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Article

Antiallergic Properties of Biflavonoids Isolated from the Flowers of Mesua ferrea Linn.

by
Yoshiaki Manse
1,
Yusuke Sakamoto
1,
Taiki Miyachi
1,
Mitsuyo Nire
1,
Yoshinori Hashimoto
1,
Saowanee Chaipech
1,2,
Yutana Pongpiriyadacha
3 and
Toshio Morikawa
1,*
1
Pharmaceutical Research and Technology Institute, Kindai University, 3-4-1 Kowakae, Higashi-Osaka 577-8502, Osaka, Japan
2
Faculty of Agro-Industry, Rajamangala University of Technology Srivijaya, Thungyai, Nakhon Si Thammarat 80240, Thailand
3
Faculty of Science and Technology, Rajamangala University of Technology Srivijaya, Thungyai, Nakhon Si Thammarat 80240, Thailand
*
Author to whom correspondence should be addressed.
Separations 2022, 9(5), 127; https://doi.org/10.3390/separations9050127
Submission received: 27 April 2022 / Revised: 17 May 2022 / Accepted: 17 May 2022 / Published: 18 May 2022
(This article belongs to the Section Purification Technology)
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Abstract

The methanolic extract from the flowers of Mesua ferrea Linn. (Calophyllaceae) showed significant hyaluronidase inhibitory activity. Following a bioassay-guided separation of the extract, two biflavonoids, viz., mesuaferrone-A (1) and mesuaferrone-B (2), were isolated, along with ten flavonoids (3–12), two xanthones (13 and 14), three triterpenes (15–17), a phenylpropanoid (18), and five aromatics (19–24). Among the isolates, 1 and 2 (IC50 = 51.1 µM and 54.7 µM, respectively) exhibited hyaluronidase inhibitory activity equivalent to that of the commercially available antiallergic agents disodium cromoglycate (64.8 μM) and ketotifen fumarate (76.5 μM). These biflavonoids (1 and 2) are 8-8″ linked dimers that are composed of naringenin (1a) or apigenin (3), with their corresponding monomers lacking inhibitory activity (IC50 > 300 μM). In addition, 1 and 2 (IC50 = 49.4 µM and 49.2 µM, respectively) inhibited the release of β-hexosaminidase, which is a marker of antigen-IgE-mediated degranulation, in rat basophilic leukemia (RBL-2H3) cells. These inhibitory activities were more potent than those of the antiallergic agents tranilast and ketotifen fumarate (IC50 = 282 μM and 158 μM, respectively), as well as one of the corresponding monomers (1a; IC50 > 100 μM). Nonetheless, these effects were weaker than those of the other monomer (3; IC50 = 6.1 μM).
Keywords: Mesua ferrea; mesuaferrone; biflavonoid; hyaluronidase inhibitor; degranulation inhibitor; Calophyllaceae Mesua ferrea; mesuaferrone; biflavonoid; hyaluronidase inhibitor; degranulation inhibitor; Calophyllaceae

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MDPI and ACS Style

Manse, Y.; Sakamoto, Y.; Miyachi, T.; Nire, M.; Hashimoto, Y.; Chaipech, S.; Pongpiriyadacha, Y.; Morikawa, T. Antiallergic Properties of Biflavonoids Isolated from the Flowers of Mesua ferrea Linn. Separations 2022, 9, 127. https://doi.org/10.3390/separations9050127

AMA Style

Manse Y, Sakamoto Y, Miyachi T, Nire M, Hashimoto Y, Chaipech S, Pongpiriyadacha Y, Morikawa T. Antiallergic Properties of Biflavonoids Isolated from the Flowers of Mesua ferrea Linn. Separations. 2022; 9(5):127. https://doi.org/10.3390/separations9050127

Chicago/Turabian Style

Manse, Yoshiaki, Yusuke Sakamoto, Taiki Miyachi, Mitsuyo Nire, Yoshinori Hashimoto, Saowanee Chaipech, Yutana Pongpiriyadacha, and Toshio Morikawa. 2022. "Antiallergic Properties of Biflavonoids Isolated from the Flowers of Mesua ferrea Linn." Separations 9, no. 5: 127. https://doi.org/10.3390/separations9050127

APA Style

Manse, Y., Sakamoto, Y., Miyachi, T., Nire, M., Hashimoto, Y., Chaipech, S., Pongpiriyadacha, Y., & Morikawa, T. (2022). Antiallergic Properties of Biflavonoids Isolated from the Flowers of Mesua ferrea Linn. Separations, 9(5), 127. https://doi.org/10.3390/separations9050127

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