Haslam’s previous accounts of this area of flavonoid chemistry (Haslam, 1975, 1982a) eloquently summarized the historical developments in the chemistry and biochemistry of this important and complex group of plant phenolics. Also covered were their relationship with condensed tannins and aspects of their characteristic chemical and spectroscopic properties and metabolism.

Flavans and proanthocyanidins

Products from tea catechins ((+)-catechin, (−)-epicatechin, (−)-epigallocatechin, (−)-epicatechin gallate, and (−)-epigallocatechin gallate) after heat treatment were individually isolated by preparative HPLC and subsequent crystallization. FAB-MS, elemental, 1H- and 13C-NMR, and optical rotation analyses indicated these products to be the C-2 epimers of the original catechins. The effects of temperature, time, pH, and concentration on this conversion of tea catechins to their epimers were examined. It was determined that the epimerization reaction should be conducted with 1% each of the tea catechin solution (pH5) at l20°C for 30 min.

Preparation of Epimers of Tea Catechins by Heat Treatment

The present study investigated the antinociceptive effects of the flavonoid myricitrin in chemical behavioral models of pain in mice and rats. Myricitrin given by i.p. or p.o. routes produced dose-related antinociception when assessed on acetic acid-induced visceral pain in mice. In addition, the i.p. administration of myricitrin exhibited significant inhibition of the neurogenic pain induced by intraplantar (i.pl.) injection of capsaicin. Like-wise, myricitrin given by i.p. route reduced the nociception produced by i.pl. injection of glutamate and phorbol myristate acetate (PMA). Western blot analysis revealed that myricitrin treatment fully prevented the protein kinase C (PKC) alpha and PKCepsilon activation by PMA in mice hind paws. Myricitrin given i.p. also inhibited the mechanical hyperalgesia induced by bradykinin, without affecting similar responses caused by epinephrine and prostaglandin E(2). The antinociception caused by myricitrin in the acetic acid test was significantly attenuated by i.p. treatment of mice with the nitric oxide precursor, L-arginine. In contrast, myricitrin antinociception was not affected by naloxone (opioid receptor antagonist) or neonatal pretreatment of mice with capsaicin and myricitrin antinociceptive effects is not related to muscle relaxant or sedative action. Together, these results indicate that myricitrin produces pronounced antinociception against chemical and mechanical models of pain in rodents. The mechanisms involved in their actions are not completely understood but seem to involve an interaction with nitric oxide-L-arginine and protein kinase C pathways.

https://jpet.aspetjournals.org/content/jpet/early/2005/10/31/jpet.105.092825.full.pdf

Analysis of the antinociceptive effect of the flavonoid myricitrin: evidence for a role of the L-arginine-nitric oxide and protein kinase C pathways.

Two new lavandulylated flavanones, (2S)-2'-methoxykurarinone (1) and (-)-kurarinone (2), were isolated from the root of Sophora flavescens, together with two known lavandulyl flavanones, sophoraflavanone G (3) and leachianone A (4), and two known isoflavonoids, formononetin and l-maakiain. The structures of 1 and 2 were determined on the basis of optical rotation and spectral evidence and by comparison with known compounds. Compounds 1-4 exhibited cytotoxic activity against human myeloid leukemia HL-60 cells.

Cytotoxic Lavandulyl Flavanones from Sophora flavescens

The ecological biochemistry of flavonoids, in which I have been engaged for 25 years, is summarized in this review article. The review covers (1) a survey of rare bio-active flavonoids in higher plants; (2) the fungal metabolism of prenylated flavonoids; (3) flavonoids antidoting against benzimidazole fungicides; (4) dihydroflavonol ampelopsin in Salix sachalinensis as a feeding stimulant towards willow beetles; and (5) flavones as signaling substances in the life-cycle development of the phytopathogenic Peronosporomycete Aphanomyces cochlioides, a cause of spinach root rot and sugar beet damping-off diseases. Finally recent trends in the ecological biochemistry of flavonoids are briefly described.

https://www.tandfonline.com/doi/pdf/10.1271/bbb.70028

Pawan K. Agrawal

Papers

Chapter Five – Other Flavonoids

Chapter Nine – Flavonoid Structure and Carbon-13 NMR Spectroscopy

Chapter Eight - Flavanoids

Chapter Seven – Chalconoids