Eryngium L. is the largest and arguably the most taxonomically complex genus of the family Apiaceae. The genus has approximately 250 species throughout the world, with the center of diversity in South America. Some Eryngium species are cultivated as ornamental, vegetable, or medicinal crops for folk uses. With increasing chemical and biological investigations, Eryngium has shown its potential as pharmaceutical crops. This review focuses on phytochemistry and pharmacological activities of 127 compounds isolated and identified from 23 species of Eryngium, particularly nonessential oil compounds such as terpenoids, triterpenoid saponins, flavonoids, coumarins, polyacetylenes, and steroids. Eryngium extracts or isolates have shown in vitro bioactivitities such as cytotoxicity against various human tumor cell lines, anti-inflammatory, anti-snake and scorpion venoms, antibacterial, antifungal, and antimalarial, antioxidant, and antihyperglycemic effects. In vivo studies through various animal models have also shown promising results. However, chemical constituents and their bioactivities of most species of this highly diversified genus have not been investigated. The molecular mechanism of bioactivities (particularly cytotoxicity and anti-snake and scorpion venoms) of Eryngium isolates remains elusive. Also, anti-tumor activity of polyhydroxylated triterpenoid saponins isolated from Eryngium needed to be furthur explored.

2,4-Di-tert-butylphenol or 2,4-bis(1,1-dimethylethyl)-phenol (2,4-DTBP) is a common toxic secondary metabolite produced by various groups of organisms. The biosources and bioactivities of 2,4-DTBP have been well investigated, but the phenol has not been systematically reviewed. This article provides a comprehensive review of 2,4-DTBP and its analogs with emphasis on natural sources and bioactivities. 2,4-DTBP has been found in at least 169 species of bacteria (16 species, 10 families), fungi (11 species, eight families), diatom (one species, one family), liverwort (one species, one family), pteridiphyta (two species, two families), gymnosperms (four species, one family), dicots (107 species, 58 families), monocots (22 species, eight families), and animals (five species, five families). 2,4-DTBP is often a major component of violate or essential oils and it exhibits potent toxicity against almost all testing organisms, including the producers; however, it is not clear why organisms produce autotoxic 2,4-DTBP and its analogs. The accumulating evidence indicates that the endocidal regulation seems to be the primary function of the phenols in the producing organisms.

Two new sesquiterpenes, sarcandralactones A (1) and B (2), and five new dimeric sesquiterpenoids, sarcandrolides A-E (3-7), along with 10 known compounds were isolated from the whole plants of Sarcandra glabra. Their structures were elucidated on the basis of spectroscopic analysis. Some of the new isolates exhibit significant cytotoxicities when tested against a small panel of tumor cell lines.

Five new diterpenes, trigonochinenes A-E (1-5), and two known ones, 3,4- seco-sonderianol (6) and 3,4- seco-sonderianic acid (7), were isolated from the aerial part of Trigonostemon chinensis. Compounds 1-4 possess a rare 3,4-seco-cleistanthanic skeleton, and compound 5 is a highly aromatized tetranorditerpene. Structures of these compounds were elucidated by spectroscopic analysis. The antimicrobial activities of compounds 1-7 were evaluated against a panel of bacteria and fungi.

Eucalyptin A (1), together with two known compounds 2 and 3 exhibiting potent inhibition on HGF/c-Met axis, was discovered from the fruits of Eucalyptus globulus. 1 possessed an unprecedented carbon framework of phloroglucinol-coupled sesquiterpenoid, and its structure was elucidated by spectroscopic method and ECD calculation. A brief structure-activity relationship discussion indicated that the coupling of a phloroglucinol and a sesquiterpenoid is essential for the activity.

Vaccinium L., comprising approximately 450 species primarily in the Northern Hemisphere, is a genus of shrubs or lianas in the family Ericaceae. The berries of many species are harvested for household consumption and commercial sale. The genus produces a wide range of compounds such as anthocyanins, flavonoids, chromones, coumarins, lignans, benzoic acids, iridoids, sterols, and triterpenoids, but is best known for the production of anthocyanins and flavonoids. Extracts and isolates of anthocyanins and flavonoids from Vaccinium fruits or leaves showed antioxidative, anti-inflammatory, antitumor, antiviral, vasoprotective, and antifungal activities. To data, more than 116 anthocyanins and flavonoids compounds have been isolated and identified primarily from the fruits or leaves of Vaccinium. This article reviews phytochemistry and pharmaceutical properties of these compounds.

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