P. Annécie Benatrehina

The Ohio State University

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A. Douglas Kinghorn

The Ohio State University

C. Benjamin Naman

Scripps Institution of Oceanography

Heebyung Chai

Xi'an Medical University

Liva Harinantenaina

The Ohio State University

Chunhua Yuan

Shanghai Sunshine Rehabilitation Center

Tran Ngoc Ninh

Vietnam Academy of Science and Technology

Djaja D. Soejarto

University of Illinois Chicago

TN Ninh

Vietnam Academy of Science and Technology

William J. Keller

Nova Southeastern University

Garima Agarwal

Jaypee Hospital

Cooperative Institutions

The Ohio State University

University of Illinois Chicago

American Association of Colleges of Pharmacy

Medicina

South China Agricultural University

Vietnam Academy of Science and Technology

Chinese Academy of Medical Sciences & Peking Union Medical College

University of North Carolina Wilmington

University of Illinois Urbana-Champaign

Indonesian Institute of Sciences

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Investigation of the antiproliferative activity of Linociera ramiflora and its isolates

Planta Medica (2015)

P. Annécie Benatrehina Lan Pan CB Naman HB Chai TN Ninh

Following the primary screening of Vietnamese plant extracts against the HT-29 human colon cancer cell line assay, the branch sample of Linociera cf. ramiflora (Roxb.) Wall. (Oleaceae) (sample A06576; voucher specimen DDS 14374) was selected as a candidate for further study. The methanol extract of this plant sample was subjected to a bioactivity-guided fractionation aiming at the isolation of potential anticancer agents. Liquid-liquid partitions of this extract led to an active chloroform fraction (IC50= 7.7 µg/mL). Further separation of this fraction through successive column chromatography afforded numerous active sub-fractions, from which several new and known lignans and arylglycerol-substituted lignan derivatives together with some aromatic compounds were isolated. The structure determination as well as the antiproliferative and quinone reductase inducting activities of these compounds will be described.

Fraction (chemistry)

Oleaceae

Active compound

10.1055/s-0035-1556492

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Bioactivity-Guided Isolation of Totarane-Derived Diterpenes from Podocarpus neriifolius and Structure Revision of 3-Deoxy-2α-hydroxynagilactone E

Natural Products and Bioprospecting (2019)

P. Annécie Benatrehina Weilun Chen Austin Czarnecki Steven J. Kurina Heebyung Chai

Bioactivity-guided phytochemical investigation of Podocarpus neriifolius D. Don. (Podocarpaceae) has led to the isolation of one new (2) and three known (1, 3, and 4) B-type podolactones, along with three totarane-type diterpenes (5-7). Their structures were determined by interpretation of High Resolution ElectroSpray Ionization Mass Spectrometry (HRESIMS) and 1D and 2D NMR data, and comparison with the values reported in the literature. The structure of compound 1, previously identified as 3-deoxy-2α-hydroxynagilactone E (8), was revised as its 2β-epimer, which has been reported recently as a new compound. All of the isolates were evaluated for their antiproliferative activity against a panel of four human cancer cell lines, namely, ovarian (OVCAR3), breast (MDA-MB-231), colon (HT-29), and melanoma (MDA-MB-435), and compounds 1 and 3 were found to be cytotoxic with IC50 values in the low micromolar range for most of the cell lines used. The major compound, inumakilactone A (3), was further tested in vivo using the HT-29, MDA-MB-435, and OVCAR3 cells in a murine hollow fiber model, for the first time.

Phytochemical

Epimer

Podocarpaceae

Absolute Configuration

10.1007/s13659-019-0198-x

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Citations (6)

Pharmaceuticals, Plant Drugs

Elsevier eBooks (2016)

C. Benjamin Naman P. Annécie Benatrehina A. Douglas Kinghorn

10.1016/b978-0-12-394807-6.00163-5

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Bioassay-Guided Isolation of Antioxidant and Cytoprotective Constituents from a Maqui Berry (Aristotelia chilensis) Dietary Supplement Ingredient As Markers for Qualitative and Quantitative Analysis

Journal of Agricultural and Food Chemistry (2017)

Jie Li Chunhua Yuan Pan Li P. Annécie Benatrehina Heebyung Chai

Bioassay-guided phytochemical investigation of a commercially available maqui berry (Aristotelia chilensis) extract used in botanical dietary supplement products led to the isolation of 16 compounds, including one phenolic molecule, 1, discovered for the first time from a natural source, along with several known compounds, 2–16, including three substances not reported previously in A. chilensis, 2, 14, and 15. Each isolate was characterized by detailed analysis of NMR spectroscopic and HRESIMS data and tested for their in vitro hydroxyl radical scavenging and quinone-reductase inducing biological activities. A sensitive and accurate LC–DAD-MS method for the quantitative determination of the occurrence of six bioactive compounds, 6, 7, 10–12, and 14, was developed and validated using maqui berry isolates purified in the course of this study as authentic standards. The method presented can be utilized for dereplication efforts in future natural product research projects or to evaluate chemical markers for quality assurance and batch-to-batch standardization of this botanical dietary supplement component.

