DETAILED ACTION
Notice of Pre-AIA or AIA Status
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Status of the Application
Receipt of the Response and Amendment after Non-Final Office Action filed 02/23/2026 is acknowledged.
The status of the claims upon entry of the present amendment stands as follows:
Pending claims: 1-10
Withdrawn claims: None
Previously canceled claims: None
Newly canceled claims: None
Amended claims: None
New claims: None
Claims currently under consideration: 1-10
Currently rejected claims: 1-10
Allowed claims: None
Claim Rejections - 35 USC § 103
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
Claims 1-10 are rejected under 35 U.S.C. 103 as being unpatentable over Xu et al. (Xu et al., “Selective enzymatic α-1,6- monoglucosylation of mogroside IIIE for the bio-creation of α-siamenoside I, a potential high-intensity sweetener,” Food Chemistry, 359, (2021) 129938) in view of Jia et al. (U.S. 2011/0027413 A1).
Regarding claims 1 and 2, Xu et al. discloses isomogroside V (p. 1, column 2, ¶2). Jia et al. discloses “iso-mogroside V” ([0011]) as having the same structure as formula (I) as claimed except for having a β-1,6-glucosidic bond between the 24-O-glucosyl moiety and the attached glucose unit instead of an α-1,6-glucosidic bond.
Xu et al. does not specifically disclose the claimed structure.
However, Xu et al. in view of Jia et al. provides motivation for producing the claimed structure, thus rendering it obvious, according to the following rationale.
First, Xu et al. mentions isomogroside V once in the introduction, along with mogrosides IIIE, IV, V, and siamenoside I (p. 1, column 2, ¶2). The reference indicates all those compounds “have an acceptable taste quality” but that a mixture of “a diverse set of mogrosides” “still has a slight aftertaste, thus suggesting it is necessary to develop a kind of pure mogroside possessing a high sweetness intensity as well as a satisfactory taste”. Id. Xu et al. then describes mogroside V as having “excellent sweetness intensity, good taste, and sufficient availability” before noting that siamenoside I was sweeter (pp. 1-2, bridging paragraph). Xu et al. noted a motivation for identifying new glycosides from luo han guo, including synthesizing such compounds via glycosylating or deglycosylating mogrosides (p. 2, column 1, ¶2). Since siamenoside I “possess[es] the best sweetness and taste among all known mogrosides” due to having four glucosyl moieties, the research group monoglycosylated mogroside IIIE to obtain isomers of siamenoside I. Id.
Xu et al. then noted earlier work wherein “α-1,6-momoglucosylation of rubusoside not only brought about a remarkable increase in the sweetness intensity, but also upgraded its sensory quality” and stated a hypothesis that “the β-1,6-glucosidic linkage in the G2 unit of [siamenoside I] could be a crucial factor that affects taste and sweetness”, before aiming to synthesize α-siamenoside I, which has an α-1,6-glucosidic linkage between the 24-O-glucosyl moiety and the attached glucose unit (p. 2, column 1, ¶3; p. 3, Table 1). Upon synthesizing α-siamenoside I, Xu et al. disclosed that it “demonstrated a higher sweetness than [siamenoside I] as well as an outstanding taste”, thus positioning the compound for use as a sweetener (p. 2, column 1, ¶4). Xu et al. concluded broadly that “the distinguished sensory profile of [α-siamenoside I] provides a clue that like β-glucosylation, α-transglucosylation can enhance the sweet taste of mogroside”. (p. 2, column 1, ¶4; p. 7, column 1, ¶2).
Since Xu et al. did not provide any additional instruction regarding isomogroside V in particular, a skilled practitioner would be motivated to consult Jia et al. for more specific information. Jia et al. discloses that isomogroside V has “high sweetening properties” and “particularly high flavour enhancing effect on sweeteners” when compared to mogroside V ([0006]-[0008]).
Given the combined indications that (i) α-transglucosylation can enhance the sweet taste of mogroside (Xu et al., p. 2, column 1, ¶4) and (ii) isomogroside V has superior taste attributes compared to mogroside V (Jia et al., [0006]-[0008]), a skilled practitioner would be motivated to modify isomogroside V to have an α-1,6-glucosidic bond between the 24-O-glucosyl moiety and the attached glucose unit. Such a modification would yield a compound identical to that claimed, thus rendering the claimed compound of formula (I) obvious.
