Abstract

Hipposponlachnins A (1) and B (2), possessing an unprecedented tetracyclo [9.3.0.02,8.03,7] tetradecane ring system, and the probable biogenetic precursor [3, (1R*,2E,4R*,7E,10S*,11S*,12R*)-10, 18-diacetoxydolabella-2,7-dien-6-one] of 1‒2 were isolated from the South China Sea marine sponge Hippospongia lachne. The structures of the novel compounds were determined using integrated spectroscopic methods in combination with single-crystal X-ray diffraction analysis. Compounds 1‒2 showed potent inhibitory activity on the release of β-hexosaminidase, a biomarker for degranulation, as well as the production of pro-inflammatory cytokine IL-4 and lipid mediator LTB4 in DNP-IgE-stimulated RBL-2H3 cells.

Highlights

  • Allergy is an abnormal adaptive immune response against allergens, such as pollen, food, dust mites, cosmetics, mold spores, and animal hairs1,2. β-Hexosaminidase, typically released in addition to histamine by mast cells after stimulation with antigen, has been used as a biomarker for antigen-induced degranulation in rat basophilic leukemia (RBL-2H3) cells[3]

  • Only a few natural compounds with anti-allergic activity have been isolated to date[5]

  • As part of our searching for anti-allergic secondary metabolites from marine sponges, we investigated the sponge Hippospongia lachne, collected from the Xisha Islands of China in March 2013

Read more

Summary

Results and Discussion

The planar structure of 1 was elucidated via a detailed analysis of 2D NMR data (Fig. 2). The overall appearance of the NMR spectrum of 2 revealed close structural similarity between 1 and 2, indicating the presence of the same tetracyclo [9.3.0.02,8.03,7]. Detailed analysis of the single-crystal X-ray diffraction patterns of 2 confirmed this hypothesis and established the absolute configuration of 2 as 1R,2R,3S,4R,7S,8S,10S,11S,12R (Fig. 3). Only one diterpenoid with a similar skeleton, namely vulgarisin A, derived from the Chinese Medicinal Plant Prunella vulgaris, has been reported to date[19] These two novel compounds represented an unprecedented tetracyclo [9.3.0.02,8.03,7] tetradecane ring system from marine source for the first time. The potent inhibitory activity on the release of β-hexosaminidase for 1‒​2 suggested that these two bioactive diterpenoids can be the potential therapeutic agents for the treatment of allergy

Methods
Author Contributions
Additional Information
Full Text
Published version (Free)

Talk to us

Join us for a 30 min session where you can share your feedback and ask us any queries you have

Schedule a call