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Compounds with antidiabetic activity in frangipani and preparation method thereof

An anti-diabetic and frangipani technology, applied in the field of compounds, can solve the problem of few reports on the active ingredients of frangipani

Active Publication Date: 2022-05-24
GUILIN MEDICAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] According to literature reports, the anti-diabetic activity of frangipani is mostly related to various crude extracts of frangipani, and there are very few reports on the specific active ingredients of frangipani

Method used

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  • Compounds with antidiabetic activity in frangipani and preparation method thereof
  • Compounds with antidiabetic activity in frangipani and preparation method thereof
  • Compounds with antidiabetic activity in frangipani and preparation method thereof

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Embodiment Construction

[0034] Structure identification of compound 1 by high-resolution mass spectrometry (HR-ESI-MS m / z : 617.4229 [M – H] ‒ , calcdfor C 40 H 57 O 5 ‒ 617.4211) can be inferred that its molecular formula is C 40 H 58 O 5 , with 12 degrees of unsaturation; +26.77 ( c 0.43, DMSO). IR (KBr) data showed OH ( υ max 3422 cm ‒1 ), COOH ( υ max 1715cm ‒1 ), meta-substituted benzene ring ( υ max 964, 882, 750 cm ‒1 ). UV (methanol) λ max (log ε ) 220 (3.46), 275 (1.89). 1 HNMR (500 MHz, pyridine- d 5 ) δ H : 0.90 (1H, m, H-1a), 1.62 (1H, m, H-1b), 1.77 (2H, m, H-2), 4.78 (1H, dd, J = 11.7, 4.8 Hz, H-3), 0.78 (1H, m, H-5), 1.35 (1H, m, H-6a), 1.45 (1H, m, H-6b), 1.35 (2H, m, H-7), 1.28 (1H, m, H-9), 1.29 (2H, m, H-11), 1.14 (2H, m, H-12), 1.62 (1H, m, H-13), 0.97 (1H, m, H-15a), 1.67 (1H, m, H-15b), 1.42 (1H, m, H-16a), 1.50 (1H, m, H-16b), 1.42 (1H, m, H -18), 2.48 (1H, td, J = 11.0, 5.8 Hz, H-19), 1.41 (2H, m, H-21), 1.26 (1H, m, H-22a) 1.40 (1H, ...

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Abstract

The invention discloses compounds with antidiabetic activity in Plumeria frangipani and a preparation method thereof. There are four compounds, wherein compounds 1, 2 and 4 are new compounds, which are respectively triterpenoid lup‑20(29)‑ en-3 β -(1-(2 S ‑hydroxypropionate)‑benzoic acid)(1), iridoids β -dihydroplumericin A(2), β ‑dihydroplumericinic acid(3), pyrones tetrahydro‑4 S ‑hydroxy‑6 β ‑heptadecyl‑2H‑pyran‑2‑one (4), and further study the antidiabetic effect of the above-mentioned compound 1‑4 of frangipani by light absorption detection method. The results showed that compound 1‑4 was α ‑Glucosidase inhibitory effect is stronger than the positive control acarbose, especially the activity of compound 1 is particularly prominent; the inhibitory effect of compound 1 on PTP1B is stronger than the positive control oleanolic acid, which has stronger activity. The invention discovers a compound with novel structure and anti-diabetic activity from Plumeria frangipani, which lays the foundation for the preparation of new anti-diabetic drugs.

Description

technical field [0001] The invention relates to compounds, in particular to a triterpenoid, iridoid and pyrone compound with anti-diabetic activity extracted and isolated from frangipani and a preparation method thereof. Background technique [0002] The source of frangipani is the oleander family Plumeria ( Plumeria rubra L.) of the dried flowers. The flowers are white and yellow, with a mellow aroma and a slightly bitter taste. It is a genuine medicinal material in Guangxi. It is mainly distributed in Guangdong, Guangxi, Yunnan, Fujian and other places. Folks in Guangdong and Guangxi often pick its flowers and dry them to make tea. Plumeria has both excellent ornamental and many ethnic medicinal properties, such as the treatment of diarrhea, dysentery, abdominal pain, toothache and earache cancer. According to "Chinese Ethnography Essentials", its taste is sweet, light, and cool in nature. In Mexico, frangipani decoction is used to treat and prevent diabetes. In recen...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J63/00C07D493/20C07D309/30A61P3/10
CPCC07J63/008C07D493/20C07D309/30A61P3/10
Inventor 谭钦刚张胜男赖春华
Owner GUILIN MEDICAL UNIVERSITY
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