Furanaphin: a novel naphtho[2,3-c]furan-4(1H)-one derivative from the aphid Aphis spiraecola Patch

Horikawa, Mitsuyo; Noguchi, Tadashi; Takaoka, Shigeru; Kawase, Masaki; Sato, Masao; Tsunoda, Tetsuto

doi:10.1016/j.tet.2003.11.061

Cited by 19 publications

(14 citation statements)

References 38 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Acid hydrolysis and GC analysis led to the identification of D-glucose and D-apiose. Comparison with reported data suggested the skeleton was 6-hydroxymusizin [6].…”

Section: Acid Hydrolysis and Sugar Identificationmentioning

confidence: 68%

Phenolic Constituents from Fallopia multiflora (Thunberg) Haraldson

Nguyen

Pham²,

Thao³

et al. 2018

Journal of Chemistry

View full text Add to dashboard Cite

Four naphtolic glycosides (1–4), three anthraquinones (5–7), two stilbenes (8-9), one benzyl glycoside (10), and one flavonoid (11) were isolated from the roots of Fallopia multiflora. The new compounds were elucidated to be 6-hydroxymusizin 8-O-α-D-apiofuranosyl-(1→6)-β-D-glucopyranoside (1) and 6-methoxy-3-methyl-1,6,8-trihydroxy-2-naphthoic acid 8-O-β-D-glucopyranoside (3). Compound 3 could be an important marker for chemotaxonomy of F. multiflora. Benzyl gentiobioside (10) was isolated for the first time from the family Polygonaceae.

show abstract

“…Acid hydrolysis and GC analysis led to the identification of D-glucose and D-apiose. Comparison with reported data suggested the skeleton was 6-hydroxymusizin [6].…”

Section: Acid Hydrolysis and Sugar Identificationmentioning

confidence: 68%

Phenolic Constituents from Fallopia multiflora (Thunberg) Haraldson

Nguyen

Pham²,

Thao³

et al. 2018

Journal of Chemistry

View full text Add to dashboard Cite

show abstract

“…Cassiaglycoside II (2) C-NMR spectra were similar to those of 6-hydroxymusizin, 21) except for the signals around the 6 and 8-positions. The positions of two glucopyranoses were confirmed by HMBC spectroscopy analysis.…”

Section: Structures Of Cassiaglycosides I-iv (1-4)mentioning

confidence: 73%

Structures of Aromatic Glycosides from the Seeds of <i>Cassia auriculata</i>

Nakamura

Zhang

Nakashima

et al. 2016

CHEMICAL & PHARMACEUTICAL BULLETIN

View full text Add to dashboard Cite

“…All spectroscopic data ( 1 H, 13 C NMR, IR, and HRMS) for the synthetic furanaphin (1) agreed with those reported previously in the literature. 11 In summary, we have achieved the total synthesis of furanaphin (1) by utilizing the Fries rearrangement as a key step and found that the BF 3 ·2AcOH complex satisfactorily provided the desired product. Further applications of this reaction and biological activities of 1 are under investigation in our laboratory and will be reported in due course.…”

Section: Scheme 1 Retrosynthesis Ofmentioning

confidence: 86%

“…1.5 mm long) as a yellowish hydrophobic compound having a unique naphthofuran ring system, which was found to be active (IC 50 25 μM) against HL-60 cells. 11 To continue our investigations into the biological activities of 1, including antiviral, antibacterial, and antifungal activities, an adequate supply of 1 was required. Herein, we report the total synthesis of 1 by utilizing the Fries rearrangement as a key step.…”

mentioning

confidence: 99%