

Spectral Measurements ◽

Dpph Assay ◽

Meoh Extract ◽

Mass Spectral ◽

Cucumis Melo L ◽

First Time

Re-investigation of the MeOH extract of the seeds of Cucumis melo L. var. reticulatus (Cucurbitaceae) led to the isolation of a new chromone derivative (5,7-dihydroxy-2-[2-(3-methoxy-4-hydroxyphenyl)ethyl]chromone (5) and a triglyceride (1,3-di-(6 Z,9 Z)-docosa-6,9-dienoyl-2-(6 Z) hexacos-6-enoylglycerol (1), together with three known compounds; α-spinasterol (2), stigmasta-7,22,25-trien-3-ol (3), and D:B-friedoolean-5-ene-3-β-ol (4), are reported from this species for the first time. Their structures were determined by extensive 1D (1H, 13C, and DEPT) and 2D (1H-1H COSY, HMQC, and HMBC) NMR and mass spectral measurements. Compound 5 displayed significant cytotoxic activity against L5178Y cells, with an ED50 of 5 μM. The MeOH extract and 5 showed antioxidant activity using the DPPH assay.

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STUDY ON CHEMICAL CONSTITUENTS AND CYTOTOXICITY OF ASPIDISTRA LETREAE

HUE UNIVERSITY JOURNAL OF SCIENCE NATURAL SCIENCE ◽

10.26459/hueuni-jns.v129i2a.5656 ◽

2020 ◽

Vol 129 (1B) ◽

Author(s):

Duc Viet Ho

Keyword(s):

Methanol Extract ◽

Human Cancer ◽

Chemical Constituents ◽

Hep G2 ◽

Pure Compound ◽

Human Cancer Cell Lines ◽

Phytochemical Investigation ◽

Reported Data ◽

First Time

A phytochemical investigation of whole Aspidistra letreae plants led to the isolation of 2H-chromen-2-one (1), α-tocopherol (2), (E)-phytol (3), asparenydiol (4) and (25S)-spirost-1β,3α,5β-triol (5). Their structures were determined on the basis of NMR spectral evidences and in comparison with the reported data. Of these, asparenydiol (4) was isolated from the genus Aspidistra for the first time. This is also the first report on the separation and structural determination of (25S)-spirost-1β,3α,5β-triol (5) as a pure compound. The methanol extract exhibited a moderate cytotoxicity against the LU-1, HeLa, MDA-MB-231, Hep-G2, and MKN-7 human cancer cell lines with IC50 values ranging from 52.58 ± 3.65 to 64.78 ± 4.89 μg/mL.

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Chemical constituents and cytotoxicity of Aspidistra letreae

HUE UNIVERSITY JOURNAL OF SCIENCE NATURAL SCIENCE ◽

10.26459/hueuni-jns.v129i1b.5656 ◽

2020 ◽

Vol 129 (1B) ◽

pp. 31-39

Author(s):

Duc Viet Ho ◽

Hanh Nhu Thi Hoang ◽

Khue Minh Vo ◽

Anh Tuan Le ◽

Hoai Thi Nguyen

Keyword(s):

Human Cancer ◽

Chemical Constituents ◽

Hep G2 ◽

Human Cancer Cell Lines ◽

Phytochemical Investigation ◽

Ic50 Values ◽

Reported Data ◽

Whole Plants ◽

First Time

A phytochemical investigation of whole Aspidistra letreae plants led to the isolation of 2H-chromen-2-one (1), α-tocopherol (2), (E)-phytol (3), asparenydiol (4) and (25S)-spirost-1β,3α,5β-triol (5). Their structures were determined on the basis of NMR spectral evidences and in comparison with the reported data. Of these, asparenydiol (4) was isolated from the genus Aspidistra for the first time. This is also the first report on the separation and structural determination of (25S)-spirost-1β,3α,5β-triol (5) as a pure compound. The methanol extract from the whole plants of Aspidistra letreae exhibits moderate cytotoxicity against the LU-1, HeLa, MDA-MB-231, Hep-G2, and MKN-7 human cancer cell lines with IC50 values ranging from 52.58 ± 3.65 to 64.78 ± 4.89 μg/mL.

