https://pubs.rsc.org/en/content/articlepdf/2016/np/c6np00059b

Diterpenoids of terrestrial origin

An overview of grayanane diterpenoids and their biological activities from the Ericaceae family in the last seven years.

Terpenoids with lactone moieties have been indicated to possess high bioactivity. Certain terpenoid lactones exist in nature, in plants and animals, but they can also be obtained by chemical synthesis. Terpenoids possessing lactone moieties are known for their cytotoxic, anti-inflammatory, antimicrobial, anticancer, and antimalarial activities. Moreover, one terpenoid lactone, artemisinin, is used as a drug against malaria. Because of these abilities, there is constant interest in new terpenoid lactones that are both isolated and synthesized, and their biological activities have been verified. In some cases, the activity of the terpenoid lactone is specifically connected to the lactone moiety. Recent works have revealed that new terpenoid lactones can demonstrate such functions and are thus considered to be potential active agents against many diseases.

Biological Activity of Selected Natural and Synthetic Terpenoid Lactones.

Thirteen new grayanane diterpenoids (1-13) and 15 known analogues (14-28) were isolated from a leaf extract of Pieris japonica. Their structures were determined by spectrometric and spectroscopic methods, including HRESIMS, NMR, IR, and UV. The absolute configurations of 1, 3, 7-9, and 16 were defined by single-crystal X-ray diffraction analysis. 17-Hydroxygrayanotoxin XIX (1) represents the first example of a 17-hydroxygrayan-15(16)-ene diterpenoid. Diterpenoids 1-28 were evaluated for their antinociceptive activities, and 4, 9, 13, 21, and 26-28 displayed significant antinociceptive activities at a dose of 5.0 mg/kg (ip) in the HOAc-induced writhing test in mice. 17-Hydroxygrayanotoxin XIX (1) exhibited potent antinociceptive effects with writhe inhibition rates of 56.3% and 64.8% at doses of 0.04 and 0.2 mg/kg, respectively, which were almost equivalent to the positive control, morphine. Rhodomollein X (26) and rhodojaponin VI (27) showed more potent antinociceptive effects than morphine at doses of 0.04 and 0.2 mg/kg. A preliminary structure-activity relationship for the antinociceptive effects of diterpenoids 1-28 is discussed.

Antinociceptive Grayanane Diterpenoids from the Leaves of Pieris japonica.

The family Ericaceae is comprised of about 70 genera of which about 20 are found throughout China. Of these Ledum, Rhododendron, Enkianthus, Pieris, Craibiodendron, Gaultheria, Vaccinium, and Leucothoe are regarded as poisonous. Many species of these poisonous genera are used as Chinese herbal medicines for the treatment of, for example, inflammation, asthma, and coughs. Modem research has demonstrated that the toxic ingredients of these poisonous genera are chiefly tetracyclic diterpenes, which have adverse effects on the digestive, cardiovascular and nervous systems. Because various species of these poisonous genera also have medicinal functions, extensive studies of these plants have led to the identification of many kinds of compound. This paper compiles 306 compounds from the eight poisonous genera, reported in 141 references.

https://journals.sagepub.com/doi/pdf/10.1177/1934578X1400900333

Phytochemicals and Biological Activities of Poisonous Genera of Ericaceae in China

Two new chlorinated multiacylated 3,4-seco-grayanane diterpenoids, neopierisoids A and B (1 and 2), were isolated from flowers of the poisonous plant Pieris japonica and were identified from spectroscopic analysis and X-ray diffraction data. Both compounds showed obvious antifeedant activity against Pieris brassicae with an EC50 of 10.07 mu g/cm(2) for 1 and 5.33 mu g/cm(2) for 2, indications of toxic properties. Chlorinated 3,4-seco-grayanane diterpenoids in P. japonica may play a defensive role against herbivores.

Neopierisoids A and B, Two New Chlorinated 3,4-seco-Grayanane Diterpenoids with Antifeedant Activity from Flowers of Pieris japonica

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Neopierisoids A and B, Two New Chlorinated 3,4-seco-Grayanane Diterpenoids with Antifeedant Activity from Flowers of Pieris japonica