The High Content of Ent-11α-hydroxy-15-oxo-kaur- 16-en-19-oic Acid in Adenostemma lavenia (L.) O. Kuntze Leaf Extract: With Preliminary in Vivo Assays

Abstract

Background: Ent-11α-hydroxy-15-oxo-kaur-16-en-19-oic acid (11αOH-KA) is a multifunctional biochemical found in some ferns, Pteris semipinnata, and its congeneric species. Although a number of therapeutic applications of 11αOH-KA have been proposed (e.g., anti-cancer, anti-inflammation, and skin whitening), the content of 11αOH-KA in these ferns is not high. Adenostemma lavenia (L.) O. Kuntze, an Asteraceae, has also been reported to contain 11αOH-KA. The decoction (hot water extract) of whole plants of A. lavenia is used as a folk remedy for inflammatory disorders, such as hepatitis and pneumonia, suggesting that 11αOH-KA may be the ingredient responsible for the medicinal properties of this plant. Methods: The anti-melanogenic activities of the water extracts of A. lavenia leaves and Pteris dispar Kunze (a cognate of P. semipinnata) leaves were compared in mouse B16F10 melanoma cells. The amount of 11αOH-KA was measured by using liquid chromatography spectrometry. C57BL/6J mice were treated with the water extract of A. lavenia leaf, and the blood concentration of 11αOH-KA was measured. The in vivo efficacy of the water extract of A. lavenia leaf was evaluated according to tis anti-melanogenic activity by monitoring hair color. Results: Although both the extracts (A. lavenia and P. dispar Kunze) showed high anti-melanogenic activities, only A. lavenia contained a high amount of 11αOH-KA, approximately 2.5% of the dry leaf weight. 11αOH-KA can be purified from A. lavenia leaves in two steps: water extraction followed by chloroform distribution. The treatment of mice with the water extract of A. lavenia leaf suppresses pigmentation in their hairs. Conclusions: Despite the small number of mice examined, the present preliminary result of the suppressed hair pigmentation suggests that the water extract of A. lavenia leaf and the ingredient that is possibly responsible for this—11αOH-KA—are new materials for oral cosmetics. The results may also be helpful in the future development of functional foods and methods to treat patients suffering from hyperpigmentation disorders, such as melasma.

The Antiaging Effect of Active Fractions and Ent-11α-Hydroxy-15-Oxo-Kaur-16-En-19-Oic Acid Isolated from Adenostemma lavenia (L.) O. Kuntze at the Cellular Level

“…To examine whether 11αOH-KA, a major ingredient in A. lavenia fractions [ 4 ], conferred H 2 O 2 resistance and longevity to S. pombe , we performed similar experiments and a chronological life span (CLS) assay with 11αOH-KA. In spot assays, the 11αOH-KA treatment (45 µg mL −1 ) significantly extended the yeast lifespan at both day 7 and 11 ( Figure 3 A).…”

“…The A. lavenia leaf extract contained a high amount of 11αOH-KA (approximately 2.5% of dry leaf weight), and the compound showed antimelanogenic activity [ 4 ]. The in vitro antioxidant and antiglycation capacities of Awf and Acf were relatively weak compared to positive controls [ 3 ].…”

“…A. lavenia was collected from Bogor, West Java, Indonesia. 11αOH-KA, isolated from A. lavenia leaves with a purity of >95%, judging from the NMR spectra in Gifu University [ 4 ], was dissolved in dimethyl sulfoxide (DMSO). Briefly, a dried powder (100 g) obtained from A. lavenia leaves was soaked in distilled water 1:30 ( w/v ) at 55 °C for 12 h. The water-soluble fraction ( A. lavenia water fraction) was recovered after filtration with coffee filtrates, and 11αOH-KA was purified by chloroform extraction ( A. lavenia chloroform fraction) followed by silica gel chromatography.…”

“…A recent study showed that A. lavenia extract had anti-inflammatory activity in LPS-treated RAW 264.7 cells and mice [ 2 ]. In addition, the leaf extract of this plant has antimelanogenic activities in B16F10 cells and suppresses hair pigmentation in infant mice [ 3 , 4 ]. Notably, A. lavenia leaf extract contains a higher amount of ent -11α-hydroxy-15-oxo-kaur-16-en-19-oic acid (11αOH-KA), which may be responsible for 50% of the antimelanogenic activity in the extracts [ 4 ] ( Figure 1 ).…”

“…The 11αOH-KA belongs to diterpene/kaurane class, which is found in some plants, including the compositae ( Gochnatia decora ) and ferns ( Pteris semipinnata ), as well as A. lavenia [ 5 , 6 ]. Interestingly, 11αOH-KA exhibits various pharmaceutical potentials, such as anticancer, anti-inflammation, and skin whitening [ 4 , 5 ]. Despite the broad activities of 11αOH-KA, the potential of this compound as an antioxidant and antiaging material in skin care has not been clarified yet.…”