Phytochemical

Ingredient

Natural product

10.1021/acs.jafc.7b03261

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Citations (23)

Antiproliferative diterpenoids from the roots of Podocarpus neriifolius

Planta Medica (2016)

P. Annécie Benatrehina TN Ninh Carla Slebodnick DD Soejarto Liva Harinantenaina

Plant samples collected in the Southeast Asian rainforests were subjected to initial screening against the HT-29 human colon cancer cell line, and Podocarpus neriifolius D. Don (Podocarpaceae), obtained from Vietnam, with an IC50 value of 8.2 µg/mL, was selected for further investigation aiming for the discovery of potential anticancer lead agents. Bioactivity-guided purification of the active ethyl acetate fraction (IC50= 4.3 µg/mL) from the dried root sample of P. neriifolius has so far afforded three type-B podolactones, namely, makilactones E (1) and G (2) and inumakilactone A (3), all characterized by the presence of a 7α,8α-epoxy-9(11)-enolide functionality [1 – 3]. Their structures were determined by interpretation of spectroscopic data and comparison with the existing literature [1,2]. In addition, the X-ray crystallography data of 1 was obtained to confirm its absolute configuration. While 3 has shown termiticidal and cytotoxic activity against murine leukemia cells P388 in vitro [1,2], in this study, it exhibited potent activity against HT-29 with an IC50 value of 1.1µM. On the other hand, compounds 1 and 2 were non-cytotoxic in this assay. In this presentation, the isolation and structure determination of these compounds are described as well as the dereplication of additional active sub-fractions, which suggests the presence of different active podolactones and totarane-type diterpenes.

IC50

Podocarpaceae

Podocarpus

10.1055/s-0036-1596515

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Natural Products

Springer eBooks (2017)

A. Douglas Kinghorn P. Annécie Benatrehina Garima Agarwal

10.1007/978-3-662-46875-3_3977

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Computer-Assisted Structure Elucidation of Black Chokeberry (Aronia melanocarpa) Fruit Juice Isolates with a New Fused Pentacyclic Flavonoid Skeleton

Organic Letters (2015)

C. Benjamin Naman Jie Li Arvin Moser Jeffery M. Hendrycks P. Annécie Benatrehina

Melanodiol 4″-O-protocatechuate (1) and melanodiol (2) represent novel flavonoid derivatives isolated from a botanical dietary supplement ingredient, dried black chokeberry (Aronia melanocarpa) fruit juice. These noncrystalline compounds possess an unprecedented fused pentacyclic core with two contiguous hemiketals. Due to having significant hydrogen deficiency indices, their structures were determined using computer-assisted structure elucidation software. The in vitro hydroxyl radical-scavenging and quinone reductase-inducing activity of each compound are reported, and a plausible biogenetic scheme is proposed.

Ingredient

10.1021/acs.orglett.5b01284

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Citations (32)

Isolation and Analysis of Antioxidant Phytochemicals from Black Chokeberry, Maqui, and Goji Berry Dietary Supplements

ACS symposium series (2018)

Jie Li P. Annécie Benatrehina Andrea L. Rague Pan Li A. Douglas Kinghorn

The analysis of antioxidant and potentially cancer chemopreventive, or cytoprotective, phytochemicals that were isolated from berries including black chokeberry (Aronia melanocarpa), maqui (Aristotelia chilensis), and goji (Lyceum barbarum) has been reported recently. This chapter describes the research conducted, rationale, and draws connections from the summation of all three projects. For example, the re-isolation of some phytochemicals from multiple dietary supplement ingredients highlights the need for dereplication methods to be used in the course of research, yet understanding the distribution of these molecules in human dietary and supplementation ingredients remains important. The observation of low- and sub-micromolar ED50 (concentration yielding half efficacy) values for hydroxyl radical-scavenging and CD (concentration required to double activity) values for quinone-reductase inducing in vitro activities, summarized for the molecules isolated, highlights the potential health impact of phytochemicals from dietary supplement ingredients such as the three berries examined. Some of the phytochemicals described should eventually be evaluated in vivo for bioactivities, metabolism, and pharmaceutical properties, and can serve as marker compounds for chemical analysis.

10.1021/bk-2018-1286.ch001

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Citations (2)

Usage, biological activity, and safety of selected botanical dietary supplements consumed in the United States

Journal of Traditional and Complementary Medicine (2018)

P. Annécie Benatrehina Pan Li C. Benjamin Naman Jie Li A. Douglas Kinghorn

In view of the continuous growth of the botanical dietary supplement industry and the increased popularity of lesser known or exotic botanicals, recent findings are described on the phytochemical composition and biological activities of five selected fruits consumed in the United States, namely, açaí, noni, mangosteen, black chokeberry, and maqui berry. A review of the ethnomedicinal uses of these plants has revealed some similarities ranging from wound-healing to the treatment of fever and infectious diseases. Laboratory studies on açaí have shown both its antioxidant and anti-inflammatory activities in vitro, and more importantly, its neuroprotective properties in animals. Anthraquinones and iridoid glucosides isolated from noni fruit induce the phase II enzyme quinone reductase (QR), and noni fruit juice exhibited antitumor and antidiabetic activities in certain animal models. Antitumorigenic effects of mangosteen in animal xenograft models of human cancers have been attributed to its xanthone content, and pure α-mangostin was shown to display antineoplastic activity in mice despite a reported low oral bioavailability. Work on the less extensively investigated black chokeberry and maqui berry has focused on recent isolation studies and has resulted in the identification of bioactive secondary metabolites with QR-inducing and hydroxyl-radical scavenging properties. On the basis of the safety studies and toxicity case reports described herein, these fruits may be generally considered as safe. However, cases of adulteration found in a commercialized açaí product and some conflicting results from mangosteen safety studies warrant further investigation on the safety of these marketed botanical dietary supplements.

Phytochemical

Nutraceutical

Anthraquinones

Garcinia Mangostana

Phytotherapy

Dietary supplement

10.1016/j.jtcme.2018.01.006

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Citations (38)

Natural Products

Springer eBooks (2015)

A. Douglas Kinghorn P. Annécie Benatrehina Garima Agarwal

10.1007/978-3-642-27841-9_3977-3

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