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Chemical Constituents of the Aerial Parts of Scutellaria lateriflora and their α-Glucosidase Inhibitory Activities

Natural Product Communications ◽

10.1177/1934578x1200700413 ◽

2012 ◽

Vol 7 (4) ◽

pp. 1934578X1200700 ◽

Cited By ~ 4

Author(s):

Minpei Kuroda ◽

Katsura Iwabuchi ◽

Yoshihiro Mimaki

Keyword(s):

Methyl Ester ◽

Chemical Constituents ◽

Meoh Extract ◽

Aerial Parts ◽

Screening Experiments ◽

Data Analyses ◽

Nmr Data ◽

Scutellaria Lateriflora ◽

Inhibitory Activities ◽

First Time

MeOH extracts of 37 herbs were tested in screening experiments for rat intestinal α-glucosidase. The MeOH extract of the aerial parts of Scutellaria lateriflora L. (Lamiaceae) significantly inhibited sucrase and maltase activities, using sucrose and maltase as the substrates. Enzyme inhibition guided-fractionation of the MeOH extract of S lateriflora resulted in the isolation of a new diterpene glucoside, deacetylajugarin-IV 18- O-β-D-glucopyranoside (1), along with 20 known phenolics (2-21). The structures of 1-21 were elucidated on the basis of MS and NMR data analyses. Baicalein (4) and baicalin (10), a glycoside of 4, showed moderate sucrase inhibitory activities at IC50 values of 14.9 and 36.3 μM, respectively, whereas luteolin (3), acteoside (16), leucosceptoside A (18), and isoacteoside (20) showed weak inhibitory activities at IC50 values of 811, 522, 727, and 443 μM, respectively. This is the first report on mammalian α-glucosidase inhibitory activities of S lateriflora extract and identification of the constituents responsible for the activities. Apigenin (2), luteolin (3), 6-methoxyluteolin 4'-methyl ether (6), isoscutellarin 8- O-β-D-glucuronide (7), luteolin 7- O-β-D-glucuronide (9), wogonin 7- O-β-D-glucuronide methyl ester (12), eriodictyol (13), naringenin (14), naringenin 7- O-β-D-glucuronide (15), jionoside D (17), leucosceptoside A (18), and (+)-syringaresinol 4'- O-β-D-glucopyranoside (21) were isolated from this plant for the first time. The inhibitory properties of S lateriflora extract against α-glucosidase provide a prospect for its antidiabetic usage.

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Berberine Induces Apoptotic Cell Death via Activation of Caspase-3 and -8 in HL-60 Human Leukemia Cells: Nuclear Localization and Structure–Activity Relationships

The American Journal of Chinese Medicine ◽

10.1142/s0192415x17500811 ◽

2017 ◽

Vol 45 (07) ◽

pp. 1497-1511 ◽

Cited By ~ 18

Author(s):

Shinya Okubo ◽

Takuhiro Uto ◽

Aya Goto ◽

Hiroyuki Tanaka ◽

Tsuyoshi Nishioku ◽

...

Keyword(s):

Cell Death ◽

Dna Fragmentation ◽

Antiproliferative Activity ◽

Caspase 3 ◽

Apoptotic Cell ◽

Apoptotic Cell Death ◽

Leukemia Cells ◽

Caspase 8 ◽

Human Leukemia ◽

Caspase 9

Berberine (BBR), an isoquinoline alkaloid, is a well-known bioactive compound contained in medicinal plants used in traditional and folk medicines. In this study, we investigated the subcellular localization and the apoptotic mechanisms of BBR were elucidated. First, we confirmed the incorporation of BBR into the cell visually. BBR showed antiproliferative activity and promptly localized to the nucleus from 5[Formula: see text]min to 15[Formula: see text]min after BBR treatment in HL-60 human promyelocytic leukemia cells. Next, we examined the antiproliferative activity of BBR (1) and its biosynthetically related compounds (2-7) in HL-60 cells. BBR exerted strongest antiproliferative activity among 1-7 and the results of structures and activity relation suggested that a methylenedioxyl group in ring A, an [Formula: see text]-alkyl group at C-9 position, and the frame of isoquinoline may be necessary for antiproliferative activity. Moreover, BBR showed the most potent antiproliferative activity in HL-60 cells among human cancer and normal cell lines tested. Next, we examined the effect of BBR on molecular events known as apoptosis induction. In HL-60 cells, BBR induced chromatin condensation and DNA fragmentation, and triggered the activation of PARP, caspase-3 and caspase-8 without the activation of caspase-9. BBR-induced DNA fragmentation was abolished by pretreatment with inhibitors against caspase-3 and caspase-8, but not against caspase-9. ERK and p38 were promptly phosphorylated after 15 min of BBR treatment, and this was correlated with time of localization to the nucleus of BBR. These results demonstrated that BBR translocated into nucleus immediately after treatments and induced apoptotic cell death by activation of caspase-3 and caspase-8.

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