Anatolicin, a Highly Potent and Selective Cytotoxic Sesquiterpene Coumarin from the Root Extract of Heptaptera anatolica

Abstract

Seven known sesquiterpene coumarins and a new sesquiterpene coumarin, anatolicin (8), were isolated from the dichloromethane extract of the roots of Heptaptera anatolica. Structures of these compounds were elucidated based on their spectral properties. While some of these sesquiterpene coumarins showed modest cytotoxic activity against COLO205, KM12, A498, UO31, and TC32 cancer cell lines, selective cytotoxicity of anatolicin (8) and 14′-acetoxybadrakemin (7) were observed at nanomolar level against the UO31 kidney cancer cell line.

Next Chapter in the Legend of Silphion: Preliminary Morphological, Chemical, Biological and Pharmacological Evaluations, Initial Conservation Studies, and Reassessment of the Regional Extinction Event

“…Umbelliprenin 16Antigenotoxic [89], antioxidant, anti-inflammatory, lipoxygenase inhibitor [90], matrix metalloproteinase inhibitor [91], antitumor [92], cytotoxic activity against CH1 (ovarian), A549 (lung), SK-MEL-28 (melanoma) [93], M4Beu (metastatic pigmented malignant melanoma), QU-DB (large cell lung) [94], and UO31 (renal) [48] cancer cell lines, modulator of melanogenesis [95], antihypertension [96], cancer chemoprevention [97], antiangiogenic [98], antimetastatic and immunostimulatory [99].…”

“…Badrakemone (20) Cytotoxic against UO31 (renal) cancer cell line [48], cancer chemoprevention [97], weak matrix metalloproteinase inhibitor [91].…”

Cytotoxic activity of the root and fruit extracts of heptaptera anisoptera (dc.) tutin

“…, colladin, 14-acetoxybadrakemin, 14-acetoxybadrakemone, 14-hydroxycolladonin from the chloroform extract of the roots and more polar compounds samarcandin, samarcandone, conferol, conferone, feselol, 9,10,11-trihydroxyumbelliprenin, 9,10,11-5'-tetrahydroxyumbelliprenin, 9, 10, 5'-triacetoxy-11-hydroxyumbellipreni, 10, 11, 5'-trihydroxyumbelliprenin from the chloroform extract of the fruits of H. anisoptera collected from Diyarbakır in June 1991 3,11,12 . Cytotoxic activity of certain sesquiterpene coumarins were described earlier 4,5 , thus, the cytotoxic compound(s) of the roots and fruits of H. anisoptera may be this type of compound(s). Bioactivity guided fractionation of the dichloromethane extracts of the roots and fruits of H. anisoptera is planned to isolate and identify their cytotoxic principles.…”

“…Tutin are growing in Turkey 1,2 . Heptaptera species are known to contain sesquiterpene coumarin derivatives 3,4 , these compounds have various biological activities such as; cytotoxicity, P-glycoprotein inhibitory, cancer chemoprevention, anti-inflammatory, antibacterial, antileishmanial, antiviral, antidiabetic, etc. [5][6][7][8][9] .…”

Neopapillarine, an Unusual Coumarino-Alkaloid from the Root Extract of Neocryptodiscus papillaris with Cytotoxic Activity on Renal Cancer Cells

“…As part of a long-term collaboration to explore the phytochemistry of rare, endemic, and medicinal Turkish plants, we evaluated the anticancer properties of extracts and pure compounds using cancer cell growth inhibition assays as well as molecularly targeted assays. We have focused on the family Apiaceae, a notably diverse plant family in Turkey, with 100 genera, e.g., [2]. Over 140 extracts from over 40 species of Turkish Apiaceae were tested by both cell growth and biochemical assays at the Molecular Targets Program, National Cancer Institute (NCI).…”