As for claim 3, Jia et al. discloses a method of sweetening an ingestible composition comprising introducing to the ingestible composition a sweetening compound ([0013], ¶(14)), where use of the sweetening compound of claim 1 in place of isomogroside V would be obvious as detailed previously in relation to claim 1.
As for claim 4, Jia et al. discloses the concentration of the sweetening compound introduced to the ingestible composition as ranging from 0.1-1000 ppm ([0022]).
As for claim 5, Jia et al. discloses the composition as further comprising monk fruit extract (i.e., swingle extract) ([0044]).
As for claim 6, Jia et al. discloses the composition as comprising one or more bitter tastants (e.g., acesulfame potassium) ([0028], [0029]).
As for claim 7, Jia et al. discloses an ingestible composition comprising isomogroside V ([0013], ¶(11)), where use of the sweetening compound of claim 1 in place of isomogroside V would be obvious as detailed previously in relation to claim 1.
As for claim 8, Jia et al. discloses the concentration of the sweetening compound in the ingestible composition as ranging from 0.1-1000 ppm ([0022]).
As for claim 9, Jia et al. discloses a flavored product comprising isomogroside V ([0013], ¶(11)), where use of the sweetening compound of claim 1 in place of isomogroside V would be obvious as detailed previously in relation to claim 1.
As for claim 10, Jia et al. discloses the flavored product as being a beverage product ([0013], ¶(11)).
Response to Arguments
Claim Rejections - 35 U.S.C. § 103 of claims 1-10 over Xu et al. and Jia et al.: Applicant’s arguments have been fully considered but they are not persuasive.
Applicant first noted that Wang et al. (Wang et al., “Cucurbitane Glycosides Derived from Mogroside IIE: Structure-Taste Relationships, Antioxidant Activity, and Acute Toxicity,” Molecules, 2014, 19, 12676-12689), which was cited in Xu et al., allegedly teaches that mogroside compounds with five glucose units having α-glycosidic bonds have substantially reduced sweetness compared to mogroside V (Applicant’s Remarks, p. 4, ¶3). Applicant asserted that Wang et al. concluded “that the β-glycosidic bond enhances the sweet taste experience, while the α-glycosidic bond does not have this ability”. Id. Applicant argued that the conclusions of Wang et al. would discourage a skilled practitioner from preparing a mogroside with five glucose units, wherein α-glycosidic bonds were present, which are characteristics of the claimed compound. Id. Applicant argued that the teaching in Wang et al. would discourage modification of the compound of Jia et al. (Applicant’s Remarks, p. 4, ¶4).
Wang et al. teaches that experimental compounds 4 and 5 were the only pentasaccharide compositions and that each contained three α-glycosidic bonds (p. 12682, ¶1). However, Wang et al. was unable to discern the exact molecular structure of the compounds, so it is unclear where the glucose subunits are attached. Id. The conclusion that “the β-glycosidic bond enhances the sweet taste experience, while the α-glycosidic bond does not have this ability” is thus limited to what the data actually supports—that compounds with three α-glycosidic bonds do not enhance the sweet taste experience, where it is unclear where such α-glycosidic bonds may even appear in a compound. The claimed compound and that of Jia et al. as modified according to Xu et al. do not have three α-glycosidic bonds. The limited instruction of Wang et al. therefore cannot be said to teach against a mogroside with five glucose units, where a single α-glycosidic bond is present, especially where Xu et al. specifically teaches that “an α-glycosidic bond at a specific site is capable of enhancing the sweetness and taste of mogroside, which experimentally supplemented previous findings of the effect of structure on sweetness and taste in α-glucosidic analogs (Wang et al., 2014; Cicek, 2020)” (p. 7, column 1, ¶2). Applicant’s arguments are thus unpersuasive.
The rejections of claims 1-10 have been maintained herein.
Conclusion
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
Claims 1-10 are rejected.
No claims are allowed at this time.
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/JEFFREY P MORNHINWEG/Primary Examiner, Art Unit 1793
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